4-(4H-1,2,4-triazol-4-yl)-4-bromophenylmethanimine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(4H-1,2,4-triazol-4-yl)-4-bromophenylmethanimine
• 英文别名: 1-(4-bromophenyl)-N-(1,2,4-triazol-4-yl)ethanimine
• 化学式: C₁₀H₉BrN₄
• 分子量: 265.112
• InChiKey: AUIKQINUYAMYGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  43.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  吡啶 、 4-(4H-1,2,4-triazol-4-yl)-4-bromophenylmethanimine 在 copper(l) iodide 、 氧气 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 110.0 ℃ 、101.33 kPa 条件下， 反应 36.0h， 以49%的产率得到2-(4-溴苯基)咪唑并[1,2-a]吡啶
  参考文献：
  名称：

  铜催化的好氧氧化C ？H取代吡啶的功能化：咪唑并吡啶衍生物的合成

  摘要：

  一种新型的，有效的，实用的方法为咪唑并吡啶衍生物的合成已经通过铜催化氧化有氧下显影 ħ取代吡啶与官能化ñ - （亚烷基）-4- ħ -1,2,4-三唑-4-胺。该程序通过N的切割发生 N键在Ñ（亚烷基）-4 - ħ -1,2,4-三唑-4-胺和活化的芳基C的在取代的吡啶H键。这是通过使用吡啶作为由过渡金属催化的C中的基板咪唑并吡啶衍生物的制备的第一个例子H功能化。该方法应为合成其他氮杂环化合物提供新颖有效的策略。

  DOI：

  10.1002/chem.201302737
• 作为产物：
  描述：

  4-氨基-1,2,4-三氮唑 、 4-溴苯乙酮 以 乙醇 为溶剂， 反应 4.0h， 以30%的产率得到4-(4H-1,2,4-triazol-4-yl)-4-bromophenylmethanimine
  参考文献：
  名称：

  Dominant Role of C−Br···N Halogen Bond in Molecular Self-Organization. Crystallographic and Quantum-Chemical Study of Schiff-Base-Containing Triazoles

  摘要：

  Three Schiff-base-containing triazole derivatives have been synthesized and investigated by X-ray crystallography. Structural motifs (zigzag or linear chains) formed in the solid state are stabilized by C-Br...N halogen bond interactions, while hydrogen bonds do not seem to play a significant role in the molecular self-organization of studied compounds. Quantum-chemical studies confirm that these interactions are sufficient to account for both the arrangement of structural motifs and very short Br...N distances observed experimentally. It is also shown that Br...N interactions can lead to generally shorter donor-acceptor distances than Cl...N contacts.

  DOI：

  10.1021/jp049742v

文献信息

• Copper‐Catalyzed Aerobic Oxidative CH Functionalization of Substituted Pyridines: Synthesis of Imidazopyridine Derivatives
  作者：Jipan Yu、Yunhe Jin、Hao Zhang、Xiaobo Yang、Hua Fu

  DOI：10.1002/chem.201302737

  日期：2013.12.2

  practical method for the synthesis of imidazopyridine derivatives has been developed through the copper‐catalyzed aerobic oxidative CH functionalization of substituted pyridines with N‐(alkylidene)‐4H‐1,2,4‐triazol‐4‐amines. The procedure occurs by cleavage of the NN bond in the N‐(alkylidene)‐4H‐1,2,4‐triazol‐4‐amines and activation of an aryl CH bond in the substituted pyridines. This is the first example

  一种新型的，有效的，实用的方法为咪唑并吡啶衍生物的合成已经通过铜催化氧化有氧下显影 ħ取代吡啶与官能化ñ - （亚烷基）-4- ħ -1,2,4-三唑-4-胺。该程序通过N的切割发生 N键在Ñ（亚烷基）-4 - ħ -1,2,4-三唑-4-胺和活化的芳基C的在取代的吡啶H键。这是通过使用吡啶作为由过渡金属催化的C中的基板咪唑并吡啶衍生物的制备的第一个例子H功能化。该方法应为合成其他氮杂环化合物提供新颖有效的策略。
• Dominant Role of C−Br···N Halogen Bond in Molecular Self-Organization. Crystallographic and Quantum-Chemical Study of Schiff-Base-Containing Triazoles
  作者：Sławomir Berski、Zbigniew Ciunik、Krzysztof Drabent、Zdzisław Latajka、Jarosław Panek

  DOI：10.1021/jp049742v

  日期：2004.8.1

  Three Schiff-base-containing triazole derivatives have been synthesized and investigated by X-ray crystallography. Structural motifs (zigzag or linear chains) formed in the solid state are stabilized by C-Br...N halogen bond interactions, while hydrogen bonds do not seem to play a significant role in the molecular self-organization of studied compounds. Quantum-chemical studies confirm that these interactions are sufficient to account for both the arrangement of structural motifs and very short Br...N distances observed experimentally. It is also shown that Br...N interactions can lead to generally shorter donor-acceptor distances than Cl...N contacts.