(2'S,8S,10S,13S,14S,17R)-2',10,13-trimethyl-3-oxospiro[2,6,7,8,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthrene-17,3'-oxirane]-2'-carboxylic acid | 144490-18-6

• 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: (2'S,8S,10S,13S,14S,17R)-2',10,13-trimethyl-3-oxospiro[2,6,7,8,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthrene-17,3'-oxirane]-2'-carboxylic acid
• CAS: 144490-18-6
• 化学式: C₂₂H₂₈O₄
• 分子量: 356.462
• InChiKey: UGHPMDNMFVKICQ-INDCHNRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  66.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2'S,8S,10S,13S,14S,17R)-2',10,13-trimethyl-3-oxospiro[2,6,7,8,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthrene-17,3'-oxirane]-2'-carboxylic acid 在 三氯化铝 chromium(VI) oxide 、 三乙胺 作用下， 以 四氢呋喃 、 溶剂黄146 、 丙酮 为溶剂， 反应 73.0h， 生成 孕甾-4,9(11),16-三烯-3,20-二酮
  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：

  3-Oxo-23,24-dinor-4,9(11),17(20)-cholatrien-22-oic acid 在 sodium tungstate 、 双氧水 作用下， 以 吡啶 为溶剂， 反应 0.25h， 以1039 mg的产率得到(2'S,8S,10S,13S,14S,17R)-2',10,13-trimethyl-3-oxospiro[2,6,7,8,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthrene-17,3'-oxirane]-2'-carboxylic acid
  参考文献：
  名称：

  Synthesis of 17α-hydroxy-20-oxo-pregnanes from 17(20)-dehydro-23,24-dinorcholan-22-oic acids

  摘要：

  Title transformation involving catalytic epoxidation, Curtius rearrangement and acidic hydrolysis has been accomplished. This synthetic sequence offers a novel route from a partial microbial side chain degradation product of natural sterols into useful precursors of antiinflammatory, antiandrogen and gestagen pharmaceuticals

  DOI：

  10.1016/s0040-4039(00)79150-7

文献信息

• Synthesis of 17α-hydroxy-20-oxo-pregnanes from 17(20)-dehydro-23,24-dinorcholan-22-oic acids
  作者：András Toró、Gábor Ambrus

  DOI：10.1016/s0040-4039(00)79150-7

  日期：1992.9

  Title transformation involving catalytic epoxidation, Curtius rearrangement and acidic hydrolysis has been accomplished. This synthetic sequence offers a novel route from a partial microbial side chain degradation product of natural sterols into useful precursors of antiinflammatory, antiandrogen and gestagen pharmaceuticals
• 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
  作者：András Toró、István Pallagi、Gábor Ambrus

  DOI：10.1016/s0040-4039(00)78366-3

  日期：1994.10

  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.