Benzoic acid (1S,3aS,3bS,5aS,7R,9aR,9bS,11aS)-1-acetyl-9a,11a-dimethyl-hexadecahydro-indeno[4,5-c]thiochromen-7-yl ester | 892864-09-4

• 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: Benzoic acid (1S,3aS,3bS,5aS,7R,9aR,9bS,11aS)-1-acetyl-9a,11a-dimethyl-hexadecahydro-indeno[4,5-c]thiochromen-7-yl ester
• 英文别名: [(1S,3aS,3bS,5aS,7R,9aR,9bS,11aS)-1-acetyl-9a,11a-dimethyl-1,2,3,3a,3b,4,5a,6,7,8,9,9b,10,11-tetradecahydroindeno[4,5-c]thiochromen-7-yl] benzoate
• CAS: 892864-09-4
• 化学式: C₂₇H₃₆O₃S
• 分子量: 440.647
• InChiKey: FXXDWHBTFHQDSZ-HVPCJGPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  68.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Benzoic acid (1S,3aS,3bS,5aS,7R,9aR,9bS,11aS)-1-acetyl-9a,11a-dimethyl-hexadecahydro-indeno[4,5-c]thiochromen-7-yl ester 在 Oxone 、 sodium thiomethoxide 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.08h， 生成 S-oxo-3α-hydroxy-6-thia-5α-pregnan-20-one
  参考文献：
  名称：

  Synthesis of 6-thia analogs of the natural neurosteroid allopregnanolone

  摘要：

  A procedure is described for the preparation of 6-thiapregnanes in five steps from pregnenolone via a 5-oxo-7-iodo-secopregnane intermediate. The 6-thiasteroid obtained was converted into 6-thia-allopregnanolone and its sulfoxide and sulforic derivatives. The trans stereochemistry at the A/B ring junction was accomplished by stereoselective reduction of an intermediate hemithioketal with triethylsilane/BF3 center dot Et2O. The compounds synthesized are analogs of natural neurosteroids, and exhibited GABA(A) receptor activity comparable to allopregnanolone. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.03.025
• 作为产物：
  描述：

  3α-benzoyloxy-19-hydroxy-6-thia-5α-pregnan-20-one 在 4-二甲氨基吡啶 、 di(1H-imidazol-2-yl)methanethione 、 偶氮二异丁腈 、 二苯基硅烷 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 9.5h， 生成 Benzoic acid (1S,3aS,3bS,5aS,7R,9aR,9bS,11aS)-1-acetyl-9a,11a-dimethyl-hexadecahydro-indeno[4,5-c]thiochromen-7-yl ester
  参考文献：
  名称：

  Synthesis of 6-thia analogs of the natural neurosteroid allopregnanolone

  摘要：

  A procedure is described for the preparation of 6-thiapregnanes in five steps from pregnenolone via a 5-oxo-7-iodo-secopregnane intermediate. The 6-thiasteroid obtained was converted into 6-thia-allopregnanolone and its sulfoxide and sulforic derivatives. The trans stereochemistry at the A/B ring junction was accomplished by stereoselective reduction of an intermediate hemithioketal with triethylsilane/BF3 center dot Et2O. The compounds synthesized are analogs of natural neurosteroids, and exhibited GABA(A) receptor activity comparable to allopregnanolone. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.03.025

文献信息

• Synthesis of 6-thia analogs of the natural neurosteroid allopregnanolone
  作者：Fernando J. Durán、Alberto A. Ghini、Hector Coirini、Gerardo Burton

  DOI：10.1016/j.tet.2006.03.025

  日期：2006.5

  A procedure is described for the preparation of 6-thiapregnanes in five steps from pregnenolone via a 5-oxo-7-iodo-secopregnane intermediate. The 6-thiasteroid obtained was converted into 6-thia-allopregnanolone and its sulfoxide and sulforic derivatives. The trans stereochemistry at the A/B ring junction was accomplished by stereoselective reduction of an intermediate hemithioketal with triethylsilane/BF3 center dot Et2O. The compounds synthesized are analogs of natural neurosteroids, and exhibited GABA(A) receptor activity comparable to allopregnanolone. (c) 2006 Elsevier Ltd. All rights reserved.