3-(2-carboxyvinyl)benzoic acid | 25974-99-6

• 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-(2-carboxyvinyl)benzoic acid
• 英文别名: m-carboxycinnamic acid；3-carboxy-cinnamic acid；Zimtsaeure-carbonsaeure-(3)；3-Carboxy-zimtsaeure；β-(3-Carboxy-phenyl)-acrylsaeure；Zimtsaeure-m-carbonsaeure；Benzoic acid, 3-[(1E)-2-carboxyethenyl]-；3-(2-carboxyethenyl)benzoic acid
• CAS: 25974-99-6
• 化学式: C₁₀H₈O₄
• 分子量: 192.171
• InChiKey: KLWPBEWWHJTYDC-UHFFFAOYSA-N

物化性质

• 熔点：
  268-270 °C
• 沸点：
  433.9±28.0 °C(Predicted)
• 密度：
  1.396±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2-carboxyvinyl)benzoic acid 在 potassium diazodicarboxylate 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 以91%的产率得到3-(2-羧乙基)苯甲酸
  参考文献：
  名称：

  Cinnamic acid derivatives as inhibitors for chorismatases and isochorismatases

  摘要：

  Chorismatases and isochorismatases catalyse the hydrolysis of chorismate or isochorismate leading to unsaturated cyclohexenoic acid derivatives. Based on simplification of the physiological substrates, two cinnamic acid-derived compounds, differing in the saturation of the side chain, were developed. In contrast to earlier inhibitor studies, the compounds described here do not have an ether bond and therefore can be synthesised very easily in one or two steps without the need for protective groups. Both substances demonstrate inhibition of the isochorismatase EntB from Escherichia coli and the chorismatases FkbO and Hyg5 from Streptomyces. For chorismatases, the unsaturated compound shows IC50 values in the millimolar range, while the saturated compound is the better inhibitor with IC50 values in the micromolar/low millimolar range; for the isochorismatase tested both compounds inhibit in the micromolar range. Further, an analysis of the apparent K-m values for FkbO and EntB was performed, showing that both inhibitors act in a competitive manner. Due to the ease of modifying these new inhibitors they are a suitable starting point for exploring further functionalised derivatives. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.12.059
• 作为产物：
  描述：

  3-羧基苯甲醛 在 sodium acetate 、 乙酸酐 作用下， 生成 3-(2-carboxyvinyl)benzoic acid
  参考文献：
  名称：

  Simonis, Chemische Berichte, 1912, vol. 45, p. 1586

  摘要：

  DOI：

文献信息

• Synthesis and Solvolysis of o-, m-, and p-Ethynylbenzyl Chloride and Closely Related Structures. The Electronic Nature of the Acetylene Group¹
  作者：John A. Landgrebe、Ronald H. Rynbrandt

  DOI：10.1021/jo01346a032

  日期：1966.8
• Titley, Journal of the Chemical Society, 1928, p. 2576
  作者：Titley

  DOI：——

  日期：——
• Synthesis of substituted cinnamic acids by the Heck reaction in aqueous media
  作者：N. A. Bumagin、N. P. Andryukhova、I. P. Beletskaya

  DOI：10.1007/bf00961965

  日期：1988.6
• Simonis, Chemische Berichte, 1912, vol. 45, p. 1586
  作者：Simonis

  DOI：——

  日期：——
• Cinnamic acid derivatives as inhibitors for chorismatases and isochorismatases
  作者：Florian Hubrich、Silja Mordhorst、Jennifer N. Andexer

  DOI：10.1016/j.bmcl.2012.12.059

  日期：2013.3

  Chorismatases and isochorismatases catalyse the hydrolysis of chorismate or isochorismate leading to unsaturated cyclohexenoic acid derivatives. Based on simplification of the physiological substrates, two cinnamic acid-derived compounds, differing in the saturation of the side chain, were developed. In contrast to earlier inhibitor studies, the compounds described here do not have an ether bond and therefore can be synthesised very easily in one or two steps without the need for protective groups. Both substances demonstrate inhibition of the isochorismatase EntB from Escherichia coli and the chorismatases FkbO and Hyg5 from Streptomyces. For chorismatases, the unsaturated compound shows IC50 values in the millimolar range, while the saturated compound is the better inhibitor with IC50 values in the micromolar/low millimolar range; for the isochorismatase tested both compounds inhibit in the micromolar range. Further, an analysis of the apparent K-m values for FkbO and EntB was performed, showing that both inhibitors act in a competitive manner. Due to the ease of modifying these new inhibitors they are a suitable starting point for exploring further functionalised derivatives. (c) 2012 Elsevier Ltd. All rights reserved.