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Chemoselective N-Heterocyclic Carbene Catalyzed Cascade of Enals with Nitroalkenes Zijun Wu, Xu Wang, Fangyi Li, Jicheng Wu, Jian Wang* Department of Pharmacology and Pharmaceutical Sciences School of Medicine and School of Life Sciences Tsinghua University, Beijing, 184 (China) wangjian212@tsinghua.edu.cn Supporting Information Contents: A. General Information... S2 B. Experimental Procedure for the N-Heterocyclic Catalyzed Addition of Enal with Nitroalkene to Give 3,4-Dihydrocoumarin... S3 C: Characterization Data.... S4 D. Reference:... S22 E. NMR Spectra... S23 F. HPLC Spectra... S52

A. General Information Chemicals and solvents were purchased from commercial suppliers and used as received. 1 H and 13 C NMR spectra were recorded on a Bruker ACF3 (3 MHz) or AMX5 (5 MHz) spectrometer. Chemical shifts were reported in parts per million (ppm), and the residual solvent peak was used as an internal reference: proton (chloroform δ 7.26), carbon (chloroform δ 77.) or tetramethylsilane (TMS δ.) was used as a reference. Multiplicity was indicated as follows: s (singlet), d (doublet), t (triplet), q (quartet), m (multiplet), dd (doublet of doublet), bs (broad singlet). Coupling constants were reported in Hertz (Hz). Low resolution mass spectra were obtained on a Finnigan/MAT LCQ spectrometer in ESI mode, and a Finnigan/MAT 95XL-T mass spectrometer in EI mode. All high resolution mass spectra were obtained on a Finnigan/MAT 95XL-T spectrometer. For thin layer chromatography (TLC), Merck pre-coated TLC plates (Merck 6 F254) were used, and compounds were visualized with a UV light at 254 nm. Flash chromatography separations were performed on Merck 6 (.4-.63 mm) mesh silica gel. The enantiomeric excesses of products were determined by chiral phase HPLC analysis. ptical rotations were recorded on Jasco DIP-1 polarimeter. The nitroalkenes were prepared according to literature procedures 1, 2, 3. S2

B. Experimental Procedure for the N- Heterocyclic Catalyzed Addition of Enal 1a with Nitroalkene 2a to Give 3,4-Dihydrocoumarin To a dry Schlenk reaction tube equipped with a magnetic stir bar, was added cinnamaldehyde 1a (45 mg,.34 mmol), nitroalkene 2a (28 mg,.17 mmol), triazolium salt NHC (7.4 mg,.17 mmol), KHC 3 (3.4 mg,.34 mmol). The Schlenk tube was closed with a septum, evacuated and refilled with N 2. Freshly distilled anhydrous THF (1 ml) was added and the mixture was stirred at room temperature and monitored by TLC until 2a was fully consumed. A small portion of mixture was collected for 1 H NMR to determine the reaction of the cis/trans-isomers. The reaction mixture was passed through a pad of silica gel and washed with ethyl acetate. The solvent was removed under reduced pressure and residue was subjected silica gel chromatography (petroleum ether/ethyl acetate) to give the desired product 3aa as colorless oil (45.5 mg, 9% yield). Racemic samples for the standard of chiral HPLC spectra were prepared using racemic NHC precursor D as catalyst. N N BF 4 N D S3

C: Characterization Data. (3R,4R)-3-benzyl-4-(nitromethyl)chroman-2-one (3aa): 45.5 mg, 9% yield, colorless oil; 1 H NMR (4 MHz, CDCl 3 ) δ = 7.43 7.41 (m, 1H), 7.39 7.3 (m, 3H), 7.26 7.15 (m, 3H), 7.7 (d, J = 6.6 Hz, 2H), 4.46 4.37 (m, 2H), 3.58 (t, J = 7.2 Hz, 1H), 3.19 (ddd, J = 1.6, 5.5, 1.4 Hz, 1H), 3.8 (dd, J = 13.7, 5.5 Hz, 1H), 2.61 (dd, J = 13.6, 1.7 Hz, 1H). 13 C NMR (1 MHz, CDCl 3 ): δ = 167.8, 15.9, 135.7, 13.4, 129.4, 129., 128.9, 127.6, 125.6, 118.5, 117.4, 77.9, 44.4, 37.6, 35.5. TLC (1:4 EtAc/Petroleum ether): R f =.47; HRMS (ESI): calcd for C 17 H 15 N 4 Na + (M+Na + ): 32.893, found 32.898. HPLC (Chiralpak IB, i-propanol/hexane = 5/95, flow rate 1. ml/min, λ = 22 nm): t R (mionor) = 2.2 min, t R (major) = 22.3 min, ee = 99%, dr > 19:1; [α] D 25 = + 8.4 (c =.67 in CHCl 3 ). F 2 N (3R,4R)-3-(4-fluorobenzyl)-4-(nitromethyl)chroman-2-one (3ab): 42.9 mg, 8% yield, colorless oil; 1 H NMR (4 MHz, CDCl 3 ): δ 7.46 7.39 (m, 1H), 7.27 7.19 (m, 2H), 7.17 (d, J = 8.2 Hz, 1H), 7.4 (d, J = 6.9 Hz, 4H), 4.49 4.4 (m, 2H), 3.58 (t, J = 7.5 Hz, 1H), 3.17 (dd, J = 1.2, 5.9 Hz, 1H), 3.3 (dd, J = 13.9, 5.8 Hz, 1H), S4

2.63 (dd, J = 13.8, 1.3 Hz, 1H). 13 C NMR (1 MHz, CDCl 3 ): δ =167.6, 162.1 (d, J C-F = 245 Hz), 15.9, 131.4 (d, J C-F = 4 Hz), 13.5, 13.4, 129.3, 125.7, 118.3, 117.4, 116., 115.8, 77.8, 44.4, 37.7, 34.9. TLC (1:4 EtAc/Petroleum ether): R f =.44. HRMS (ESI): calcd for C 17 H 14 FN 4 Na + (M+Na + ): 338.85, found 338.87. HPLC (Chiralpak IB, i-propanol/hexane = 5/95, flow rate 1. ml/min, λ = 254 nm): t R (minor) = 21.1 min, t R (major) = 28.8 min, ee = 99%, dr > 19:1; [α] D 25 = + 73.2 (c =.3 in CHCl 3 ). Cl 2 N (3R,4R)-3-(4-chlorobenzyl)-4-(nitromethyl)chroman-2-one (3ac): 46.2 mg, 82% yield, foam; 1 H NMR (4 MHz, CDCl 3 ): δ = 7.46 7.39 (m, 1H), 7.35 7.27 (m, 2H), 7.23 (qd, J = 7.6, 1.5 Hz, 2H), 7.16 (t, J = 8.3 Hz, 1H), 7.1 (d, J = 8.3 Hz, 2H), 4.53 4.36 (m, 2H), 3.57 (dd, J = 11.3, 4. Hz, 1H), 3.18 (ddd, J = 1.2, 5.9, 1.4 Hz, 1H), 3.2 (dd, J = 13.8, 5.9 Hz, 1H), 2.62 (dd, J = 13.8, 1.3 Hz, 1H). 13 C NMR (1 MHz, CDCl 3 ): δ = 167.5, 15.9, 134.2, 133.5, 13.5, 13.2, 129.3, 129.2, 125.7, 118.2, 117.5, 77.7, 44.2, 37.7, 35.. TLC (1:4 EtAc/Petroleum ether): R f =.44. HRMS (ESI): calcd for C 17 H 15 ClN 4 Na + (M+Na + ): 355.582, found 355.587. HPLC (Chiralpak IB, i-propanol/hexane = 1/9, flow rate 1. ml/min, λ = 22 nm): t R (minor) = 15.5 min, t R (major) = 2.8 min, ee = 99%, dr > 19:1; [α] D 25 = +22.8 (c = 1.1 in CHCl 3 ). S5

Br 2 N (3R,4R)-3-(4-bromobenzyl)-4-(nitromethyl)chroman-2-one (3ad): 56.4 mg, 88% yield, white solid, mp 125-127 C; 1 H NMR (4 MHz, CDCl 3 ): δ = 7.49 7.39 (m, 3H), 7.27 7.15 (m, 3H), 7.1 6.94 (m, 2H), 4.49 4.4 (m, 2H), 3.56 (t, J = 7.7 Hz, 1H), 3.18 (ddd, J = 1.3, 5.9, 1.4 Hz, 1H), 3.1 (dd, J = 13.8, 5.9 Hz, 1H), 2.6 (dd, J = 13.8, 1.3 Hz, 1H). 13 C NMR (1 MHz, CDCl 3 ): δ = 167.4, 15.9, 134.7, 132.2, 13.6, 13.5, 129.3, 125.7, 121.6, 118.2, 117.5, 77.7, 44.1, 37.7, 35.. TLC (1:4 EtAc/Petroleum ether): R f =.37. HRMS (ESI): calcd for C 17 H 14 BrN 4 Na + (M+Na + ): 398.4, found 397.9994. HPLC (Chiralpak IC, i-propanol/hexane = 5/95, flow rate 1. ml/min, λ = 22 nm): t R (minor) = 16.4 min, t R (major) = 22.5 min, ee = 99%, dr > 2:1; [α] 25 D = - 7.9 (c = 1.5 in CHCl 3 ). CH 3 2 N (3R,4R)-3-(4-methylbenzyl)-4-(nitromethyl)chroman-2-one (3ae): 41.8 mg, 79% yield, colorless oil; 1 H NMR (4 MHz, CDCl 3 ): δ = 7.46 7.39 (m, 1H), 7.26 7.2 (m, 2H), 7.2 7.15 (m, 2H), 7.14 (s, 1H), 6.95 (d, J = 8. Hz, 2H), 4.48 4.39 (m, 2H), 3.58 (td, J = 7.7, 1.3 Hz, 1H), 3.16 (ddd, J = 1.7, 5.5, 1.5 Hz, 1H), 3.3 (dt, J = 14.7, 7.3 Hz, 1H), 2.55 (dt, J = 15.9, 7.9 Hz, 1H), 2.36 (s, 3H). 13 C NMR (1 MHz, S6

