(3S,3'R,8R,9S,10R,13S,14S,17R)-3-hydroxy-3',10,13-trimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydrospiro[cyclopenta[a]phenanthrene-17,2'-oxirane]-3'-carboxylic acid | 162316-75-8

• 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: (3S,3'R,8R,9S,10R,13S,14S,17R)-3-hydroxy-3',10,13-trimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydrospiro[cyclopenta[a]phenanthrene-17,2'-oxirane]-3'-carboxylic acid
• CAS: 162316-75-8
• 化学式: C₂₂H₃₂O₄
• 分子量: 360.494
• InChiKey: MIONZIQFHAIDQK-LEPVRUAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.92
• 重原子数：
  26.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  70.06
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (3S,3'R,8R,9S,10R,13S,14S,17R)-3-hydroxy-3',10,13-trimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydrospiro[cyclopenta[a]phenanthrene-17,2'-oxirane]-3'-carboxylic acid 在 三氯化铝 三乙胺 作用下， 以 吡啶 为溶剂， 反应 24.0h， 以50%的产率得到(R)-2-Hydroxy-2-((3S,8R,9S,10R,17R)-3-hydroxy-10,17-dimethyl-2,3,4,7,8,9,10,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)-propionic acid
  参考文献：
  名称：

  Synthesis of 16-dehydro-20-oxopregnanes from 17α,20-epoxy-23,24-dinorcholan-22-oic acids. Highly stereospecific oxirane → allyl alcohol isomerization of an epoxycarboxylic acid

  摘要：

  A microbial degradation product of natural sterols was converted into traditional precursor of steroid syntheses by a simple sequence. The title isomerization, the key step, was investigated to demonstrate a concerted mechanism, in which a cyclic transition state, involving the oxirane oxygen, the beta- and gamma-carbon, the gamma-proton to be removed and the catalyst coordinated by the carboxylate group, is postulated.

  DOI：

  10.1016/s0040-4039(00)78366-3
• 作为产物：
  描述：

  在 sodium tungstate sodium chlorite 、 双氧水 、 二异丁基氢化铝 作用下， 以 吡啶 为溶剂， 生成 (3S,3'R,8R,9S,10R,13S,14S,17R)-3-hydroxy-3',10,13-trimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydrospiro[cyclopenta[a]phenanthrene-17,2'-oxirane]-3'-carboxylic acid
  参考文献：
  名称：

  Synthesis of 16-dehydro-20-oxopregnanes from 17α,20-epoxy-23,24-dinorcholan-22-oic acids. Highly stereospecific oxirane → allyl alcohol isomerization of an epoxycarboxylic acid

  摘要：

  A microbial degradation product of natural sterols was converted into traditional precursor of steroid syntheses by a simple sequence. The title isomerization, the key step, was investigated to demonstrate a concerted mechanism, in which a cyclic transition state, involving the oxirane oxygen, the beta- and gamma-carbon, the gamma-proton to be removed and the catalyst coordinated by the carboxylate group, is postulated.

  DOI：

  10.1016/s0040-4039(00)78366-3