4-phenyl-6-(trifluoromethyl)quinoline

• 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: 4-phenyl-6-(trifluoromethyl)quinoline
• 英文别名: 6-trifluoromethyl-4-phenylquinoline
• 化学式: C₁₆H₁₀F₃N
• 分子量: 273.257
• InChiKey: VKISQRCYNUKFCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-phenyl-6-trifluoromethyl-1,2,3,4-tetrahydroquinoline 在 氧气 、 sodium t-butanolate 作用下， 以 二甲基亚砜 为溶剂， 60.0 ℃ 、101.33 kPa 条件下， 反应 4.0h， 以11%的产率得到4-phenyl-6-(trifluoromethyl)quinoline
  参考文献：
  名称：

  DMSO / t-BuONa / O2介导的饱和N-杂环的好氧脱氢。

  摘要：

  芳族N-杂环如喹啉，异喹啉和二氢吲哚是通过叔丁醇钠促进的DMSO溶液中饱和杂环的氧化脱氢而合成的。该反应在温和的反应条件下进行并且具有良好的官能团耐受性。机理研究表明，一种自由基途径涉及从底物的N–H键或α–C–H夺取二甲基自由基的氢以及随后氮或α-氨基烷基自由基的氧化。

  DOI：

  10.1021/acs.joc.9b03447

文献信息

• Direct Synthesis of Quinolines via Co(III)-Catalyzed and DMSO-Involved C–H Activation/Cyclization of Anilines with Alkynes
  作者：Xuefeng Xu、Yurong Yang、Xu Zhang、Wei Yi

  DOI：10.1021/acs.orglett.7b03673

  日期：2018.2.2

  activation/cyclization of simple, cheap, and easily available anilines with alkynes for direct and highly efficient synthesis of privileged quinolines with exclusive regioselectivity and broad substrate/functional group tolerance and in good to excellent yields, where DMSO was employed as both the solvent and the C1 building block of quinoline products, is reported. Mechanistic experiments revealed that

  独特的Co（III）催化和DMSO参与的C–H活化/环化，具有炔烃的简单，廉价且易于获得的苯胺，可直接高效地合成特权喹啉，具有独特的区域选择性和广泛的底物/官能团耐受性，且在据报道，使用DMSO作为溶剂和喹啉产品的C 1结构单元时，收率良好。机理实验表明，通用反应可能采用2-乙烯基苯甲胺类物质作为活性中间体。
• The one-pot synthesis of quinolines via Co(<scp>iii</scp>)-catalyzed C–H activation/carbonylation/cyclization of anilines
  作者：Xuefeng Xu、Yurong Yang、Xin Chen、Xu Zhang、Wei Yi

  DOI：10.1039/c7ob02310c

  日期：——

  We herein disclose a novel Co(III)-catalyzed C–H activation/carbonylation/cyclization of anilines with ketones using paraformaldehyde as the carbonyl source, giving direct access to diverse quinolines with broad functional group tolerance and in good to excellent yields. Moreover, exclusive site-/region-selectivity was observed in this versatile transformation.

  我们在此公开了一种新型的Co（III）催化的使用低聚甲醛作为羰基来源的苯酮与苯胺的C–H活化/羰基化/环化反应，可直接获得具有宽泛的官能团耐受性且产率高至优异的各种喹啉。此外，在这种多功能的转化中观察到了唯一的位点/区域选择性。
• Microwave-Assisted Metal-Free Rapid Synthesis of C4-Arylated Quinolines via Povarov Type Multicomponent Reaction
  作者：Devesh Chandra、Ankit Kumar Dhiman、Rakesh Kumar、Upendra Sharma

  DOI：10.1002/ejoc.201900325

  日期：2019.4.30

  Quinoline Synthesis: Three component reaction of aniline, alkynes, and formaldehyde under microwave irradiation promoted by CSA led to the formation of 4‐arylated quinolines via Povarov type reaction.

  喹啉合成：在CSA促进的微波辐射下，苯胺，炔烃和甲醛的三组分反应通过Povarov型反应导致4芳基化喹啉的形成。
• Copper-mediated formal [5+1] annulation of 2-vinylanilines and glyoxylic acid: A facile approach for the synthesis of 4-arylated quinolines
  作者：Yunyu Xiang、Puying Luo、Tianxin Hao、Weikang Xiong、Xiaolin Song、Qiuping Ding

  DOI：10.1016/j.tet.2020.131832

  日期：2021.1

  A copper-mediated formal [5 + 1] oxidative annulation of 2-vinylanilines and glyoxylic acid to 4-arylated quinolines was developed. A series of 4-arylated quinoline derivatives were obtained in good to excellent yields. This protocol could be carried out efficiently on gram scale. The transformation probably underwent nucleophilic addition/6π electrocyclization/oxidative aromatization and the elimination

  开发了铜介导的2-乙烯基苯胺和乙醛酸的正式[5 +1]氧化环化成4-芳基化的喹啉。获得了一系列4-芳基化的喹啉衍生物，收率良好至优异。该协议可以在克规模上有效地执行。该转化可能经历了亲核加成/6π电环化/氧化芳构化和消除了CO 2级联过程。
• Tertiary amines as a C1 synthon: metal-free synthesis of quinolines and 2-substituted quinolines <i>via</i> [3+2+1] aerobic cyclization and C–N bond cleavage
  作者：Jing-Yuan Liu、Zhen-Ying Wang、Qiang Li、Dacheng Li、Jianmin Dou

  DOI：10.1039/d2nj04119g

  日期：——

  An I2-mediated [3+2+1] aerobic cyclization reaction of anilines with alkynes and tertiary amines without any peroxides has been reported. This protocol employed tertiary amines as a C1 building block for the direct synthesis of 2-non, 2-alkyl, and even 2-aryl substituted quinolines via C–N bond cleavage. Differing from the traditional methods, both terminal and internal alkynes were compatible in this

  已经报道了在没有任何过氧化物的情况下， I 2介导的苯胺与炔烃和叔胺的 [3+2+1] 有氧环化反应。该方案采用叔胺作为 C1 结构单元，通过C-N 键断裂直接合成 2-非、2-烷基甚至 2-芳基取代的喹啉。与传统方法不同，末端和内部炔烃在这种无金属三组分体系中是相容的。2-乙烯基苯胺可能作为该过程中的一种活性中间体产生。