CDCl 3 ): δ = 168., 151., 137.2, 132.6, 13.3, 129.7, 129.4, 128.7, 125.6, 118.5, 117.4, 78., 44.5, 37.5, 21.1. TLC (1:4 EtAc/Petroleum ether): R f =.46. HRMS (ESI): calcd for C 18 H 17 N 4 Na + (M+Na + ): 334.155, found 334.159. HPLC (Chiralpak IB, i-propanol/hexane = 1/9, flow rate 1. ml/min, λ = 22 nm): t R (minor) = 11.2 min, t R (minor) = 13.1 min, ee =99%, dr > 19:1; [α] 25 D = + 47.3 (c = 5.3 in CHCl 3 ). (3R,4R)-3-(2-methoxybenzyl)-4-(nitromethyl)chroman-2-one (3af): Major isomer, 42.3 mg, 76% yield, foam; 1 H NMR (4 MHz, CDCl 3 ): δ = 7.44 7.38 (m, 1H), 7.31 7.25 (m, 1H), 7.25 7.18 (m, 2H), 7.16 (dd, J = 7.7, 5.5 Hz, 1H), 6.92 6.84 (m, 3H), 4.49 4.38 (m, 2H), 3.83 (s, 3H), 3.59 (td, J = 7.8, 1.3 Hz, 1H), 3.4 3.29 (m, 1H), 3.8 (dd, J = 13.4, 6.4 Hz, 1H), 2.73 2.61 (m, 1H). 13 C NMR (1 MHz, CDCl 3 ): δ = 168.1, 157.6, 151., 13.8, 13.2, 129.4, 129., 125.3, 124.1, 12.6, 118.9, 117.2, 11.5, 78.1, 55.1, 42.4, 38.3, 31.3. TLC (1:4 EtAc/Petroleum ether): R f =.44. HRMS (ESI): calcd for C 18 H 17 N 5 Na + (M+Na + ): 35.14, found 35.16. HPLC (Chiralpak IB, i-propanol/hexane = 5/95, flow rate 1. ml/min, λ = 24 nm): t R (minor) = 18.3 min, t R (major) = 19.6 min, ee = 99%, dr >19:1; [α] 25 D = + 111. (c =.3 in CHCl 3 ). S7

(3R,4R)-3-(3-fluorobenzyl)-4-(nitromethyl)chroman-2-one 3ag: 41.3 mg, 77% yield, colorless oil; 1 H NMR (4 MHz, CDCl 3 ): δ = 7.46 7.4 (m, 1H), 7.36 7.29 (m, 1H), 7.23 (q, J = 5.8 Hz, 2H), 7.18 (d, J = 8.2 Hz, 1H), 7.1 (td, J = 8.5, 2.3 Hz, 1H), 6.87 (d, J = 7.6 Hz, 1H), 6.79 (d, J = 9.4 Hz, 1H), 4.52 4.39 (m, 2H), 3.59 (t, J = 7.5 Hz, 1H), 3.25 3.15 (m, 1H), 3.5 (dd, J = 13.8, 5.8 Hz, 1H), 2.63 (dd, J = 13.7, 1.4 Hz, 1H). 13 C NMR (1 MHz, CDCl 3 ): δ = 167.4, 163. (d, J C-F = 24.6 Hz), 15.9, 138.2 (d, J C-F = 7 Hz), 13.6, 13.5, 13.5, 129.4, 125.8, 124.6, 124.5, 118.2, 117.4, 116., 115.8, 114.7, 114.5, 77.8, 44.2, 37.8, 35.3. TLC (1:4 EtAc/Petroleum ether): R f =.44. HRMS (ESI): calcd for C 17 H 14 FN 4 Na + (M+Na + ): 338.85, found 338.85. HPLC (Chiralpak IB, i-propanol/hexane = 5/95, flow rate 1. ml/min, λ = 22 nm): t R (minor) = 14.4 min, t R (major) = 17.2 min, ee = 99 %, dr > 19:1; [α] 25 D = + 17.3 (c =.8 in CHCl 3 ). (3R,4R)-3-(2-nitrobenzyl)-4-(nitromethyl)chroman-2-one 3ah: 45.4 mg, 78% yield, white solid, mp 142-145 C; 1 H NMR (4 MHz, CDCl 3 ): δ = 8.7 (dt, J = 11.6, 5.8 Hz, 1H), 7.6 (td, J = 7.5, 1.3 Hz, 1H), 7.53 7.41 (m, 2H), 7.29 (d, J = 7. Hz,1H), 7.27 7.16 (m, 3H), 4.63 4.41 (m, 2H), 3.82 (td, J = 7.7, 1. Hz, 1H), 3.47 3.36 S8

(m, 1H), 3.21 (dd, J = 13.6, 6.5 Hz, 1H), 3.11 (dd, J = 13.6, 9. Hz, 1H). 13 C NMR (1 MHz, CDCl 3 ): δ = 166.8, 15.7, 148.9, 133.7, 132.7, 131.6, 13.6, 129.4, 128.9, 125.7, 125.7, 118.4, 117.5, 77.8, 43.7, 39.5, 34.. TLC (1:4 EtAc/Petroleum ether): R f =.17. HRMS (ESI): calcd for C 17 H 14 N 2 6 Na + (M+Na + ): 365.75, found 365.748. HPLC (Chiralpak ID, i-propanol/hexane = 1/9, flow rate 1. ml/min, λ = 22 nm): t R (major) = 71.3 min, t R (minor) = 81.6 min, ee = 99%, dr > 19:1; [α] 25 D = + 56.7 (c =.7 in CHCl 3 ). 2 N (3R,4R)-3-(naphthalen-2-ylmethyl)-4-(nitromethyl)chroman-2-one (3ai): 51.9 mg, 88% yield, white solid, mp 121-124 C; 1 H NMR (4 MHz, CDCl 3 ): δ = 7.94 7.6 (m, 2H), 7.59 (d, J = 8.3 Hz, 1H), 7.57 7.52 (m, 2H), 7.51 7.39 (m, 2H), 7.33 7.18 (m, 3H), 7.1 (t, J = 7.1 Hz, 1H), 4.37 (d, J = 7.7 Hz, 2H), 3.66 3.49 (m, 2H), 3.39 (ddd, J = 1.5, 5., 1.3 Hz, 1H), 3.3 (dd, J = 13.9, 1.6 Hz, 1H). 13 C NMR (1 MHz, CDCl 3 ): δ = 168.1, 151., 134.2, 131.7, 131.4, 13.5, 129.7, 129.2, 128.6, 127.7, 126.8, 126.1, 125.6, 125.3, 123., 118.6, 117.5, 78., 43.6, 37.9, 32.9. TLC (1:4 EtAc/Petroleum ether): R f =.4. HRMS (ESI): calcd for C 21 H 17 N 4 Na + (M+Na + ): 37.155, found 37.151. HPLC (Chiralpak IC, i-propanol/hexane = 1/9, flow rate 1. ml/min, λ = 254 nm): t R (major) = 26.2 min, t R (minor) = 3.5 min, ee = 99%, dr > 19:1; [α] 25 D = + 44.5 (c = 1.5 in CHCl 3 ). S9

2 N N (3R,4R)-4-(nitromethyl)-3-(pyridin-3-ylmethyl)chroman-2-one (3aj): 4.1 mg, 79% yield, white solid, mp 15-152 C; 1 H NMR (4 MHz, CDCl 3 ): δ 8.58 8.57 (m, 1H), 8.31 (d, J = 2. Hz, 1H), 7.5 7.45 (m, 1H), 7.45 7.43 (m, 1H), 7.31 (dt, J = 8.5, 4.2 Hz, 1H), 7.26 7.14 (m, 2H), 7.16 (dd, J = 12., 6.2 Hz, 1H), 4.48 4.45 (m, 2H), 3.59 (ddd, J = 25.8, 13., 4.2 Hz, 1H), 3.22 3.19 (m, 1H), 3.7 3.2 (m, 1H), 2.7 (td, J = 13.9, 8.9 Hz, 1H). 13 C NMR (1 MHz, CDCl 3 ): δ = 167.1, 15.8, 15.1, 149.1, 136.3, 131.4, 13.7, 129.3, 125.9, 123.9, 118., 117.5, 77.6, 43.9, 37.9, 32.9. TLC (1:2 EtAc/Petroleum ether): R f =.29. HRMS (ESI): calcd for C 16 H 14 N 2 4 Na + (M+Na + ): 321.851, found 321.851. HPLC (Chiralpak IB, i-propanol/hexane = 2/8, flow rate 1. ml/min, λ = 254 nm): t R (minor) =25.2 min, t R (major) = 33.5 min, ee = 99%, dr > 19:1; [α] 25 D = + 48.8 (c = 1. in CHCl 3 ). (3R,4R)-3-(furan-2-ylmethyl)-4-(nitromethyl)chroman-2-one (3ak): 36.6 mg, 75% yield, colorless oil; 1 H NMR (4 MHz, CDCl 3 ): δ = 7.41 (ddd, J = 8.2, 6.9, 2.3 Hz, 1H), 7.36 (dd, J = 1.9,.8 Hz, 1H), 7.26 7.19 (m, 2H), 7.17 7.12 (m, 1H), 6.34 6.28 (m, 1H), 6.13 6.4 (m, 1H), 4.59 4.43 (m, 2H), 3.68 (td, J = 7.5, 2. Hz, 1H), 3.32 (ddd, J = 9.6, 5.6, 2. Hz, 1H), 3.4 (td, J = 14.7, 6.1 Hz, 1H), 2.87 2.75 (m, S1

