ethyl N-[3-phenyl-1-oxo-2-propen-1-yl] glycinate | 62430-51-7

• 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-phenyl-1-oxo-2-propen-1-yl] glycinate
• 英文别名: Cinnamoylglycinethylester；N-(3-phenyl-acryloyl)-glycine ethyl ester；N-cinnamoyl-glycine ethyl ester；N-Cinnamoyl-glycin-aethylester；Cinnamoylaminoessigsaeure-aethylester；Cinnamylamido-essigsaeure-ethylester；Ethyl 2-(3-phenylprop-2-enoylamino)acetate
• CAS: 62430-51-7
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: KIIVDCMVGMHQLJ-UHFFFAOYSA-N

物化性质

• 熔点：
  102-104 °C
• 沸点：
  432.3±45.0 °C(Predicted)
• 密度：
  1.133±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl N-[3-phenyl-1-oxo-2-propen-1-yl] glycinate 在 alkaline solution 作用下， 生成 肉桂酰甘氨酸
  参考文献：
  名称：

  Klages, Journal fur praktische Chemie (Leipzig 1954), 1902, vol. <2> 65, p. 192

  摘要：

  DOI：
• 作为产物：
  描述：

  肉桂酰氯 在 乙醇 、 sodium 作用下， 生成 ethyl N-[3-phenyl-1-oxo-2-propen-1-yl] glycinate
  参考文献：
  名称：

  Notes- Adducts with N-Substituted Acrylamides

  摘要：

  DOI：

  10.1021/jo01080a611

文献信息

• [3 + 2] Cycloaddition of Nitrile Ylides with Diazonium Salts: Copper-Catalyzed One-Pot Synthesis of Fully Substituted 1,2,4-Triazoles
  作者：Huihuang Li、Xueli Wu、Weiwei Hao、Haiyan Li、Yanwei Zhao、Yaxiong Wang、Pengcheng Lian、Yonggao Zheng、Xiaoguang Bao、Xiaobing Wan

  DOI：10.1021/acs.orglett.8b02172

  日期：2018.9.7

  A novel [3 + 2] cycloaddition between nitrile ylides and diazonium salts was well-established. This copper-catalyzed three-component reaction was distinguished by mild conditions, ready availability, and operational simplicity, thus opening access to 1,2,4-triazoles with a diverse set of substitution patterns.

  在腈和重氮盐之间建立新颖的[3 + 2]环加成反应已广为人知。这种铜催化的三组分反应的特点是条件温和，易得性和操作简便性，从而使获得具有多种取代方式的1,2,4-三唑成为可能。
• Lissel, Manfred; Gau, Achim, Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1986, vol. 41, # 3, p. 367 - 370
  作者：Lissel, Manfred、Gau, Achim

  DOI：——

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

  DOI：——

  日期：——
• Kondrat'ewa,G.Y.; Tschshi-Chen,K., Journal of general chemistry of the USSR, 1962, vol. 32, p. 2315 - 2320
  作者：Kondrat'ewa,G.Y.、Tschshi-Chen,K.

  DOI：——

  日期：——
• Tyrosinase inhibitory effects and antioxidative activities of novel cinnamoyl amides with amino acid ester moiety
  作者：Qian Fan、Hong Jiang、Er-dong Yuan、Jian-xun Zhang、Zheng-xiang Ning、Sui-jian Qi、Qing-yi Wei

  DOI：10.1016/j.foodchem.2012.03.021

  日期：2012.9

  Nine cinnamoyl amides with amino acid ester (CAAE) moiety were synthesized by the conjugation of the corresponding cinnamic acids (cinnamic acid, 4-hydroxy cinnamic acid, ferulic acid and caffeic acid) with amino acid esters, and their inhibitory effects on the activities of mushroom tyrosinase were investigated, using L-3,4-dihydroxyl-phenylalanine (L-DOPA) as the substrate. Among these CAAE amides, ethyl N-[3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propen-1-yl]-L-phenylalaninate (b(4)) showed the strongest inhibitory activity; the IC50 was 0.18 mu M. The IC50 values, inhibition types, inhibition mechanisms and kinetics of all these CAAE amides were evaluated. A structure-activity relationship (SAR) study found that the inhibitory effects were potentiated with the increasing length of hydrocarbon chains at the amino acid esters and also influenced by the substituents at the styrene groups. Furthermore, the hydroxyl radical scavenging and anti-lipid peroxidation activities of four CAAE derivatives were also investigated. Among these compounds, b(3) (ethyl N-[3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]-L-phenylalaninate) and b(4) exhibited potential antioxidant activities. (C) 2012 Elsevier Ltd. All rights reserved.