Reaktionsgleichung
[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]=1Komponenten
Versuchsvorschrift
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.
Quellen und Nachweise
- ORD-Eintrag
- ord-819a3df950a04881b8332ff8daac245c
- Quelldatensatz
- uspto-grants-2016_05
- Patentnummer
- US09328061B2
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