1-(p-chlorophenyl)-4-(2-tetrahydropyrimidinyl)-5-phenyl-1,2,3-triazole | 137669-22-8

• 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-tetrahydropyrimidinyl)-5-phenyl-1,2,3-triazole
• 英文别名: 2-(1-(4-Chlorophenyl)-5-phenyl-1H-1,2,3-triazol-4-yl)-1,4,5,6-tetrahydropyrimidine；2-[1-(4-chlorophenyl)-5-phenyltriazol-4-yl]-1,4,5,6-tetrahydropyrimidine
• CAS: 137669-22-8
• 化学式: C₁₈H₁₆ClN₅
• 分子量: 337.812
• InChiKey: NUFHHRRFCCGPFF-UHFFFAOYSA-N

物化性质

• 沸点：
  591.0±60.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 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 、 1-phenyl-2-(tetrahydropyrimidin-2(1H)-ylidene)ethan-1-one 反应 6.0h， 以7%的产率得到3-benzoyl-4,5,6,7-tetrahydro<1,2,3>triazolo<1,5-a>pyrimidine
  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