N-(dicyanomethylene)aniline | 19769-98-3

• 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-(dicyanomethylene)aniline
• 英文别名: N-Phenyl-imido-malonsaeuredinitril；N-dicyanomethylenaniline；2-phenyliminopropanedinitrile
• CAS: 19769-98-3
• 化学式: C₉H₅N₃
• 分子量: 155.159
• InChiKey: KAVGWBDYNOLGTJ-UHFFFAOYSA-N

物化性质

• 沸点：
  269.0±23.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  59.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(dicyanomethylene)aniline 、 胍 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以53%的产率得到5-苯基偶氮嘧啶-2,4,6-三胺
  参考文献：
  名称：

  Design, synthesis and biological evaluation of pyrimidine-based derivatives as antitumor agents

  摘要：

  In this paper we made a contentious effort to afford heterocyclic compounds with interesting biological activities. The reaction of guanidine with either activated methylene groups, arylhydrazono derivatives, dicyanopropene derivatives, malononitrile dimer or arylhydarazononitrile derivatives afforded diaminopyrimidine derivatives, aryldiazenyl pyrimidine derivatives, fused pyridopyrimidne derivatives and pyrimidopyridazine derivatives respectively.Also the reaction of guanidine with phenylhydrazono carbonyl compounds produced phenyldiazenyl pyrimidine derivatives. The latter products were directed toward the reaction with either acetic anhydride or ethylcyanoacetate to form acetamidopyrimidine derivatives and cyanoacetamidopyrimidine derivatives respectively. The latter products underwent cyclization via reaction with either activated methylene groups or activated methylene carbonyl compounds afforded pyridopyrimidne derivatives.The structures of the newly synthesized compounds were established using IR, H-1 NMR, C-13 NMR and mass spectrometry and their antitumor activity was investigated. Some of these compounds showed promising inhibitory effects on the three different cell lines.

  DOI：

  10.33224/rrch.2020.65.3.02
• 作为产物：
  描述：

  1-氰基硫代甲酰苯胺 在 氯 作用下， 生成 N-(dicyanomethylene)aniline
  参考文献：
  名称：

  Kuehle,E. et al., Angewandte Chemie, 1969, vol. 81, p. 18 - 32

  摘要：

  DOI：

文献信息

• Tetracyanoethylene oxide. IV. Nucleophilic ring opening
  作者：W. J. Linn、E. Ciganek

  DOI：10.1021/jo01259a026

  日期：1969.7
• Periselectivity in cycloadditions to vinylmethylketene and structurally related vinylketene imines
  作者：Gaetano Barbaro、Arturo Battaglia、Patrizia Giorgianni

  DOI：10.1021/jo00391a020

  日期：1987.7
• Synthesis and reactivity of N-mesitylcyclopropylideneazomethine
  作者：Arturo Battaglia、Gaetano Barbaro、Patrizia Giorgianni、Elisabetta Foresti、Piera Sabatino、Alessandro Dondoni

  DOI：10.1021/jo00225a071

  日期：1985.12
• Koutentis, Panayiotis A.; Rees, Charles W., Journal of the Chemical Society. Perkin transactions I, 1999, # 2, p. 111 - 117
  作者：Koutentis, Panayiotis A.、Rees, Charles W.

  DOI：——

  日期：——
• BARBARO, GAETANO;BATTAGLIA, ARTURO;GIORGIANNI, PATRIZIA, J. ORG. CHEM., 52,(1987) N 15, 3289-3296
  作者：BARBARO, GAETANO、BATTAGLIA, ARTURO、GIORGIANNI, PATRIZIA

  DOI：——

  日期：——

表征谱图