3-cyclohexyl-imidazolo-<4,5-b>-pyridine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: 3-cyclohexyl-imidazolo-<4,5-b>-pyridine
• 英文别名: 3-cyclohexyl-3H-imidazo[4,5-b]pyridine；3-Cyclohexylimidazo[4,5-b]pyridine
• 化学式: C₁₂H₁₅N₃
• 分子量: 201.271
• InChiKey: FRDNXHUZOGNHSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-cyclohexyl-imidazolo-<4,5-b>-pyridine 在 二氯双[二叔丁基-(4-二甲基氨基苯基)膦]钯(II) 、 叔丁基锂 、 cesium fluoride 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 为溶剂， -78.0~110.0 ℃ 、200.0 kPa 条件下， 反应 2.48h， 生成 3-cyclohexyl-2-(3-(ethylsulfonyl)phenyl)-3H-imidazo[4,5-b]pyridine
  参考文献：
  名称：

  Microwave enhanced Suzuki coupling: a diversity-oriented approach to the synthesis of highly functionalised 3-substituted-2-aryl/heteroaryl imidazo[4,5-b]pyridines

  摘要：

  A modified approach for the synthesis of 3-substituted 2-aryl/heteroaryl imidazo[4,5-b]pyridines utilising palladium catalysed cross-coupling reactions under microwave enhanced conditions has been achieved. utilisation of (A-(ta)phos)(2)PdCl2-catalysed cross-coupling reactions enables rapid derivatization of this (imidazo[4,5-b]pyridines) pharmaceutically relevant core. This catalytic system is compatible with a broad spectrum of arylboronic acids electron rich, electron poor, and heteroarylboronic acids. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.12.051
• 作为产物：
  描述：

  甲酸 、 N²-cyclohexylpyridine-2,3-diamine 在 碳酸氢钠 作用下， 以 水 为溶剂， 以92%的产率得到3-cyclohexyl-imidazolo-<4,5-b>-pyridine
  参考文献：
  名称：

  Microwave enhanced Suzuki coupling: a diversity-oriented approach to the synthesis of highly functionalised 3-substituted-2-aryl/heteroaryl imidazo[4,5-b]pyridines

  摘要：

  A modified approach for the synthesis of 3-substituted 2-aryl/heteroaryl imidazo[4,5-b]pyridines utilising palladium catalysed cross-coupling reactions under microwave enhanced conditions has been achieved. utilisation of (A-(ta)phos)(2)PdCl2-catalysed cross-coupling reactions enables rapid derivatization of this (imidazo[4,5-b]pyridines) pharmaceutically relevant core. This catalytic system is compatible with a broad spectrum of arylboronic acids electron rich, electron poor, and heteroarylboronic acids. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.12.051

文献信息

• Ethoxymethylenemalonates and Malononitriles (EMM reagents) as formic acid equivalents: Synthesis of fused-imidazoles under neutral or mildly acidic con
  作者：Barb E. Segelstein、Bert L. Chenard、John E. Macor、Ronald J. Post

  DOI：10.1016/s0040-4039(00)91957-9

  日期：1993.3

  The use of ethoxymethylenemalonates and malononitriles (EMM reagents)for the efficient synthesis of fused imidazoles and related compounds is described.
• Microwave enhanced Suzuki coupling: a diversity-oriented approach to the synthesis of highly functionalised 3-substituted-2-aryl/heteroaryl imidazo[4,5-b]pyridines
  作者：Ayyiliath M. Sajith、A. Muralidharan

  DOI：10.1016/j.tetlet.2011.12.051

  日期：2012.2

  A modified approach for the synthesis of 3-substituted 2-aryl/heteroaryl imidazo[4,5-b]pyridines utilising palladium catalysed cross-coupling reactions under microwave enhanced conditions has been achieved. utilisation of (A-(ta)phos)(2)PdCl2-catalysed cross-coupling reactions enables rapid derivatization of this (imidazo[4,5-b]pyridines) pharmaceutically relevant core. This catalytic system is compatible with a broad spectrum of arylboronic acids electron rich, electron poor, and heteroarylboronic acids. (C) 2011 Elsevier Ltd. All rights reserved.