1H). 13 C NMR (1 MHz, CDCl 3 ): δ = 167.3, 15.7, 149.4, 142.6, 13.4, 129.3, 125.6, 118.4, 117.4, 11.5, 18.4, 77.8, 42.1, 38.2, 28.4. TLC (1:4 EtAc/Petroleum ether): R f =.41. HRMS (ESI): calcd for C 15 H 13 N 5 Na + (M+Na + ): 31.691, found 31.693. HPLC (Chiralpak IB, i-propanol/hexane = 2/98, flow rate 1. ml/min, λ = 22 nm): t R (major) = 34.6 min, t R (minor) = 37.6 min, ee = 98%, dr > 19:1; [α] 25 D = + 58.8 (c =.3 in CHCl 3 ). 2 N S (3R,4R)-4-(nitromethyl)-3-(thiophen-2-ylmethyl)chroman-2-one (3al): 36.1 mg, 7% yield, red oil; 1 H NMR (4 MHz, CDCl 3 ): δ = 7.45 7.41 (m, 1H), 7.25 (dd, J = 13.5, 7.6 Hz, 3H), 7.16 (t, J = 7.5 Hz, 1H), 7.3 6.94 (m, 1H), 6.81 6.73 (m, 1H), 4.63 4.34 (m, 2H), 3.7 (t, J = 7.6 Hz, 1H), 3.33 3.14 (m, 2H), 3.2 2.82 (m, 1H). 13 C NMR (1 MHz, CDCl 3 ): δ = 167.4, 15.8, 137.6, 13.5, 129.5, 127.4, 126.9, 125.7, 125.3, 118.2, 117.4, 77.8, 44.8, 37.6, 29.7. TLC (1:4 EtAc/Petroleum ether): R f =.4. HRMS (ESI): calcd for C 15 H 13 N 4 SNa + (M+Na + ): 326.463, found 326.463. HPLC (Chiralpak IF, i-propanol/hexane = 3/97, flow rate 1. ml/min, λ = 22 nm): t R (major) = 26.3 min, t R (minor) = 33.7 min, ee = 99%, dr > 19:1; [α] 25 D = +39.3 (c =.6 in CHCl 3 ). 2 N S11

(3R,4R)-3-(benzofuran-2-ylmethyl)-4-(nitromethyl)chroman-2-one (3am): 41.9 mg, 73% yield, red oil; 1 H NMR (4 MHz, CDCl 3 ): δ = 7.52 (d, J = 7.4 Hz, 1H), 7.44 (d, J = 8. Hz, 1H), 7.42 7.35 (m, 1H), 7.33 7.26 (m, 1H), 7.22 (dt, J = 14.7, 7. Hz, 3H), 7.15 (d, J = 8. Hz, 1H), 6.48 (s, 1H), 4.62 4.44 (m, 2H), 3.8 3.69 (m, 1H). 13 C NMR (1 MHz, CDCl 3 ): δ = 167.1, 155., 152.3, 15.7, 13.4, 129.2, 128.1, 125.6, 124.3, 123., 12.8, 118.3, 117.4, 111.1, 15.5, 77.6, 41.6, 38.2, 29.. TLC (1:4 EtAc/Petroleum ether): R f =.37. HRMS (ESI): calcd for C 19 H 15 N 5 Na + (M+Na + ): 36.848, found 36.842. HPLC (Chiralpak IC, i-propanol/hexane = 1/9, flow rate 1. ml/min, λ = 22 nm): t R (major) = 31.6 min, t R (major) = 38. min, ee = 99%, dr > 19:1; [α] 25 D = + 1.1 (c =.5 in CHCl 3 ). 2 N S (3R,4R)-3-(benzo[b]thiophen-2-ylmethyl)-4-(nitromethyl)chroman-2-one (3an): 37.2 mg, 62% yield, red oil; 1 H NMR (4 MHz, CDCl 3 ): δ = 7.8 (dd, J = 1.5, 9.3 Hz, 1H), 7.77 7.67 (m, 1H), 7.49 7.4 (m, 1H), 7.35 (ddd, J = 14.2, 7.1, 1.4 Hz, 2H), 7.25 (d, J = 4.2 Hz, 2H), 7.21 7.16 (m, 1H), 6.99 (s, 1H), 4.61 4.41 (m, 2H), 3.84 3.64 (m, 1H), 3.44 3.24 (m, 2H), 2.96 (dt, J = 27.4, 13.6 Hz, 1H). 13 C NMR (1 MHz, CDCl 3 ): δ = 167.2, 15.8, 139.8, 139.6, 138.6, 13.5, 129.5, 125.8, 124.6, 124.5, 123.7, 123.4, 122.4, 118.1, 117.5, 77.7, 44.2, 37.6, 3.6. TLC (1:4 EtAc/Petroleum ether): R f =.35. HRMS (ESI): calcd for C 19 H 15 N 4 SNa + (M+Na + ): S12

376.619, found 376.621. HPLC (Chiralpak IB, i-propanol/hexane = 5/95, flow rate 1. ml/min, λ = 22 nm): t R (minor) = 34.4 min, t R (major) = 36.2 min, ee = 99%, dr > 19:1; [α] 25 D = + 18.3(c =.6 in CHCl 3 ). (3R,4R)-3-((E)-but-2-en-1-yl)-4-(nitromethyl)chroman-2-one (3ao): 31.5 mg, 71% yield, colorless oil; 1 H NMR (4 MHz, CDCl 3 ): δ = 7.41 7.38 (m, 1H), 7.38 7.24 (m, 2H), 7.19 (dd, J = 7.8, 4.7 Hz, 1H), 5.67 5.52 (m, 2H), 4.9 4.74 (m, 2H), 3.8 3.69 (m, 1H), 2.71 2.65 (m, 1H), 2.63 (t, J = 6. Hz, 1H), 2.41 2.34 (m, 1H), 1.74 (dd, J = 12.2, 7.1 Hz, 3H). 13 C NMR (1 MHz, CDCl 3 ): δ = 169.1, 151.4, 13.3, 129.7, 129.2, 127.3, 126.8, 126.5, 12.5, 75.3, 45.3, 42.4, 37., 36.6, 17.8. TLC (1:4 EtAc/Petroleum ether): R f =.48. HRMS (ESI): calcd for C 14 H 15 N 4 Na + (M+Na + ): 284.897, found 284.895. HPLC (Chiralpak IF, i-propanol/hexane = 3/97, flow rate 1. ml/min, λ = 254 nm): t R (minor) = 26.3 min, t R (major) = 3.7 min, ee = 92%, dr > 19:1; [α] 25 D = -2.93 (c =.5 in CHCl 3 ). (3R,4R)-3-butyl-4-(nitromethyl)chroman-2-one (3ap): 37.1 mg, 83% yield, colorless oil; 1 H NMR (4 MHz, CDCl 3 ): 1 H NMR (4 MHz, CDCl 3 ) δ 7.39 (ddd, J = 8.1, 7.4, 1.7 Hz, 1H), 7.28 7.23 (m, 1H), 7.22 7.16 (m, 1H), 7.15 7.1 (m, 1H), 4.45 4.35 (m, 2H), 3.82 3.68 (m, 1H), 2.95 2.82 (m, 1H), 1.6 (tdd, J = 9.2, S13

8.6, 5.4 Hz, 1H), 1.52 1.37 (m, 3H), 1.34 1.27 (m, 3H),.89 (t, J = 7.2 Hz, 3H). 13 C NMR (1 MHz, CDCl 3 ): δ = 168.1, 15.8, 13.2, 129.2, 125.4, 118.8, 117.3, 78.1, 42.7, 39.5, 29.9, 28.9, 22.1, 13.7. TLC (1:4 EtAc/Petroleum ether): R f =.54. HRMS (ESI): calcd for C 14 H 17 N 4 Na + (M+Na + ): 286.155, found 286.159. HPLC (Chiralpak IC, i-propanol/hexane = 1/9, flow rate 1. ml/min, λ = 19 nm): t R (major) = 17.5 min, t R (minor) = 21.3 min, ee = 99%, dr > 19:1; [α] 25 D = + 45.4 (c =.5 in CHCl 3 ). 2 N (3R,4R)-3-(cyclohexylmethyl)-4-(nitromethyl)chroman-2-one (3aq): 41.8 mg, 81% yield, colorless oil; 1 H NMR (4 MHz, CDCl 3 ): δ = 7.41 7.35 (m, 1H), 7.25 (dd, J = 7.6, 1.7 Hz, 1H), 7.19 (td, J = 7.5, 1.1 Hz, 1H), 7.11 (dd, J = 8.2,.8 Hz, 1H), 4.6 4.41 (m, 2H), 3.69 (dt, J = 14.2, 3.5 Hz, 1H), 3.4 (td, J = 7.6, 1.4 Hz, 1H), 1.79 (d, J = 12.6 Hz, 1H), 1.72 1.6 (m, 4H), 1.5 1.4 (m, 1H), 1.36 1.14 (m, 5H),.93.82 (m, 2H). 13 C NMR (1 MHz, CDCl 3 ): δ = 168.4, 15.8, 13.2, 129.3, 125.3, 118.8, 117.2, 78.1, 4., 39.6, 37.5, 34.7, 33., 32.8, 26.3, 25.9. TLC (1:4 EtAc/Petroleum ether): R f =.48. HRMS (ESI): calcd for C 17 H 21 N 4 Na + (M+Na + ): 326.1368, found 326.1362. HPLC (Chiralpak IC, i-propanol/hexane = 1/9, flow rate 1. ml/min, λ = 254 nm): t R (major) = 11.4 min, t R (minor) = 13.7 min, ee = 98%, dr > 19:1; [α] 25 D = + 38.3 (c = 1.2 in CHCl 3 ). S14

