(Z)-ethyl 3-(4-nitrobenzamido)acrylate | 1402150-53-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-ethyl 3-(4-nitrobenzamido)acrylate
• 英文别名: ethyl (Z)-3-[(4-nitrobenzoyl)amino]prop-2-enoate
• CAS: 1402150-53-1
• 化学式: C₁₂H₁₂N₂O₅
• 分子量: 264.238
• InChiKey: DZSHMYHWNMDJKN-FPLPWBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  对硝基苯甲酰胺 、 丙炔酸乙酯 在 sodium acetate 、 palladium diacetate 、 三氟乙酸 作用下， 以 甲苯 为溶剂， 以72%的产率得到(Z)-ethyl 3-(4-nitrobenzamido)acrylate
  参考文献：
  名称：

  Stereoselective Synthesis of Enamides by Pd-Catalyzed Hydroamidation of Electron Deficient Terminal Alkynes

  摘要：

  Hydroamidation of electron-deficient terminal alkynes by amides in presence of Pd catalyst has been exploited for the stereoselective synthesis of Z-enamides. The possible intramolecular hydrogen bonding between the amido proton and carbonyl oxygen of ester group provides the extra stability to the Z-isomer of vinyl palladium complex, which subsequently undergoes protodepalladation and leads to the Z-enamide selectively. This process is found to be mild and operationally simple with broad substrate scope.

  DOI：

  10.1021/jo301772f

文献信息

• Stereoselective Synthesis of Enamides by Pd-Catalyzed Hydroamidation of Electron Deficient Terminal Alkynes
  作者：Niranjan Panda、Raghavender Mothkuri

  DOI：10.1021/jo301772f

  日期：2012.10.19

  Hydroamidation of electron-deficient terminal alkynes by amides in presence of Pd catalyst has been exploited for the stereoselective synthesis of Z-enamides. The possible intramolecular hydrogen bonding between the amido proton and carbonyl oxygen of ester group provides the extra stability to the Z-isomer of vinyl palladium complex, which subsequently undergoes protodepalladation and leads to the Z-enamide selectively. This process is found to be mild and operationally simple with broad substrate scope.