2-perfluoropenthyl-6-nitroquinoline | 1548899-36-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-perfluoropenthyl-6-nitroquinoline
• 英文别名: 6-Nitro-2-(1,1,2,2,3,3,4,4,5,5,5-undecafluoropentyl)quinoline
• CAS: 1548899-36-0
• 化学式: C₁₄H₅F₁₁N₂O₂
• 分子量: 442.188
• InChiKey: ADHOFZDPZVQESQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  58.7
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  1-(4-nitrophenylimino)-3-phenoxy-3-perfluoropenthylprop-2-ene 、 乙烷,三氯氟- 以 二氯甲烷 为溶剂， 反应 6.0h， 以0.983 g的产率得到6-methyl-2-undecafluoropentylquinoline
  参考文献：
  名称：

  Synthesis of substituted 1-trifluoromethyl and 1-perfluoroalkyl-3-(arylamino)prop-2-en-1-one: advances in the mechanism of Combes 2-trifluoromethyl and 2-perfluoroalkyl quinolines synthesis

  摘要：

  We report a new synthesis and our study of the mechanism of formation of substituted 1-trifluoromethyl and 1-perfluoroalkyl-3-(phenylamino)prop-2-en-1-one starting from 3-(R-phenoxy)-3-perfluoroalkyl-prop-2-enals and arylamines. Reactivity study of the intermediates confirmed that 3-perfluoroalkyl-N,N'-diphenyl-1,5-diazapentadienes are the synthetic intermediates of the synthesis of 2-perfluoroalkylquinolines. The mechanism of the reaction of 1-trifluoromethyl and 1-perfluoroalkyl-3-(phenylamino)prop-2-en-1-one with POCl3 was studied. To our knowledge this is the first detection and isolation of N,N'-diaryldiazapentadiene derivatives as intermediates in the Combes F-alkyl substituted quinoline synthesis starting from enaminoketones. Finally, we succeeded isolating and identifying unsymmetrically substituted 2-perfluorolakyldiazapentadiene. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.12.073