p-Toluenesulfinic acid → (E)-P,P-Diphenyl-N-(1-tosylhex-2-en-1-yl)phosphinic amide
反応式
[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]=1参加物
実験手順
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.
出典と根拠
- ORDレコード
- ord-819a3df950a04881b8332ff8daac245c
- 出典データセット
- uspto-grants-2016_05
- 特許番号
- US09328061B2
反応ノート
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