3-(4-hydroxy-3-methoxy-phenyl)-acrylic acid methoxycarbonylmethyl 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: 3-(4-hydroxy-3-methoxy-phenyl)-acrylic acid methoxycarbonylmethyl ester
• 英文别名: (2-methoxy-2-oxoethyl) (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• 化学式: C₁₃H₁₄O₆
• 分子量: 266.251
• InChiKey: YFWLSODMCVAHSD-GQCTYLIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(4-hydroxy-3-methoxy-phenyl)-acrylic acid methoxycarbonylmethyl ester 在 吡啶 、 lithium iodide 作用下， 反应 4.5h， 以45%的产率得到2-[(E)-3-(4-hydroxy-3-methoxy-phenyl)prop-2-enoyl]oxyacetic acid
  参考文献：
  名称：

  Caffeoylglycolic and caffeoylamino acid derivatives, halfmers of l-chicoric acid, as new HIV-1 integrase inhibitors

  摘要：

  Human immunodeficiency virus (HIV) integrase (IN) catalyzes the integration of HIV DNA copy into the host cell DNA. L-Chicoric acid (1) has been found to be one of the most potent HIV-1 integrase inhibitor. Caffeoylglycolic and caffeoylamino acid derivatives' halfmeric structures Of L-chicoric acid 2 were synthesized for the purpose of simplifying the structure Of L-Chicoric acid. Among synthesized, compounds 2c and 3f showed HIV-1 IN inhibitory activities with IC50 values of 10.5 and 12.0 mu M, respectively, comparable to that of parent compound L-chicoric acid (IC50 = 15.7 mu M). (c) 2007 Elsevier Masson SAS. All fights reserved.

  DOI：

  10.1016/j.ejmech.2007.02.016
• 作为产物：
  描述：

  阿魏酸 、 溴乙酸甲酯 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以79%的产率得到3-(4-hydroxy-3-methoxy-phenyl)-acrylic acid methoxycarbonylmethyl ester
  参考文献：
  名称：

  Caffeoylglycolic and caffeoylamino acid derivatives, halfmers of l-chicoric acid, as new HIV-1 integrase inhibitors

  摘要：

  Human immunodeficiency virus (HIV) integrase (IN) catalyzes the integration of HIV DNA copy into the host cell DNA. L-Chicoric acid (1) has been found to be one of the most potent HIV-1 integrase inhibitor. Caffeoylglycolic and caffeoylamino acid derivatives' halfmeric structures Of L-chicoric acid 2 were synthesized for the purpose of simplifying the structure Of L-Chicoric acid. Among synthesized, compounds 2c and 3f showed HIV-1 IN inhibitory activities with IC50 values of 10.5 and 12.0 mu M, respectively, comparable to that of parent compound L-chicoric acid (IC50 = 15.7 mu M). (c) 2007 Elsevier Masson SAS. All fights reserved.

  DOI：

  10.1016/j.ejmech.2007.02.016