N-phenyl-2-(trifluoromethyl)quinolin-4-amine | 87658-38-6

• 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: N-phenyl-2-(trifluoromethyl)quinolin-4-amine
• 英文别名: 4-Quinolinamine, N-phenyl-2-(trifluoromethyl)-
• CAS: 87658-38-6
• 化学式: C₁₆H₁₁F₃N₂
• 分子量: 288.272
• InChiKey: MQFDNUVQKUWJHE-UHFFFAOYSA-N

物化性质

• 熔点：
  139.5-140 °C
• 沸点：
  358.6±42.0 °C(Predicted)
• 密度：
  1.332±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  24.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,2,2-三氟-N-苯基亚氨代乙酰氯 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成 N-phenyl-2-(trifluoromethyl)quinolin-4-amine
  参考文献：
  名称：

  Catalyst‐Free, Heating‐Induced Desulfurization Annulation of CF ₃ ‐Imidoyl Sulfoxonium Ylides with Isothiocyanates for the Synthesis of 2‐Trifluoromethyl‐4‐aminoquinolines

  摘要：

  AbstractA heating‐induced desulfurization annulation of readily available CF3‐imidoyl sulfoxonium ylides and isothiocyanates for the construction of 2‐trifluoromethylquinolines has been achieved. The developed transformation was performed under metal‐ and additive‐free conditions, producing a variety of biologically valuable 2‐trifluoromethylquinoline derivatives with high efficiency.

  DOI：

  10.1002/ejoc.202300090

文献信息

• Anticancer-Active <i>N</i>-Heteroaryl Amines Syntheses: Nucleophilic Amination of <i>N</i>-Heteroaryl Alkyl Ethers with Amines
  作者：Xia Wang、Qiu-Xia Yang、Cheng-Yu Long、Yan Tan、Yi-Xin Qu、Min-Hui Su、Si-Jie Huang、Weihong Tan、Xue-Qiang Wang

  DOI：10.1021/acs.orglett.9b01711

  日期：2019.7.5

  A mild amination protocol of N-heteroaryl alkyl ethers with various amines is described. This transformation is achieved by utilizing simple and readily available base as promoter via C–O bond cleavage, offering a new amination strategy to access several anticancer-active compounds. This work is highlighted by the excellent functional group compatibility, scalability, wide substrate scope, and easy

  描述了N-杂芳基烷基醚与各种胺的温和胺化方案。通过使用简单易用的碱基作为启动子通过C–O键裂解来实现这种转化，从而提供了一种新的胺化策略来使用多种抗癌活性化合物。出色的官能团兼容性，可扩展性，广泛的底物范围以及多种药物的容易衍生化，突出了这项工作。
• Synthesis of 2‐Trifluoromethyl‐4‐aminoquinolines via Heating‐Promoted Multi‐component Reaction of CF₃‐Imidoyl Sulfoxonium Ylides and Amines with Difluorocarbene as a C1 Synthon^†
  作者：Guangming Wei、Chen Li、Haoyuan Wang、Zhengkai Chen、Xiao‐Feng Wu

  DOI：10.1002/cjoc.202300373

  日期：2023.12

  developed, allowing a facile access to 2-trifluoromethyl-4-aminoquinolines in high yields. The reaction proceeds smoothly with or without the addition of sulfur and utilizes difluorocarbene as a C1 synthon under simply heating conditions. Mechanistic study reveals that in-situ generated thiocarbonyl fluoride, isothiocyanate or gem-difluoroalkene might act as the key reaction intermediates.

  开发了CF 3 取代的亚氨基亚锍叶立德(TFISY)、胺和(三苯基膦)二氟乙酸酯(PDFA)的热诱导多组分反应，可以轻松地以高产率获得2-三氟甲基-4-氨基喹啉。无论添加或不添加硫，该反应均顺利进行，并在简单的加热条件下利用二氟卡宾作为C1合成子。机理研究表明，原位生成的硫代碳酰氟、异硫氰酸酯或偕二氟烯烃可能是关键的反应中间体。
• Cycloadditions and nucleophilic attack on Z-2H-heptafluorobut-2-ene
  作者：Richard D. Chambers、Andrew R. Edwards

  DOI：10.1016/s0040-4020(98)00201-4

  日期：1998.5

  Chemistry of Z-2H-Heptafluorobut-2-ene 1 is surveyed; cycloaddition reactions occur with a variety of benzenoid compounds, in some cases leading directly to aromatics. Addition to cyclopentadiene, followed by eliminations of hydrogen fluoride and ethyne, lead to isomeric bistrifluoromethylcyclopentadienes. Nucleophilic reactions occur readily with oxygen, nitrogen and sulphur nucleophiles and aniline provides a quinoline synthesis. (C) 1998 Elsevier Science Ltd. All rights reserved.
• CN116813544
  申请人：——

  公开号：——

  公开（公告）日：——
• Catalyst‐Free, Heating‐Induced Desulfurization Annulation of CF ₃ ‐Imidoyl Sulfoxonium Ylides with Isothiocyanates for the Synthesis of 2‐Trifluoromethyl‐4‐aminoquinolines
  作者：Guangming Wei、Yue Sun、Dongling Zheng、Shiqi Qiu、Zhengkai Chen、Xiao‐Feng Wu

  DOI：10.1002/ejoc.202300090

  日期：2023.3.7

  AbstractA heating‐induced desulfurization annulation of readily available CF3‐imidoyl sulfoxonium ylides and isothiocyanates for the construction of 2‐trifluoromethylquinolines has been achieved. The developed transformation was performed under metal‐ and additive‐free conditions, producing a variety of biologically valuable 2‐trifluoromethylquinoline derivatives with high efficiency.