5-chloro-2-(pyridin-3-yl)benzonitrile | 1227701-06-5

• 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: 5-chloro-2-(pyridin-3-yl)benzonitrile
• 英文别名: 5-Chloro-2-pyridin-3-ylbenzonitrile
• CAS: 1227701-06-5
• 化学式: C₁₂H₇ClN₂
• 分子量: 214.654
• InChiKey: MNSCLYPXLCURIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  36.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline 、 5-chloro-2-(pyridin-3-yl)benzonitrile 在 2-双环己基膦-2',6'-二甲氧基联苯 、 potassium phosphate 、 palladium diacetate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以33%的产率得到5-(2-methylquinolin-7-yl)-2-(pyridin-3-yl)benzonitrile
  参考文献：
  名称：

  Structure–activity relationships in a novel series of 7-substituted-aryl quinolines and 5-substituted-aryl benzothiazoles at the metabotropic glutamate receptor subtype 5

  摘要：

  The metabotropic glutamate receptor subtype 5 (mGluR5) has been implicated in numerous neuropsychiatric disorders including addiction. We have discovered that the rigid diaryl alkyne template, derived from the potent and selective noncompetitive mGluR5 antagonist 2-methyl-6-(phenylethynyl) pyridine (MPEP), can serve to guide the design of novel quinoline analogues and pharmacophore optimization has resulted in potent mGluR5 noncompetitive antagonists (EC(50) range 60-100 nM) in the quinoline series. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2010.03.053
• 作为产物：
  描述：

  3-吡啶硼酸 、 2-溴-5-氯硝基苯 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 以75%的产率得到5-chloro-2-(pyridin-3-yl)benzonitrile
  参考文献：
  名称：

  Structure–activity relationships in a novel series of 7-substituted-aryl quinolines and 5-substituted-aryl benzothiazoles at the metabotropic glutamate receptor subtype 5

  摘要：

  The metabotropic glutamate receptor subtype 5 (mGluR5) has been implicated in numerous neuropsychiatric disorders including addiction. We have discovered that the rigid diaryl alkyne template, derived from the potent and selective noncompetitive mGluR5 antagonist 2-methyl-6-(phenylethynyl) pyridine (MPEP), can serve to guide the design of novel quinoline analogues and pharmacophore optimization has resulted in potent mGluR5 noncompetitive antagonists (EC(50) range 60-100 nM) in the quinoline series. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2010.03.053