1-[2,2-bis(ethyloxy)ethyl]-4-bromo-1H-imidazole

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 1-[2,2-bis(ethyloxy)ethyl]-4-bromo-1H-imidazole
• 英文别名: 1,1-diethoxy-2-(4-bromoimidazolyl)ethane；4-Bromo-1-(2,2-diethoxyethyl)-1h-imidazole；4-bromo-1-(2,2-diethoxyethyl)imidazole
• 化学式: C₉H₁₅BrN₂O₂
• 分子量: 263.134
• InChiKey: GHPOEGJBERBALY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[2,2-bis(ethyloxy)ethyl]-4-bromo-1H-imidazole 、 二乙基(3-吡啶基)-硼烷 在 potassium phosphate 、 palladium diacetate 、 四丁基碘化铵 、 三环己基膦 、 盐酸 作用下， 以 水 、 N,N-二甲基甲酰胺 、 乙醇 、 二氯甲烷 、 甲基叔丁基醚 为溶剂， 以81%的产率得到3-{1-[2,2-bis(ethyloxy)ethyl]-1H-imidazol-4-yl}pyridine hydrochloride
  参考文献：
  名称：

  Regioselective Synthesis of 1-Aklyl-4-(3-pyridyl)-Substituted Imidazole

  摘要：

  A practical and regioselective synthesis of 1-alkyl-4-(3-pyridyl) imidazole via a Suzuki coupling reaction employing 3-pyridyl-boronates has been investigated. The use of sec-butyllithium in place of n-butyllithium for complete selectivity in removing bromines on tribromoimidazole to provide a key bromoimidazole coupling unit is described. For effective Suzuki coupling reaction, the nature of pyridylboronates and the conditions employed are discussed. The factors affecting the outcome of the Suzuki coupling reaction are presented.

  DOI：

  10.1021/op0498767
• 作为产物：
  描述：

  1-[2,2-bis(ethyloxy)ethyl]-2,4,5-tribromo-1H-imidazole 在 仲丁基锂 、 水 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 反应 0.5h， 以4.95 g的产率得到1-[2,2-bis(ethyloxy)ethyl]-4-bromo-1H-imidazole
  参考文献：
  名称：

  Regioselective Synthesis of 1-Aklyl-4-(3-pyridyl)-Substituted Imidazole

  摘要：

  A practical and regioselective synthesis of 1-alkyl-4-(3-pyridyl) imidazole via a Suzuki coupling reaction employing 3-pyridyl-boronates has been investigated. The use of sec-butyllithium in place of n-butyllithium for complete selectivity in removing bromines on tribromoimidazole to provide a key bromoimidazole coupling unit is described. For effective Suzuki coupling reaction, the nature of pyridylboronates and the conditions employed are discussed. The factors affecting the outcome of the Suzuki coupling reaction are presented.

  DOI：

  10.1021/op0498767
• 作为试剂：
  描述：

  3-吡啶硼酸 在 potassium phosphate 、 1-[2,2-bis(ethyloxy)ethyl]-4-bromo-1H-imidazole 、 palladium diacetate 、 四丁基碘化铵 、 三环己基膦 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 以100%的产率得到3,3'-联吡啶
  参考文献：
  名称：

  Regioselective Synthesis of 1-Aklyl-4-(3-pyridyl)-Substituted Imidazole

  摘要：

  A practical and regioselective synthesis of 1-alkyl-4-(3-pyridyl) imidazole via a Suzuki coupling reaction employing 3-pyridyl-boronates has been investigated. The use of sec-butyllithium in place of n-butyllithium for complete selectivity in removing bromines on tribromoimidazole to provide a key bromoimidazole coupling unit is described. For effective Suzuki coupling reaction, the nature of pyridylboronates and the conditions employed are discussed. The factors affecting the outcome of the Suzuki coupling reaction are presented.

  DOI：

  10.1021/op0498767

文献信息

• Regioselective Synthesis of 1-Aklyl-4-(3-pyridyl)-Substituted Imidazole
  作者：Hengxu Wei、Ravinder Sudini、Hao Yin

  DOI：10.1021/op0498767

  日期：2004.11.1

  A practical and regioselective synthesis of 1-alkyl-4-(3-pyridyl) imidazole via a Suzuki coupling reaction employing 3-pyridyl-boronates has been investigated. The use of sec-butyllithium in place of n-butyllithium for complete selectivity in removing bromines on tribromoimidazole to provide a key bromoimidazole coupling unit is described. For effective Suzuki coupling reaction, the nature of pyridylboronates and the conditions employed are discussed. The factors affecting the outcome of the Suzuki coupling reaction are presented.