N,1-diisopropyl-1H-benzo[d]imidazol-2-amine | 1284224-09-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: N,1-diisopropyl-1H-benzo[d]imidazol-2-amine
• 英文别名: N,1-diisopropyl-1H-2-aminobenzimidazole；N,1-di(propan-2-yl)benzimidazol-2-amine
• CAS: 1284224-09-4
• 化学式: C₁₃H₁₉N₃
• 分子量: 217.314
• InChiKey: OYHRXTULHWTOQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  29.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,3-diisopropyl-2-phenylguanidine 在 [双(三氟乙酰氧基)碘]苯 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以72%的产率得到N,1-diisopropyl-1H-benzo[d]imidazol-2-amine
  参考文献：
  名称：

  Oxidant-Switchable Selective Synthesis of 2-Aminobenzimidazoles via C–H Amination/Acetoxylation of Guanidines

  摘要：

  The iodine(III) compound promoted CH amination and tandem CH amination/acetoxylation of guanidines are achieved for the first time to provide efficiently 2-aminobenzimidazoles and acetoxyl-substituted 2-aminobenzimidazoles, respectively. The amount and type of iodine(III) compounds control the selective syntheses of two types of 2-aminobenzimidazoles. This reaction shows good regioselectivity when unsymmetrical substrates are used.

  DOI：

  10.1021/ol502815p

文献信息

• A Protocol to 2-Aminobenzimidazoles via Copper-Catalyzed Cascade Addition and Cyclization of <i>o</i>-Haloanilines and Carbodiimides
  作者：Fei Wang、Shangjun Cai、Qian Liao、Chanjuan Xi

  DOI：10.1021/jo200014v

  日期：2011.5.6

  for the synthesis of a variety of 2-animobenzimidazole derivatives has been developed. The reaction proceeded from o-haloanilines and carbodiimides via copper(I)-catalyzed domino reaction in the presence of tert-butoxide to afford the corresponding 2-animobenzimidazole derivatives in good to excellent yields. o-Haloanilines could be o-iodoaniline, o-bromoaniline, and o-chloroaniline derivatives. Carbodiimides

  已经开发了一种有效的策略，用于合成多种2-苯甲酰苯并咪唑衍生物。在叔丁醇的存在下，由邻卤代苯胺和碳二亚胺通过铜（I）催化的多米诺反应进行反应，以良好或优异的收率得到相应的2-苯胺基苯并咪唑衍生物。邻卤代苯胺可以是邻碘苯胺，邻溴苯胺和邻氯苯胺衍生物。碳二亚胺可以是具有芳基或烷基取代基的对称和不对称底物。当使用不对称的碳二亚胺时，该反应表现出良好的区域选择性。
• Eco-friendly strategy: design and synthesis of biologically potent benzimidazole–amine hybrids via visible-light generated oxidative C–H arylamylation of analenic amidines
  作者：I.R. Siddiqui、Farah Ibad、Afshan Ibad、Malik Abdul Waseem、Geeta Watal

  DOI：10.1016/j.tetlet.2015.10.042

  日期：2016.1

  An operationally simple visible light mediated intramolecular cyclization of benzimidazole to 2-amino benzimidazole hybrid. The disclosed procedure is rapid and the convenient synthesis of benzimidazole-amine hybrids from easily available substituted cyclic, acyclic amines, and benzimidazole under neat conditions in the presence of catalyst tris(2,2-bipyridine)ruthenium(II) chloride. Indubitably this methodology gives a facile and straightforward pathway to construct benzimidazole-amine hybrid derivatives in an eco-friendly fashion. The reaction proved to be economical interims of product yield, low loading of catalyst under solvent free condition. The solvent free method has supreme importance in industrial research. The scope and efficiency of this new green method is significantly better than the existing methods. (C) 2015 Published by Elsevier Ltd.
• Oxidant-Switchable Selective Synthesis of 2-Aminobenzimidazoles via C–H Amination/Acetoxylation of Guanidines
  作者：Yue Chi、Wen-Xiong Zhang、Zhenfeng Xi

  DOI：10.1021/ol502815p

  日期：2014.12.19

  The iodine(III) compound promoted CH amination and tandem CH amination/acetoxylation of guanidines are achieved for the first time to provide efficiently 2-aminobenzimidazoles and acetoxyl-substituted 2-aminobenzimidazoles, respectively. The amount and type of iodine(III) compounds control the selective syntheses of two types of 2-aminobenzimidazoles. This reaction shows good regioselectivity when unsymmetrical substrates are used.