3-{1-[2,2-bis(ethyloxy)ethyl]-1H-imidazol-4-yl}pyridine | 794508-41-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-{1-[2,2-bis(ethyloxy)ethyl]-1H-imidazol-4-yl}pyridine
• 英文别名: 3-[1-(2,2-Diethoxyethyl)imidazol-4-yl]pyridine
• CAS: 794508-41-1
• 化学式: C₁₄H₁₉N₃O₂
• 分子量: 261.324
• InChiKey: BNEIIVUYSPFHQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  49.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  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(邻甲基苯基)磷 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 96.0h， 以17%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

• Cesium Carbonate as an Efficient Base for Alkylation of 3-(1H-Imidazol-4-yl)pyridine
  作者：Ravinder Sudini、Hengxu Wei

  DOI：10.1080/00397910902945352

  日期：2009.12.15

  Regioselective 1-alkylation of 3-(1H-imidazol-4-yl)pyridine using bromoacetaldehyde diethyl acetal in the presence of cesium carbonate has been achieved. Selective isolation of the desired 1-alkylated 3-(1H-imidazol-4-yl)pyridine product as a hydrochloride salt, there by avoiding the need for chromatography, is described.
• 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.