2-chloro-6-(4-fluorophenyl)-4-methylnicotinonitrile | 943117-82-6

• 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: 2-chloro-6-(4-fluorophenyl)-4-methylnicotinonitrile
• 英文别名: 2-chloro-6-(4-fluorophenyl)-4-methylpyridine-3-carbonitrile
• CAS: 943117-82-6
• 化学式: C₁₃H₈ClFN₂
• 分子量: 246.671
• InChiKey: VJICUXZBAOMUCC-UHFFFAOYSA-N

物化性质

• 沸点：
  385.9±42.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  36.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-chloro-6-(4-fluorophenyl)-4-methylnicotinonitrile 在 tris-(dibenzylideneacetone)dipalladium(0) 、 硫酸 、 2-(二叔丁基膦)联苯 、 sodium t-butanolate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 3.0h， 生成 5-(4-fluorophenyl)-9-methoxy-7H-benzo[h]pyrido[4,3,2-de][1,6]naphthyridine
  参考文献：
  名称：

  A facile synthesis of tetracyclic benzo-pyridonaphthyridines by domino reaction

  摘要：

  A novel methodology for the synthesis of tetracyclic benzo-pyridonaphthyridines, forming a C-C and a C-N bond in concentrated sulfuric acid at 70 degrees C in a one-pot is reported. The key substrates (9a-m) are prepared by reacting 2-chloro-6-(4-fluorophenyl)-4-methylnicotinenitrile (7) with various anilines followed by dimethylformamide dimethylacetal. The domino reaction is initiated by the protonation of the beta-carbon of the enamine group in 9a-m and terminated by the elimination of dimethylamine. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.02.016
• 作为产物：
  描述：

  2,6-二羟基-3-氰基-4-甲基吡啶 在 四(三苯基膦)钯 、 苄基三乙基氯化铵 、 potassium carbonate 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 13.5h， 生成 2-chloro-6-(4-fluorophenyl)-4-methylnicotinonitrile
  参考文献：
  名称：

  A facile synthesis of tetracyclic benzo-pyridonaphthyridines by domino reaction

  摘要：

  A novel methodology for the synthesis of tetracyclic benzo-pyridonaphthyridines, forming a C-C and a C-N bond in concentrated sulfuric acid at 70 degrees C in a one-pot is reported. The key substrates (9a-m) are prepared by reacting 2-chloro-6-(4-fluorophenyl)-4-methylnicotinenitrile (7) with various anilines followed by dimethylformamide dimethylacetal. The domino reaction is initiated by the protonation of the beta-carbon of the enamine group in 9a-m and terminated by the elimination of dimethylamine. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.02.016

文献信息

• A facile synthesis of tetracyclic benzo-pyridonaphthyridines by domino reaction
  作者：Vishnu Basetti、Rangarao Pallepati、Subramanya Hosahalli、Vijay Potluri

  DOI：10.1016/j.tetlet.2013.02.016

  日期：2013.4

  A novel methodology for the synthesis of tetracyclic benzo-pyridonaphthyridines, forming a C-C and a C-N bond in concentrated sulfuric acid at 70 degrees C in a one-pot is reported. The key substrates (9a-m) are prepared by reacting 2-chloro-6-(4-fluorophenyl)-4-methylnicotinenitrile (7) with various anilines followed by dimethylformamide dimethylacetal. The domino reaction is initiated by the protonation of the beta-carbon of the enamine group in 9a-m and terminated by the elimination of dimethylamine. (C) 2013 Elsevier Ltd. All rights reserved.