17α-hydroxy-4-cholesten-3-one | 157636-45-8

• 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
• 英文名称: 17α-hydroxy-4-cholesten-3-one
• 英文别名: 17-Hydroxycholest-4-en-3-one；(8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
• CAS: 157636-45-8
• 化学式: C₂₇H₄₄O₂
• 分子量: 400.645
• InChiKey: JPZQAAAKHXFVKO-AHXUHXIQSA-N

物化性质

• 沸点：
  511.9±50.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5α-cholestane-5,17α-diol 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以88.8%的产率得到17α-hydroxy-4-cholesten-3-one
  参考文献：
  名称：

  Some reactions of 16α,17α-oxido-5α-cholestane derivatives, synthesis of 17α-hydroxycholest-4-en-3-one

  摘要：

  Careful epoxidation of the Delta(16)-olefins 3 and 4 yielded 16 alpha,17 alpha-epoxides 5 and 6 which were reduced by lithium aluminium hydride, oxidized, and dehydrated to 17 alpha-hhydroxycholest-4-en-3-one 20, i.e., an epitestosterone homolog containing a well tolerated alkyl group at position 17. Under catalysis of acids, epoxide 5 was rearranged to Delta(13)-16 alpha-alcohol 10. Less careful epoxidation of Delta(16)-olefin 4 with excess of peroxy acid led to products of double epoxidation (Le., epoxidation, rearrangement, and another oxidation) 7 and 12. Structures of products of rearrangement were studied mainly by NMR spectroscopy.

  DOI：

  10.1016/0039-128x(94)90123-6