Gold-Catalyzed Intramolecular Diazo Coupling: An Efficient

Macrocyclization towards Cyclic Olefins

Table of Contents

1. General Information 2. Preparation of Substrates 3. General procedure for table 2 4. References 5. 1H NMR and 13C NMR Spectra of compounds

Electronic Supplementary Material (ESI) for ChemComm.This journal is © The Royal Society of Chemistry 2015

General Information All of the reactions were carried out in a flame-dried tube. Solvents were dried prior to use. For column chromatography, 200-300 mesh silica gel was used. 1H NMR were recorded on Bruker 400MHz spectrometer and 13C NMR were recorded on Bruker 100MHz, 125MHz spectrometer in CDCl3. HRMS were performed on Agilent 6230 TOF mass spectrometer, Waters Micromass GCT Premier and Thermo Fisher Scientific LTQ FT Ultra mass spectrometer. GC analysis was recorded on Agilent 7890/5975C-GC/MSD. Melting points were determined on a SGW X-4B melting point apparatus. Preparation of Substrate Preparation of diazo compounds: 1a-1m[1], 1n-1v[2] were prepared according to the literature procedures.

OO

OO

O

O

N2

N21e

1e: 1H NMR (400 MHz, CDCl3) δ 6.94 (m, 4H), 4.82 (s, 2H), 4.57-4.47 (m, 4H), 4.25-4.20 (m, 4H). 13C NMR (100 MHz, CDCl3) δ 148.94, 129.72, 122.41, 116.03, 67.88, 63.36, 62.21. HRMS (APCI) calcd. for C14H15O6 [M+H-2N2]+: 279.0863, found: 279.0869.

O

O

1h

OO

O

ON2

N2

1h: 1H NMR (400 MHz, CDCl3) δ 6.92-6.87 (m, 4H), 4.74 (s, 1H), 4.36-4.24 (m, 4H), 4.05-4.00 (m, 4H), 2.47 (s, 1H), 1.92-1.74 (m, 8H). 13C NMR (100 MHz, CDCl3) δ 148.96, 121.29, 114.08, 68.52, 64.61, 46.16, 25.86, 25.67. HRMS (APCI) calcd. for C18H23O6 [M+H-2N2]+: 335.1489, found: 335.1475.

OO

ON2

OO

ON2

1i 1i: 1H NMR (400 MHz, CDCl3) δ 7.16 (t, J = 8.2 Hz, 1H), 6.49 (d, J = 2.3 Hz, 1H), 6.47 (d, J = 2.3 Hz, 1H), 6.44 (t, J = 2.3 Hz, 1H), 4.74 (s, 2H), 4.24 (t, J = 6.1 Hz, 4H), 3.96 (t, J = 5.7 Hz, 4H), 1.84 (dt, J = 6.0, 3.0 Hz, 8H). 13C NMR (100 MHz, CDCl3) δ 160.16, 129.88, 106.77, 101.47, 67.23, 64.53, 46.19, 25.79, 25.63. HRMS (APCI) calcd. for C18H23O6 [M+H-2N2]+: 335.1489, found: 335.1479.

O O

O

1j

O

ON2

ON2

1j: 1H NMR (400 MHz, CDCl3) δ 6.89 (s, 4H), 4.74 (s, 2H), 4.19 (t, J = 12.0 Hz, 4H), 4.01 (t, J = 12.0 Hz, 4H), 1.84 (m, 4H), 1.73 (m, 4H), 1.60-1.50 (m, 4H). 13C NMR (100 MHz, CDCl3) δ 149.09, 121.21, 114.18, 68.93, 64.82, 46.14, 28.95, 28.60, 22.54. HRMS (APCI) calcd. for C20H27O6 [M+H-2N2]+: 363.1802, found: 363.1802.

OO

OO

O

ON2

N21k

1k: 1H NMR (400 MHz, CDCl3) δ 6.89 (s, 4H), 4.73 (s, 1H), 4.35 (s, 1H), 4.31-4.11 (m, 4H), 4.00 (m, 4H), 1.91 (m, 1H), 1.87 (m, 3H), 1.84-1.78 (m, 2H), 1.68 (m, 2H), 1.55-1.48 (m, 2H), 1.48-1.40 (m, 2H). 13C NMR (100 MHz, CDCl3) δ 173.33, 165.04, 149.20, 148.92, 121.35, 121.16, 113.99, 68.94, 68.88, 68.61, 65.40, 65.23, 64.63, 46.17, 29.19, 28.78, 28.25, 25.87, 25.62. HRMS (APCI) calcd. for C20H27O6 [M+H-2N2]+: 363.1802, found: 363.1801.

