8-甲基-2-(三氟甲基)喹啉 | 1860-46-4

• 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
• 中文名称: 8-甲基-2-(三氟甲基)喹啉
• 英文名称: 8-methyl-2-(trifluoromethyl)quinoline
• 英文别名: 2-trifluoromethyl-8-methylquinoline
• CAS: 1860-46-4
• 化学式: C₁₁H₈F₃N
• 分子量: 211.186
• InChiKey: QLTYGFJHXYCNMR-UHFFFAOYSA-N

物化性质

• 沸点：
  50 °C(Press: 35 Torr)
• 密度：
  1.267±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  0
• 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：
  4

安全信息

• 海关编码：
  2933499090

反应信息

• 作为产物：
  描述：

  3-trifluoromethyl-1-(2-methylphenylamino)-3-(2-methylphenylimino)propene 在 溶剂黄146 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 6.0h， 生成 8-甲基-2-(三氟甲基)喹啉
  参考文献：
  名称：

  New Regiospecific Synthesis of 2-Trifluoromethyl-1,5 Diazapentadiene Compounds and of 2-Trifluoromethylquinolines, Their Cyclization Products

  摘要：

  2-Trifluoromethylquinolines 5 are synthesized in high yields using a perfluoroalkylated gemiodoacetoxy derivative 3 and arylamines 4. The intermediate of this reaction, 2-trifluoromethyl-1,5-diazapentadiene compound 6, was isolated. The procedures are easy, and yields are in general high. This sequence represents a valuable new synthesis of substituted 2-trifluoromethylquinolines and of 2-trifluoromethyl-diazapentadienes (vinamidine compounds).

  DOI：

  10.1021/jo050586d

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。
• 2-Position-Selective C–H Perfluoroalkylation of Quinoline Derivatives
  作者：Takahiro Shirai、Motomu Kanai、Yoichiro Kuninobu

  DOI：10.1021/acs.orglett.8b00339

  日期：2018.3.16

  We developed 2-position-selective, direct C–H trifluoromethylation, pentafluoroethylation, and heptafluoropropylation of quinoline derivatives. Regioselective transformation was achieved without derivatization of the quinolines. The reaction proceeded at room temperature with high functional group tolerance, even in gram scale. Notably, the reaction was applicable to substrates containing a functional

  我们开发了喹啉衍生物的2位选择性，直接C–H三氟甲基化，五氟乙基化和七氟丙基化。在不衍生喹啉的情况下实现了区域选择性转化。该反应在室温下以即使以克为单位的高官能团耐受性进行。值得注意的是，该反应适用于含有对氧化敏感的官能团和药物分子的底物。
• [EN] N-AROYL CYCLIC AMINES AS OREXIN RECEPTOR ANTAGONISTS<br/>[FR] AMINES CYCLIQUES N-AROYLE UTILISEES COMME ANTAGONISTES DU RECEPTEUR D'OREXINE
  申请人：GLAXO GROUP LTD

  公开号：WO2004026866A1

  公开（公告）日：2004-04-01

  This invention relates to N-aroyl cyclic amine derivatives and their use as pharmaceuticals.

  这项发明涉及N-芳酰环氨基衍生物及其作为药物的用途。
• 2-(Trifluoromethyl)quinolines from anilines: A novel mode of isomerization and cyclization
  作者：Holger Keller、Manfred Schlosser

  DOI：10.1016/0040-4020(96)00168-8

  日期：1996.3

  in the presence of phosphoryl trichloride, the resulting 4-anilino-1,1,1-trifluorobut-3-en-2-ones undergo an N → ortho shift of the side chain followed by cyclization and dehydration to afford 2-(trifluoromethyl)quinolines.

  N-亚乙基-叔丁胺用二异丙基氨基锂去质子化，然后与三氟乙酸乙酯缩合，得到4-叔丁基氨基-1,1,1-三氟丁-3-烯-2-酮。当在弱酸性条件下用苯胺处理后一化合物时，会发生氨基取代基的交换。当在三氯化磷的存在下加热时，所得的4-苯胺基-1,1,1-三氟丁-3-烯-2-酮经过侧链的N →邻位移位，然后环化和脱水，得到2-（三氟甲基）喹啉。
• 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.