5-(4-fluorophenyl)-10-(methylthio)-7H-benzo[h]pyrido[4,3,2-de][1,6]naphthyridine | 1428522-70-6

• 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: 5-(4-fluorophenyl)-10-(methylthio)-7H-benzo[h]pyrido[4,3,2-de][1,6]naphthyridine
• 英文别名: 11-(4-Fluorophenyl)-4-methylsulfanyl-8,10,16-triazatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2(7),3,5,9(17),10,12,14-octaene；11-(4-fluorophenyl)-4-methylsulfanyl-8,10,16-triazatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2(7),3,5,9(17),10,12,14-octaene
• CAS: 1428522-70-6
• 化学式: C₂₁H₁₄FN₃S
• 分子量: 359.427
• InChiKey: QXQJSHMSYKESFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  63.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  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)-10-(methylthio)-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

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.