4-carbethoxy-3-methyl-1,3-cyclohexadienyl carboxylic acid | 143287-95-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-carbethoxy-3-methyl-1,3-cyclohexadienyl carboxylic acid
• 英文别名: 4-Ethoxycarbonyl-3-methylcyclohexa-1,3-diene-1-carboxylic acid
• CAS: 143287-95-0
• 化学式: C₁₁H₁₄O₄
• 分子量: 210.23
• InChiKey: YYSJRMKWAIGMRA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  一氧化碳 、 Ethyl 2-methyl-4-(trifluoromethylsulfonyloxy)cyclohexa-1,3-diene-1-carboxylate 在 bis(triphenylphosphine) palladium (Il) acetate potassium acetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以89%的产率得到4-carbethoxy-3-methyl-1,3-cyclohexadienyl carboxylic acid
  参考文献：
  名称：

  Palladium-catalysed hydroxycarbonylation of vinyl and aryl triflates: synthesis of α,β-unsaturated and aromatic carboxylic acids

  摘要：

  The palladium-catalyzed hydroxycarbonylation of vinyl and aryl triflates, under a CO balloon, in the presence of potassium acetate affords alpha,beta-unsaturated and aromatic carboxylic acids with one more carbon in good to high yield. The nature of the solvent and of the ligand have been proved to be crucial for the success of the reaction. Vinyl triflates undergo the hydroxycarbonylation at room temperature in DMF in the presence of Pd(OAc)2(PPh3)2. Aryl triflates produce best results at 60-degrees-C in DMSO in the presence of Pd(OAC)2 and 1,1-bis (diphenylphosphino)ferrocene (dppf).

  DOI：

  10.1016/s0040-4039(00)74824-6

文献信息

• Palladium-catalysed hydroxycarbonylation of vinyl and aryl triflates: synthesis of α,β-unsaturated and aromatic carboxylic acids
  作者：Sandro Cacchi、Alessandro Lupi

  DOI：10.1016/s0040-4039(00)74824-6

  日期：1992.6

  The palladium-catalyzed hydroxycarbonylation of vinyl and aryl triflates, under a CO balloon, in the presence of potassium acetate affords alpha,beta-unsaturated and aromatic carboxylic acids with one more carbon in good to high yield. The nature of the solvent and of the ligand have been proved to be crucial for the success of the reaction. Vinyl triflates undergo the hydroxycarbonylation at room temperature in DMF in the presence of Pd(OAc)2(PPh3)2. Aryl triflates produce best results at 60-degrees-C in DMSO in the presence of Pd(OAC)2 and 1,1-bis (diphenylphosphino)ferrocene (dppf).