(E)-3-(4-amino-5-chloro-2-methoxy-phenyl)-acrylic acid methyl ester | 1253180-87-8

• 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)-3-(4-amino-5-chloro-2-methoxy-phenyl)-acrylic acid methyl ester
• 英文别名: 3-(4-amino-5-chloro-2-methoxyphenyl)acrylic acid methyl ester；methyl (E)-3-(4-amino-5-chloro-2-methoxyphenyl)prop-2-enoate
• CAS: 1253180-87-8
• 化学式: C₁₁H₁₂ClNO₃
• 分子量: 241.674
• InChiKey: NEESXIGJRSIEJR-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-氨基-5-氯-2-甲氧基苯甲酸 、 丙烯酸甲酯（MA） 在 氧气 、 palladium diacetate 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 120.0 ℃ 、101.33 kPa 条件下， 反应 10.0h， 以64%的产率得到(E)-3-(4-amino-5-chloro-2-methoxy-phenyl)-acrylic acid methyl ester
  参考文献：
  名称：

  Pd-Catalyzed Dearboxylative Heck Coupling with Dioxygen as the Terminal Oxidant

  摘要：

  Pd-catalyzed decarboxylative Heck coupling of aromatic carboxylic acids with various olefins is developed using O-2 as the terminal oxidant. Enhancement of O-2 pressure leads to improving reaction turnover in this transformation and allows significantly reducing catalyst loading for efficient conversion of electron-rich benzoic acids. A Pd catalyst supported by a carbene ligand enables using electron-deficient benzoic acids as coupling partners.

  DOI：

  10.1021/ol102158n

文献信息

• Pd-catalyzed decarboxylative arylation of silyl enol ester sp3β-C–H bond under aerobic conditions
  作者：Zhengjiang Fu、Shijun Huang、Jian Kan、Weiping Su、Maochun Hong

  DOI：10.1039/c0dt01234c

  日期：——

  Pd-catalyzed aerobic oxidative coupling of various benzoic acids with silyl enol esters proceeds via a combination of decarboxylation with sp3 β-C–H bond activation to give Heck-type products. Mechanistic studies reveal this coupling involves in situ generation of olefin from aerobic oxidation of silyl enolate, followed by decarboxylative Heck coupling.

  钯各种苯甲酸与甲硅烷基烯醇酯的催化催化好氧氧化偶联是通过脱羧与sp 3 β-C–H键活化的结合进行的，从而得到Heck型产物。机理研究表明，这种偶联涉及从烯基甲硅烷基的好氧氧化中原位生成烯烃，然后进行脱羧化Heck偶联。
• Pd-Catalyzed Dearboxylative Heck Coupling with Dioxygen as the Terminal Oxidant
  作者：Zhengjiang Fu、Shijun Huang、Weiping Su、Maochun Hong

  DOI：10.1021/ol102158n

  日期：2010.11.5

  Pd-catalyzed decarboxylative Heck coupling of aromatic carboxylic acids with various olefins is developed using O-2 as the terminal oxidant. Enhancement of O-2 pressure leads to improving reaction turnover in this transformation and allows significantly reducing catalyst loading for efficient conversion of electron-rich benzoic acids. A Pd catalyst supported by a carbene ligand enables using electron-deficient benzoic acids as coupling partners.