4,5-dibromo-1-methyl-2-(1-naphthyl)imidazole

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4,5-dibromo-1-methyl-2-(1-naphthyl)imidazole
• 英文别名: 4,5-Dibromo-1-methyl-2-naphthalen-1-ylimidazole；4,5-dibromo-1-methyl-2-naphthalen-1-ylimidazole
• 化学式: C₁₄H₁₀Br₂N₂
• 分子量: 366.055
• InChiKey: CCWILTNOYQWQME-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4,5-dibromo-1-methyl-2-(1-naphthyl)imidazole 在 正丁基锂 、 potassium hydroxide 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 四苯基硼化三叔丁基膦 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.5h， 生成 5-ethoxycarbonyl-1-methyl-4-(4-methylphenyl)-2-(1-naphthyl)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
• 作为产物：
  描述：

  4,5-二溴-1-甲基-1H-咪唑 、 1-碘萘 在 palladium(II) acetate*1,10-phenanthroline 、 caesium carbonate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 反应 20.0h， 以90%的产率得到4,5-dibromo-1-methyl-2-(1-naphthyl)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.