3-(p-chlorobenzoyl)-5,6-dihydro-4H-imidazo-<1,2-c><1,2,3>triazole | 132111-57-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(p-chlorobenzoyl)-5,6-dihydro-4H-imidazo-<1,2-c><1,2,3>triazole
• 英文别名: (4-chlorophenyl)(5,6-dihydro-4H-imidazo[1,2-c][1,2,3]triazol-3-yl)methanone；(4-chlorophenyl)-(5,6-dihydro-4H-imidazo[1,2-c]triazol-3-yl)methanone
• CAS: 132111-57-0
• 化学式: C₁₁H₉ClN₄O
• 分子量: 248.672
• InChiKey: HYFHHKLPZCIZQL-UHFFFAOYSA-N

物化性质

• 熔点：
  207-209 °C
• 沸点：
  513.9±60.0 °C(Predicted)
• 密度：
  1.59±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  59.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(p-chlorobenzoylmethylene)imidazolidine 在 对甲苯磺酰叠氮 、 碳酸氢钠 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 以74%的产率得到3-(p-chlorobenzoyl)-5,6-dihydro-4H-imidazo-<1,2-c><1,2,3>triazole
  参考文献：
  名称：

  烯胺和甲苯磺酰叠氮化物向N-杂环熔融和5-氨基1,2,3-三唑的无金属过渡态

  摘要：

  的多功能5-氨基官能化的1,2,3-三唑，无论是在N杂环稠合的和非环状的氨基官能化形式形式的合成，已经通过的环反应实现宝石二氨基烯胺酮和甲苯磺酰叠氮化物下transition-无金属的条件。

  DOI：

  10.1002/ejoc.202000938

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.
• An efficient one-pot synthesis of heterocycle-fused 1,2,3-triazole derivatives as anti-cancer agents
  作者：Sheng-Jiao Yan、Yong-Jiang Liu、Yu-Lan Chen、Lin Liu、Jun Lin

  DOI：10.1016/j.bmcl.2010.06.141

  日期：2010.9

  A series of heterocycle-fused 1,2,3-triazoles were easily prepared by the 1,3-dipolar cycloaddition of heterocyclic ketene aminals or N,O-acetals with sodium azide and polyhalo isophthalonitriles in a one-pot reaction at room temperature without a catalyst and evaluated in vitro against a panel of human tumour cell lines. 1,3-Oxazoheterocycle fused 1,2,3-triazoles were more potent against the tumour cell lines Skov-3, HL-60, A431, A549 and HepG-2 than 1,3-diazoheterocycle fused 1,2,3-triazoles. 4-Methoxyphenyl substituted 1,3-oxazoheterocycle fused 1,2,3-triazole 6j was found to be the most potent derivative with IC50 values lower than 1.9 mu g/mL against A431 and K562 human tumour cell lines. (C) 2010 Elsevier Ltd. All rights reserved.