1-(p-chlorophenyl)-4-(2-imidazolinyl)-5-phenyl-1,2,3-triazole | 132111-44-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(p-chlorophenyl)-4-(2-imidazolinyl)-5-phenyl-1,2,3-triazole
• 英文别名: 1-(4-Chlorophenyl)-4-(4,5-dihydro-1H-imidazol-2-yl)-5-phenyl-1H-1,2,3-triazole；1-(4-chlorophenyl)-4-(4,5-dihydro-1H-imidazol-2-yl)-5-phenyltriazole
• CAS: 132111-44-5
• 化学式: C₁₇H₁₄ClN₅
• 分子量: 323.785
• InChiKey: XKOGPZMSQJGTRV-UHFFFAOYSA-N

物化性质

• 沸点：
  542.5±60.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  55.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-叠氮-4-氯苯 、 2-benzoylmethyleneimidazolidine 反应 24.0h， 以13%的产率得到3-benzoyl-5,6-dihydro-4H-imidazo<1,2-c><1,2,3>triazole
  参考文献：
  名称：

  The reaction of benzoyl-substituted heterocyclic ketene aminals with aryl azides

  摘要：

  The reaction between heterocyclic ketene animals, 2-(benzoylmethylene)imidazolidines 3, -hexahydropyrimidines 4, and phenyl azides 5 was investigated. Both the reaction rate and products were strongly dependent on the substituents on 3 or 4 and 5. The reaction rate decreased with the decrease of the electron-withdrawing ability of the Y on the aryl azide 5 with the order NO2 > Cl > H > CH3O, as well as with the decrease of the electron-donating ability of the X on the 3 or 4 following the order CH3O > CH3 > H > Cl. Substituents X and Y affected the course of the reaction. Thus, 3 or 4 reacted with p-nitrophenyl azide 5a to give exclusively highly substituted 1,2,3-triazole derivatives 6aa-da and 7aa-da. The reaction between 3 or 4 and other aryl azides 5b-d afforded respectively fused triazoles 8a-d or 9a-d (6-31%) in addition to triazoles 6ab-bd or 7ab-bd (8-76%). It is concluded that 3 and 4 behave mostly as nucleophiles rather than 1,3-dipolarophiles in reaction with aryl azides 5. Only in the case of unfavorable electronic factors may 3 and 4 act as 1,3-dipolarophiles toward 5.

  DOI：

  10.1021/jo00027a035

文献信息

• The reaction of benzoyl-substituted heterocyclic ketene aminals with aryl azides
  作者：Zhitang Huang、Meixiang Wang

  DOI：10.1021/jo00027a035

  日期：1992.1

  The reaction between heterocyclic ketene animals, 2-(benzoylmethylene)imidazolidines 3, -hexahydropyrimidines 4, and phenyl azides 5 was investigated. Both the reaction rate and products were strongly dependent on the substituents on 3 or 4 and 5. The reaction rate decreased with the decrease of the electron-withdrawing ability of the Y on the aryl azide 5 with the order NO2 > Cl > H > CH3O, as well as with the decrease of the electron-donating ability of the X on the 3 or 4 following the order CH3O > CH3 > H > Cl. Substituents X and Y affected the course of the reaction. Thus, 3 or 4 reacted with p-nitrophenyl azide 5a to give exclusively highly substituted 1,2,3-triazole derivatives 6aa-da and 7aa-da. The reaction between 3 or 4 and other aryl azides 5b-d afforded respectively fused triazoles 8a-d or 9a-d (6-31%) in addition to triazoles 6ab-bd or 7ab-bd (8-76%). It is concluded that 3 and 4 behave mostly as nucleophiles rather than 1,3-dipolarophiles in reaction with aryl azides 5. Only in the case of unfavorable electronic factors may 3 and 4 act as 1,3-dipolarophiles toward 5.