(E)-ethyl 2-cyano-3-(2,3,4-trihydroxyphenyl)acrylate

• 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)-ethyl 2-cyano-3-(2,3,4-trihydroxyphenyl)acrylate
• 化学式: C₁₂H₁₁NO₅
• 分子量: 249.223
• InChiKey: AJDJAQGMANWVCW-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.27
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  110.78
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  2,3,4-三羟基苯甲醛 、 氰乙酸乙酯 在 N-(propylcarbamoyl)sulfamic acid bonded on silica 作用下， 反应 0.25h， 以95%的产率得到(E)-ethyl 2-cyano-3-(2,3,4-trihydroxyphenyl)acrylate
  参考文献：
  名称：

  Silica bonded N-(propylcarbamoyl)sulfamic acid (SBPCSA) as a highly efficient and recyclable solid catalyst for the synthesis of Benzylidene Acrylate derivatives: Docking and reverse docking integrated approach of network pharmacology

  摘要：

  A green approach has been developed for the synthesis of a series of benzylidene acrylate 3(a-p) from differently substituted aromatic/heterocyclic aldehydes and ethyl cyanoacetate in excellent yields (90-98%), and employing silica bonded N-(Propylcarbamoyl)sulfamic acid as a recyclable catalyst under solvent-free condition. The molecular structure of compounds 3b, 3d and 3i were well supported by single-crystal X-ray crystallographic analysis. The present protocol bears wide substrate tolerance and is believed to be more practical, efficient, eco-friendly, and compatible as compared to existing methods. In-silico approaches were implemented to find the biochemical and physiological effects, toxicity, and biological profiles of the synthesized compounds to determine the expected biological nature and confirm a drug-like compound. A molecular docking study of the expected biologically active compound was performed to know the hypothetically binding mode with the receptor. Also, reverse docking is applied to recognize receptors from unknown protein targets for drug-like compounds to explain poly-pharmacology and binding postures with different receptors.

  DOI：

  10.1016/j.bpc.2020.106443