1-cinnamoyl-4-phenylsemicarbazide | 119558-73-5

• 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: 1-cinnamoyl-4-phenylsemicarbazide
• 英文别名: 4-phenyl-1-cinnamoylsemicarbazide；1-Phenyl-3-(3-phenylprop-2-enoylamino)urea
• CAS: 119558-73-5
• 化学式: C₁₆H₁₅N₃O₂
• 分子量: 281.314
• InChiKey: MBKLOEAYDCDTSL-UHFFFAOYSA-N

物化性质

• 熔点：
  45 °C
• 密度：
  1.263±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  70.2
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-cinnamoyl-4-phenylsemicarbazide 在 硫酸 作用下， 反应 2.0h， 以78%的产率得到N-phenyl-5-styryl-1,3,4-oxadiazol-2-amine
  参考文献：
  名称：

  Synthesis and cyclisation of 1,4-disubstituted semicarbazides

  摘要：

  Semicarbazides, besides possessing medicinal properties, also find wide applications in agriculture and industry. We report in this article the synthesis of the four 1,4-disubstituted semicarbazides: 1-cinnamoyl-4-phenyl semicarbazide (1), 1-oleyl-4-phenyl semicarbazides (2), 1,1',1''-tricitryl-4,4',4''-triphenyl semicarbazide (3) and 1-benzoyl-4-phenyl semicarbazide (4), by the condensation of four different hydrazides: cinnamic acid hydrazide (5), oleic acid hydrazide (6), citric acid hydrazide (7) and benzoic acid hydrazide (8). The acid hydrazides were prepared by the condensation of four different acids with phenyl isocyanate. The semicarbazides were also subjected to acid catalysed intramolecular cyclisation. The cyclisation of (1) and (2) afforded substituted 1,3,4-oxadizoles: 2-cinnamoyl-5-aminophenyl 1,3,4-oxadizoles (9) and 2-oleyl-5-aminophenl 1,3,4-oxadizoles (10), respectively, in high yield, while no cyclisation occurred in the cases of (3) and (4). The products in each case have been identified on the basis of melting points and IR spectral studies.

  DOI：

  10.1080/14786410802435935
• 作为产物：
  描述：

  3-phenylacrylic acid hydrazide 、 异氰酸苯酯 以 乙醇 为溶剂， 反应 15.0h， 生成 1-cinnamoyl-4-phenylsemicarbazide
  参考文献：
  名称：

  Mounir, M.; El-Asmy, A. A.; El-Basiouny, M. S., Bulletin de la Societe Chimique de France, 1989, # 3, p. 309 - 311

  摘要：

  DOI：

文献信息

• El-Asmy, A. A.; Babaqi, A. S.; Shaiba, Y. M., Bulletin de la Societe Chimique de France, 1988, # 3, p. 428 - 431
  作者：El-Asmy, A. A.、Babaqi, A. S.、Shaiba, Y. M.、Al-Ansi, T. Y.

  DOI：——

  日期：——
• Mounir, M.; El-Asmy, A. A.; El-Basiouny, M. S., Bulletin de la Societe Chimique de France, 1989, # 3, p. 309 - 311
  作者：Mounir, M.、El-Asmy, A. A.、El-Basiouny, M. S.

  DOI：——

  日期：——
• Synthesis and cyclisation of 1,4-disubstituted semicarbazides
  作者：Syeda Farina Asghar、Khawaja Ansar Yasin、Habib-ur-Rehman、Shahid Aziz

  DOI：10.1080/14786410802435935

  日期：2010.3.10

  Semicarbazides, besides possessing medicinal properties, also find wide applications in agriculture and industry. We report in this article the synthesis of the four 1,4-disubstituted semicarbazides: 1-cinnamoyl-4-phenyl semicarbazide (1), 1-oleyl-4-phenyl semicarbazides (2), 1,1',1''-tricitryl-4,4',4''-triphenyl semicarbazide (3) and 1-benzoyl-4-phenyl semicarbazide (4), by the condensation of four different hydrazides: cinnamic acid hydrazide (5), oleic acid hydrazide (6), citric acid hydrazide (7) and benzoic acid hydrazide (8). The acid hydrazides were prepared by the condensation of four different acids with phenyl isocyanate. The semicarbazides were also subjected to acid catalysed intramolecular cyclisation. The cyclisation of (1) and (2) afforded substituted 1,3,4-oxadizoles: 2-cinnamoyl-5-aminophenyl 1,3,4-oxadizoles (9) and 2-oleyl-5-aminophenl 1,3,4-oxadizoles (10), respectively, in high yield, while no cyclisation occurred in the cases of (3) and (4). The products in each case have been identified on the basis of melting points and IR spectral studies.