OO

O O

ON2

ON2

1l 1l: 1H NMR (400 MHz, CDCl3) δ 7.15 (t, J = 8.2 Hz, 1H), 6.48 (d, J = 2.3 Hz, 1H), 6.46 (d, J = 2.3 Hz, 1H), 6.44 (t, J = 2.2 Hz, 1H), 4.74 (s, 2H), 4.18 (t, J = 6.6 Hz, 4H), 3.94 (t, J = 6.4 Hz, 4H), 1.84-1.76 (m, 4H), 1.76-1.67 (m, 4H), 1.58-1.48 (m, 4H). 13C NMR (100 MHz, CDCl3) δ 160.27, 129.84, 106.71, 101.47, 67.59, 64.76, 46.17, 28.89, 28.58, 22.54. HRMS (APCI) calcd. for C20H27O6 [M+H-2N2]+: 363.1802, found: 363.1805.

OO

OO

ON2

ON2

1m 1m: 1H NMR (400 MHz, CDCl3) δ 6.81 (s, 4H), 4.73 (s, 2H), 4.17 (t, J = 6.6 Hz, 4H), 3.90 (t, J = 6.4 Hz, 4H), 1.76 (dd, J = 14.4, 6.6 Hz, 4H), 1.68 (dd, J = 14.3, 7.0 Hz, 4H), 1.54-1.36 (m, 8H). 13C NMR (100 MHz, CDCl3) δ 153.18, 115.41, 68.41, 64.88, 46.16, 29.28, 28.77, 25.77, 25.67. HRMS (APCI) calcd. for C22H31O6 [M+H-2N2]+: 391.2115, found: 391.2109.

O N2

O N2

O

O1r

1r: 1H NMR (400 MHz, CDCl3) δ 6.88 (s, 4H), 5.36 (s, 2H), 4.02 (t, J = 6.1 Hz, 4H), 2.57 (s, 4H), 2.24-2.04 (m, 4H). 13C NMR (100 MHz, CDCl3) δ 194.42, 148.84, 121.49, 114.29, 68.05, 54.57, 24.80. HRMS (DART) calcd. for C16H19N4O4 [M+H]+: 331.1401, found: 331.1399.

O

O

1s

O

ON2

N2

1s: 1H NMR (400 MHz, CDCl3) δ 6.87 (s, 4H), 5.29 (s, 2H), 3.98 (t, J = 12.0 Hz, 4H), 2.34 (s, 4H), 1.88-1.77 (m, 4H), 1.70 (m, 4H), 1.56-1.46 (m, 4H). 13C NMR (100 MHz, CDCl3) δ 195.04, 149.07, 121.19, 114.15, 68.90, 29.71, 29.08, 25.74, 24.95. HRMS (DART) calcd. for C20H27N4O4 [M+H]+: 387.2027, found:387.2026.

General procedure for table 2 To a solution of 1 (1 mmol) in 10 mL of 1,2-dichloroethane (DCE) was added 2.5 mol% of

tBuXphosAuCl/ NaBArF at room temperature. Then the mixture was heated 80oC and stirred for 12 h under argon atmosphere. The mixture was cooled to room temperature and solvent was removed under vacuum. The crude residue was purified by column chromatography to afford product 2.

OO

O

O

2a 2a:[1] This compound was prepared via general procedure (Yield: 65%). 1H NMR (400 MHz, CDCl3) δ 6.13 (s, 2H), 4.26-4.12 (m, 4H), 1.77-1.65 (m, 4H), 1.51-1.46 (m, 4H). 13C NMR (100 MHz, CDCl3) δ 165.21, 128.92, 66.37, 24.57, 24.19.

O

O

O

OO

2b 2b:[1] This compound was prepared via general procedure (Yield: 63%). 1H NMR (400 MHz, CDCl3) δ 6.32 (s, 2H), 4.42-4.30 (m, 4H), 3.93-3.82 (m, 4H). 13C NMR (100 MHz, CDCl3) δ 165.13, 129.81, 71.57, 66.06.

OO

O

O

2c

2c:[1] This compound was prepared via general procedure (Yield: 62%). 1H NMR (400 MHz, CDCl3) δ 6.24 (s, 2H), 4.32-4.24 (m, 4H), 1.73-1.64 (m, 4H), 1.41 (s, 8H). 13C NMR (100 MHz, CDCl3) δ 165.28, 129.58, 64.02, 26.81, 24.84, 21.65.

