N-(4-bromophenyl)-2-methylbenzamidine | 1021397-24-9

• 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: N-(4-bromophenyl)-2-methylbenzamidine
• 英文别名: N'-(4-bromophenyl)-2-methylbenzenecarboximidamide
• CAS: 1021397-24-9
• 化学式: C₁₄H₁₃BrN₂
• 分子量: 289.175
• InChiKey: CBGXNFMJPHNAQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  38.4
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(4-bromophenyl)-2-methylbenzamidine 在 氧气 、 copper diacetate 、 溶剂黄146 作用下， 以 二甲基亚砜 为溶剂， 反应 18.0h， 以89%的产率得到5-bromo-2-(2-methylphenyl)benzimidazole
  参考文献：
  名称：

  CH官能化/ CN键形成：铜催化am合成苯并咪唑。

  摘要：

  DOI：

  10.1002/anie.200705420
• 作为产物：
  描述：

  邻甲基苯腈 、 4-溴苯胺 在 aluminum (III) chloride 作用下， 反应 0.5h， 生成 N-(4-bromophenyl)-2-methylbenzamidine
  参考文献：
  名称：

  Transition-Metal-Free Three-Component Reaction: Additive Controlled Synthesis of Sulfonylated Imidazoles

  摘要：

  Two efficient transition-metal-free highly regioselective pathways for constructing sulfonylated imidazoles via three-component reactions of amidines, ynals, and sodium sulfonates have been developed. The generations of different sulfonylated imidazoles were simply controlled by additives. In addition, this method features environmental friendliness, good functional group tolerance, and high atom economy, which makes it practical.

  DOI：

  10.1021/acs.joc.9b01818

文献信息

• Controllable Site-Selective Construction of 4- and 5-Hydroxyalkyl-Substituted Imidazoles from Amidines, Ynals, and Water
  作者：Wei Liu、Jiaming He、Xiang Liu、Yue Yu、Yongyan Pei、Baofu Zhu、Hua Cao

  DOI：10.1021/acs.joc.0c01715

  日期：2020.12.4

  site-selective pathways to construct 4- and 5-hydroxyalkyl-substituted imidazoles through a three-component reaction of amidines, ynals, and water has been documented. Particularly, the high regioselectivity of the reaction was simply switched by changing the additives. In addition, further 18O-labeled experiments to probe a plausible mechanism and the gram-scale synthesis were studied.

  通过am，乙醛和水的三组分反应来构建4-和5-羟烷基取代的咪唑的可控位点选择性途径的第一个实例已有文献报道。特别地，通过改变添加剂，可以简单地切换反应的高区域选择性。此外，还研究了18个O标记的实验，以探讨可能的机理和克级合成。
• Synergic effect of copper-based metal–organic frameworks for highly efficient C–H activation of amidines
  作者：Fen Xu、Wei-Fen Kang、Xiao-Ning Wang、Hao-Dong Kou、Zhen Jin、Chun-Sen Liu

  DOI：10.1039/c7ra10682c

  日期：——

  functionalization of substituted amidines was developed for the facile and efficient synthesis of benzimidazoles. More importantly, this transformation is compatible with various substrates derived from aryl nitriles without ortho substituents. Under reaction conditions devoid of O2 atmosphere or specific groups, 537-MOF has been revealed as a key parameter for expanding the reaction scope and increasing

  Cu-MOF催化的取代am的C-H官能团的开发是为了简便高效地合成苯并咪唑。更重要的是，这种转变与衍生自无邻位取代基的芳基腈的各种底物相容。在没有O 2气氛或特定基团的反应条件下，已发现537-MOF是扩大反应范围并将产率提高至96％的关键参数。重要的是，该策略还为进一步利用MOF作为挑战性有机反应的催化剂提供了许多机会。