3,3-bis(2,4-dimethoxyphenyl)acrylic acid methyl ester | 1262097-80-2

• 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: 3,3-bis(2,4-dimethoxyphenyl)acrylic acid methyl ester
• 英文别名: Methyl 3,3-bis(2,4-dimethoxyphenyl)prop-2-enoate；methyl 3,3-bis(2,4-dimethoxyphenyl)prop-2-enoate
• CAS: 1262097-80-2
• 化学式: C₂₀H₂₂O₆
• 分子量: 358.391
• InChiKey: FNCVGEIUJSRZQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2,4-dimethoxybenzenediazonium tetrafluoroborate 、 丙烯酸甲酯（MA） 在 palladium diacetate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以95%的产率得到3,3-bis(2,4-dimethoxyphenyl)acrylic acid methyl ester
  参考文献：
  名称：

  Facile synthesis of symmetrical 3,3-diarylacrylates by a Heck-Matsuda reaction: an expedient route to biologically active indanones

  摘要：

  A simple and straightforward synthesis of symmetrical 3,3-diarylacrylates based on a Heck-Matsuda reaction of arenediazonium salts bearing electron-donating groups with methylacrylates is described. The reaction employs Pd(OAc)(2) as catalyst and goes to completion within 1 h affording the corresponding unsaturated diaryl esters in good to high yields. This method permitted the expeditious and efficient synthesis of the anticancer 3-arylindanone 5 in two operative steps in 43% overall yield. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.05.039

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。
• Facile synthesis of symmetrical 3,3-diarylacrylates by a Heck-Matsuda reaction: an expedient route to biologically active indanones
  作者：Jason G. Taylor、Rodrigo da Silva Ribeiro、Carlos Roque D. Correia

  DOI：10.1016/j.tetlet.2011.05.039

  日期：2011.7

  A simple and straightforward synthesis of symmetrical 3,3-diarylacrylates based on a Heck-Matsuda reaction of arenediazonium salts bearing electron-donating groups with methylacrylates is described. The reaction employs Pd(OAc)(2) as catalyst and goes to completion within 1 h affording the corresponding unsaturated diaryl esters in good to high yields. This method permitted the expeditious and efficient synthesis of the anticancer 3-arylindanone 5 in two operative steps in 43% overall yield. (C) 2011 Elsevier Ltd. All rights reserved.