N-(3-aminophenyl)-2-cyanoacetamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(3-aminophenyl)-2-cyanoacetamide
• 化学式: C₉H₉N₃O
• 分子量: 175.19
• InChiKey: UMBLPHBYULDGOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  78.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-cyanoacetyl-3,5-dimethylpyrazole 、 间苯二胺 以 甲苯 为溶剂， 以85%的产率得到N-(3-aminophenyl)-2-cyanoacetamide
  参考文献：
  名称：

  Transmonocyanoacetylation of phenylenediamines: a simple and efficient synthesis of novel N-(aminophenyl)-2-cyanoacetamides and their derivatives

  摘要：

  Herein, we report a simple and efficient method for the transmonocyanoacetylation of phenylenediamines using inexpensive, commercially available 1-cyanoacetyl-3,5-dimethylpyrazole as a cyanoacetylating agent. This method provides operationally simple and efficient access to N-(aminophenyl)-2-cyanoacetamides under mild conditions with short reaction times. Also, a series of novel N-(functionalized phenyl)-2-cyanoacetamide derivatives have been synthesized through the reaction of N-(4-aminophenyl)-2-cyanoacetamide with various electrophiles, such as carbonyl, acyl chloride, and isothiocyanate derivatives. In all cases, good yields of products were obtained and reaction times were significantly reduced compared with similar reactions. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.11.098

文献信息

• US4189427A
  申请人：——

  公开号：US4189427A

  公开（公告）日：1980-02-19
• Transmonocyanoacetylation of phenylenediamines: a simple and efficient synthesis of novel N-(aminophenyl)-2-cyanoacetamides and their derivatives
  作者：Yousry A. Ammar、Samir Y. Abbas、Mostafa M. Ghorab、Mansour S. Al Said

  DOI：10.1016/j.tetlet.2015.11.098

  日期：2016.1

  Herein, we report a simple and efficient method for the transmonocyanoacetylation of phenylenediamines using inexpensive, commercially available 1-cyanoacetyl-3,5-dimethylpyrazole as a cyanoacetylating agent. This method provides operationally simple and efficient access to N-(aminophenyl)-2-cyanoacetamides under mild conditions with short reaction times. Also, a series of novel N-(functionalized phenyl)-2-cyanoacetamide derivatives have been synthesized through the reaction of N-(4-aminophenyl)-2-cyanoacetamide with various electrophiles, such as carbonyl, acyl chloride, and isothiocyanate derivatives. In all cases, good yields of products were obtained and reaction times were significantly reduced compared with similar reactions. (C) 2015 Elsevier Ltd. All rights reserved.