3β-hydroxy-A-homo-5αH-pregnan-20-one | 1234504-45-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3β-hydroxy-A-homo-5αH-pregnan-20-one
• 英文别名: 1-[(1S,2S,5R,8S,11R,12S,15S,16S)-5-hydroxy-2,16-dimethyl-15-tetracyclo[9.7.0.02,8.012,16]octadecanyl]ethanone
• CAS: 1234504-45-0
• 化学式: C₂₂H₃₆O₂
• 分子量: 332.527
• InChiKey: KVFBEKSKNXEUOG-XQJOZJDQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 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：

  3β-hydroxy-A-homo-5-pregnen-20-one 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 25.0 ℃ 、413.69 kPa 条件下， 反应 22.0h， 以80%的产率得到3β-hydroxy-A-homo-5αH-pregnan-20-one
  参考文献：
  名称：

  Synthesis and GABAA receptor activity of A-homo analogues of neuroactive steroids

  摘要：

  A procedure is described for the preparation of A-homo-5-pregnenes via an acid catalyzed rearrangement of cyclopropylcarbinols assisted by microwave irradiation. 3 alpha-Hydroxy and 4 alpha-hydroxy-A-homo-5-pregnen-20-one, analogues of the neuroactive steroid allopregnanolone, were obtained by means of a regioselective epoxidation of a double bond in the expanded A-ring, using a fructose-derived chiral ketone as catalyst and oxone as oxidant. Although both these compounds were marginally active in inhibiting TBPS binding to GABA(A) receptors, 3 beta-hydroxy-A-homo-5-pregnen-20-one was almost as active as allopregnanolone. Reduction of the double bond of the latter compound resulted in a ten fold loss of activity. (c) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.03.037

文献信息

• Synthesis and GABAA receptor activity of A-homo analogues of neuroactive steroids
  作者：María V. Dansey、Pablo H. Di Chenna、Adriana S. Veleiro、Zdena Krištofíková、Hana Chodounska、Alexander Kasal、Gerardo Burton

  DOI：10.1016/j.ejmech.2010.03.037

  日期：2010.7

  A procedure is described for the preparation of A-homo-5-pregnenes via an acid catalyzed rearrangement of cyclopropylcarbinols assisted by microwave irradiation. 3 alpha-Hydroxy and 4 alpha-hydroxy-A-homo-5-pregnen-20-one, analogues of the neuroactive steroid allopregnanolone, were obtained by means of a regioselective epoxidation of a double bond in the expanded A-ring, using a fructose-derived chiral ketone as catalyst and oxone as oxidant. Although both these compounds were marginally active in inhibiting TBPS binding to GABA(A) receptors, 3 beta-hydroxy-A-homo-5-pregnen-20-one was almost as active as allopregnanolone. Reduction of the double bond of the latter compound resulted in a ten fold loss of activity. (c) 2010 Elsevier Masson SAS. All rights reserved.