(3R,5R,6S,8S,9S,10R,13S,14S,17R)-17-Isopropenyl-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthrene-3,6-diol | 63060-77-5

• 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: (3R,5R,6S,8S,9S,10R,13S,14S,17R)-17-Isopropenyl-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthrene-3,6-diol
• CAS: 63060-77-5
• 化学式: C₂₂H₃₆O₂
• 分子量: 332.527
• InChiKey: BPLUNBAPJGKEFT-VKGRLEKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.55
• 重原子数：
  24.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  3α,6α-diacetoxy-5β-cholan-24-oic acid 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 (3R,5R,6S,8S,9S,10R,13S,14S,17R)-17-Isopropenyl-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthrene-3,6-diol
  参考文献：
  名称：

  咪唑啉化物的光化学II。羧酸链的C2-C3裂解。一种方便的胆汁酸和羊毛甾醇侧链降解的新方法。

  摘要：

  AbstractIrradiation of N‐stearoylimidazole (1) gave hexadec‐1‐ene (4) in 45% yield, whereas irradiation of N‐(4‐methylstearoyl)imidazole (13) possessing a tertiary hydrogen atom γ to the carbonyl group led to 2‐methylhexadec‐1‐ene (14) in 62% yield. These results are explained by a two‐stage process: acyl migration, followed by Norrish Type II eliminatior. The reaction has been utilized for the side chain degradation of bile acids and of lanosterol, in which the second stage of the reaction was shown to proceed in up to 70% yield.

  DOI：

  10.1002/hlca.19760590814