23-dehydrocholesterol | 58507-61-2

• 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: 23-dehydrocholesterol
• 英文别名: Δ23-cholesterol；cholesta-5,22-dien-3-ol；5,23-Cholestadien-3beta-ol；(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylhept-4-en-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
• CAS: 58507-61-2
• 化学式: C₂₇H₄₄O
• 分子量: 384.646
• InChiKey: QWRSWWMDQCPOTC-DPAQBDIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  6β-methoxy-3α,5-cyclocholestan-24-ol 在 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 以24%的产率得到24ξ-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

文献信息

• Side chain modified sterols as probes into insect molting hormone metabolism. II: Synthesis of monofluorocholesterols
  作者：Glenn D. Prestwich、Hong Ming Shieh、Apurba K. Gayen

  DOI：10.1016/0039-128x(83)90018-1

  日期：1983.1

  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.