3β-fluoro-androsta-5,16-diene

• 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: 3β-fluoro-androsta-5,16-diene
• 英文别名: (3S,8S,9S,10R,13R,14S)-3-fluoro-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15-decahydro-1H-cyclopenta[a]phenanthrene
• 化学式: C₁₉H₂₇F
• 分子量: 274.422
• InChiKey: VKUOQOXDVMBKNF-DYKIIFRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (3S,8S,9S,10R,13R,14S)-10,13-二甲基-2,3,4,7,8,9,11,12,14,15-十氢-1H-环戊并[a]菲-3-醇 在 全氟丁基磺酰氟 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以68%的产率得到androsta-3,5,16-triene
  参考文献：
  名称：

  PREPARATION OF 3α-FLUORO- AND 3β-FLUORO DERIVATIVES OF 5α-ANDROST-16-ENES AND ANDROSTA-5,16-DIENES

  摘要：

  n-Perfluorobutanesulfonyl fluoride, in the presence of DBU, is shown to be a convenient and satisfactory reagent for the preparation of a variety of unsaturated 3-fluorosteroids of defined stereochemistry. 3-Fluoro-16,17-dehydrosteroids are reported for the first time. Fluorodehydroxylation proceeded with retention of configuration for 5,6,16,17-tetradehydro-3beta-sterols, but with inversion for their 3alpha-analogues, as it did for several 16,17-dehydrosterols.

  DOI：

  10.1081/scc-120005419

文献信息

• Preparation of 3,17‐ and 3,20‐Difluoro‐Derivatives of the Androst‐5‐ene and Pregn‐5‐ene Series
  作者：Richard A. Decréau、Charles M. Marson

  DOI：10.1081/scc-200039449

  日期：2004.12.31

  Unsaturated mono- and difluorosteroids have been prepared in high yield using n-perfluorobutanesulfonyl fluoride 1. The 3,17- and 3,20-difluoro-5,6-dehydrosteroids are reported for the first time. 3-Fluoroderivatives of the androst-5-ene-17-one and 5alpha-androst-17-one series have been prepared, and yields obtained with 1 have been compared with those reported with other fluorinating agents.