(5R,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-二羟基-17-[(2R)-7-羟基-6-甲基庚烷-2-基]-10,13-二甲基-1,2,4,5,6,7,8,9,11,12,14,15,16,17-十四氢环戊烯并[a]菲-3-酮 | 78094-12-9

• 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: (5R,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-二羟基-17-[(2R)-7-羟基-6-甲基庚烷-2-基]-10,13-二甲基-1,2,4,5,6,7,8,9,11,12,14,15,16,17-十四氢环戊烯并[a]菲-3-酮
• 英文名称: 7α,12α,26-trihydroxy-5β-cholestan-3-one
• 英文别名: (5R,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-dihydroxy-17-[(2R,6R)-7-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
• CAS: 78094-12-9
• 化学式: C₂₇H₄₆O₄
• 分子量: 434.66
• InChiKey: UCVRZTRGVBWBPR-QGLFLVSTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (25R)-3α,7α,12α-trihydroxy-5β-cholestan-26-oic acid 在 Celite 、 silver carbonate 、 diborane(6) 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 3.25h， 生成 (5R,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-二羟基-17-[(2R)-7-羟基-6-甲基庚烷-2-基]-10,13-二甲基-1,2,4,5,6,7,8,9,11,12,14,15,16,17-十四氢环戊烯并[a]菲-3-酮
  参考文献：
  名称：

  Synthesis of biological precursors of cholic acid II

  摘要：

  This paper describes the partial syntheses of 3 alpha, 7 alpha, 12 alpha-trihydroxy-5 beta-cholestan-26-al, 7 alpha, 12 alpha, 26-trihydroxy-5 beta-cholestan-3-one and 7 alpha, 12 alpha-dihydroxy-3-oxo-5 beta-cholestan-26-al via Ag2CO3/Celite oxidation of 5 beta-cholestane-3 alpha, 7 alpha, 12 alpha, 26-tetrol. These bile alcohols were resolved by analytical and preparative TLC, characterized by gas-liquid chromatography and mass spectrometry. These compounds will be useful to delineate further the mechanism of oxidation of 5 beta-cholestane-3 alpha, 7 alpha, 12 alpha, 25-tetrol on the pathway to cholic acid.

  DOI：

  10.1016/s0039-128x(81)80018-9

文献信息

• Synthesis of biological precursors of cholic acid II
  作者：B. Dayal、G.S. Tint、A.K. Batta、S. Shefer、G. Salen

  DOI：10.1016/s0039-128x(81)80018-9

  日期：1981.2

  This paper describes the partial syntheses of 3 alpha, 7 alpha, 12 alpha-trihydroxy-5 beta-cholestan-26-al, 7 alpha, 12 alpha, 26-trihydroxy-5 beta-cholestan-3-one and 7 alpha, 12 alpha-dihydroxy-3-oxo-5 beta-cholestan-26-al via Ag2CO3/Celite oxidation of 5 beta-cholestane-3 alpha, 7 alpha, 12 alpha, 26-tetrol. These bile alcohols were resolved by analytical and preparative TLC, characterized by gas-liquid chromatography and mass spectrometry. These compounds will be useful to delineate further the mechanism of oxidation of 5 beta-cholestane-3 alpha, 7 alpha, 12 alpha, 25-tetrol on the pathway to cholic acid.