(3R,4R)-3-benzyl-6-methyl-4-(nitromethyl)chroman-2-one (3ba): 43.4 mg, 82% yield, foam; 1 H NMR (4 MHz, CDCl 3 ): δ = 7.39-7.3 (m, 3H), 7.22 (dd, J = 8.31, 1.67 Hz, 1H), 7.9 (dd, J = 9.24, 2.48 Hz, 3H), 7.3 (d, J = 17.27 Hz, 1H), 4.47-4.35 (m, 2H), 3.54 (dd, J = 11.9, 4.33 Hz, 1H), 3.17 (ddd, J = 1.48, 5.55, 1.39 Hz, 1H), 3.6 (dd, J = 13.65, 5.56 Hz, 1H), 2.62 (dd, J = 13.65, 1.54 Hz, 1H), 2.38 (s, 3H). 13 C NMR (1 MHz, CDCl 3 ): δ = 168., 148.8, 135.9, 135.5, 13.9, 129.6, 129., 127.5, 118., 117.1, 78., 44.5, 36.7, 35.6, 2.8. TLC (1:4 EtAc/Petroleum ether): R f =.45. HRMS (ESI): calcd for C 18 H 17 N 4 Na + (M+Na + ): 334.155, found 334.159. HPLC (Chiralpak IB, i-propanol/hexane = 5/95, flow rate 1. ml/min, λ = 22 nm): t R (minor) = 16.8 min, t R (major) = 18. min, ee = 99%, dr > 19:1; [α] D 25 = +71.4 (c =.7 in CHCl 3 ). (3R,4R)-3-benzyl-6-methoxy-4-(nitromethyl)chroman-2-one (3ca): 47.3 mg, 85% yield, colorless oil; 1 H NMR (4 MHz, CDCl 3 ): δ = 7.37 7.28 (m, 3H), 7.22 7.8 (t, J = 7.8 Hz, 3H), 6.81 6.74 (m, 1H), 6.71 (d, J = 2.1 Hz, 1H), 4.48 4.32 (m, 2H), 3.84 (d, J = 3.4 Hz, 3H), 3.51 (t, J = 7.5 Hz, 1H), 3.14 (d, J = 7.1 Hz, 1H), 3.5 (d, J = 7.1 Hz, 1H), 2.62 (dd, J = 13.4, 1.7 Hz, 1H). 13 C NMR (1 MHz, CDCl 3 ): δ = 168., S15

157., 144.7, 135.8, 129., 128.9, 127.6, 119.3, 118.3, 115.4, 114.2, 77.8, 55.8, 44.3, 37.8, 35.5. TLC (1:4 EtAc/Petroleum ether): R f =.38. HRMS (ESI): calcd for C 18 H 17 N 5 Na + (M+Na + ): 35.14, found 35.18. HPLC (Chiralpak IC, i-propanol/hexane = 1/9, flow rate 1. ml/min, λ = 22 nm): t R (major) = 31.3 min, t R (minor) = 33.2 min, ee = 99%, dr > 19:1; [α] 25 D = + 54.6 (c =.3 in CHCl 3 ). (3R,4R)-3-benzyl-6-chloro-4-(nitromethyl)chroman-2-one (3da): 46.8 mg, 83% yield, white solid, 98-1 C; 1 H NMR (4 MHz, CDCl 3 ): δ = 7.41 7.32 (m, 4H), 7.24 7.18 (m, 1H), 7.17 7.5 (m, 3H), 4.5 4.36 (m, 2H), 3.63 3.5 (m, 1H), 3.26 3.15 (m, 1H), 3.7 (dt, J = 15.3, 7.6 Hz, 1H), 2.62 (dd, J = 13.7, 1.5 Hz, 1H). 13 C NMR (1 MHz, CDCl 3 ): δ = 167.1, 149.5, 135.4, 13.7, 13.5, 129.1, 129.1, 128.8, 127.7, 12.2, 118.8, 77.5, 44.1, 37.4, 35.6. TLC (1:4 EtAc/Petroleum ether): R f =.43. HRMS (ESI): calcd for C 17 H 14 ClN 4 Na + (M+Na + ): 354.59, found 354.57. HPLC (Chiralpak IC, i-propanol/hexane = 1/9, flow rate 1. ml/min, λ = 22 nm): t R (major) = 25.6 min, t R (minor) = 29.5 min, ee = 96%, dr > 19:1; [α] 25 D = + 34.3 (c =.5 in CHCl 3 ). (3R,4R)-3-benzyl-6-bromo-4-(nitromethyl)chroman-2-one (3ea): 54.4 mg, 85% S16

yield, white solid, 15-17 C; 1 H NMR (4 MHz, CDCl 3 ): δ = 7.56 7.53 (m, 1H), 7.38 7.28 (m, 4H), 7.1 7.5 (m, 3H), 4.49 4.38 (m, 2H), 3.56 (tt, J = 8.8, 4.4 Hz, 1H), 3.26 3.13 (m, 1H), 3.7 (dd, J = 13.7, 5.6 Hz, 1H), 2.62 (dd, J = 13.7, 1.5 Hz, 1H). 13 C NMR (1 MHz, CDCl 3 ): δ = 167.1, 15.1, 135.4, 133.5, 132., 129.1, 128.8, 127.7, 12.6, 119.2, 118., 77.5, 44.1, 37.4, 35.7. TLC (1:4 EtAc/Petroleum ether): R f =.43. HRMS (ESI): calcd for C 17 H 14 BrN 4 Na + (M+Na + ): 398.4, found 398.. HPLC (Chiralpak IB, i-propanol/hexane = 5/95, flow rate 1. ml/min, λ = 22 nm): t R (minor) = 31.7 min, t R (major) = 33. min, ee = 95%, dr > 19:1; [α] 25 D = + 2.8 (c =.8 in CHCl 3 ). (3R,4R)-3-benzyl-7-(diethylamino)-4-(nitromethyl)chroman-2-one (3fa): 37.6 mg, 6% yield, red oil; 1 H NMR (4 MHz, CDCl 3 ): δ = 7.33 (td, J = 14.24, 7.11, 7.11 Hz, 4H), 7.11 (d, J = 7.7 Hz, 2H), 6.98 (d, J = 8.5 Hz, 1H), 6.47 (d, J = 8.64 Hz, 1H), 6.4 (s, 1H), 4.37 (d, J = 7.68 Hz, 2H), 3.43 (dd, J = 14.6, 6.13 Hz, 1H), 3.41 3.27 (m, 4H), 3.9 (ddd, J = 18.84, 11.94, 5.4 Hz, 2H), 2.74 2.58 (m, 1H), 1.21 (dd, J = 14.85, 7.77 Hz, 6H). 13 C NMR (1 MHz, CDCl 3 ): δ = 168.7, 152.2, 149.4, 136.3, 129.8, 129., 129., 127.3, 18.5, 13.5, 99.4, 78.5, 44.9, 44.5, 37., 35.7, 12.5. TLC (1:4 EtAc/Petroleum ether): R f =.23. HRMS (ESI): calcd for C 21 H 24 N 2 4 Na + (M+Na + ): 391.1634, found 391.1638. HPLC (Chiralpak IB, i-propanol/hexane = S17

1/9, flow rate 1. ml/min, λ = 254nm): t R (major) = 9.6 min, t R (major) = 11.5 min, ee = 98%, dr > 19:1; [α] 25 D = + 16.2 (c = 2.5 in CHCl 3 ). 2 N Et (3R,4R)-3-benzyl-8-ethoxy-4-(nitromethyl)chroman-2-one (3ga): 47.6 mg, 82% yield, colorless oil; 1 H NMR (4 MHz, CDCl 3 ): δ = 7.37 7.3 (m, 3H), 7.15 (t, J = 8. Hz, 1H), 7.12 7.3 (m, 2H), 7.1 (dt, J = 6., 2.6 Hz, 1H), 6.79 6.71 (m, 1H), 4.47 4.37 (m, 2H), 4.22 4.9 (m, 2H), 3.6 3.5 (m, 1H), 3.22 3.4 (m, 2H), 2.6 (dt, J = 32.2, 16.1 Hz, 1H), 1.51 (dd, J = 14., 7. Hz, 3H). 13 C NMR (1 MHz, CDCl 3 ): δ = 167.5, 147.2, 14.3, 135.8, 129., 128.9, 127.5, 125.6, 12.3, 119.5, 114., 77.8, 64.8, 44.2, 37.7, 35.4, 14.8. TLC (1:4 EtAc/Petroleum ether): R f =.43. HRMS (ESI): calcd for C 19 H 19 N 5 Na + (M+Na + ): 364.1161, found 364.1167. HPLC (Chiralpak AD-H, i-propanol/hexane = 1/9, flow rate 1. ml/min, λ = 22 nm): t R (minor) = 1.4 min, t R (major) = 11.5 min, ee = 99%, dr > 19:1; [α] 25 D = + 11.7 (c = 2.5 in CHCl 3 ). (1R,2R)-2-benzyl-1-(nitromethyl)-1H-benzo[f]chromen-3(2H)-one (3ha): 29.5 mg, 5% yield, colorless oil; 1 H NMR (4 MHz, CDCl 3 ): δ = 7.93 (t, J = 7.65, 7.65 Hz, S18

