methyl cis-2-(5-carbomethoxy-1-cyclohexen-3-yl)propanoate | 133967-42-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: methyl cis-2-(5-carbomethoxy-1-cyclohexen-3-yl)propanoate
• 英文别名: methyl (1S,5S)-5-(1-methoxy-1-oxopropan-2-yl)cyclohex-3-ene-1-carboxylate
• CAS: 133967-42-7
• 化学式: C₁₂H₁₈O₄
• 分子量: 226.273
• InChiKey: FAYTUQGANFVXBR-XVBQNVSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (E)-(1-methoxyprop-1-enyloxy)trimethylsilane 、 cis-methyl 5-acetoxycyclohex-3-enecarboxylate 在 1,1'-bis(diphenylphosphino)ferrocene-Pd 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 methyl syn-2-(3-carbomethoxybicyclo<3.1.0>hexane-6-yl)propanoate 、 methyl cis-2-(5-carbomethoxy-1-cyclohexen-3-yl)propanoate 、 methyl trans-2-(5-carbomethoxy-1-cyclohexen-3-yl)propanoate
  参考文献：
  名称：

  The regio- and stereoselectivities of the reaction of allyl acetates and silyl ketene acetals catalyzed by palladium(0) complexes: a new route to cyclopropane derivatives

  摘要：

  Pd(0) complexes of chelating phosphines catalyzed the coupling of allyl acetates and ketene silyl acetals to yield alpha-allylated carboxylic acid esters. Unexpectedly alkylation of the central carbon atom (C2) of the allyl groups was also observed with concomitant formation of cyclopropane derivatives. In both cases the silyl enolate attacked the allyl group from the side opposite Pd. The yield of the reaction was sensitive to the nature of the ligand coordinated with palladium. The 1,1'-bis(diphenylphosphino)ferrocene-Pd complex was the most effective catalyst.

  DOI：

  10.1021/jo00012a027

文献信息

• The regio- and stereoselectivities of the reaction of allyl acetates and silyl ketene acetals catalyzed by palladium(0) complexes: a new route to cyclopropane derivatives
  作者：C. Carfagna、L. Mariani、A. Musco、G. Sallese、R. Santi

  DOI：10.1021/jo00012a027

  日期：1991.6

  Pd(0) complexes of chelating phosphines catalyzed the coupling of allyl acetates and ketene silyl acetals to yield alpha-allylated carboxylic acid esters. Unexpectedly alkylation of the central carbon atom (C2) of the allyl groups was also observed with concomitant formation of cyclopropane derivatives. In both cases the silyl enolate attacked the allyl group from the side opposite Pd. The yield of the reaction was sensitive to the nature of the ligand coordinated with palladium. The 1,1'-bis(diphenylphosphino)ferrocene-Pd complex was the most effective catalyst.