3β,4β-epoxy-20β-hydroxy-A-homo-5-pregnene | 1234504-30-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3β,4β-epoxy-20β-hydroxy-A-homo-5-pregnene
• 英文别名: (1R)-1-[(1S,2R,5S,7R,12S,13S,16S,17S)-2,17-dimethyl-6-oxapentacyclo[10.7.0.02,9.05,7.013,17]nonadec-9-en-16-yl]ethanol
• CAS: 1234504-30-3
• 化学式: C₂₂H₃₄O₂
• 分子量: 330.511
• InChiKey: UPTUAKIDOLKZIM-COIMCIHDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3β,4β-epoxy-20β-hydroxy-A-homo-5-pregnene 在 lithium aluminium tetrahydride 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.33h， 以63%的产率得到3β,20β-dihydroxy-A-homo-5-pregnene
  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：

  20β-hydroxy-A-homopregna-3,5-diene 在 Oxone 、 Shi's ketone 、 四丁基醋酸铵 、 edetate disodium 、 potassium carbonate 作用下， 以 乙二醇二甲醚 、 水 、 乙腈 为溶剂， 反应 0.5h， 以35%的产率得到3β,4β-epoxy-20β-hydroxy-A-homo-5-pregnene
  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