A-homo-5-pregnene-4,20-dione | 1234504-41-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: A-homo-5-pregnene-4,20-dione
• 英文别名: (1S,2R,11S,12S,15S,16S)-15-acetyl-2,16-dimethyltetracyclo[9.7.0.02,8.012,16]octadec-8-en-6-one
• CAS: 1234504-41-6
• 化学式: C₂₂H₃₂O₂
• 分子量: 328.495
• InChiKey: ARIUIGWOURYMLV-GFJXEVPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  A-homo-5-pregnene-4,20-dione 在 potassium tri-sec-butyl-borohydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以70%的产率得到1-((1S,3aS,3bS,7R,10aR,10bS,12aS)-7-hydroxy-10a,12a-dimethyl-1,2,3,3a,3b,4,6,7,8,9,10,10a,10b,11,12,12a-hexadecahydrocyclohepta[a]cyclopenta[f]naphthalen-1-yl)ethan-1-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
• 作为产物：
  描述：

  4β,20β-dihydroxy-A-homo-5-pregnene 在 barium carbonate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以75%的产率得到A-homo-5-pregnene-4,20-dione
  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.