2H), 7.73 (d, J = 8.53 Hz, 1H), 7.65 (d, J = 6.95 Hz, 1H), 7.58 7.5 (m, 1H), 7.3 7.28 (m, 5H), 6.95 (dd, J = 5.81, 2.62 Hz, 2H), 4.54 4.39 (m, 2H), 4.29 4.17 (m, 1H), 3.43 3.3 (m, 1H), 3.1 (d, J = 5.43 Hz, 1H), 2.68 2.55 (m, 1H). 13 C NMR (1 MHz, CDCl 3 ): δ = 167.9, 149.5, 135.7, 131.5, 131.3, 13.6, 129.5, 129., 128.6, 127.7, 126., 121.5, 117.3, 11.9, 76.4, 44.3, 35.9, 34.. TLC (1:4 EtAc/Petroleum ether): R f =.5. HRMS (ESI): calcd for C 21 H 17 N 4 Na + (M+Na + ): 37.155, found 37.151. HPLC (Chiralpak IB, i-propanol/hexane = 1/9, flow rate 1. ml/min, λ = 22 nm): t R (major) = 16.7 min, t R (minor) = 19.9 min, ee = 99%, dr > 19:1; [α] 25 D = + 21.3 (c = 2.7 in CHCl 3 ). (8R,9R)-8-benzyl-2-methyl-9-(nitromethyl)-8,9-dihydro-7H-furo[3,2-f]chromen-7 -one (3ia): 38.8 mg, 65% yield, colorless oil; 1 H NMR (4 MHz, CDCl 3 ): δ = 7.41 (d, J = 8.8 Hz, 1H), 7.35 7.3 (m, 3H), 6.99 (dd, J = 5.32, 3.5 Hz, 1H), 6.28 (s, 1H), 4.45 (d, J = 7.57 Hz, 2H), 3.78 (t, J = 7.41, 7.41 Hz, 1H), 3.22 (dd, J = 1.49, 5.9 Hz, 1H), 3.8 (dd, J = 13.59, 5.32 Hz, 1H), 2.59 (dd, J = 13.51, 1.94 Hz, 1H), 2.51 (s, 3H). 13 C NMR (1 MHz, CDCl 3 ): δ = 168.2, 158.9, 151.7, 146.9, 135.9, 129.1, 129., 129., 128.6, 127.6, 112.6, 112.1, 18.8, 1.5, 77.3, 44.6, 35.7, 35.6, 14.5. TLC (1:4 EtAc/Petroleum ether): R f =.45. HRMS (ESI): calcd for C 2 H 17 N 5 Na + (M+Na + ): 374.14, found 374.12. HPLC (Chiralpak IC, i-propanol/hexane = 1/9, flow rate 1. ml/min, λ = 22 nm): t R (major) = 13.7 min, S19

t R (minor) = 16.7 min, ee = 99%, dr > 19:1; [α] 25 D = + 11.1 (c =.7 in CHCl 3 ). (1R,2R)-2-benzyl-1-(nitromethyl)-8,9,1,11-tetrahydro-1H-benzofuro[3,2-f]chro men-3(2h)-one (3ja): 34.6 mg, 52% yield, colorless oil; 1 H NMR (4 MHz, CDCl 3 ): δ = 7.43 7.37 (m, 1H), 7.37 7.3 (m, 3H), 7.23 7.9 (m, 1H), 7.3 6.91 (m, 2H), 4.53 4.38 (m, 2H), 3.95 3.86 (m, 1H), 3.35 3.23 (m, 1H), 3.19 3.5 (m, 1H), 2.81 2.71 (m, 2H), 2.62 2.49 (m, 1H), 2.48 2.23 (m, 1H), 1.94 1.84 (m, 2H), 1.83 1.72 (m, 2H). 13 C NMR (1 MHz, CDCl 3 ): δ = 167.1, 163.2, 159.1, 149.6, 146.2, 134.9, 127.9, 126.5, 115., 111.5, 111., 76.2, 42.8, 34.2, 32.8, 29., 27.8, 26.8, 23.. TLC (1:4 EtAc/Petroleum ether): R f =.43. HRMS (ESI): calcd for C 23 H 21 N 5 Na + (M+Na + ): 414.1317, found 414.1317. HPLC (Chiralpak IB, i-propanol/hexane = 1/9, flow rate 1. ml/min, λ = 22 nm): t R (major) = 9.8 min, t R (minor) = 1.8 min, ee = 94%, dr > 19:1; [α] 25 D = + 32. (c =.5 in CHCl 3 ). N 2 (1R,2R)-2-benzyl-1-(nitromethyl)-1,2,9,1,11,12-hexahydrocyclohepta[4,5]furo[3, 2-f]chromen-3(8H)-one (3ka): 31. mg, 48% yield, colorless oil; 1 H NMR (4 MHz, CDCl 3 ): δ = 7.41 7.34 (m, 1H), 7.31 (m, 3H), 7. 6.99 (m, 1H), 4.55 4.37 (m, 2H), 4.17 4.6 (m, 1H), 3.27 3.21 (m, 1H), 3.19 3.8 (m, 1H), 3.1 2.85 (m, S2

2H), 2.62 2.45 (m, 3H), 1.92 1.69 (m, 6H). 13 C NMR (1 MHz, CDCl 3 ): δ = 168.1, 16.1, 15.6, 147.2, 135.9, 129., 127.6, 116.1, 112.5, 112., 19.1, 77.3, 43.8, 35.2, 33.8, 3.1, 29.7, 28.8, 25.5, 24.. TLC (1:4 EtAc/Petroleum ether): R f =.4. HRMS (ESI): calcd for C 24 H 23 N 5 Na + (M+Na + ): 428.1474, found 428.1476. HPLC (Chiralpak IB, i-propanol/hexane = 1/9, flow rate 1. ml/min, λ = 254 nm): t R (major) = 37.5 min, t R (minor) = 44. min, ee = 99%, dr > 19:1; [α] 25 D = + 5.7 (c = 1.5 in CHCl 3 ). (9R,1R)-9-benzyl-1-(nitromethyl)-9,1-dihydro-8H-pyrano[2,3-h]quinolin-8- one (3la): 3.8 mg, 52% yield, colorless oil; 1 H NMR (4 MHz, CDCl 3 ): δ = 8.93 (dd, J = 4.21, 1.62 Hz, 1H), 8.19 (dd, J = 8.23, 1.58 Hz, 1H), 7.84 (d, J = 8.95 Hz, 1H), 7.46 (dd, J = 8.24, 4.26 Hz, 1H), 7.24 7.19 (m, 3H), 7.2 (dd, J = 6.8, 2.38 Hz, 2H), 4.79 (d, J = 4.14 Hz, 1H), 4.65 (dd, J = 9.29, 6.47 Hz, 2H), 3.44 (s, 1H), 3.6 (d, J = 6.2 Hz, 1H), 2.82 2.72 (m, 1H). 13 C NMR (1 MHz, CDCl 3 ): δ = 167.8, 161.3, 136.4, 13., 129., 128.7, 128.6, 128.3, 137.4, 121., 118., 77.2, 44.6, 37.4, 33.7. TLC (1:4 EtAc/Petroleum ether): R f =.15. HRMS (ESI): calcd for C 2 H 16 N 2 4 Na + (M+Na + ): 371.18, found 371.111. HPLC (Chiralpak ID, i-propanol/hexane = 2/8, flow rate 1. ml/min, λ = 22 nm): t R (minor) = 2.2 min, t R (major) = 25.9 min, ee = 97%, dr > 19:1; [α] 25 D = + 11.7 (c = 2.5 in CHCl 3 ). S21

(1R,2R)-2-benzyl-1-(nitromethyl)-1,2-dihydropyrano[2,3-c]carbazol-3(7H)-one (3ma): 36.8 mg, 56% yield, colorless oil; 1 H NMR (4 MHz, CDCl 3 ): δ = 8.25 (s, 1H), 8.6 (d, J = 5.2 Hz, 1H), 7.86 (s, 1H), 7.52 7.48 (m, 1H), 7.33 (dd, J = 7.28, 7.32 Hz, 1H), 7.25 7.23 (m, 3H), 7.1 (d, J = 7.12 Hz, 2H), 4.52 (d, J = 7.76 Hz, 2H), 3.76 (t, J = 7.64, 7.64 Hz, 1H), 3.27 3.23 (m, 1H), 3.13 3.7 (m, 1H), 2.69 (t, J = 7.79, 7.79 Hz, 1H). 13 C NMR (1 MHz, CDCl 3 ): δ = 168.4, 149.4, 14.1, 135.9, 129., 128.9, 127.5, 126.4, 126.4, 122.4, 121.2, 12.8, 12.4, 12.3, 11.8, 11.1, 99.2, 78.5, 44.6, 38., 35.5, 29.7. TLC (1:4 EtAc/Petroleum ether): R f =.25. HRMS (ESI): calcd for C 23 H 18 N 2 4 Na + (M+Na + ): 49.1164, found 49.117. HPLC (Chiralpak IB, i-propanol/hexane = 1/9, flow rate 1. ml/min, λ = 22 nm): t R (minor) = 11.4 min, t R (major) = 14.6 min, ee = 95%, dr > 19:1; [α] 25 D = + 85.9 (c = 3.1 in CHCl 3 ). D. Reference: [1] R. M. D. Nunes, M. Pineiro, L. G. Arnaut J. Am. Chem. Soc. 29, 131, 9456. [2] Q. Ni, H. Zhang, A. Grossmann, C. C. J. Loh, C. Merkens, D. Enders Angew. Chem. Int. Ed. 213, 52, 13562. [3] S. -Y. Cai, S. -L. Zhang, Y. -H. Zhao, D. Z. Wang rg. Lett. 213, 15, 266. S22

