<1R,1α,3α(E)>-(3-Phenoxyphenyl)methyl 2,2-Dimethyl-3-<3-tert-butoxy-2-(tert-butylsulfonyl)-3-oxo-1-propenyl>cyclopropanecarboxylate | 138336-44-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: <1R,1α,3α(E)>-(3-Phenoxyphenyl)methyl 2,2-Dimethyl-3-<3-tert-butoxy-2-(tert-butylsulfonyl)-3-oxo-1-propenyl>cyclopropanecarboxylate
• 英文别名: (3-phenoxyphenyl)methyl (1R,3R)-3-[(E)-2-tert-butylsulfonyl-3-[(2-methylpropan-2-yl)oxy]-3-oxoprop-1-enyl]-2,2-dimethylcyclopropane-1-carboxylate
• CAS: 138336-44-4
• 化学式: C₃₀H₃₈O₇S
• 分子量: 542.694
• InChiKey: OYHSTXLQOMCVED-XLIXZDQVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  <1R,1α,3α(E)>-(3-Phenoxyphenyl)methyl 2,2-Dimethyl-3-<3-tert-butoxy-2-(tert-butylsulfonyl)-3-oxo-1-propenyl>cyclopropanecarboxylate 在 sodium dithionite 、 甲基三辛基氯化铵 、 碳酸氢钠 作用下， 以 环己烷 、 水 为溶剂， 反应 1.25h， 以157 mg的产率得到<1R,1α,3α(Z)>-(3-Phenoxyphenyl)methyl 2,2-Dimethyl-3-(3-tert-butoxy-3-oxo-1-propenyl)cyclopropanecarboxylate
  参考文献：
  名称：

  A new way toward Z.alpha.,.beta. unsaturated esters: a pyrethroid application

  摘要：

  Use of the stereospecific condensation of beta-carbalkoxysulfones with aldehydes, followed by the stereospecific reduction of the afforded sulfonyl acrylate with sodium dithionite allows us to propose this method as a new way to prepare Z alpha,beta unsaturated esters. Steric hindrance seems to be the reason for the selectivity of the reduction and the mechanism was proved, by X-ray of an intermediate, to be a cis Michael addition of HSO2-, followed by an anti elimination of SO2 and the sulfinate group. This method discovered in the pyrethroid series for the synthesis of acrinathrin 1 could have general application.

  DOI：

  10.1021/jo00028a034
• 作为产物：
  描述：

  tert-Butyl 2-(tert-Butylsulfonyl)acetate 在 4-二甲氨基吡啶 、 sodium hydride 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 <1R,1α,3α(E)>-(3-Phenoxyphenyl)methyl 2,2-Dimethyl-3-<3-tert-butoxy-2-(tert-butylsulfonyl)-3-oxo-1-propenyl>cyclopropanecarboxylate
  参考文献：
  名称：

  A new way toward Z.alpha.,.beta. unsaturated esters: a pyrethroid application

  摘要：

  Use of the stereospecific condensation of beta-carbalkoxysulfones with aldehydes, followed by the stereospecific reduction of the afforded sulfonyl acrylate with sodium dithionite allows us to propose this method as a new way to prepare Z alpha,beta unsaturated esters. Steric hindrance seems to be the reason for the selectivity of the reduction and the mechanism was proved, by X-ray of an intermediate, to be a cis Michael addition of HSO2-, followed by an anti elimination of SO2 and the sulfinate group. This method discovered in the pyrethroid series for the synthesis of acrinathrin 1 could have general application.

  DOI：

  10.1021/jo00028a034

文献信息

• US5329017A
  申请人：——

  公开号：US5329017A

  公开（公告）日：1994-07-12