(E)-methyl 3-(2-((dimethylamino)methyl)phenyl)acrylate | 72862-50-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-methyl 3-(2-((dimethylamino)methyl)phenyl)acrylate
• 英文别名: methyl 3-(2-dimethylaminomethylphenyl)propenoate；methyl o-dimethylaminomethylcinnamate；methyl (E)-3-[2-[(dimethylamino)methyl]phenyl]prop-2-enoate
• CAS: 72862-50-1
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: HDNOBAKYRJTHQD-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-methyl 3-(2-((dimethylamino)methyl)phenyl)acrylate 、 lithium diphenyl cuprate 在 氨 、 氯化铵 作用下， 以 二氯甲烷 为溶剂， 生成 methyl 3-<2-dimethylaminomethylphenyl>-3-phenyl-propanoate
  参考文献：
  名称：

  Stereoselective addition of R2CuLi to ortho-substituted methyl cinnamates intramolecular assistance and solvent effects

  摘要：

  High chemical yields are obtained on the addition of the ortho-substituted enoates 1,2,3, and 4 to Me2CuLi or Ph2CuLi in non-coordinating solvents, CH2Cl2 or toluene. The results underline the strong effect of solvent on reactions between organocuprates and enoates as the corresponding reactions in diethyl ether afforded low yields and moderate steroselectivity. No reaction was observed when THF was used. The high steroselectivity observed with the dimethylaminoethyl substituted enoate 4 in non-coordinating solvents can be accommodated by a mechanistic model for the reaction based on chelation control, within a copper-alkene pi-complex.

  DOI：

  10.1016/s0040-4020(01)86478-4
• 作为产物：
  描述：

  N,N-二甲基苄胺 、 丙烯酸甲酯（MA） 在 palladium dichloride copper diacetate 、 溶剂黄146 作用下， 以 2,2,2-三氟乙醇 为溶剂， 反应 48.0h， 以66%的产率得到(E)-methyl 3-(2-((dimethylamino)methyl)phenyl)acrylate
  参考文献：
  名称：

  通过反应条件的酸度调节的 N,N-二甲基苄胺的邻位烯烃的间接邻位功能化

  摘要：

  取代的 N,N-二甲基苄胺的高度区域选择性烯化是通过基于对其特征的分析调整反应条件的酸度来开发的。在温和条件下，邻位官能化的 N,N-二甲基苄胺进一步转化为 3-(2'-甲苯基) 丙酸及其衍生物。这两种转化可以合二为一，3-(2'-甲苯基)丙酸及其衍生物以中等至良好的收率获得。机理研究表明，在 N,N-二甲基氨基甲基的辅助下，Pd(II) 离子对苯环的亲电攻击是该催化转化过程中的关键步骤，这受反应条件的酸性控制。

  DOI：

  10.1021/ja070588a

文献信息

• Intramolecularly assisted addition of LiMe2 Cu to methyl cinnamates
  作者：Gerd Hallnemo、Christina Ullenius

  DOI：10.1016/s0040-4039(00)84028-9

  日期：1986.1
• HALLNEMO, G.;ULLENIUS, CH., TETRAHEDRON LETT., 1986, 27, N 3, 395-398
  作者：HALLNEMO, G.、ULLENIUS, CH.

  DOI：——

  日期：——
• Indirect <i>ortho</i> Functionalization of Substituted Toluenes through <i>ortho</i> Olefination of <i>N</i>,<i>N</i>-Dimethylbenzylamines Tuned by the Acidity of Reaction Conditions
  作者：Guixin Cai、Ye Fu、Yizhou Li、Xiaobing Wan、Zhangjie Shi

  DOI：10.1021/ja070588a

  日期：2007.6.1

  substituted N,N-dimethylbenzylamines was developed by tuning the acidity of reaction conditions based on analysis of their features. The ortho-functionalized N,N-dimethylbenzylamines were further transformed into 3-(2'-tolyl)propanoic acid and its derivatives under mild conditions. These two transformations could be combined into one pot, and 3-(2'-tolyl)propanoic acid and its derivatives were obtained in

  取代的 N,N-二甲基苄胺的高度区域选择性烯化是通过基于对其特征的分析调整反应条件的酸度来开发的。在温和条件下，邻位官能化的 N,N-二甲基苄胺进一步转化为 3-(2'-甲苯基) 丙酸及其衍生物。这两种转化可以合二为一，3-(2'-甲苯基)丙酸及其衍生物以中等至良好的收率获得。机理研究表明，在 N,N-二甲基氨基甲基的辅助下，Pd(II) 离子对苯环的亲电攻击是该催化转化过程中的关键步骤，这受反应条件的酸性控制。
• Stereoselective addition of R2CuLi to ortho-substituted methyl cinnamates intramolecular assistance and solvent effects
  作者：Beritte Christenson、Gerd Hallnemo、Christina Ullenius

  DOI：10.1016/s0040-4020(01)86478-4

  日期：1991.1

  High chemical yields are obtained on the addition of the ortho-substituted enoates 1,2,3, and 4 to Me2CuLi or Ph2CuLi in non-coordinating solvents, CH2Cl2 or toluene. The results underline the strong effect of solvent on reactions between organocuprates and enoates as the corresponding reactions in diethyl ether afforded low yields and moderate steroselectivity. No reaction was observed when THF was used. The high steroselectivity observed with the dimethylaminoethyl substituted enoate 4 in non-coordinating solvents can be accommodated by a mechanistic model for the reaction based on chelation control, within a copper-alkene pi-complex.