OO

O

OO

O

2d 2d:[1] This compound was prepared via general procedure (Yield: 62%). 1H NMR (400 MHz, CDCl3) δ 6.27 (s, 2H), 4.44-4.32 (m, 4H), 3.84-3.71 (m, 4H), 3.65 (s, 4H). 13C NMR (100 MHz, CDCl3) δ 165.14, 129.61, 69.45, 68.67, 63.79.

O

O

OO

O

O2e 2e: This compound was prepared via general procedure (Yield: 68%). 1H NMR (400 MHz, CDCl3) δ 6.95 (tdd, J = 9.6, 5.9, 3.8 Hz, 4H), 6.30 (s, 2H), 4.52 (dd, J = 5.1, 3.3 Hz, 4H), 4.27 (dd, J = 5.1, 3.3 Hz, 4H). 13C NMR (100 MHz, CDCl3) δ 165.10, 149.04, 129.79, 122.40, 115.58, 67.73, 63.40. HRMS (APCI) calcd. for C14H15O6 [M+H]+: 279.0863, found: 279.0855.

OO

O

O2f

2f:[1] This compound was prepared via general procedure (Yield: 58%). 1H NMR (400 MHz, CDCl3) δ 6.23 (s, 2H), 4.34-4.23 (m, 4H), 1.74-1.62 (m, 4H), 1.39 (m, 10H). 13C NMR (100 MHz, CDCl3) δ 165.46, 129.73, 64.55, 28.30, 26.70, 25.73, 23.54.

OO

O

O2g

2g:[1] This compound was prepared via general procedure (Yield: 54%). 1H NMR (400 MHz, CDCl3) δ 6.25 (s, 2H), 4.36-4.22 (m, 4H), 1.79-1.64 (m, 4H), 1.35 (m, 12H). 13C NMR (100 MHz, CDCl3) δ 165.49, 129.95, 63.90, 28.10, 26.55, 25.33, 24.25.

O

O

OO

O

O2h

2h: This compound was prepared via general procedure as a solid (Yield: 66%), mp: 80-82°C. 1H NMR (400 MHz, CDCl3) δ 6.95-6.81 (m, 4H), 6.25 (s, 2H), 4.34 (t, J = 7.1 Hz, 4H), 4.03 (t, J = 5.3 Hz, 4H), 2.00-1.92 (m, 4H), 1.89 (m, 4H). 13C NMR (100 MHz, CDCl3) δ 165.35, 148.84, 129.69, 121.03, 113.02, 68.29, 65.61, 26.13, 25.87. HRMS (APCI) calcd. for C18H23O6 [M+H]+: 335.1489, found: 335.1519.

O

O

OO

OO

2i 2i: This compound was prepared via general procedure as a solid (Yield: 42%), mp: 113-115°C. 1H NMR (400 MHz, CDCl3) δ 7.13 (t, J = 8.2 Hz, 1H), 6.76 (s, 2H), 6.51 (d, J = 2.3 Hz, 1H), 6.49 (d, J = 2.3 Hz, 1H), 6.44 (t, J = 2.3 Hz, 1H), 4.36-4.28 (t, J = 12.0 Hz, 4H), 4.07 (t, J = 16.0 Hz, 4H), 2.01 (dd, J = 13.1, 6.3 Hz, 4H), 1.98-1.91 (m, 4H). 13C NMR (125 MHz, CDCl3) δ 164.46, 160.23, 133.35, 129.98, 108.69, 98.27, 67.62, 66.61, 28.13, 24.64. HRMS (APCI) calcd. for C18H23O6 [M+H]+: 335.1489, found: 335.1509.

O

O O

O

O

O2j

2j: This compound was prepared via general procedure (Yield: 48%). 1H NMR (400 MHz, CDCl3) δ 6.86 (s, 6H), 4.33-4.24 (t, J = 12.0 Hz, 4H), 3.97 (t, J = 12.0 Hz, 4H), 2.01-1.93 (m, 4H), 1.84-1.77 (m, 4H), 1.68 (m, 4H). 13C NMR (100 MHz, CDCl3) δ 164.74, 148.34, 133.69, 120.40, 111.55, 68.05, 65.88, 29.52, 28.16, 24.10. HRMS (APCI) calcd. for C20H27O6 [M+H]+: 363.1802, found: 363.1797.

