(E)-3-(4-dimethylaminophenyl)-3-methyl acrylic acid methyl ester

• 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-dimethylaminophenyl)-3-methyl acrylic acid methyl ester
• 英文别名: (E)-methyl 3-(4-(dimethylamino)phenyl)but-2-enoate；methyl (E)-3-(4-(dimethylamino)phenyl)but-2-enoate；methyl (2E)-3-[4-(dimethylamino)phenyl]but-2-enoate；methyl (E)-3-[4-(dimethylamino)phenyl]but-2-enoate
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: QAPHEVNFJIYJGF-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  巴豆酸甲酯 、 4-碘-N,N-二甲基苯胺 在 4-甲氧基苯脲 、 palladium diacetate 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以50%的产率得到(E)-3-(4-dimethylaminophenyl)-3-methyl acrylic acid methyl ester
  参考文献：
  名称：

  Selective reactivity of electron-rich aryl iodides in the Heck arylation of disubstituted alkenes catalyzed by palladium–arylurea complexes

  摘要：

  A catalyst consisting of 1 mol % of the 1:2 complex of Pd(OAc)(2) with N-(4-carbethoxyphenyl)urea promotes the Heck arylation of 2- or 3-substituted, conjugated esters, nitriles, aldehydes, and ketones (an uncharacteristically broad range of substrates), but only with electron-rich aryl iodides (an uncharacteristically narrow range of halides). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.09.019

文献信息

• A Versatile Catalyst for Heck Reactions of Aryl Chlorides and Aryl Bromides under Mild Conditions
  作者：Adam F. Littke、Gregory C. Fu

  DOI：10.1021/ja010988c

  日期：2001.7.1

  for Heck reactions of aryl chlorides and bromides. A sterically and electronically diverse array of aryl bromides, as well as activated aryl chlorides, couple with a range of mono- and disubstituted olefins at room temperature, furnishing the arylated product with high E/Z stereoselection. The corresponding reactions of a broad spectrum of electron-neutral and electron-rich aryl chlorides proceed at

  在 Cy2NMe 存在下，Pd/P(t-Bu)3 可作为一种非常温和且用途广泛的催化剂，用于芳基氯化物和溴化物的 Heck 反应。空间和电子上不同的芳基溴化物阵列以及活化的芳基氯化物，在室温下与一系列单取代和双取代的烯烃偶联，为芳基化产物提供高 E/Z 立体选择。广泛的电子中性和富电子芳基氯化物的相应反应在升高的温度下进行，并且具有高选择性。在范围和温和性方面，Pd/P(t-Bu)3/Cy2NMe 代表了先前报道的这些 Heck 偶联过程的催化剂的进步。
• Pd–arylurea complexes for the Heck arylation of crotonic and cinnamic substrates
  作者：Matthew R. Smith、Jung Yun Kim、Marco A. Ciufolini

  DOI：10.1016/j.tetlet.2013.01.077

  日期：2013.4

  A catalyst consisting of the 1:2 complex of Pd(OAc)(2) (1 mol %) with N-(4-carbethoxy)-phenylurea promotes the Heck arylation of a range of crotonic and cinnamic substrates, including aldehydes, ketones, esters, and nitriles, with electron-rich-but not electron-deficient-aryl iodides. (c) 2013 Elsevier Ltd. All rights reserved.
• Selective reactivity of electron-rich aryl iodides in the Heck arylation of disubstituted alkenes catalyzed by palladium–arylurea complexes
  作者：Matthew R. Smith、Young Jin Jang、Jung Yun Kim、Marco A. Ciufolini

  DOI：10.1016/j.tet.2013.09.019

  日期：2013.11

  A catalyst consisting of 1 mol % of the 1:2 complex of Pd(OAc)(2) with N-(4-carbethoxyphenyl)urea promotes the Heck arylation of 2- or 3-substituted, conjugated esters, nitriles, aldehydes, and ketones (an uncharacteristically broad range of substrates), but only with electron-rich aryl iodides (an uncharacteristically narrow range of halides). (C) 2013 Elsevier Ltd. All rights reserved.