E. NMR Spectra S23

S24

S25

S26

S27

S28

F 2 N 3ag F 2 N 3ag S29

S3

S31

S32

S33

2 N S 3al 2 N S 3al S34

S35

2 N S 3an 2 N S 3an S36

S37

S38

2 N 3aq 2 N 3aq S39

S4

S41

S42

S43

S44

S45

S46

S47

S48

S49

S5

N 2 N H 3ma N 2 N H 3ma S51

F. HPLC Spectra 1 mau 22nm,4nm 数数数数数 :WZJ-2-21-1(IB-.95).lc d 样品数 :WZJ-2-21-1(IB-.95) 样品 ID:WZJ-2-21-1(IB-.95) 75 5 25 2.74 21.789 5. 7.5 1. 12.5 15. 17.5 2. 22.5 25. 27.5 min 1 2.74 6199772 21526 48.55 47.934 2 21.789 6581842 233754 51.495 52.66 Total 12781614 44896 1. 1. mau 15 22nm,4nm 125 数数数数数 :WZJ-2-21-2(IB-.95).lc d 样品数 :WZJ-2-21-2(IB-.95) 样品 ID:WZJ-2-21-2(IB-.95) 22.296 1 75 5 25 2.225 5. 7.5 1. 12.5 15. 17.5 2. 22.5 25. 27.5 min 1 2.225 13529 744.29.5 2 22.296 469446 1472655 99.971 99.95 Total 4613975 1473399 1. 1. S52

5 mau 19nm,4nm 数数数数数 :wzj-1-99-2(unsy m)-p1.lcd 样品数 :wzj-1-99-2(unsy m)-p 样品 ID:wzj-1-99-2(UNsy m)-p 4 3 2 21.989 28.812 1 5. 7.5 1. 12.5 15. 17.5 2. 22.5 25. 27.5 3. 32.5 min 1 21.98 55544 12334 51.149 52.273 2 28.817 482833 11261 48.851 47.727 Total 988377 23595 1. 1. 5 mau 22nm,4nm 数数数数数 :wzj-1-99-2(sy m)-p1.lcd 样品数 :wzj-1-99-2(sy m)-p 样品 ID:wzj-1-99-2(sy m)-p 4 3 2 28.83 1 5. 7.5 1. 12.5 15. 17.5 2. 22.5 25. 27.5 3. 32.5 min 1 21.142 5525 11.637.58 2 28.83 861549 18871 99.363 99.42 Total 86774 18981 1. 1. 21.896 S53

5 mau 22nm,4nm 数数数数数 :wzj-2-18-2(ib-9%)1.lc d 样品数 :wzj-2-18-2(ib-9%) 样品 ID:wzj-2-18-2(IB-9%) 4 3 2 15.345 2.712 1 5. 7.5 1. 12.5 15. 17.5 2. 22.5 25. 27.5 min 1 15.345 1484848 2343712 49.78 51.164 2 2.712 18787167 223712 5.922 48.836 Total 213635216 458814 1. 1. 4 mau 22nm,4nm 35 3 数数数数数 :wzj-2-18-1(ib-9%)1.lc d 样品数 :wzj-2-18-1(ib-9%) 样品 ID:wzj-2-18-1(IB-9%) 2.772 25 2 15 1 5 15.531 5. 7.5 1. 12.5 15. 17.5 2. 22.5 25. 27.5 min 1 15.531 695995 2229.423.641 2 2.772 1637878 3137235 99.577 99.359 Total 1644833 3157464 1. 1. S54

2 mau 22nm,4nm 数数数数数 :wzj-1-97-2(asy m)-2.lc d 样品数 :wzj-1-97-2(asy m)-2 样品 ID:wzj-1-97-2(asy m)-2 175 15 125 1 16.684 22.836 75 5 25 5. 7.5 1. 12.5 15. 17.5 2. 22.5 min 1 16.684 2666475 1151994 49.864 55.34 2 22.836 2628839 929678 5.136 44.66 Total 52275314 281672 1. 1. 3 mau 22nm,4nm 数数数数数 :wzj-1-97-1(sy m)1.lcd 样品数 :wzj-1-97-1(sy m) 样品 ID:wzj-1-97-1(sy m) 25 2 15 22.529 1 5 5. 7.5 1. 12.5 15. 17.5 2. 22.5 min 1 16.428 218854 5328.28.326 2 22.529 77917267 1627876 99.72 99.674 Total 78136122 163324 1. 1. 16.428 S55

2 mau 22nm,4nm 数数数数数 :wzj-2-2-2(ib-9%)1.lc d 样品数 :wzj-2-2-2(ib-9%) 样品 ID:wzj-2-2-2(IB-9%) 175 15 125 1 11.77 13.81 75 5 25 5. 7.5 1. 12.5 15. 17.5 min 1 11.77 3814363 1243436 48.773 5.424 2 13.81 46358 1222512 51.227 49.576 Total 7826661 2465948 1. 1. 2 mau 22nm,4nm 数数数数数 :wzj-2-2-1(ib-9%)1.lc d 样品数 :wzj-2-2-1(ib-9%) 样品 ID:wzj-2-2-1(IB-9%) 175 15 125 1 13.9 75 5 25 11.195 5. 7.5 1. 12.5 15. 17.5 min 1 11.195 45312 86.137.9 2 13.9 3315518 117 99.863 99.991 Total 331583 113 1. 1. S56

2 mau 24nm,4nm 数数数数数 :WZJ-5-11-1(IB-.95). lcd 样品数 :WZJ-5-11-1(IB-.95) 样品 ID:WZJ-5-11-1(IB-.95) 175 15 125 1 75 5 25 18.616 19.589 5. 7.5 1. 12.5 15. 17.5 2. 22.5 25. 27.5 min 1 18.616 121939 4964 49.81 48.543 2 19.589 1264695 52621 5.919 51.457 Total 2483734 12261 1. 1. 25 mau 24nm,4nm 数数数数数 :WZJ-5-11-2(IB-.95). lcd 样品数 :WZJ-5-11-2(IB-.95) 样品 ID:WZJ-5-11-2(IB-.95) 2 19.587 15 1 5 5. 7.5 1. 12.5 15. 17.5 2. 22.5 25. 27.5 min 1 18.347 164 14.4.8 2 19.587 437646 167615 99.996 99.992 Total 43781 16763 1. 1. 18.472 S57

5 mau 22nm,4nm 数数数数数 :wzj-1-98-2(unsy m)1.lcd 样品数 :wzj-1-98-2(unsy m) 样品 ID:wzj-1-98-2(unsy m) 4 3 2 14.446 17.288 1 5. 7.5 1. 12.5 15. 17.5 2. 22.5 min 1 14.446 5526666 192441 49.526 49.276 2 17.288 5632486 19895 5.474 5.724 Total 11159152 39536 1. 1. 7 mau 22nm,4nm 6 数数数数数 :wzj-1-98-1(sy m)1.lcd 样品数 :wzj-1-98-1(sy m) 样品 ID:wzj-1-98-1(sy m) 17.225 5 4 3 2 1 14.389 5. 7.5 1. 12.5 15. 17.5 2. 22.5 min 1 14.389 19818 3134.589.551 2 17.225 1852377 56687 99.411 99.449 Total 18633589 569221 1. 1. S58

mau 22nm,4nm 175 15 125 数数数数数 :wzj-2-11-2(id-9%)1.lc d 样品数 :wzj-2-11-2(id-9%) 样品 ID:wzj-2-11-2(ID-9%) 7.87 84.441 1 75 5 25 4. 45. 5. 55. 6. 65. 7. 75. 8. 85. 9. 95. min 1 7.87 3173743 1748 49.922 53.274 2 84.441 31836265 153313 5.78 46.726 Total 63573695 328113 1. 1. 25 mau 22nm,4nm 数数数数数 :wzj-2-11-1(id-9%)1.lcd 样品数 :wzj-2-11-1(id-9%) 样品 ID:wzj-2-11-1(ID-9%) 2 15 71.287 1 5 4. 45. 5. 55. 6. 65. 7. 75. 8. 85. 9. 95. min 1 71.287 244754 134643 99.746 99.595 2 81.555 6129 548.254.45 Total 2465783 135191 1. 1. 81.555 S59

5 mau 254nm,4nm 数数数数数 :wzj-1-119-2(ic)-1.lcd 样品数 :wzj-1-119-2(ic)-1 样品 ID:wzj-1-119-2(IC)-1 4 3 2 1 26.582 3.847 15. 17.5 2. 22.5 25. 27.5 3. 32.5 min 1 26.582 461981 9581 5.723 52.572 2 3.847 44886 8644 49.277 47.428 Total 91787 18225 1. 1. 2 mau 254nm,4nm 175 数数数数数 :WZJ-1-119-1.lcd 样品数 :wzj-1-119-1(ic) 样品 ID:wzj-1-119-1(IC) 15 125 1 26.28 75 5 25 15. 17.5 2. 22.5 25. 27.5 3. 32.5 min 1 26.28 5759534 98557 99.83 99.812 2 3.471 9782 186.17.188 Total 5769317 98743 1. 1. 3.471 S6