O

O

O

O

O

O

2k 2k: This compound was prepared via general procedure as a solid (Yield: 58%), mp: 97-99°C. 1H NMR (400 MHz, CDCl3) δ 6.90 (d, J = 1.4 Hz, 4H), 6.88 (s, 2H), 4.30-4.26 (m, 2H), 4.26-4.22 (m, 2H), 4.03 (t, J = 3.9 Hz, 2H), 4.00 (t, J = 4.6 Hz, 2H), 2.04-1.96 (m, 2H), 1.93-1.84 (m, 4H), 1.76 (dd, J = 11.0, 5.6 Hz, 2H), 1.57-1.49 (m, 4H). 13C NMR (125 MHz, CDCl3) δ 164.86, 149.40, 133.80, 133.75, 121.35, 121.26, 115.00, 114.11, 69.96, 68.52, 66.08, 64.60, 29.84, 27.26, 27.05, 26.84, 26.03, 25.41. HRMS (APCI) calcd. for C20H27O6 [M+H]+: 363.1802, found: 363.1796.

O

O O

O

O

O

2l 2l: This compound was prepared via general procedure (Yield: 52%). 1H NMR (400 MHz, CDCl3) δ 7.18 (t, J = 8.1 Hz, 1H), 6.82 (s, 2H), 6.50 (d, J = 2.3 Hz, 1H), 6.48 (d, J = 2.1 Hz, 1H), 6.48-6.45 (m, 1H), 4.32-4.21 (t, J = 12.0 Hz, 4H), 4.03 (t, J = 12.0 Hz, 4H), 1.84-1.70 (m, 8H), 1.64 (dt, J = 9.0, 4.6 Hz, 4H). 13C NMR (100 MHz, CDCl3) δ 164.96, 160.19, 133.52, 129.94, 106.33, 103.74, 67.29, 64.89, 28.20, 27.85, 22.54. HRMS (APCI) calcd. for C20H27O6 [M+H]+: 363.1802, found: 363.1799.

O

O OO

OO

2m 2m: This compound was prepared via general procedure (Yield: 45%). 1H NMR (400 MHz, CDCl3) δ 6.80 (s, 4H), 6.70 (s, 2H), 4.27-4.18 (t, J = 12.0 Hz, 4H), 4.00 (t, J = 12.0 Hz, 4H), 1.73 (m, 4H), 1.65 (m, 4H), 1.51 (m, 4H), 1.47-1.37 (m, 4H). 13C NMR (100 MHz, CDCl3) δ 165.05, 152.69, 133.37, 116.17, 67.74, 64.92, 28.34, 27.72, 24.82, 24.75. HRMS (APCI) calcd. for C22H31O6 [M+H]+: 391.2115, found: 391.2107.

O O

2n

2n:[2] This compound was prepared via general procedure (Yield: 62%). 1H NMR (400 MHz, CDCl3) δ 6.40 (s, 2H), 2.57 (s, 4H), 1.90 (m, 4H). 13C NMR (125 MHz, CDCl3) δ 204.69, 136.82, 40.34, 23.37.

O

O2o 2o:[2] This compound was prepared via general procedure (Yield: 55%). 1H NMR (400 MHz, CDCl3) δ 7.35-7.23 (m, 4H), 6.18 (s, 2H), 3.95 (s, 4H). 13C NMR (100 MHz, CDCl3) δ 200.06, 134.39, 133.00, 130.84, 128.36, 48.63.

O

O

2p 2p:[2] This compound was prepared via general procedure (Yield: 65%). 1H NMR (400 MHz,

CDCl3) δ 7.51 (d, J = 7.7 Hz, 1H), 7.47-7.44 (m, 1H), 7.32 (d, J = 7.6 Hz, 1H), 7.17 (d, J = 7.6 Hz, 1H), 6.59 (q, J = 13.7 Hz, 2H), 3.25 (dd, J = 7.4, 5.5 Hz, 2H), 2.86 (dd, J = 7.4, 5.5 Hz, 2H). 13C NMR (125 MHz, CDCl3) δ 204.00, 194.74, 137.43, 135.04, 132.58, 130.48, 129.14, 127.73, 48.41, 28.45.

O

O

2q 2q:[3] This compound was prepared via general procedure (Yield: 45%). 1H NMR (400 MHz, CDCl3) δ 7.03 (s, 2H), 2.71-2.59 (m, 4H), 1.89-1.71 (m, 4H), 1.46 (m, 4H), 1.28 (m, 4H). 13C NMR (100 MHz, CDCl3) δ 203.18, 137.22, 39.12, 24.75, 24.51, 24.18.

