2-(2,4-dinitrophenyl)-1H-1,2,3-benzotriazole | 13417-40-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(2,4-dinitrophenyl)-1H-1,2,3-benzotriazole
• 英文别名: 2-(2,4-dinitrophenyl)-2H-benzotriazole；2-(2,4-dinitro-phenyl)-2H-benzotriazole；2-<2,4-Dinitrophenyl>-benzotriazol；2-(2,4-Dinitrophenyl)-benzotriazol；2-(2,4-Dinitrophenyl)benzotriazole
• CAS: 13417-40-8
• 化学式: C₁₂H₇N₅O₄
• 分子量: 285.219
• InChiKey: RSZBFXSZXRQJMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  122
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(2,4-dinitrophenyl)-1H-1,2,3-benzotriazole 以 N,N-二甲基甲酰胺-d7 为溶剂， 反应 2616.0h， 生成 1-(2,4-dinitrophenyl)-1H-1,2,3-benzotriazole
  参考文献：
  名称：

  Synthesis, structure, and isomerism of N-2,4-dinitrophenylbenzotriazoles

  摘要：

  Both isomers of N-(2,4'-dinitrophenyl)benzotriazole, the 1(3)- and the 2-substituted, have been characterized and their reciprocal isomerism was studied. Cross-experiments in the presence of 5(6)-nitro-1H-benzotriazole proved that the isomerization of 2-(2',4'-dinitrophenyl)-2H-benzotriazole into the 1-isomer occurs by an intermolecular mechanism. The reported reaction of 5 (6) -nitro-1H-benzotriazole with 1-chloro-2,4-dinitrobenzene has been reexamined discovering that there is an error in the proportions of N-substituted isomers. A possible explanation for the observed isomerizations was proposed. Identification of all compounds by multinuclear magnetic resonance, including solid-state studies, has been achieved. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.02.083
• 作为产物：
  描述：

  T406石油添加剂 、 1-氯-2,4-二硝基苯 在 十六烷基三甲基溴化铵 、 potassium hydrogencarbonate 作用下， 以 甲苯 为溶剂， 反应 10.0h， 生成 1-(2,4-dinitrophenyl)-1H-1,2,3-benzotriazole 、 2-(2,4-dinitrophenyl)-1H-1,2,3-benzotriazole
  参考文献：
  名称：

  在相转移催化条件下苯并三唑与活化的芳基卤化物的选择性 N(1)-芳基化

  摘要：

  1H-1,2,3-苯并三唑与活化的卤代芳烃在相转移催化条件下，使用无机碱和十六烷基三甲基溴化铵作为相转移催化剂进行了芳基化研究。芳基化提供N(1)-和N(2)-芳基化产物。它们的比例取决于碱的性质和芳基化剂的反应性。在催化量的苯基环丙烷羧酸铜存在下，芳基化在 N(1) 原子上区域选择性地进行。

  DOI：

  10.1007/bf02496407

文献信息

• Efficient Synthesis of <i>N</i>-2-Aryl-1,2,3-Triazole Fluorophores via Post-Triazole Arylation
  作者：Yuxiu Liu、Wuming Yan、Yunfeng Chen、Jeffrey L. Petersen、Xiaodong Shi

  DOI：10.1021/ol802246q

  日期：2008.12.4

  Efficient post-triazole regloselective N-2 arylation was developed from C-4, C-5 disubstituted-1,2,3-NH-triazoles. Three different approaches had been investigated, including SNAr, Cu(I) catalyzed aryl amidation and Cu(II) mediated boronic acid coupling. The N-2-aryl triazoles were successfully synthesized with excellent yields. The structures were characterized by X-ray crystallography and some N-2-triazole products gave strong fluorescence with various emission controlled by the C-5 groups.