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化学学报
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化学学报 ›› 1989, Vol. 47 ›› Issue (1): 89-92. 上一篇    下一篇

研究论文

17α-羟基-16β-甲基-5,9(11)-孕甾二烯-3,20-二缩酮的D环高碳化

倪元;夏克敏;彭贵章   

  1. 中国科学院上海有机化学研究所;上海第十二制药厂
  • 发布日期:1989-01-15

D-Homoannulation of 17α-hydroxy-16β -methyl-5,9(11)-pregnadiene-3,20-dione-bis(diethylene ketal)

NI YUAN;XIA KEMING;PENG GUIZHANG   

  • Published:1989-01-15

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报导了17α-羟基-16β-甲基-4,9(11)孕甾二烯-3,20-二缩酮(1)用70%醋酸进行的水解反应. 结果得相应的3,20-二酮化合物(2). 当用98%醋酸处理(1)不能获得(2). 而是重排成17α-羟基-16β, 17β-二甲基-D-高孕甾二烯二酮(3). 当化合物(1)和(2)与含有CaCl2的70%醋酸反应获得16β, 17β-二甲-D-高-4,9(11), 15-孕甾三烯-3,17-二酮, 其得率取决于CaCl2的浓度和反应时间.

关键词: 反应机理, 甾族化合物, 重排反应, 乙酸, 娠烯二酮

17a-Hydroxy-16b-methyl-5,9(11)-pregnadiene-3, 20-dione-bis(diethylene ketal) (I) on treatment with 70% acetic acid was hydrolyzed to the parent 3,20-dione (II) in 88% yield, while compound I or II on treatment with 98% acetic acid was rearranged to 17a-hydroxy-16b,17b-dimethyl-D-homo-4,9(11)-androstanediene-3,17a- dione (III) in 68 or 89% yields, resp. I and II reacted with 70% acetic acid containing CaCl2 to give 16b,17ab-dimethyl-D-homo-4,9(11),15-androstrien-3,17-dione (IV) in 90% yield. The yield of compound IV is dependent on the concentration of CaCl2 and the time of reaction.

Key words: REACTION MECHANISM, STEROIDS, REARRANGEMENT REACTION, ACETIC ACID, PREGNENEDIONE

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