O

O

2r 2r:[3] This compound was prepared via general procedure as a solid (Yield: 61%). 1H NMR (400 MHz, CDCl3) δ 6.99 (s, 2H), 2.71-2.56 (m, 4H), 1.88-1.67 (m, 4H), 1.40-1.26 (m, 12H). 13C NMR (125 MHz, CDCl3) δ 202.52, 136.13, 41.11, 26.32, 26.19, 25.66, 24.59.

O

O

O

O

2s 2s: This compound was prepared via general procedure as a solid (Yield: 72%), mp: 108-110°C. 1H NMR (400 MHz, CDCl3) δ 7.34 (s, 2H), 6.90 (m, 2H), 6.86-6.80 (m, 2H), 4.05-4.03 (t, J = 8.0 Hz, 4H), 2.84 (t, J = 12.0 Hz, 4H), 2.27-2.15 (m, 4H). 13C NMR (100 MHz, CDCl3) δ 202.00, 148.09, 137.12, 121.12, 112.01, 67.34, 38.51, 25.70. HRMS (EI) calcd. for C16H18O4 [M]: 274.1205, found: 274.1199.

O

O

2t 2t:[3] This compound was prepared via general procedure as a solid (Yield: 56%). 1H NMR (400 MHz, CDCl3) δ 7.00 (s, 2H), 2.65-2.59 (m, 4H), 1.78-1.69 (m, 4H), 1.26 (m, 16H). 13C NMR (125MHz, CDCl3) δ 201.88, 136.07, 41.64, 27.23, 27.10, 26.92, 26.62, 24.63.

O

O

2u 2u: This compound was prepared via general procedure as white solid (Yield: 61%), mp: 121-123°C. 1H NMR (400 MHz, CDCl3) δ 6.94 (s, 2H), 2.63 (t, J = 12.0 Hz, 4H), 1.70 (dd, J = 13.7, 6.9 Hz, 4H), 1.29 (m, 20H). 13C NMR (125 MHz, CDCl3) δ 201.62, 136.31, 41.14, 29.71, 27.59, 27.50, 27.44, 27.42, 24.39. HRMS (APCI) calcd. for C18H31O2 [M+H]+: 279.2319, found: 279.2316.

O

O

OO

2v 2v: This compound was prepared via general procedure as a solid (Yield: 69%), mp: 83-85°C. 1H NMR (400 MHz, CDCl3) δ 6.99 (s, 2H), 6.93-6.75 (m, 4H), 3.96 (t, J = 5.5 Hz, 4H), 2.67-2.64 (t, J = 12.0 Hz, 4H), 1.88-1.70 (m, 8H), 1.51 (m, 4H). 13C NMR (100 MHz, CDCl3) δ 202.21, 148.54, 136.57, 120.66, 112.36, 67.94, 41.48, 29.57, 26.33, 26.13. HRMS (EI) calcd. for C20H26O4 [M]: 330.1831, found: 330.1829. References: [1] Li, G.; Che, C. Org. Lett., 2004, 6, 1621. [2] Chandler, C. L.; List, B. J. Am. Chem. Soc., 2008, 130, 6737. [3] Sunanta, K.; Anthony, M. Chem. Comm., 1978, 23, 1069.

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121.16

121.35

148.92

149.20

165.04

173.33

-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)

-1000

0

1000

2000

3000

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5000

6000

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8000

9000

10000

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18000

19000

20000

210002015-6-114sjt61/36 LK1-276

3.99

4.35

3.99

4.04

4.00

1.67

0.99

0.93

1.01

0.98

-0.00

1.25

1.49

1.51

1.52

1.53

1.54

1.55

1.55

1.57

1.68

1.70

1.72

1.73

1.75

1.76

1.78

1.80

1.82

1.83

3.92

3.94

3.95

4.17

4.18

4.20

4.74

6.43

6.44

6.44

6.46

6.47

6.48

6.49

7.13

7.15

7.17

7.26

-100102030405060708090100110120130140150160170180190200210f1 (ppm)

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0

50

100

150

200

250

300

350

400

450

500

5502015-6-114sjt61/37 LK1-276

22.54

28.58

28.89

46.17

64.76

67.59

76.77

77.09

77.40

101.47

106.71

129.84

160.27

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.5f1 (ppm)

Desktop4sjt31/14 kn5-219-1

8.15

3.85

4.02

4.00

3.96

1.67

4.00

0.00

1.391.401.421.431.451.471.481.491.501.511.631.641.661.681.691.711.731.751.761.78

3.883.903.924.154.174.19

4.73

6.81

7.26

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Desktop4sjt31/36 KN005-219-1

