1-benzyl-4,5-dibromo-2-(4-methoxyphenyl)-1H-imidazole | 1448032-39-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-benzyl-4,5-dibromo-2-(4-methoxyphenyl)-1H-imidazole
• 英文别名: 1-Benzyl-4,5-dibromo-2-(4-methoxyphenyl)imidazole；1-benzyl-4,5-dibromo-2-(4-methoxyphenyl)imidazole
• CAS: 1448032-39-0
• 化学式: C₁₇H₁₄Br₂N₂O
• 分子量: 422.119
• InChiKey: VAMRLVHKINXWOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  1-benzyl-4,5-dibromo-2-(4-methoxyphenyl)-1H-imidazole 、 3-硝基苯硼酸 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 5.0h， 以60%的产率得到1-benzyl-2-(4-methoxyphenyl)-4,5-di(3-nitrophenyl)-1H-imidazole
  参考文献：
  名称：

  Selective Sequential Cross-Coupling Reactions on Imidazole towards Neurodazine and Analogues

  摘要：

  Polysubstituted imidazoles represent a common structural motif in bioactive molecules. A modular and flexible strategy towards 2,4,5-triarylated imidazoles is reported applying a Suzuki-Miyaura cross-coupling protocol. Employing 1-protected 2,4,5-tribromoimidazole as starting material, both stepwise and one-pot protocols towards the title compounds are disclosed. The utility of the approach was demonstrated by synthesizing neurodazine, a biologically active molecule affecting neuronal cell differentiation.

  DOI：

  10.1055/s-0032-1316906
• 作为产物：
  描述：

  溴甲苯 在 四(三苯基膦)钯 、 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 水 、 甲苯 为溶剂， 反应 11.0h， 生成 1-benzyl-4,5-dibromo-2-(4-methoxyphenyl)-1H-imidazole
  参考文献：
  名称：

  Selective Sequential Cross-Coupling Reactions on Imidazole towards Neurodazine and Analogues

  摘要：

  Polysubstituted imidazoles represent a common structural motif in bioactive molecules. A modular and flexible strategy towards 2,4,5-triarylated imidazoles is reported applying a Suzuki-Miyaura cross-coupling protocol. Employing 1-protected 2,4,5-tribromoimidazole as starting material, both stepwise and one-pot protocols towards the title compounds are disclosed. The utility of the approach was demonstrated by synthesizing neurodazine, a biologically active molecule affecting neuronal cell differentiation.

  DOI：

  10.1055/s-0032-1316906

文献信息

• Selective Sequential Cross-Coupling Reactions on Imidazole towards Neurodazine and Analogues
  作者：Michael Schnürch、Marko Mihovilovic、Lisa-Maria Recnik、Mohammed Abd El Hameid、Maximilian Haider

  DOI：10.1055/s-0032-1316906

  日期：——

  Polysubstituted imidazoles represent a common structural motif in bioactive molecules. A modular and flexible strategy towards 2,4,5-triarylated imidazoles is reported applying a Suzuki-Miyaura cross-coupling protocol. Employing 1-protected 2,4,5-tribromoimidazole as starting material, both stepwise and one-pot protocols towards the title compounds are disclosed. The utility of the approach was demonstrated by synthesizing neurodazine, a biologically active molecule affecting neuronal cell differentiation.