(3S,3'S,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 | 162316-73-6

• 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'S,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: 162316-73-6
• 化学式: C₂₂H₃₂O₄
• 分子量: 360.494
• InChiKey: MIONZIQFHAIDQK-MXGVOXBCSA-N

物化性质

• 沸点：
  523.0±50.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

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'S,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 periodate reagent 、 三乙胺 作用下， 以 氘代吡啶 为溶剂， 生成 16-妊娠双烯醇酮
  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：

  16-脱氢孕烯醇酮乙酸酯 在 sodium tungstate 、 palladium on activated charcoal 吡啶 、 sodium chlorite 、 氢气 、 双氧水 、 二异丁基氢化铝 、 三氯氧磷 作用下， 以 吡啶 为溶剂， 生成 (3S,3'S,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