2-(perfluoroethyl)quinoline | 136949-42-3

• 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-(perfluoroethyl)quinoline
• 英文别名: 2-(pentafluoroethyl)quinoline；2-(1,1,2,2,2-pentafluoroethyl)quinoline
• CAS: 136949-42-3
• 化学式: C₁₁H₆F₅N
• 分子量: 247.167
• InChiKey: GVJDLIPCGMCJIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (2-(2,2,3,3,3-pentafluoropropanamido)phenethyl)triphenylphosphonium bromide 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以30%的产率得到2-(perfluoroethyl)quinoline
  参考文献：
  名称：

  Synthesis of Trifluoromethyl Derivatives of Quinoline and Isoquinoline

  摘要：

  DOI：

  10.3987/com-21-14598

文献信息

• 3-Trifloxy-3-trifluoromethylpropeniminium Triflate: Reaction with Aromatic Amines – An Efficient Synthesis of 2-Trifluoromethylquinolines
  作者：Ivan L. Baraznenok、Valentine G. Nenajdenko、Elizabeth S. Balenkova

  DOI：10.1002/(sici)1099-0690(199904)1999:4<937::aid-ejoc937>3.0.co;2-3

  日期：1999.4

  The reaction of iminium triflates 2 and 7 with various aromatic amines were investigated. The 2-Rf-substituted quinolines 3 and 8 were prepared in excellent yields by the reaction of 2 and 7, respectively, with substituted anilines. The reactions of 2 and 7 with diarylamines proceeds, suprisingly, to afford the corresponding 3-Rf-substituted cinnamaldehydes 4 and 9.

  研究了亚胺三氟甲磺酸酯 2 和 7 与各种芳香胺的反应。2-Rf 取代的喹啉 3 和 8 分别通过 2 和 7 与取代苯胺的反应以极好的收率制备。令人惊讶的是，2 和 7 与二芳胺的反应进行，得到相应的 3-Rf 取代的肉桂醛 4 和 9。
• A Convenient Method for Catalytic Aromatic Pentafluoroethylation Using Potassium (Pentafluoroethyl)trimethoxyborate
  作者：Hideki Amii、Tsuyuka Sugiishi、Daisuke Kawauchi、Mizuki Sato、Tatsuya Sakai

  DOI：10.1055/s-0036-1588131

  日期：——

  pentafluoroethylation of aryl iodides using potassium (pentafluoroethyl)trimethoxyborate has been developed. The borate was found to be a convenient pentafluoroethyl source. In parallel, it was found that the solvent, as well as ligand, makes significant impact on the catalytic perfluoroalkylations. A method for the copper-catalyzed pentafluoroethylation of aryl iodides using potassium (pentafluoroethyl)trimethoxyborate

  摘要 已经开发出使用（五氟乙基）三甲氧基硼酸钾的铜催化的芳基碘化物的五氟乙基化的方法。发现硼酸盐是方便的五氟乙基源。平行地，发现溶剂以及配体对催化全氟烷基化产生显着影响。 已经开发出使用（五氟乙基）三甲氧基硼酸钾的铜催化的芳基碘化物的五氟乙基化的方法。发现硼酸盐是方便的五氟乙基源。平行地，发现溶剂以及配体对催化全氟烷基化产生显着影响。
• A class of effective decarboxylative perfluoroalkylating reagents: [(phen)₂Cu](O₂CR_F)
  作者：Yangjie Huang、Manjaly J. Ajitha、Kuo-Wei Huang、Zhongxing Zhang、Zhiqiang Weng

  DOI：10.1039/c6dt00277c

  日期：——

  [(phen)2Cu](O2CRF) (1) for the decarboxylative perfluoroalkylation of aryl and heteroaryl halides. Treatment of copper tert-butyloxide with phenanthroline ligands, with subsequent addition of perfluorocarboxylic acids afforded air-stable copper(I) perfluorocarboxylato complexes 1. These complexes reacted with a variety of aryl and heteroaryl halides to form perfluoroalkyl(hetero)arenes in moderate to high

  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。
• Preparation of perfluoroalkyl azaarenes with a perfluoroalkyllithium-boron trifluoride system
  作者：Hidemitsu Uno、Shin-ichiro Okada、Hitomi Suzuki

  DOI：10.1016/s0040-4020(01)86555-8

  日期：1991.8

  In the presence of boron trifluoride, perfluoroalkyllithiums generated in situ from tbe reaction of n-perfluoroalkyl iodides with methyllithium-lithium bromide smoothly added to a carbon-nitrogen double bond of bicyclic azaarenes and diazines to give the corresponding perfluoroalkylated dihydro heterocycles, which often underwent spontaneous aromatization in air. Perfluoroalkylation occurred preferentially

  在三氟化硼的存在下，由正全氟烷基碘与甲基锂-溴化锂的反应原位生成的全氟烷基锂被平稳地添加到双环氮杂芳烃和二嗪的碳氮双键中，得到相应的全氟烷基化的二氢杂环，这些杂环经常自发地发生。空气中的芳香化。即使在碳原子被烷基取代基占据的情况下，全氟烷基化也优先发生在氮杂芳烃中氮旁边的碳上。仅观察到一个例外是of啶的反应，其中在9位引入了全氟烷基。
• Cupration of C₂F₅H: Isolation, Structure, and Synthetic Applications of [K(DMF)₂][(<i>t</i>-BuO)Cu(C₂F₅)]. Highly Efficient Pentafluoroethylation of Unactivated Aryl Bromides
  作者：Anton Lishchynskyi、Vladimir V. Grushin

  DOI：10.1021/ja407017j

  日期：2013.8.28

  Pentafluoroethane, C2F5H (HFC-125), is smoothly cuprated with preisolated or in situ-generated [K(DMF)][(t-BuO)(2)Cu] to give [K(DMF)(2)][(t-BuO)Cu(C2F5)] (1) in nearly quantitative yield. Complex 1 has been isolated, structurally characterized, and demonstrated to be an exceedingly versatile pentafluoroethylating reagent for a variety of substrates, including unactivated aryl bromides.