ethyl N-[3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propen-1-yl] glycinate | 42381-62-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl N-[3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propen-1-yl] glycinate
• 英文别名: ethyl 2-[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoylamino]acetate
• CAS: 42381-62-4
• 化学式: C₁₄H₁₇NO₅
• 分子量: 279.293
• InChiKey: HZHDIEUXNNJOKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.09
• 重原子数：
  20.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  84.86
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  阿魏酸 、 甘氨酸乙酯盐酸盐 在 1-羟基苯并三唑 、 三乙胺 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 ethyl N-[3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propen-1-yl] glycinate
  参考文献：
  名称：

  Synthesis of N-hydroxycinnamoyl amino acid ester analogues and their free radical scavenging and antioxidative activities

  摘要：

  Hydroxycinnamic acids have a variety of biological activities, including antioxidant activity. To find more active antioxidants with hydroxycinnamoyl moiety, we synthesized a series of N-hydroxycinnamoyl amino acid esters and evaluated their antioxidative activities by 2,2-diphenyl-1-picryl hydrazyl (DPPH) radical scavenging and human red blood cells (RBCs) haemolysis methods. It was found that N-caffeoyl amides exhibited the highest DPPH-scavenging activities, whereas N-feruloyl amides demonstrated the highest antihaemolysis activities among the three different hydroxycinnamamides (caffeoyl, feruloyl, and p-coumaroyl), and that hydroxycinnamoyl amides were more effective than their corresponding free acid and ester compounds in both DPPH and RBC haemolysis tests.

  DOI：

  10.1007/s00044-011-9713-2

文献信息

• Wei; Jiang; Zhang, Asian Journal of Chemistry, 2012, vol. 24, # 6, p. 2383 - 2388
  作者：Wei、Jiang、Zhang、Zhang、Guo

  DOI：——

  日期：——
• Synthesis of N-hydroxycinnamoyl amino acid ester analogues and their free radical scavenging and antioxidative activities
  作者：Qing-Yi Wei、Hong Jiang、Jian-Xun Zhang、Peng-Fei Guo、Huan Wang

  DOI：10.1007/s00044-011-9713-2

  日期：2012.8

  Hydroxycinnamic acids have a variety of biological activities, including antioxidant activity. To find more active antioxidants with hydroxycinnamoyl moiety, we synthesized a series of N-hydroxycinnamoyl amino acid esters and evaluated their antioxidative activities by 2,2-diphenyl-1-picryl hydrazyl (DPPH) radical scavenging and human red blood cells (RBCs) haemolysis methods. It was found that N-caffeoyl amides exhibited the highest DPPH-scavenging activities, whereas N-feruloyl amides demonstrated the highest antihaemolysis activities among the three different hydroxycinnamamides (caffeoyl, feruloyl, and p-coumaroyl), and that hydroxycinnamoyl amides were more effective than their corresponding free acid and ester compounds in both DPPH and RBC haemolysis tests.