(E)-ethyl 3-(N-methylformamido)acrylate

• 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: (E)-ethyl 3-(N-methylformamido)acrylate
• 英文别名: ethyl (E)-3-[formyl(methyl)amino]prop-2-enoate
• 化学式: C₇H₁₁NO₃
• 分子量: 157.169
• InChiKey: IGLCEKFODQZCQE-SNAWJCMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-甲基甲酰胺 、 丙炔酸乙酯 在 sodium acetate 、 palladium diacetate 、 三氟乙酸 作用下， 以 甲苯 为溶剂， 反应 36.0h， 以41%的产率得到(E)-ethyl 3-(N-methylformamido)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

• Alkenylation of Imides and Activated Amides
  作者：Wilhelm FLITSCH、Stefan R. SCHINDLER

  DOI：10.1055/s-1975-23889

  日期：——

  The reaction of imides and activated amides with phosphoranes provides a simple route to enamides, bis[alkenyl]amines, and enamines. Experiments to determine the scope and limitations of these reactions are summarised in this review. Some of the results are taken from investigations with other aims. As well as the dependance on structure, configurational and tautomeric aspects of the reaction are described. The Wittig alkenylation of the imides is compared with other methods of alkenylation. 1. Introduction 2. Wittig Alkenylation of Imides 2.1. General Comments 2.2. Non-Stabilised Phosphoranes 2.3. Ethoxycarbonylmethylenetriphenylphosphorane and Cyanomethylenetriphenylphosphorane 2.3.1. Open Chain Imides 2.3.2. Five-Membered Ring Imides: Phthalimides, Succinimides, and Maleimides 2.3.3. Six-Membered and Larger Ring Imides 2.3.4. Bicyclic N-Bridgehead Imides 2.3.5. N-Acylimides 2.4. Benzoylmethylenetriphenylphosphorane 3. Alkenylation of Imides with the Wittig-Horner Reagent 4. Alkenylation of Activated Amides 4.1. N-Sulfonyllactams 4.2. N-Acylpyrroles 5. Conclusions

  酰亚胺和活化酰胺与磷烯的反应为酞胺、双[烯烃基]胺和烯胺提供了一条简单的合成路线。本文总结了确定这些反应的适用范围和局限性的实验结果。一些结果来自于其他目的的研究。除了对结构的依赖，本文还描述了反应的构象和互变异构方面。将酰亚胺的Wittig烯基化与其他烯基化方法进行了比较。 1. 引言 2. 酰亚胺的Wittig烯基化 2.1. 一般评论 2.2. 非稳定磷烯 2.3. 乙氧羰基亚甲基三苯基磷烯和氰亚甲基三苯基磷烯 2.3.1. 开链酰亚胺 2.3.2. 五元环酰亚胺：邻苯二甲酰亚胺、琥珀酰亚胺和马来酰亚胺 2.3.3. 六元及更大环酰亚胺 2.3.4. 自环桥头N-桥联酰亚胺 2.3.5. N-酰基酰亚胺 2.4. 苯甲酰基亚甲基三苯基磷烯 3. 使用Wittig-Horner试剂对酰亚胺进行烯基化 4. 活化酰胺的烯基化 4.1. N-磺酰亚乳胺 4.2. N-酰基吡咯 5. 结论