25.67

25.77

28.77

29.28

46.16

64.88

68.41

115.41

153.18

-1.0-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)

0

5000

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35000

40000

45000

500002015-4-94sjt54/2 zch3-70

4.14

4.00

4.22

1.80

4.06

-0.00

1.68

2.10

2.12

2.13

2.15

2.17

2.57

4.01

4.02

4.04

5.36

6.86

6.89

7.26

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0

100

200

300

400

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800

900

1000

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2015-4-104sjt54/13 zch3-70

24.80

54.57

68.05

76.74

77.06

77.37

114.29

121.49

148.84

194.42

-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)

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0

10000

20000

30000

40000

50000

60000

70000

80000

90000

100000

110000

120000

2015-4-304sjt56/34 zch3-96

4.35

4.69

4.35

4.06

4.00

1.70

4.21

-0.01

1.21

1.23

1.25

1.49

1.51

1.53

1.68

1.70

1.72

1.80

1.82

1.83

2.34

3.96

3.98

3.99

5.29

6.87

7.26

-100102030405060708090100110120130140150160170180190200210f1 (ppm)

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50

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150

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350

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550

600

650

700

2015-4-304sjt56/35 zch3-96

24.95

25.74

29.08

29.71

68.90

114.15

121.19

149.07

195.04

-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.5f1 (ppm)

0

5000

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15000

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35000

40000

45000

146-H4xuhd47/5 ZCH-146

3.93

4.30

4.31

2.00

1.47

1.48

1.48

1.49

1.50

1.52

1.70

1.71

1.72

4.18

4.19

4.20

6.13

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0

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4sjt284sjt28/45 zch-146 24

.224.6

66.4

128.9

165.2

-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)

4sjt294sjt29/27 LK1-241-4

4.38

4.31

2.00

3.873.883.89

4.354.364.37

6.32

7.27

-100102030405060708090100110120130140150160170180190200210f1 (ppm)

4sjt294sjt29/28 LK1-241-4

66.1

71.6

129.8

165.1

-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)

0

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40000

45000

50000

55000

4sjt294sjt29/38 zch-164

8.28

4.27

4.22

2.00

1.41

1.61

1.66

1.67

1.69

4.27

4.28

4.29

6.24

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0

50

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400

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4sjt294sjt29/39 zch-164 21

.724.8

26.8

64.0

129.6

165.3

-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.5f1 (ppm)

-5000

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5000

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45000

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55000

60000

65000

70000

75000

80000

85000

90000桌面4sjt30/15 zch-2-1a

4.36

4.33

4.22

2.00

3.65

3.76

3.77

3.78

4.37

4.38

4.39

6.27

7.27

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-50

0

50

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300

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400

450

500

550

600

6502014-6-304sjt30/19 zch-2-1A 63

.868.7

69.5

129.6

165.1

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.5f1 (ppm)

FileRecv4sjt30/50 kn5-214-1

4.04

4.00

1.90

4.00

0.00

1.60

4.264.274.274.284.514.524.534.54

6.306.926.936.946.946.956.966.97

7.26

-100102030405060708090100110120130140150160170180190200210f1 (ppm)

4sjt314sjt31/9 kn5-214-1

63.40

67.73

115.58

122.40

129.79

149.04

165.10

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.5f1 (ppm)

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4sjt294sjt29/41 zch-163-2A

10.22

4.05

4.25

2.00

0.00

1.38

1.38

1.40

1.58

1.67

1.68

1.70

4.27

4.28

4.30

6.23

7.27

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100

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14sjt29/42 zch-163-2A 23

.525.7

26.7

28.3

64.5

129.7

165.5

-1.0-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)

0

5000

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15000

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30000

35000

40000

450004sjt294sjt29/5 zch-148-2

13.35

4.40

4.38

2.00

0.00

1.35

1.35

1.59

1.69

1.70

1.71

4.28

4.30

4.31

6.25

7.27

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-20

0

20

40

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14sjt29/15 zch-148-2 24

.225.3

26.6

28.1

63.9

130.0

165.5

-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)

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16000

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20000

22000

24000

26000

280002014-7-44sjt30/40 zch-2-11-2

4.05

4.02

4.32

4.26

2.00

4.08

0.01

1.61

1.87

1.87

1.89

1.89

1.91

1.92

1.92

1.94

1.96

1.98

1.98

4.02

4.03

4.04

4.32

4.34

4.36

6.25

6.86

6.87

6.87

6.88

6.89

6.90

6.91

6.92

7.27

0102030405060708090100110120130140150160170180f1 (ppm)

