methyl (4aR,4bR,5S,8aS,10aR)-5-benzyloxy-1-chloro-8a-cyano-4a-methyl-8-methylene-2-oxoperhydrophenanthrene-1-carboxylate | 1609534-04-4

• 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: methyl (4aR,4bR,5S,8aS,10aR)-5-benzyloxy-1-chloro-8a-cyano-4a-methyl-8-methylene-2-oxoperhydrophenanthrene-1-carboxylate
• 英文别名: methyl (4aR,4bR,5S,8aS,10aR)-1-chloro-8a-cyano-4a-methyl-8-methylidene-2-oxo-5-phenylmethoxy-4,4b,5,6,7,9,10,10a-octahydro-3H-phenanthrene-1-carboxylate
• CAS: 1609534-04-4
• 化学式: C₂₆H₃₀ClNO₄
• 分子量: 455.982
• InChiKey: XHALAXDEDJUSES-INROKVMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  76.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (4aR,4bR,5S,8aS,10aR)-5-benzyloxy-1-chloro-8a-cyano-4a-methyl-8-methylene-2-oxoperhydrophenanthrene-1-carboxylate 在 2,6-二叔丁基-4-甲基苯酚 、 sodium chloride 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 4.0h， 生成 (4aR,4bR,5S,8aS)-5-benzyloxy-4a-methyl-8-methylene-2-oxo-2,3,4,4a,4b,5,6,7,8,8a,9,10-dodecahydrophenanthrene-8a-carbonitrile
  参考文献：
  名称：

  Divergent synthesis of pseudoenantiomers for ABC-ring moiety of steroids

  摘要：

  Steroid family has various bioactivities and characteristic polycyclic structure. Although several synthetic methods have been reported, more efficient way is desired for medicinal chemistry. In this Letter, we synthesized pseudoenantiomers of tricyclic enones toward both enantiomers for ABC-ring moiety of steroids utilizing D-mannitol as a chiral source. The key steps are radical domino cyclization of polyalkenyl-beta-keto ester into tricyclic keto ester and subsequent dealkoxycarbonylation. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.04.018
• 作为产物：
  描述：

  (2Z)-(4S)-4-benzyloxy-2-[(E)-5-bromo-4-methylpent-3-enyl]octa-2,7-dienenitrile 在 正丁基锂 、 copper(II) acetate monohydrate 、 manganese(III) triacetate dihydrate 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 、 mineral oil 为溶剂， 反应 7.33h， 生成 methyl (4aR,4bR,5S,8aS,10aR)-5-benzyloxy-1-chloro-8a-cyano-4a-methyl-8-methylene-2-oxoperhydrophenanthrene-1-carboxylate
  参考文献：
  名称：

  Divergent synthesis of pseudoenantiomers for ABC-ring moiety of steroids

  摘要：

  Steroid family has various bioactivities and characteristic polycyclic structure. Although several synthetic methods have been reported, more efficient way is desired for medicinal chemistry. In this Letter, we synthesized pseudoenantiomers of tricyclic enones toward both enantiomers for ABC-ring moiety of steroids utilizing D-mannitol as a chiral source. The key steps are radical domino cyclization of polyalkenyl-beta-keto ester into tricyclic keto ester and subsequent dealkoxycarbonylation. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.04.018

文献信息

• Divergent synthesis of pseudoenantiomers for ABC-ring moiety of steroids
  作者：Miyu Furuta、Kengo Hanaya、Takeshi Sugai、Mitsuru Shoji

  DOI：10.1016/j.tetlet.2014.04.018

  日期：2014.5

  Steroid family has various bioactivities and characteristic polycyclic structure. Although several synthetic methods have been reported, more efficient way is desired for medicinal chemistry. In this Letter, we synthesized pseudoenantiomers of tricyclic enones toward both enantiomers for ABC-ring moiety of steroids utilizing D-mannitol as a chiral source. The key steps are radical domino cyclization of polyalkenyl-beta-keto ester into tricyclic keto ester and subsequent dealkoxycarbonylation. (C) 2014 Elsevier Ltd. All rights reserved.