15 mau 254nm,4nm 数数数数数 :wzj-1-96-2(unsy m)1.lcd 样品数 :wzj-1-96-2(unsy m) 样品 ID:wzj-1-96-2(unsy m) 125 1 75 5 25.93 34.51 25 1. 15. 2. 25. 3. 35. 4. 45. min 1 25.93 2122727 4993 49.316 55.26 2 34.51 2181636 4491 5.684 44.794 Total 434363 9395 1. 1. 5 mau 254nm,4nm 数数数数数 :wzj-1-96-2(sy m)2.lcd 样品数 :wzj-1-96-2(sy m) 样品 ID:wzj-1-96-2(sy m) 4 3 33.58 2 1 25.178 1. 15. 2. 25. 3. 35. 4. 45. min 1 25.178 13872 2263.859.989 2 33.58 11985518 226564 99.141 99.11 Total 1289389 228827 1. 1. S61

1 mau 22nm,4nm 数数数数数 :wzj-1-12-2(ib-.98)1.lcd 样品数 :wzj-1-12-2(ib-.98) 样品 ID:wzj-1-12-2(IB-.98) 75 5 25 34.565 37.74 1. 15. 2. 25. 3. 35. 4. 45. min 1 34.565 994443 2735 5.341 53.59 2 37.74 98974 177589 49.659 46.941 Total 19754144 378324 1. 1. 5 mau 22nm,4nm 45 4 35 数数数数数 :wzj-1-12-1(ib-.98)1.lcd 样品数 :wzj-1-12-1(ib-.98) 样品 ID:wzj-1-12-1(IB-.98) 3 25 34.575 2 15 1 5 1. 15. 2. 25. 3. 35. 4. 45. min 1 34.575 1341798 266252 99.157 99.7 2 37.567 114111 2499.843.93 Total 1353291 26875 1. 1. 37.567 S62

1 mau 22nm,4nm 数数数数数 :wzj-2-4-2(if-h-97%)1.lcd 样品数 :wzj-2-4-2(if-h-97%) 样品 ID:wzj-2-4-2(IF-H-97%) 75 5 26.359 34.89 25 1. 15. 2. 25. 3. 35. 4. 45. min 1 26.359 34875 62235 5.441 56.216 2 34.89 29946628 484686 49.559 43.784 Total 642672 116991 1. 1. 1 mau 22nm,4nm 数数数数数 :wzj-2-4-1(if-h-97%)1.lcd 样品数 :wzj-2-4-1(if-h-97%) 样品 ID:wzj-2-4-1(IF-H-97%) 75 26.39 5 25 1. 15. 2. 25. 3. 35. 4. 45. min 1 26.39 3575243 74835 99.977 99.96 2 33.661 8216 283.23.4 Total 3576646 75117 1. 1. 33.661 S63

8 mau 254nm,4nm 数数数数数 :wzj-6-11-1.lcd 样品数 :wzj-6-11-1 样品 ID:wzj-6-11-1 7 6 5 4 3 2 1 31.517 37.649 25. 27.5 3. 32.5 35. 37.5 4. 42.5 45. min 4 1 31.517 175912 38756 51.228 54.863 2 37.649 16746667 318441 48.772 45.137 Total 34336769 75497 1. 1. mau 254nm,4nm 数数数数数 :wzj-6-11-2.lcd 样品数 :wzj-6-11-2 样品 ID:wzj-6-11-2 3 31.655 2 1 25. 27.5 3. 32.5 35. 37.5 4. 42.5 45. min 1 31.655 1389677 227742 99.527 99.642 2 38.42 49351 818.473.358 Total 143928 22856 1. 1. 38.42 S64

1 mau 22nm,4nm 数数数数数 :wzj-2-1-2(ib-95%)1.lc d 样品数 :wzj-2-1-2(ib-95%) 样品 ID:wzj-2-1-2(IB-95%) 75 5 32.467 34.726 25 1. 12.5 15. 17.5 2. 22.5 25. 27.5 3. 32.5 35. min 1 32.467 31154934 4837 49.46 5.296 2 34.726 3194455 474388 5.594 49.74 Total 635939 954425 1. 1. 数数数数数 :wzj-2-6(ib-95%)1.lcd 样品数 :wzj-2-6(ib-95%) 样品 ID:wzj-2-6(IB-95%) mau 22nm,4nm 9 8 7 6 5 4 3 2 36.26 1 34.432 1. 12.5 15. 17.5 2. 22.5 25. 27.5 3. 32.5 35. 37.5 min 1 34.432 68639 1857.124.23 2 36.26 5586228 911686 99.876 99.797 Total 55154866 913542 1. 1. S65

5 mau 254nm,4nm 数数数数数 :wzj-2-7(if-h-97%)1.lcd 样品数 :wzj-2-7(if-h-97%) 样品 ID:wzj-2-7(IF-H-97%) 4 3 2 1 26.162 31.189 1. 12.5 15. 17.5 2. 22.5 25. 27.5 3. 32.5 min 1 26.162 687311 14561 44.917 51.826 2 31.189 842876 13535 55.83 48.174 Total 153187 2896 1. 1. 1 mau 22nm,4nm 9 8 7 数数数数数 :wzj-1-17-2(if-h-97%)1.lcd 样品数 :wzj-1-17-2(if-h-97%) 样品 ID:wzj-1-17-2(IF-H-97%) 6 5 3.667 4 3 2 1 1. 12.5 15. 17.5 2. 22.5 25. 27.5 3. 32.5 min 1 26.291 1599813 41761 4.329 7.3 2 3.667 35357326 53281 95.671 92.7 Total 36957139 57243 1. 1. 26.291 S66

15 mau 254nm,4nm 数数数数数 :wzj-6-19-1.lcd 样品数 :wzj-6-19-1 样品 ID:wzj-6-19-1 125 1 75 5 25 17.74 2.418 15. 16. 17. 18. 19. 2. 21. 22. 23. 24. min 1 17.74 9872186 396843 47.45 53.239 2 2.418 11112334 348556 52.955 46.761 Total 298452 7454 1. 1. 15 mau 254nm,4nm 数数数数数 :wzj-6-19-2.lcd 样品数 :wzj-6-19-2 样品 ID:wzj-6-19-2 125 1 75 17.541 5 25 15. 16. 17. 18. 19. 2. 21. 22. 23. 24. min 1 17.541 1534377 581724 99.567 99.682 2 21.342 66712 1854.433.318 Total 154789 583578 1. 1. 21.342 S67

2 N 3aq 4 mau 254nm,4nm 数数数数数 :WZJ-2-31-2(IC-.9).lc d 样品数 :WZJ-2-31-2(IC-.9) 样品 ID:WZJ-2-31-2(IC-.9) 35 3 25 2 15 1 11.371 13.478 5. 2.5 5. 7.5 1. 12.5 15. 17.5 2. 22.5 25. 27.5 min 1 11.371 3439766 274464 49.9 55.483 2 13.478 34447731 1664439 5.1 44.517 Total 68757497 373893 1. 1. mau 254nm,4nm 数数数数数 :WZJ-2-31-1(IC-.9).lc d 样品数 :WZJ-2-31-1(IC-.9) 样品 ID:WZJ-2-31-2(IC-.9)1 2 15 1 11.354 5 13.724. 2.5 5. 7.5 1. 12.5 15. 17.5 2. 22.5 25. 27.5 min 1 11.354 1417133 852871 98.784 99.242 2 13.724 172551 6511 1.216.758 Total 14189684 859382 1. 1. S68

1 mau 22nm,4nm 数数数数数 :wzj-1-18-2(ib)2.lcd 样品数 :wzj-1-18-2(ib) 样品 ID:wzj-1-18-2(IB) 75 16.114 17.372 5 25 5. 7.5 1. 12.5 15. 17.5 2. 22.5 min 1 16.114 2155497 636564 48.15 5.69 2 17.372 2174213 63481 51.85 49.931 Total 4185971 1271365 1. 1. 15 mau 22nm,4nm 125 数数数数数 :wzj-1-18-1(ib)1.lcd 样品数 :wzj-1-18-1(ib) 样品 ID:wzj-1-18-1(IB) 18.1 1 75 5 25 5. 7.5 1. 12.5 15. 17.5 2. 22.5 min 1 16.777 85768 4172.233.37 2 18.1 36735733 1353582 99.767 99.693 Total 3682151 1357754 1. 1. 16.777 S69

5 mau 22nm,4nm 数数数数数 :jqf -1-87-1(IC-.9).lcd 样品数 :jqf -1-87-1(IC-.9) 样品 ID:jqf -1-87-1(IC-.9) 4 3 2 31.86 33.16 1 5. 1. 15. 2. 25. 3. 35. 4. 45. min 1 31.86 9879867 233385 5.727 51.775 2 33.16 9596568 217387 49.273 48.225 Total 19476435 45772 1. 1. 5 mau 22nm,4nm 数数数数数 :jqf -1-87-2(IC-.9).lcd 样品数 :jqf -1-87-2(IC-.9) 样品 ID:jqf -1-87-2(IC-.9) 4 31.28 3 2 1 5. 1. 15. 2. 25. 3. 35. 4. 45. min 1 31.28 1645213 36429 99.977 99.967 2 33.248 3846 12.23.33 Total 164959 36433 1. 1. 33.248 S7

