3α,17β-dihydroxy-5α-androstan-16-one 3-benzoate 17-acetate | 95717-09-2

• 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: 3α,17β-dihydroxy-5α-androstan-16-one 3-benzoate 17-acetate
• CAS: 95717-09-2
• 化学式: C₂₈H₃₆O₅
• 分子量: 452.591
• InChiKey: JAGKMJBCFBDCPK-RUDDPOLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.37
• 重原子数：
  33.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  69.67
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3α,17β-dihydroxy-5α-androstan-16-one 3-benzoate 17-acetate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 5α-androstane-3α,16α,17β-triol
  参考文献：
  名称：

  Synthesis of 5α-Androstane-3α,16α,17β-triol from 3β-hydroxy-5-androsten-17-one

  摘要：

  5 alpha-Androstane-3 alpha, 16 alpha, 17 beta-triol was synthesized from 3 beta-hydroxy-5-androsten-17-one. The procedure involved catalytic hydrogenation of 3 beta-hydroxy-5-androsten-17-one to 3 beta-hydroxy-5 alpha-androstan-17-one. This was followed by conversion of the 3 beta-hydroxy group to 3 alpha-benzoyloxy group by the Mitsunobu reaction. Further treatment with isopropenyl acetate yielded 5 alpha-androsten-16-ene-3 alpha, 17-diol 3-benzoate 17-acetate. This was then converted to 3 alpha, 17-dihydroxy-5 alpha-androstan-16-one 3-benzoate 17-acetate via the unstable epoxide intermediate after treatment with m-cloroperoxybenzoic acid. LiA1H4 reduction of this compound formed 5 alpha-androstane-3 alpha, 16 alpha, 17 beta-triol. 1H and 13C NMR of various steroids are presented to confirm the structure of this compound.

  DOI：

  10.1016/0039-128x(84)90018-7
• 作为产物：
  描述：

  去氢表雄酮 在 palladium on activated charcoal 氢气 、 对甲苯磺酸 、 间氯过氧苯甲酸 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 水 、 苯 为溶剂， 反应 12.0h， 生成 3α,17β-dihydroxy-5α-androstan-16-one 3-benzoate 17-acetate
  参考文献：
  名称：

  Synthesis of 5α-Androstane-3α,16α,17β-triol from 3β-hydroxy-5-androsten-17-one

  摘要：

  5 alpha-Androstane-3 alpha, 16 alpha, 17 beta-triol was synthesized from 3 beta-hydroxy-5-androsten-17-one. The procedure involved catalytic hydrogenation of 3 beta-hydroxy-5-androsten-17-one to 3 beta-hydroxy-5 alpha-androstan-17-one. This was followed by conversion of the 3 beta-hydroxy group to 3 alpha-benzoyloxy group by the Mitsunobu reaction. Further treatment with isopropenyl acetate yielded 5 alpha-androsten-16-ene-3 alpha, 17-diol 3-benzoate 17-acetate. This was then converted to 3 alpha, 17-dihydroxy-5 alpha-androstan-16-one 3-benzoate 17-acetate via the unstable epoxide intermediate after treatment with m-cloroperoxybenzoic acid. LiA1H4 reduction of this compound formed 5 alpha-androstane-3 alpha, 16 alpha, 17 beta-triol. 1H and 13C NMR of various steroids are presented to confirm the structure of this compound.

  DOI：

  10.1016/0039-128x(84)90018-7