3-(3-aminophenyl)-2-cyanoacrylic acid | 861314-15-0

• 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-(3-aminophenyl)-2-cyanoacrylic acid
• 英文别名: 3-Amino-α-cyan-zimtsaeure；3-Amino-benzalmalonsaeure-mononitril；3-(3-Amino-phenyl)-2-cyan-acrylsaeure；3-(3-Aminophenyl)-2-cyanoprop-2-enoic acid
• CAS: 861314-15-0
• 化学式: C₁₀H₈N₂O₂
• 分子量: 188.186
• InChiKey: MLAQFTUNJKPUAF-UHFFFAOYSA-N

物化性质

• 沸点：
  430.4±40.0 °C(Predicted)
• 密度：
  1.373±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  87.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(3-aminophenyl)-2-cyanoacrylic acid 在 盐酸 作用下， 生成 3-(3-acetylamino-phenyl)-2-cyano-acrylic acid ethyl ester
  参考文献：
  名称：

  Kauffmann, Chemische Berichte, 1916, vol. 49, p. 1324

  摘要：

  DOI：
• 作为产物：
  描述：

  3-(3-amino-phenyl)-2-cyano-acrylic acid ethyl ester 在 硫酸 作用下， 生成 3-(3-aminophenyl)-2-cyanoacrylic acid
  参考文献：
  名称：

  Kauffmann, Chemische Berichte, 1916, vol. 49, p. 1336

  摘要：

  DOI：

文献信息

• Highly selective colorimetric/fluorometric chemodosimeters for cyanide ions in aqueous solution based on Michael addition to C-atom possessing different polar substituents
  作者：R. Manivannan、A. Satheshkumar、Kuppanagounder P. Elango

  DOI：10.1016/j.tetlet.2014.09.096

  日期：2014.11

  Two simple chemosensors, 3-(4-aminophenyl)-2-cyanoacrylic acid (1) and 3-(3-aminophenyl)-2-cyanoacrylic acid (2), exhibited visual colour and fluorescence changes selectively with cyanide ions in aqueous solution. Their anion sensing properties were investigated using UV-vis, fluorescence and H-1 & C-13 NMR spectral studies and theoretical studies. The mechanism of sensing involves Michael addition of CN- to C=C bond. The addition reaction was found to occur relatively easier with p-NH2C6H4 group (Taft's sigma* 0.16) substituted C=C bond than that with m-NH2C6H4 group (sigma* 0.58) substituted compound. The detection limits were calculated to be 33 pM and 0.2 nM for the receptors 1 and 2, respectively, which are lower than the maximum permissible concentration of cyanide ion in drinking water (1.9 mu M) set by the World Health Organization (WHO). (C) 2014 Elsevier Ltd. All rights reserved.