2-(benzofuran-2-yl)-1-ethyl-1H-benzo[d]imidazole | 1321985-55-0

• 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: 2-(benzofuran-2-yl)-1-ethyl-1H-benzo[d]imidazole
• CAS: 1321985-55-0
• 化学式: C₁₇H₁₄N₂O
• 分子量: 262.311
• InChiKey: WQAXCTDFLFMIJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.47
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  30.96
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  1-乙基苯并咪唑 、 2-(2,2-dibromovinyl)phenol 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(I) bromide 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 10.0h， 以83%的产率得到2-(benzofuran-2-yl)-1-ethyl-1H-benzo[d]imidazole
  参考文献：
  名称：

  Highly efficient copper/palladium-catalyzed tandem Ullman reaction/arylation of azoles via C–H activation: synthesis of benzofuranyl and indolyl azoles from 2-(gem-dibromovinyl)phenols(anilines) with azoles

  摘要：

  In this paper, a novel and highly efficient copper/palladium-catalyzed tandem intramolecular Ullman-type C-O(N) coupling reaction of 2-(gem-dibromovinyl)phenols(anilines) followed by an intermolecular arylation of azoles through C-H activation has been developed. In the presence of CuBr with Pd(PPh3)(2)Cl-2 used as co-catalyst, and (LiOBu)-Bu-t as a base, the one-pot reactions of 2-(gem-dibromovinyl)phenols and 2-(gem-dibromovinyl)anilines with a variety of azoles, including oxazoles, imidazoles, thiazoles, and oxadiazoles underwent smoothly in toluene at 100 degrees C to generate the corresponding biheteroaryl products in high yields. A tentative mechanism of copper/palladium-catalyzed tandem reaction was described. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.06.044