<1R,1α,3α(Z)>-(3-Phenoxyphenyl)methyl 2,2-Dimethyl-3-<3-tert-butoxy-2-(phenylsulfenyl)-3-oxo-1-propenyl>cyclopropanecarboxylate | 138336-37-5

• 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(Z)>-(3-Phenoxyphenyl)methyl 2,2-Dimethyl-3-<3-tert-butoxy-2-(phenylsulfenyl)-3-oxo-1-propenyl>cyclopropanecarboxylate
• CAS: 138336-37-5
• 化学式: C₃₂H₃₄O₅S
• 分子量: 530.685
• InChiKey: PYFYKZYYEARGGJ-HHCXTUBUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.81
• 重原子数：
  38.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  <1R,1α,3α(Z)>-(3-Phenoxyphenyl)methyl 2,2-Dimethyl-3-<3-tert-butoxy-2-(phenylsulfenyl)-3-oxo-1-propenyl>cyclopropanecarboxylate 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以95%的产率得到<1R,1α,3α(Z)>-(3-Phenoxyphenyl)methyl 2,2-Dimethyl-3-<3-tert-butoxy-2-(phenylsulfonyl)-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 (phenylthio)acetate 在 4-二甲氨基吡啶 、 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(Z)>-(3-Phenoxyphenyl)methyl 2,2-Dimethyl-3-<3-tert-butoxy-2-(phenylsulfenyl)-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