20ξ-fluoro-6β-methoxy-3α,5-cyclo-5α-cholestane | 88674-21-9

• 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
• 英文名称: 20ξ-fluoro-6β-methoxy-3α,5-cyclo-5α-cholestane
• CAS: 88674-21-9；88729-20-8
• 化学式: C₂₈H₄₇FO
• 分子量: 418.679
• InChiKey: PAVBANUHGHYEKH-IDKNOLKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.82
• 重原子数：
  30.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  20ξ-fluoro-6β-methoxy-3α,5-cyclo-5α-cholestane 在 对甲苯磺酸 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 4.0h， 以80%的产率得到Cholest-5-en-3-ol, 20-fluoro-, (3b,20R)-
  参考文献：
  名称：

  Side chain modified sterols as probes into insect molting hormone metabolism. II: Synthesis of monofluorocholesterols

  摘要：

  The hydroxylations of the cholesterol side chain at C-20, 22, and 25 are key terminal events in ecdysone biogenesis. We have prepared the C-20, C-22, C-24, and C-25 monofluorinated cholesterols as potential inhibitors of these hydroxylation events, and preliminary bioassay results in Manduca sexta are reported. The synthesis of [26(14)C]-20-fluorocholesterol is also described. Although the 20-, 22-, and 25-monofluorocholesterols do not appear to affect larval growth and development, the 24-fluoro isomer shows a moderate retardation of growth and a modest increase in mortality.

  DOI：

  10.1016/0039-128x(83)90018-1
• 作为产物：
  描述：

  6-methoxy-20ξ-isohexyl-3α,5-cyclo-5α-pregnan-20-ol 在 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到20ξ-fluoro-6β-methoxy-3α,5-cyclo-5α-cholestane
  参考文献：
  名称：

  Side chain modified sterols as probes into insect molting hormone metabolism. II: Synthesis of monofluorocholesterols

  摘要：

  The hydroxylations of the cholesterol side chain at C-20, 22, and 25 are key terminal events in ecdysone biogenesis. We have prepared the C-20, C-22, C-24, and C-25 monofluorinated cholesterols as potential inhibitors of these hydroxylation events, and preliminary bioassay results in Manduca sexta are reported. The synthesis of [26(14)C]-20-fluorocholesterol is also described. Although the 20-, 22-, and 25-monofluorocholesterols do not appear to affect larval growth and development, the 24-fluoro isomer shows a moderate retardation of growth and a modest increase in mortality.

  DOI：

  10.1016/0039-128x(83)90018-1