-50

0

50

100

150

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250

300

350

400

2014-7-44sjt30/41 zch-2-8 25

.926.1

65.6

68.3

113.0

121.0

129.7

148.8

165.4

1.52.02.53.03.54.04.55.05.56.06.57.07.5f1 (ppm)

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20000

21000新建文件夹4sjt31/19 zch-2-22-1

4.16

4.19

4.26

4.22

1.02

0.99

1.07

2.00

1.08

1.93

1.94

1.95

1.96

1.97

1.99

2.00

2.02

2.03

4.05

4.07

4.09

4.30

4.31

4.33

6.43

6.44

6.44

6.48

6.49

6.50

6.51

6.76

7.11

7.13

7.15

7.27

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2-22-1-Csunjt44/23 zch-2-22-1

24.64

28.13

66.61

67.62

98.27

108.69

129.98

133.35

160.23

164.46

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)

4sjt314sjt31/3 lk1-277-1

3.97

4.08

3.97

4.11

4.00

6.08

1.581.661.681.691.701.791.801.811.951.971.981.981.99

3.953.973.984.274.284.30

6.86

7.26

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FileRecv4sjt31/43 lk1-277-1

24.1

28.2

29.5

65.9

68.1

111.5

120.4

133.7

148.3

164.7

-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)

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13000

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15000

2014-7-184sjt32/4 zch-2-34A

4.16

2.14

4.19

2.16

2.08

2.18

2.08

2.13

2.00

3.82

0.01

1.53

1.55

1.56

1.57

1.85

1.87

1.88

1.89

1.90

1.98

2.00

2.02

3.98

4.00

4.01

4.02

4.02

4.04

4.23

4.24

4.26

4.26

4.28

4.29

6.88

6.90

6.90

7.27

102030405060708090100110120130140150160170180f1 (ppm)

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26sunjt44/26 zch-2-34A

25.41

26.03

26.84

27.05

27.26

29.84

64.60

66.08

68.52

69.96

114.11

115.00

121.26

121.35

133.75

133.80

149.40

164.86

1.41.61.82.02.22.42.62.83.03.23.43.63.84.04.24.44.64.85.05.25.45.65.86.06.26.46.66.87.07.27.4f1 (ppm)

新建文件夹4sjt31/28 lk1-280-1

3.99

7.96

4.00

3.94

0.96

0.83

0.94

1.78

1.00

1.591.621.621.641.661.681.731.741.751.771.781.80

4.014.034.044.244.264.27

6.466.476.476.486.496.506.516.82

7.167.187.207.27

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FileRecv4sjt31/37 lk1-280-1

22.54

27.85

28.20

64.89

67.29

76.72

77.04

77.35

103.74

106.33

129.94

133.52

160.19

164.96

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.5f1 (ppm)

Desktop4sjt31/21 kn5-220-1

4.33

4.23

4.11

3.98

3.99

4.00

1.84

3.92

0.000.07

1.401.411.421.431.441.451.481.501.521.541.601.631.641.661.671.711.721.741.75

3.984.004.014.214.224.24

6.706.80

7.26

O

O OO

O

O

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Desktop4sjt31/32 kn5-220-1

24.75

24.82

27.72

28.34

64.92

67.74

76.72

77.03

77.35

116.17

133.37

152.69

165.05

O

O OO

O

O

1.52.02.53.03.54.04.55.05.56.06.57.07.5f1 (ppm)

-2000

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30000

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zch4sjt55/22 zch3-72

4.12

4.00

1.75

1.56

1.88

1.89

1.90

1.91

2.57

6.40

7.26

-100102030405060708090100110120130140150160170180190200210f1 (ppm)

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30000sunjt45sunjt45/2 zch3-72

23.37

40.34

76.77

77.03

77.28

136.82

204.69

-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)

-2000

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22000

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28000

30000

32000

2015-4-174sjt54/50 zch3-81-1

4.14

2.00

5.06

-0.00

3.95

6.18

7.25

7.26

7.26

7.27

7.28

7.29

7.29

7.30

-100102030405060708090100110120130140150160170180190200210f1 (ppm)

-50

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50

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550

600

650

700

7502015-4-174sjt54/51 zch3-81-1

48.63

76.73

77.04

77.36

128.36

130.84

133.00

134.39

200.06

1.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)

