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化学学报
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化学学报 ›› 1963, Vol. 29 ›› Issue (2): 109-113. 上一篇    下一篇

论文

甾体中6-羥基、6-甲基的构型

韓广甸, 黄鳴龍   

  1. 中国科学院有机化学研究所
  • 投稿日期:1962-08-01 发布日期:2013-06-03

THE CONFIGURATION OF 6-METHYL-6-HYDROXY-STEROID

HAN KUANG-TIENG, HUANG-MINLON   

  1. Institute of Organic Chemistry, Academic Sinica
  • Received:1962-08-01 Published:2013-06-03

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466

被引次数

1

根据下列实验结果,即(1)3β,5α-二羟基胆甾-6-酮-3-乙酸酯(Ⅵb)的Grignard反应产物(Ⅶa)与β-氧环物(Ⅸ)的酸水解产物相同,(2)用碱消除X之5α-羟基后所得之物(Ⅺ)与用碱剖开Ⅻ之α-氧环后之物(ⅩⅢ)互异,证明C6-酮基甾体进行Grignard反应时,生成具6β-羟基的化合物。此与Fieser[2]和盐田三千夫[4]的推论相符,而与Sneen[3a]的推论相反。同时亦证明酸水解6-甲基-5§,6§-环氧化合物遵守双竪向剖环规则。

Acid cleavage of β-epoxide (IX) gave ba-methyl cholestan-3β, 5a, 6β-triol (VⅡa) identical with that obtained by treatment of 3β-acetoxy-5a-hydroxy-cholestan-6one (VIb) with methyl magnesium iodide.Elimination of 5a-hydroxy of compound X with alkali gave XI which is the isomer of XⅢ obtained from XⅡ by treatment with alkali.These results confirm the conclusion of Fieser[2], Shiota[4] that Grignard reaction of 6-oxo-5a-steroid involves the least hindered a-attack by the reagent.