4,5-dibromo-1-methyl-2-(4-methoxyphenyl)imidazole | 1246624-38-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4,5-dibromo-1-methyl-2-(4-methoxyphenyl)imidazole
• 英文别名: 4,5-Dibromo-2-(4-methoxyphenyl)-1-methylimidazole；4,5-dibromo-2-(4-methoxyphenyl)-1-methylimidazole
• CAS: 1246624-38-3
• 化学式: C₁₁H₁₀Br₂N₂O
• 分子量: 346.021
• InChiKey: LTQGNYJXYVQWDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  丙烯酸异丁酯 、 4,5-dibromo-1-methyl-2-(4-methoxyphenyl)imidazole 在 palladium diacetate 、 三乙胺 、 三环己基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以85%的产率得到
  参考文献：
  名称：

  Synthesis of 2,5,6-Trisubstituted Benzimidazoles by Heck and Subsequent 6π-Electrocyclization-Dehydrogenation Reactions of 2,4,5-Tribromo-N-methylimidazole and 2-Aryl-4,5-dibromo-N-methylimidazoles

  摘要：

  2,5,6-三取代苯并咪唑是通过2,4,5-三溴-N-甲基咪唑和2-芳基-4,5-二溴-N-甲基咪唑的Heck反应以及随后的6α-电环化-脱氢反应制备的。

  DOI：

  10.1055/s-0030-1258092
• 作为产物：
  描述：

  4,5-二溴-1-甲基-1H-咪唑 、 4-碘苯甲醚 在 [Pd(1,10-phenanthroline)₂](PF₆)₂ 、 caesium carbonate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 20.0h， 以57 mg的产率得到4,5-dibromo-1-methyl-2-(4-methoxyphenyl)imidazole
  参考文献：
  名称：

  Facile Synthetic Method for Diverse Polyfunctionalized Imidazoles by Means of Pd-Catalyzed C–H Bond Arylation of N-Methyl-4,5-dibromoimidazole

  摘要：

  C-H bond-selective arylation reaction of 4,5-dibromoimidazole with aryl iodides, catalyzed by the palladium-1,10-phenanthroline complex [Pd(phen)(2)](PF6)(2), has been developed. The process tolerates the presence of a variety of functional groups on the aryl halide substrates. The products formed in these reactions were transformed to a variety of polyfunctionalized imidazoles by taking advantage of selective reactions of remaining C-Br bonds.

  DOI：

  10.1021/jo5013493

文献信息

• Facile Synthetic Method for Diverse Polyfunctionalized Imidazoles by Means of Pd-Catalyzed C–H Bond Arylation of <i>N</i>-Methyl-4,5-dibromoimidazole
  作者：Takayuki Yamauchi、Fumitoshi Shibahara、Toshiaki Murai

  DOI：10.1021/jo5013493

  日期：2014.8.1

  C-H bond-selective arylation reaction of 4,5-dibromoimidazole with aryl iodides, catalyzed by the palladium-1,10-phenanthroline complex [Pd(phen)(2)](PF6)(2), has been developed. The process tolerates the presence of a variety of functional groups on the aryl halide substrates. The products formed in these reactions were transformed to a variety of polyfunctionalized imidazoles by taking advantage of selective reactions of remaining C-Br bonds.
• Synthesis of 2,5,6-Trisubstituted Benzimidazoles by Heck and Subsequent 6π-Electrocyclization-Dehydrogenation Reactions of 2,4,5-Tribromo-N-methylimidazole and 2-Aryl-4,5-dibromo-N-methylimidazoles
  作者：Peter Langer、Serge-Mithérand Toguem

  DOI：10.1055/s-0030-1258092

  日期：2010.7

  2,5,6-Trisubstituted benzimidazoles were prepared by Heck reactions of 2,4,5-tribromo-N-methylimidazole and 2-aryl-4,5-dibromo-N-methyl-imidazoles and subsequent 6π-electro­cyclization-dehydrogenation reactions.

  2,5,6-三取代苯并咪唑是通过2,4,5-三溴-N-甲基咪唑和2-芳基-4,5-二溴-N-甲基咪唑的Heck反应以及随后的6α-电环化-脱氢反应制备的。