1-(4-Chloro-2-nitro-phenyl)-5-ethoxycarbonylmethyl-1H-[1,2,3]triazole-4-carboxylic acid ethyl ester | 210989-45-0

• 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-(4-Chloro-2-nitro-phenyl)-5-ethoxycarbonylmethyl-1H-[1,2,3]triazole-4-carboxylic acid ethyl ester
• CAS: 210989-45-0
• 化学式: C₁₅H₁₅ClN₄O₆
• 分子量: 382.76
• InChiKey: WBANXZMWNKKZTN-UHFFFAOYSA-N

物化性质

• 沸点：
  544.9±60.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.11
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  126.45
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  1-(4-Chloro-2-nitro-phenyl)-5-ethoxycarbonylmethyl-1H-[1,2,3]triazole-4-carboxylic acid ethyl ester 在 水 、 三氯化铁 、 铁粉 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以93%的产率得到1-(2-Amino-4-chloro-phenyl)-5-ethoxycarbonylmethyl-1H-[1,2,3]triazole-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  1,2,3-Triazolo[1,5-a][1,4]- and 1,2,3-triazolo[1,5-a][1,5]benzodiazepine derivatives: synthesis and benzodiazepine receptor binding

  摘要：

  This paper reports the synthesis of new 1,2,3-triazolo[1,4]benzodiazepine and 1,2,3-triazolo[1,5]benzodiazepine derivatives and their evaluation toward benzodiazepine receptors, Receptor affinity gradually and remarkably increases by moving the nitrogen atom of the central ring from position 3 through 4 to position 5, to give the most effective compound 6a (K-i = 150 nM). N-methylation of the diazepine ring (7a) lowers receptorial binding. Introduction of a chlorine atom on the benzene ring doubles the K-i value (6b) which remains unaltered by the N-methylation (7b). (C) 1998 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(98)00025-1
• 作为产物：
  描述：

  4-chloro-2-nitrophenyl azide 在 乙酰基丙二酸二乙酯 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以25%的产率得到1-(4-Chloro-2-nitro-phenyl)-5-ethoxycarbonylmethyl-1H-[1,2,3]triazole-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  1,2,3-Triazolo[1,5-a][1,4]- and 1,2,3-triazolo[1,5-a][1,5]benzodiazepine derivatives: synthesis and benzodiazepine receptor binding

  摘要：

  This paper reports the synthesis of new 1,2,3-triazolo[1,4]benzodiazepine and 1,2,3-triazolo[1,5]benzodiazepine derivatives and their evaluation toward benzodiazepine receptors, Receptor affinity gradually and remarkably increases by moving the nitrogen atom of the central ring from position 3 through 4 to position 5, to give the most effective compound 6a (K-i = 150 nM). N-methylation of the diazepine ring (7a) lowers receptorial binding. Introduction of a chlorine atom on the benzene ring doubles the K-i value (6b) which remains unaltered by the N-methylation (7b). (C) 1998 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(98)00025-1