3β-acetoxy-17,17-(ethylenedioxy)-7β-hydroxy-5α-androstane | 85775-45-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 3β-acetoxy-17,17-(ethylenedioxy)-7β-hydroxy-5α-androstane
• 英文别名: [(3S,5S,7S,8R,9S,10S,13S,14S)-7-hydroxy-10,13-dimethylspiro[1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthrene-17,2'-1,3-dioxolane]-3-yl] acetate
• CAS: 85775-45-7
• 化学式: C₂₃H₃₆O₅
• 分子量: 392.536
• InChiKey: WTFAZJZKCUJRPZ-ILMCUKGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3β-acetoxy-17,17-(ethylenedioxy)-7β-hydroxy-5α-androstane 在 水 、 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 反应 12.0h， 以98%的产率得到3β-acetoxy-7β-hydroxy-5α-androstane
  参考文献：
  名称：

  Synthesis of 7β-hydroxy-epiandrosterone

  摘要：

  The synthesis of 7 beta-hydroxy-epiandrosterone (6) possessing strong anti-inflammatory properties was achieved starting from 3 beta-acetoxy-17,17-(ethylenedioxy)-5-androsten (1). This approach involved as a main step an allylic oxidation of the C-7 followed by two reduction reactions of the double bond and of the carbonyl group. This stereoselective synthesis in 5 steps gave 7 beta-hydroxy-epiandrosterone in 63% overall yield. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2010.08.003
• 作为产物：
  描述：

  (3R,5R,10S,13S)-10,13-dimethyl-7-oxohexadecahydrospiro[cyclopenta[a]phenanthrene-17,2'-[1,3]dioxolan]-3-yl acetate 在 sodium tetrahydroborate 、 cerium(III) chloride heptahydrate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以89%的产率得到3β-acetoxy-17,17-(ethylenedioxy)-7β-hydroxy-5α-androstane
  参考文献：
  名称：

  Synthesis of 7β-hydroxy-epiandrosterone

  摘要：

  The synthesis of 7 beta-hydroxy-epiandrosterone (6) possessing strong anti-inflammatory properties was achieved starting from 3 beta-acetoxy-17,17-(ethylenedioxy)-5-androsten (1). This approach involved as a main step an allylic oxidation of the C-7 followed by two reduction reactions of the double bond and of the carbonyl group. This stereoselective synthesis in 5 steps gave 7 beta-hydroxy-epiandrosterone in 63% overall yield. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2010.08.003