(4R)-4-[(5R,8R,9S,10S,12R,13R,14S,17R)-12-羟基-10,13-二甲基-3-氧代-1,2,4,5,6,7,8,9,11,12,14,15,16,17-十四氢环戊烯并[a]菲-17-基]戊酸 | 136892-43-8

• 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
• 中文名称: (4R)-4-[(5R,8R,9S,10S,12R,13R,14S,17R)-12-羟基-10,13-二甲基-3-氧代-1,2,4,5,6,7,8,9,11,12,14,15,16,17-十四氢环戊烯并[a]菲-17-基]戊酸
• 中文别名: 甲基硫酸8-[(乙基氨基甲酰)氧代]-1-甲基喹啉正离子
• 英文名称: 12β-hydroxy-3-keto-5β-cholan-24-oic acid
• 英文别名: 3-oxolithocholic acid；3-oxo-LCA；12beta-Hydroxy-3-oxo-5beta-cholan-24-oic Acid；(4R)-4-[(5R,8R,9S,10S,12R,13R,14S,17R)-12-hydroxy-10,13-dimethyl-3-oxo-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]pentanoic acid
• CAS: 136892-43-8
• 化学式: C₂₄H₃₈O₄
• 分子量: 390.563
• InChiKey: WMUMZOAFCDOTRW-RXTDITKTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  Cholan-24-oic acid, 3,3-dimethoxy-12-oxo-, (5b)- 在 sodium hydroxide 、 sodium tetrahydroborate 作用下， 反应 24.0h， 生成 12-alpha-羟基-3-氧代-5-beta-胆烷酸 、 (4R)-4-[(5R,8R,9S,10S,12R,13R,14S,17R)-12-羟基-10,13-二甲基-3-氧代-1,2,4,5,6,7,8,9,11,12,14,15,16,17-十四氢环戊烯并[a]菲-17-基]戊酸
  参考文献：
  名称：

  Synthesis of 7- and 12-hydroxy- and 7,12-dihydroxy-3-keto-5β-cholan-24-oic acids by reduction of 3,7-, 3,12- and 3,7,12-oxo derivatives

  摘要：

  7alpha-, 12alpha-, 12beta-Hydroxy and 7alpha,12alpha- and 7alpha,12beta-dihydroxy-3-ketocholanoic acids were prepared in satisfactory yields protecting the 3-keto group as dimethyl ketal and subsequent reduction with sodium borohydride of the corresponding 7- and 12-oxo functionalities. The same procedure gave also 3,12-diketo-7alpha-hydroxy-cholanoic acid.

  DOI：

  10.1016/0039-128x(93)90028-l

文献信息

• Synthesis of 7- and 12-hydroxy- and 7,12-dihydroxy-3-keto-5β-cholan-24-oic acids by reduction of 3,7-, 3,12- and 3,7,12-oxo derivatives
  作者：Giancarlo Fantin、Marco Fogagnolo、Alessandro Medici、Paola Pedrini、Umberto Cova

  DOI：10.1016/0039-128x(93)90028-l

  日期：1993.11

  7alpha-, 12alpha-, 12beta-Hydroxy and 7alpha,12alpha- and 7alpha,12beta-dihydroxy-3-ketocholanoic acids were prepared in satisfactory yields protecting the 3-keto group as dimethyl ketal and subsequent reduction with sodium borohydride of the corresponding 7- and 12-oxo functionalities. The same procedure gave also 3,12-diketo-7alpha-hydroxy-cholanoic acid.