p-Toluenesulfinic acid → (E)-P,P-Diphenyl-N-(1-tosylhex-2-en-1-yl)phosphinic amide
반응식
[C:1]1([P:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)(=[O:9])[NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:16](=O)/[CH:17]=[CH:18]/[CH2:19][CH2:20][CH3:21].[C:23]1([CH3:32])[CH:28]=[CH:27][C:26]([S:29]([OH:31])=[O:30])=[CH:25][CH:24]=1>>[C:1]1([P:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)(=[O:9])[NH:8][CH:16]([S:29]([C:26]2[CH:27]=[CH:28][C:23]([CH3:32])=[CH:24][CH:25]=2)(=[O:31])=[O:30])/[CH:17]=[CH:18]/[CH2:19][CH2:20][CH3:21])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1참가 물질
실험 절차
The title compound is synthesized following a previously reported procedure7 from P,P-diphenylphosphinic amide (2.17 g, 10.0 mmol, 1.00 equiv.), (E)-hex-2-enal (2.31 mL, 20.0 mmol, 2.00 equiv.), and p-toluenesulfinic acid (2.34 g, 15.0 mmol, 1.50 equiv.) to obtain S5 as white solid (3.22 g, 7.10 mmol, 71% yield). M.p.=138-139° C. IR (neat): 3177 (w, br), 2959 (w), 2933 (w), 2870 (w), 1661 (m), 1596 (w), 1437 (m), 1300 (m), 1281 (m), 1214 (m), 1185 (s), 1170 (m), 1138 (m), 1125 (s), 1106 (m), 1083 (m), 955 (m), 894 (m), 752 (m), 726 (s), 693 (s), 662 (m), 583 (s), 568 (m), 536 (s) cm−1; 1H NMR (400 MHz, CDCl3): δ 7.79-7.71 (4H, m), 7.59 (2H, d, J=8.4 Hz), 7.59-7.54 (2H, m), 7.50-7.43 (4H, m), 7.23 (2H, d, J=8.0 Hz), 5.90 (1H, ddd, J=13.6, 11.6, 9.6 Hz), 5.31 (1H, t, J=10.0 Hz), 4.73 (1H, dd, J=14.0, 10.4 Hz), 3.28 (1H, app td, J=10.8, 3.6 Hz), 2.42 (3H, s), 1.97-1.88 (1H, m), 1.52-1.32 (2H, m), 1.20-1.10 (1H, m), 0.82 (3H, t, J=7.2 Hz); 13C NMR (100 MHz, CDCl3): δ 144.3, 134.7, 132.8, 132.6 (d, J=2.9 Hz), 132.5 (d, J=2.9 Hz), 132.2 (d, J=10.1 Hz), 131.9 (d, J=10.1 Hz), 131.4 (d, J=128.0 Hz), 131.1 (d, J=128.0 Hz), 129.6, 129.2, 128.9 (d, J=12.9 Hz), 128.9 (d, J=13.0 Hz), 101.9 (d, J=9.9 Hz), 67.6, 29.7, 21.8, 20.0, 13.7.
출처 및 근거
- ORD 기록
- ord-819a3df950a04881b8332ff8daac245c
- 출처 데이터셋
- uspto-grants-2016_05
- 특허 번호
- US09328061B2
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