N,1-diphenyl-6-methyl-1H-2-aminobenzimidazole | 1242169-13-6

• 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-diphenyl-6-methyl-1H-2-aminobenzimidazole
• 英文别名: N,1-diphenyl-1H-2-aminobenzimidazole；6-methyl-N,1-diphenylbenzimidazol-2-amine
• CAS: 1242169-13-6
• 化学式: C₂₀H₁₇N₃
• 分子量: 299.375
• InChiKey: NEUNPYTZZRYEQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 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：

  、 苯胺 在 copper(l) iodide 、 1,10-菲罗啉 、 caesium carbonate 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 16.0h， 以52%的产率得到N,1-diphenyl-6-methyl-1H-2-aminobenzimidazole
  参考文献：
  名称：

  Copper-catalyzed synthesis of 2-aminobenzimidazoles from carbonimidoyl dichlorides and amines

  摘要：

  A new protocol for the synthesis of a variety of 2-aminobenzimidazole derivatives has been developed. O-haloaryl carbonimidoyl dichloride reacted with anilines to generate an o-haloaryl guanidine intermediate, which underwent copper catalyzed ring closure to afford 2-aminobenzimidazole derivative in moderate yields (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.07.072

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。
• Synthesis of Benzoxazole and Benzimidazole Derivatives via Ligand-Free Copper(I)-Catalyzed Cross-Coupling Reaction of o-Halophenols or o-Haloanilines with Carbodiimides
  作者：Guodong Shen、Weiliang Bao

  DOI：10.1002/adsc.201000022

  日期：——

  A novel and efficient synthesis of benzoxazole and benzimidazole derivatives via a ligand‐free, copper(I)‐catalyzed, one‐pot cascade process has been developed. A variety of carbodiimides coupled with o‐halophenols or o‐haloanilines to give the products in moderate to excellent yields under the mild conditions.

  通过无配体，铜（I）催化的一锅级联过程，开发了新颖，有效的苯并恶唑和苯并咪唑衍生物的合成方法。在温和的条件下，各种碳化二亚胺与邻卤代苯酚或邻卤代苯胺联用，可使产品具有中等至极好的收率。