2-(perfluoropentyl)quinoline | 264920-40-3

• 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-(perfluoropentyl)quinoline
• 英文别名: 2-perfluoropentyl-quinoline；2-perfluoropentylquinoline；2-(1,1,2,2,3,3,4,4,5,5,5-undecafluoropentyl)quinoline
• CAS: 264920-40-3
• 化学式: C₁₄H₆F₁₁N
• 分子量: 397.191
• InChiKey: DHENRCZLPZOSRR-UHFFFAOYSA-N

物化性质

• 沸点：
  263.5±40.0 °C(Predicted)
• 密度：
  1.527±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  26
• 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：
  12.9
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  全氟己酸 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 16.41h， 生成 2-(perfluoropentyl)quinoline
  参考文献：
  名称：

  一类有效的脱羧全氟烷基化试剂：[（phen）2 Cu]（O 2 CR F）†

  摘要：

  本文描述了用于芳基卤化物和杂芳基卤化物的脱羧全氟烷基化的一类有效试剂[（phen）2 Cu]（O 2 CR F）（1）的发明。用菲咯啉配体处理叔丁基氧化铜，随后添加全氟羧酸，得到空气稳定的全氟羧酸铜（I）络合物1。这些络合物与各种芳基和杂芳基卤化物反应，以中等至高收率形成全氟烷基（杂）芳烃。计算研究表明，第二个phen配体的配位可能会降低全氟羧酸酯脱羧的能垒，从而促进全氟烷基化。

  DOI：

  10.1039/c6dt00277c

文献信息

• A Novel Synthesis of 2-Fluoroalkyl Quinolines
  作者：Quan-Fu Wang、Yun-Yu Mao、Chao-Yue Qin、Shi-Zheng Zhu、Chang-Ming Hu

  DOI：10.1007/s007060050006

  日期：2000.1.15

  2-Fluoroalkyl quinolines are prepared by reacting aniline with alpha-fluoroalkyl aldehydes or alpha-fluoroalkyl cyclohexanones in the presence of acetic acid. Under the same reaction condition, 2-aminophenol gives the corresponding 2-fluoroalkyl-8-quinolinols; in some cases, 2-fluoroalkyl benzoxazoles are also formed as minor products.
• 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
  作者：Salem El Kharrat、Philippe Laurent、Hubert Blancou

  DOI：10.1016/j.tet.2013.12.073

  日期：2014.2

  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.