methyl 3,3-bis(3,4,5-trimethoxyphenyl)acrylate | 1318223-40-3

• 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: methyl 3,3-bis(3,4,5-trimethoxyphenyl)acrylate
• 英文别名: Methyl 3,3-bis(3,4,5-trimethoxyphenyl)prop-2-enoate
• CAS: 1318223-40-3
• 化学式: C₂₂H₂₆O₈
• 分子量: 418.444
• InChiKey: PAICQNLXVJFICG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  81.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 3,3-bis(3,4,5-trimethoxyphenyl)acrylate 在 palladium on carbon 、 水 、 氢气 、 potassium hydroxide 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 3.0h， 生成 5,6,7-Trimethoxy-3-(3,4,5-trimethoxyphenyl)-2,3-dihydroinden-1-one
  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
• 作为产物：
  描述：

  4-methoxybenzenediazonium tetrafluoroborate 、 丙烯酸甲酯（MA） 在 monoaluminum phosphate 、 palladium diacetate 作用下， 以 甲醇 为溶剂， 反应 0.57h， 以64%的产率得到methyl 3,3-bis(3,4,5-trimethoxyphenyl)acrylate
  参考文献：
  名称：

  磷酸铝原位生成钯催化Matsuda-Heck反应制备β，β-二芳基烯烃

  摘要：

  原位生成的磷酸铝钯提供了一种新颖的活性催化体系，可通过松田-赫克反应制备β，β-二芳基化烯烃。通过Response-Surface模型优化了该催化方案的反应条件。

  DOI：

  10.1021/acs.oprd.7b00279

文献信息

• <i>In Situ</i> Generated Palladium on Aluminum Phosphate as Catalytic System for the Preparation of β,β-Diarylated Olefins by Matsuda–Heck Reaction
  作者：Sandra Lucks、Heiko Brunner

  DOI：10.1021/acs.oprd.7b00279

  日期：2017.11.17

  In situ generated palladium on aluminum phosphate provides a novel and active catalytic system for the preparation of β,β-diarylated olefins using the Matsuda–Heck reaction. The reaction conditions of this catalytic protocol were optimized by a Response-Surface model.

  原位生成的磷酸铝钯提供了一种新颖的活性催化体系，可通过松田-赫克反应制备β，β-二芳基化烯烃。通过Response-Surface模型优化了该催化方案的反应条件。
• 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.