5 mau 22nm,4nm 数数数数数 :wzj-1-111-2(ic-9%)1.lc d 样品数 :wzj-1-111-2(ic-9%) 样品 ID:wzj-1-111-2(IC-9%) 4 3 2 25.686 28.546 1 7.5 1. 12.5 15. 17.5 2. 22.5 25. 27.5 3. 32.5 35. 37.5 min 1 25.686 89386 152446 48.886 5.884 2 28.546 939722 147148 51.114 49.116 Total 18213582 299593 1. 1. 1 mau 22nm,4nm 9 8 7 数数数数数 :wzj-1-111-1(ic-9%)1.lc d 样品数 :wzj-1-111-1(ic-9%) 样品 ID:wzj-1-111-1(IC-9%) 6 5 25.63 4 3 2 1 7.5 1. 12.5 15. 17.5 2. 22.5 25. 27.5 3. 32.5 35. 37.5 min 1 25.63 3862 511936 97.921 97.696 2 29.485 638793 1275 2.79 2.34 Total 3724813 52411 1. 1. 29.485 S71

1 mau 254nm,4nm 数数数数数 :wzj-1-11-2(ib)1.lcd 样品数 :wzj-1-11-2(ib) 样品 ID:wzj-1-11-2(IB) 75 5 31.418 33.34 25 1. 12.5 15. 17.5 2. 22.5 25. 27.5 3. 32.5 35. 37.5 min 1 31.418 161537 36197 5.13 49.11 2 33.34 161444 37658 49.987 5.989 Total 3229746 73855 1. 1. 15 mau 254nm,4nm 数数数数数 :wzj-1-11-1(ib)1.lcd 样品数 :wzj-1-11-1(ib) 样品 ID:wzj-1-11-1(IB) 125 1 75 33.24 5 25 1. 12.5 15. 17.5 2. 22.5 25. 27.5 3. 32.5 35. 37.5 min 1 31.685 86225 2258 2.454 2.827 2 33.24 3427285 7762 97.546 97.173 Total 351351 79878 1. 1. 31.685 S72

3 mau 254nm,4nm 数数数数数 :WZJ-5-84-2(IB-.9).lcd 样品数 :WZJ-5-84-2(IB-.9) 样品 ID:WZJ-5-84-2(IB-.9) 25 2 15 1 9.652 11.316 5. 2.5 5. 7.5 1. 12.5 15. 17.5 2. 22.5 min 1 9.652 31431587 1367674 49.422 53.19 2 11.316 3216747 1211942 5.578 46.981 Total 63598995 2579616 1. 1. 8 mau 254nm,4nm 7 6 5 数数数数数 :WZJ-5-84-1(IB-.9).lcd 样品数 :WZJ-5-84-1(IB-.9) 样品 ID:WZJ-5-84-1(IB-.9) 4 9.598 3 2 1 11.463. 2.5 5. 7.5 1. 12.5 15. 17.5 2. 22.5 min 1 9.598 73619 33249 99.94 99.51 2 11.463 6681 318.96.949 Total 7372828 335228 1. 1. S73

5 mau 22nm,4nm 45 数数数数数 :wzj-2-9-2( AD-9% ) 1.lcd 样品数 :wzj-2-9-2( AD-9% ) 样品 ID:wzj-2-9-2( AD-9% ) 4 35 3 25 2 15 1 5 1.447 11.558 8. 9. 1. 11. 12. 13. 14. 15. 16. 17. 18. 19. min 1 1.447 53157444 18116 5.565 49.97 2 11.558 51969532 187819 49.435 5.93 Total 15126975 368925 1. 1. 15 mau 22nm,4nm 数数数数数 :wzj-2-9-1( AD-9% ) 1.lcd 样品数 :wzj-2-9-1( AD-9% ) 样品 ID:wzj-2-9-1( AD-9% ) 125 1 75 11.47 5 25 1.359 8. 9. 1. 11. 12. 13. 14. 15. 16. 17. 18. 19. min 1 1.359 19328 3779.545.525 2 11.47 19951467 71633 99.455 99.475 Total 26795 719812 1. 1. S74

6 mau 22nm,4nm 数数数数数 :WZJ-5-72-2(IB-.9).lcd 样品数 :WZJ-5-72-2(IB-.9) 样品 ID:WZJ-5-72-2(IB-.9) 5 4 3 2 16.655 19.63 1 1. 12.5 15. 17.5 2. 22.5 25. 27.5 min 1 16.655 7555543 2985411 51.778 54.594 2 19.63 736144 2482968 48.222 45.46 Total 145911587 5468379 1. 1. 1 mau 254nm,4nm 数数数数数 :WZJ-5-76-3-2(IB-.9).lc d 样品数 :WZJ-5-76-3-2(IB-.9) 样品 ID:WZJ-5-76-3-2(IB-.9) 75 5 25 16.697 19.9 1. 12.5 15. 17.5 2. 22.5 25. 27.5 min 1 16.697 4929592 221895 99.665 99.641 2 19.9 16552 8.335.359 Total 4946144 222695 1. 1. S75

6 mau 22nm,4nm 数数数数数 :WZJ-5-15-1(IC-.9).lcd 样品数 :WZJ-5-15-1(IC-.9) 样品 ID:WZJ-5-15-1(IC-.9) 5 4 13.731 3 16.468 2 1 5. 7.5 1. 12.5 15. 17.5 2. 22.5 25. 27.5 min 1 13.731 72367341 39661 5.556 58.37 2 16.468 7776994 2786272 49.444 41.63 Total 143144335 6692882 1. 1. 5 mau 22nm,4nm 数数数数数 :WZJ-5-15-2(IC-.9).lcd 样品数 :WZJ-5-15-2(IC-.9) 样品 ID:WZJ-5-15-1(IC-.9) 4 3 13.68 2 1 16.721 5. 7.5 1. 12.5 15. 17.5 2. 22.5 25. 27.5 min 1 13.68 54117475 2682381 99.32 99.384 2 16.721 3836 16637.698.616 Total 54497835 269918 1. 1. S76

7 mau 22nm,4nm 数数数数数 :WZJ-5-71(IB-.9).lcd 样品数 :WZJ-5-71(IB-.9) 样品 ID:WZJ-5-71(IB-.9) 6 5 4 9.82 1.712 3 2 1 5. 7.5 1. 12.5 15. 17.5 min 1 9.82 72375522 3738646 5.243 51.527 2 1.712 71675935 35176 49.757 48.473 Total 14451457 7255653 1. 1. 5 mau 22nm,4nm 数数数数数 :WZJ-5-76-1-2(IB-.9).lc d 样品数 :WZJ-5-76-1-2(IB-.9) 样品 ID:WZJ-5-76-1-2(IB-.9) 4 3 2 1 9.843 1.832 5. 7.5 1. 12.5 15. 17.5 min 1 9.843 2132314 12569 96.711 96.435 2 1.832 724561 37921 3.289 3.565 Total 2226874 163611 1. 1. S77

15 mau 254nm,4nm 数数数数数 :WZJ-5-111-1(IB-.9). lcd 样品数 :WZJ-5-111-1(IB-.9) 样品 ID:WZJ-5-111-1(IB-.9) 125 1 75 36.982 5 44.996 25. 5. 1. 15. 2. 25. 3. 35. 4. 45. 5. 55. 6. min 1 36.982 51386668 59827 52.92 64.914 2 44.996 472634 323362 47.98 35.86 Total 9864672 921631 1. 1. 1 mau 254nm,4nm 数数数数数 :WZJ-5-111-2(IB-.9). lcd 样品数 :WZJ-5-111-2(IB-.9) 样品 ID:WZJ-5-111-2(IB-.9) 75 5 25 37.464. 5. 1. 15. 2. 25. 3. 35. 4. 45. 5. 55. 6. min 1 37.464 18932693 245669 99.653 99.521 2 44.83 65876 1183.347.479 Total 18998569 246852 1. 1. 44.83 S78

2 mau 22nm,4nm 数数数数数 :WZJ-5-128-1(ID-.8).lcd 样品数 :WZJ-5-128-1(ID-.8) 样品 ID:WZJ-5-128-1(ID-.8) 175 15 125 1 75 5 25 2.158 25.924 5. 7.5 1. 12.5 15. 17.5 2. 22.5 25. 27.5 3. 32.5 35. 37.5 min 1 2.158 24986569 779256 5.55 57.665 2 25.924 249322 57297 49.945 42.335 Total 49918571 1351353 1. 1. 15 mau 22nm,4nm 数数数数数 :snpec53.tmp 样品数 :WZJ-5-128-2(ID-.8) 样品 ID:WZJ-5-128-2(ID-.8) 125 1 75 5 25.875 25 2.2 5. 7.5 1. 12.5 15. 17.5 2. 22.5 25. 27.5 3. 32.5 35. 37.5 min 1 2.2 299691 12457 1.657 3.47 2 25.875 17782738 396344 98.343 96.953 Total 1882428 4881 1. 1. S79

2 mau 22nm,4nm 数数数数数 :WZJ-5-13-1(IB-.9). lcd 样品数 :WZJ-5-13-1(IB-.9) 样品 ID:WZJ-5-13-1(IB-.9) 175 15 125 1 75 5 25 11.93 14.582 7.5 1. 12.5 15. 17.5 2. 22.5 25. 27.5 min 1 11.93 175532 94511 48.618 54.449 2 14.582 18551349 756699 51.382 45.551 Total 3614549 166121 1. 1. 15 mau 22nm,4nm 数数数数数 :WZJ-5-13-2(IB-.9). lcd 样品数 :WZJ-5-13-2(IB-.9) 样品 ID:WZJ-5-13-2(IB-.9) 125 1 75 5 14.556 25 11.355 7.5 1. 12.5 15. 17.5 2. 22.5 25. 27.5 min 1 11.355 39991 26542 2.341 4.691 2 14.556 14188182 539297 97.659 95.39 Total 1458892 565838 1. 1. S8