-2000

-1000

0

1000

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20000

21000

22000

23000

24000zch4sjt55/23 zch3-83-2

2.38

2.25

2.00

1.19

1.39

1.45

1.26

1.57

2.84

2.86

2.86

2.88

3.24

3.25

3.25

3.27

4.09

6.54

6.57

6.61

6.64

7.16

7.18

7.26

7.31

7.33

7.42

7.43

7.44

7.45

7.46

7.50

7.52

-100102030405060708090100110120130140150160170180190200210f1 (ppm)

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15000sunjt45sunjt45/1 zch3-83-2

28.45

48.41

76.77

77.03

77.28

127.73

129.14

130.48

132.58

135.04

137.43

194.74

204.00

-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)

0

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164sjt60/16 zch 3-158

4.05

4.11

4.10

3.94

2.00

-0.00

0.07

1.25

1.28

1.29

1.44

1.45

1.46

1.47

1.56

1.78

1.80

1.81

2.63

2.64

2.65

2.65

2.66

7.03

7.26

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1300

2015-6-114sjt61/41 zch3-158

24.17

24.51

24.75

39.12

137.22

203.18

-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)

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60000

65000

70000

75000

800002015-4-94sjt54/3 zch3-71

4.26

4.16

4.28

2.13

2.20

1.97

-0.00

1.63

2.18

2.19

2.20

2.22

2.24

2.83

2.84

2.86

4.03

4.04

4.05

6.82

6.83

6.83

6.84

6.85

6.88

6.89

6.90

6.91

6.92

7.26

7.34

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-100

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550

600

650

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7502015-4-104sjt54/12 zch3-71

25.70

38.51

67.34

76.75

77.07

77.38

112.01

121.12

137.12

148.09

202.00

-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.0f1 (ppm)

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34000

36000

38000

400002015-4-304sjt56/32 zch3-100-1

4.14

8.21

4.00

4.21

4.22

1.98

0.00

1.48

1.50

1.52

1.54

1.59

1.75

1.76

1.78

1.78

1.79

1.80

1.81

1.83

1.85

2.64

2.66

2.67

3.94

3.96

3.97

6.80

6.81

6.82

6.82

6.83

6.84

6.85

6.86

6.86

6.86

6.87

6.99

7.26

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2015-4-304sjt56/33 zch3-100-1

26.13

26.33

29.57

41.48

67.94

76.72

77.04

77.36

112.36

120.66

136.57

148.54

202.21

-1.0-0.50.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.58.08.5f1 (ppm)

-500

0

500

1000

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2500

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3500

4000

4500

5000

5500

6000

6500

7000

7500

8000

8500

9000ZCH4sjt62/63 zch3-191

12.09

4.24

3.78

2.00

-0.00

0.07

1.26

1.27

1.28

1.30

1.31

1.33

1.35

1.56

1.73

1.75

1.77

2.60

2.62

2.63

6.99

7.26

-100102030405060708090100110120130140150160170180190200210f1 (ppm)

-1000

0

1000

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5000

6000

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8000

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11000

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1800028sunjt45/28 zch3-191

24.59

25.66

26.19

26.32

41.11

136.13

202.52

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.5f1 (ppm)

-2000

-1000

0

1000

2000

3000

4000

5000

6000

7000

8000

9000

10000

11000

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13000

14000

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16000

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18000

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20000

21000

22000

23000

240002015-7-24sjt63/2 zch3-189

16.02

4.27

4.16

2.00

-0.00

0.07

1.19

1.24

1.25

1.28

1.57

1.69

1.70

1.72

1.73

1.75

1.77

2.60

2.62

2.63

4.07

6.32

7.00

7.26

-100102030405060708090100110120130140150160170180190200210f1 (ppm)

0

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30000

26sunjt45/26 zch3-189

24.63

26.62

26.92

27.10

27.23

41.64

136.07

201.88

0.00.51.01.52.02.53.03.54.04.55.05.56.06.57.07.5f1 (ppm)

-1000

0

1000

2000

3000

4000

5000

6000

7000

8000

9000

10000

11000

12000

13000

14000

15000

16000

17000

18000

19000

20000

210002015-7-24sjt63/1 zch3-189-2

20.25

4.21

4.21

2.00

-0.00

0.07

1.24

1.25

1.28

1.32

1.57

1.68

1.70

1.71

1.73

2.61

2.63

2.64

4.07

6.94

7.26

-100102030405060708090100110120130140150160170180190200210f1 (ppm)

-1000

0

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1100027sunjt45/27 zch3-189-2

24.39

27.42

27.44

27.50

27.59

29.71

41.14

136.31

201.62

重氮大环information大环谱图