<1R,1α(S^*),3α(E)>-1-Cyano-1-(3-phenoxyphenyl)methyl 2,2-Dimethyl-3-<3-tert-butoxy-2-(tert-butylsulfonyl)-3-oxo-1-propenyl>cyclopropanecarboxylate | 130051-21-7

• 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(S^*),3α(E)>-1-Cyano-1-(3-phenoxyphenyl)methyl 2,2-Dimethyl-3-<3-tert-butoxy-2-(tert-butylsulfonyl)-3-oxo-1-propenyl>cyclopropanecarboxylate
• CAS: 130051-21-7
• 化学式: C₃₁H₃₇NO₇S
• 分子量: 567.703
• InChiKey: NANAFMIGULBYRX-JCJTWSFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  40.0
• 可旋转键数：
  8.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  119.76
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  <1R,1α(S^*),3α(E)>-1-Cyano-1-(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 1.0h， 以60%的产率得到(1R,3S)-3-((Z)-2-tert-Butoxycarbonyl-vinyl)-2,2-dimethyl-cyclopropanecarboxylic acid (S)-cyano-(3-phenoxy-phenyl)-methyl ester
  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， 反应 18.0h， 生成 <1R,1α(S^*),3α(E)>-1-Cyano-1-(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