21,21,21-trifluoro-3β-hydroxy-pregn-5-en-20-one | 2071-13-8

• 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: 21,21,21-trifluoro-3β-hydroxy-pregn-5-en-20-one
• 英文别名: 21,21,21-Trifluor-3β-hydroxy-pregn-5-en-20-on；2,2,2-trifluoro-1-[(3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone
• CAS: 2071-13-8
• 化学式: C₂₁H₂₉F₃O₂
• 分子量: 370.455
• InChiKey: ZHQOQRHYUTVGRL-WQBJWTDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  21,21,21-trifluoro-3β-hydroxy-pregn-5-en-20-one 在 N-甲基-4-哌啶酮 、 aluminum isopropoxide 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以72%的产率得到21,21,21-trifluoro-pregn-4-ene-3,20-dione
  参考文献：
  名称：

  Synthesis of novel 21-trifluoropregnane steroids: Inhibitors of 17α-hydroxylase/17,20-lyase (17α-lyase)

  摘要：

  Novel 21-trifluoropregnenolone (6), 21-trifluoroprogesterone (7) and related compounds 4a and 8 have been synthesized in high yields from 3 beta-acetoxyandrost-5-ene-17 beta-carbaldehyde (3). The key reaction was the conversion of 3 into the 21-trifluoromethyl-20-alcohol as a diastereomeric mixture (4) by trifluoromethyltrimethylsilane (TMS-CF3) in the presence of tetrabutylammonium fluoride (TBAF). All compounds, including 6 and 7, were unambiguously characterized by IR, H-1 and F-19 NMR, high-resolution mass spectrometry (HRMS), and elemental analysis. On this basis, we concluded that the only report of an earlier synthesis of 6 and 7(13) is erroneous. Enzyme inhibition studies showed that 20 xi-hydroxy-21-trifluoropregn-4-en-3-one (8) is a potent inhibitor (IC50 value = -0.6 mu M) of rat 17 alpha-hydroxylase/17,20-lyase. (C) 1997 by Elsevier Science Inc.

  DOI：

  10.1016/s0039-128x(97)00016-0
• 作为产物：
  描述：

  3β-acetoxy-21,21,21-trifluoro-pregn-5-en-20-one 在 氢氧化钾 作用下， 生成 21,21,21-trifluoro-3β-hydroxy-pregn-5-en-20-one
  参考文献：
  名称：

  THE REACTION OF PERCHLORYL FLUORIDE WITH ENOL ETHERS

  摘要：

  DOI：

  10.1021/ja01528a058

文献信息

• THE REACTIONS OF BROMINE ATOMS AND THE STRENGTHS OF C-H BONDS
  作者：G. C. Fettis、A. F. Trotman-Dickenson

  DOI：10.1021/ja01528a059

  日期：1959.10