(4S,6aS,6a1S,8aS,9aS,10S,12aS,12bS)-10-((S)-1-hydroxyethyl)-9a-methyl-1,2,4,5,6,6a1,8a,9,9a,10,11,12,12a,12b-tetradecahydro-7H-cyclopenta[1,2]phenanthro[4,4b-bc]furan-4-ol | 1032410-54-0

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (4S,6aS,6a1S,8aS,9aS,10S,12aS,12bS)-10-((S)-1-hydroxyethyl)-9a-methyl-1,2,4,5,6,6a1,8a,9,9a,10,11,12,12a,12b-tetradecahydro-7H-cyclopenta[1,2]phenanthro[4,4b-bc]furan-4-ol
• CAS: 1032410-54-0
• 化学式: C₂₁H₃₂O₃
• 分子量: 332.483
• InChiKey: ZHSXJFDSFGDHON-QDYCMWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  49.69
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  甲酸 、 (4S,6aS,6a1S,8aS,9aS,10S,12aS,12bS)-10-((S)-1-hydroxyethyl)-9a-methyl-1,2,4,5,6,6a1,8a,9,9a,10,11,12,12a,12b-tetradecahydro-7H-cyclopenta[1,2]phenanthro[4,4b-bc]furan-4-ol 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 以60%的产率得到3α-formyloxy-11,19-epoxypregn-4-en-20-ol
  参考文献：
  名称：

  Synthesis and GABAA receptor activity of oxygen-bridged neurosteroid analogs

  摘要：

  Three analogs of neuroactive steroids were prepared (4-6) in which 1,11- or 11,19-oxygen bridges give a constrained conformation. Their 3D structures were obtained by ab initio calculations and in the case of 3 alpha-hydroxy-11,19-epoxypregn-4- ene-20-one (4), confirmed by X-ray analysis. Biological activity of the synthetic steroids was assayed in vitro using t-[H-3] butylbicycloorthobenzoate as radiolabeled ligand for the GABA(A) receptor. The activity of compound 4 was similar to that of allopregnanolone (1). 1 alpha, 11 alpha-Epoxypregnanolone (6) was more active than pregnanolone (2). (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.01.048
• 作为产物：
  描述：

  11,19-Oxidopregn-4-ene-3,20-dione 在 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.5h， 以80%的产率得到(4S,6aS,6a1S,8aS,9aS,10S,12aS,12bS)-10-((S)-1-hydroxyethyl)-9a-methyl-1,2,4,5,6,6a1,8a,9,9a,10,11,12,12a,12b-tetradecahydro-7H-cyclopenta[1,2]phenanthro[4,4b-bc]furan-4-ol
  参考文献：
  名称：

  Synthesis and GABAA receptor activity of oxygen-bridged neurosteroid analogs

  摘要：

  Three analogs of neuroactive steroids were prepared (4-6) in which 1,11- or 11,19-oxygen bridges give a constrained conformation. Their 3D structures were obtained by ab initio calculations and in the case of 3 alpha-hydroxy-11,19-epoxypregn-4- ene-20-one (4), confirmed by X-ray analysis. Biological activity of the synthetic steroids was assayed in vitro using t-[H-3] butylbicycloorthobenzoate as radiolabeled ligand for the GABA(A) receptor. The activity of compound 4 was similar to that of allopregnanolone (1). 1 alpha, 11 alpha-Epoxypregnanolone (6) was more active than pregnanolone (2). (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.01.048