methyl 2-acetoxy-3-(4-methoxyphenyl)acrylate

• 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 2-acetoxy-3-(4-methoxyphenyl)acrylate
• 化学式: C₁₃H₁₄O₅
• 分子量: 250.251
• InChiKey: MAJRFMGJGUMFMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.77
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  4-methoxybenzenediazonium tetrafluoroborate 、 methyl 2-acetoxyacrylate 在 2,6-二叔丁基-4-甲基吡啶 、 tris-(dibenzylideneacetone)dipalladium(0) 作用下， 以 苯甲腈 为溶剂， 反应 3.0h， 以59%的产率得到methyl 2-acetoxy-3-(4-methoxyphenyl)acrylate
  参考文献：
  名称：

  The Heck–Matsuda arylation of 2-hetero-substituted acrylates

  摘要：

  The Heck-Matsuda arylation of 2-aza and 2-oxo-substituted acrylates is described. Several reaction conditions were evaluated including the influence of solvents, temperature, catalysts, and stoichiometry. While the oxygenated system was successfully arylated in benzonitrile with Pd-2(dba)(3) as catalyst, the aza-acrylate furnished methoxylated products. The methoxylated products were subjected to an elimination/reduction protocol to obtain the corresponding N,O-protected phenylalanine derivatives. A one-pot procedure for the preparation of phenylalanine derivatives from 2-aza-substituted acrylates is presented. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.10.132

文献信息

• The Heck–Matsuda arylation of 2-hetero-substituted acrylates
  作者：Francisco de Azambuja、Carlos Roque Duarte Correia

  DOI：10.1016/j.tetlet.2010.10.132

  日期：2011.1

  The Heck-Matsuda arylation of 2-aza and 2-oxo-substituted acrylates is described. Several reaction conditions were evaluated including the influence of solvents, temperature, catalysts, and stoichiometry. While the oxygenated system was successfully arylated in benzonitrile with Pd-2(dba)(3) as catalyst, the aza-acrylate furnished methoxylated products. The methoxylated products were subjected to an elimination/reduction protocol to obtain the corresponding N,O-protected phenylalanine derivatives. A one-pot procedure for the preparation of phenylalanine derivatives from 2-aza-substituted acrylates is presented. (C) 2010 Elsevier Ltd. All rights reserved.