Post on 16-Feb-2021
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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19000
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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
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-50
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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
10000
15000
20000
25000
30000
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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-100
0
100
200
300
400
500
600
700
800
900
1000
1100
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
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50
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150
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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
10000
15000
20000
25000
30000
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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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
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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
5000
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15000
20000
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30000
35000
40000
45000
50000
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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
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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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60000
65000
70000
75000
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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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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
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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
-100102030405060708090100110120130140150160170180190200210f1 (ppm)
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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
20000
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30000
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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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-40
-20
0
20
40
60
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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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2000
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6000
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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)
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0
50
100
150
200
250
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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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0
1000
2000
3000
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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
-100102030405060708090100110120130140150160170180190200210f1 (ppm)
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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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1000
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4000
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6000
7000
8000
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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
-100102030405060708090100110120130140150160170180190200210f1 (ppm)
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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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
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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
0
2000
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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)
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50
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550
600
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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
2000
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20000
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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
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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
1000
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6000
7000
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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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800
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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)
-5000
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50000
55000
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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600
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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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2000
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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
1500
2000
2500
3000
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
2000
3000
4000
5000
6000
7000
8000
9000
10000
11000
12000
13000
14000
15000
16000
17000
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
12000
13000
14000
15000
16000
17000
18000
19000
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
5000
10000
15000
20000
25000
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
1000
2000
3000
4000
5000
6000
7000
8000
9000
10000
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