Cyclohexene oxide → HCID 16738222、化合物
反応式
[O:1]1[C:5]2([CH2:9][CH2:8][NH:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[CH:10]12[O:16][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15]2>O>[O:1]1[C:5]2([CH2:9][CH2:8][N:7]([C@H:10]3[CH2:15][CH2:14][CH2:13][CH2:12][C@@H:11]3[OH:16])[CH2:6]2)[O:4][CH2:3][CH2:2]1参加物
4
反応条件
- 温度
- 80 °C
実験手順
A mixture of 1e (23.5 g, no more than 182 mmol), cyclohexene oxide (23 mL, 220 mmol) and water (8 mL) was heated at 80° C. for 2 h. The reaction mixture was then partitioned between 40% NaOH aq (60 mL) and Et2O (120 mL). The basic aqueous layer was extracted twice more with Et2O (2×120 mL). The combined organic extracts were dried and concentrated in vacuo. The residue was then heated under high vacuum at 50° C. for 1 h with stirring (to remove the excess of cyclohexene oxide) to yield 32.8 g of 2e (79% yield); as illustrated in FIG. 2. Rf 0.33 (EtOAc-iPrNrH2, 98:2,v/v); 13C NMR (50 MHz, APT, CDCl3) δ 115.5 (+), 70.0 (−), 65.0 (−), 64.5 (+), 57.0 (+), 46.5 (+), 36.0 (+), 33.5 (+), 25.0 (+), 24.0 (+), 21.5 (+); IR (film) 3457 cm−1.