2-phenyl-4-(trifluoromethyl)-6-chloroquinoline | 489429-64-3

• 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-phenyl-4-(trifluoromethyl)-6-chloroquinoline
• 英文别名: 6-chloro-2-phenyl-4-(trifluoromethyl)quinoline；Quinoline, 6-chloro-2-phenyl-4-(trifluoromethyl)-
• CAS: 489429-64-3
• 化学式: C₁₆H₉ClF₃N
• 分子量: 307.702
• InChiKey: HCNZAAVGLGDUMO-UHFFFAOYSA-N

物化性质

• 熔点：
  116.6-118.4 °C
• 沸点：
  407.0±45.0 °C(Predicted)
• 密度：
  1.352±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  21
• 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：

  1-(2-氨基-5-氯苯基)-2,2,2-三氟乙酮 在 氢溴酸 、 正丁基氯化镁 、 copper(ll) bromide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 5.5h， 生成 2-phenyl-4-(trifluoromethyl)-6-chloroquinoline
  参考文献：
  名称：

  Electrophile-driven copper-catalyzed one-pot synthesis of 3-halogen quinoline derivatives

  摘要：

  A convenient and regioselective one-pot synthesis of 3-chloride or 3-bromide quinoline derivatives was achieved through a Grignard addition reaction by alkynyl Grignard regent to o-trifluoroacetyl aniline and a Cu(ll)-catalyzed cyclization-halogenation tandem reaction with aqueous HCl or HBr as electrophilic reagent. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.06.010

文献信息

• The First Proline-Catalyzed Friedlander Annulation: Regioselective Synthesis of 2-Substituted Quinoline Derivatives
  作者：Biao Jiang、Jia-jia Dong、Yun Jin、Xiao-long Du、Min Xu

  DOI：10.1002/ejoc.200800121

  日期：2008.6

  The first proline-catalyzed Friedlander annulation for the synthesis of 2-substituted 4-trifluoromethyl quinoline derivatives is described. Excellent re gio selectivity as well as good yields were shown in a variety of cases, and a tandem aldol-cyclization pathway might be involved. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).

  描述了第一个用于合成 2-取代 4-三氟甲基喹啉衍生物的脯氨酸催化 Friedlander 环化。在各种情况下都显示出优异的区域选择性和良好的产率，并且可能涉及串联醛醇环化途径。((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)。
• NHC-Cu(I)-Catalyzed Friedländer-Type Annulation of Fluorinated <i>o</i>-Aminophenones with Alkynes on Water: Competitive Base-Catalyzed Dibenzo[<i>b</i>,<i>f</i>][1,5]diazocine Formation
  作者：Paweł Czerwiński、Michał Michalak

  DOI：10.1021/acs.joc.7b01235

  日期：2017.8.4

  good yields. Further investigations proved that o-FMKs could be efficiently transformed into a rare class of heterocyclic compounds—dibenzo[b,f][1,5]diazocines—by a base-catalyzed condensation, also on water. The developed method was applied for gram-scale synthesis of a fluorinated analogue of G protein-coupled receptor antagonist (GPR91).

  4- trifluoromethylquinolines和naphthydrines（以及它们的二氟和全氟类似物）一种高效，易于扩展的合成作为串联直接催化炔基/脱水缩合的结果Ô -aminofluoromethylketones（ø -FMKs），首次催化报道了NHC-铜（I）在水上的配合物。在反应条件下可耐受各种末端炔烃，包括β-内酰胺，甾体和糖衍生的炔烃，从而可得到所需的喹啉和萘酚，并具有良好的收率。进一步的研究证明，o -FMKs可以有效地转化为稀有的杂环化合物，即二苯并[ b，f] [1,5]重氮电影—通过碱催化的缩合反应，也可以在水上进行。所开发的方法被用于克规模的G蛋白偶联受体拮抗剂（GPR91）的氟化类似物的合成。
• Silver catalyzed synthesis of 4-trifluoromethyl substituted quinolines in water
  作者：Bing-Chuan Zhao、Qing-Zhou Zhang、Wen-Yu Zhou、Hu-Chun Tao、Zi-Gang Li

  DOI：10.1039/c3ra41991f

  日期：——

  Herein we report the first silver catalyzed fluorinated quinoline synthesis via a cascade alkyne–ketone–amino coupling/addition/condensation process in water.

  在此，我们首次报道了银催化氟化喹啉的合成过程，该过程是在水中通过级联炔酮-氨基偶联/加成/缩合进行的。
• Access to 4-Trifluoromethyl Quinolines via Cu-Catalyzed Annulation Reaction of Ketone Oxime Acetates with <i>ortho</i>-Trifluoroacetyl Anilines under Redox-Neutral Conditions
  作者：Zhen-Hua Wang、Li-Wen Shen、Ping Yang、Yong You、Jian-Qiang Zhao、Wei-Cheng Yuan

  DOI：10.1021/acs.joc.2c00128

  日期：2022.5.6

  An efficient Cu-catalyzed annulation reaction of ketone oxime acetates with ortho-trifluoroacetyl anilines has been disclosed. With the developed protocol, a series of 4-trifluoromethyl quinolines were obtained in good to excellent yields (58–99%) under redox-neutral conditions. The protocol also could be extended to ferrocene-based ketone oxime acetates for the construction of ferrocene-substituted

  已公开了酮肟乙酸酯与邻-三氟乙酰苯胺的有效Cu催化的环化反应。使用开发的方案，在氧化还原中性条件下以良好至优异的产率 (58–99%) 获得了一系列 4-三氟甲基喹啉。该协议还可以扩展到二茂铁基酮肟乙酸酯，用于构建二茂铁取代的含氟喹啉。
• Zn(II)-Mediated Alkynylation−Cyclization of <i>o</i>-Trifluoroacetyl Anilines:  One-Pot Synthesis of 4-Trifluoromethyl-Substituted Quinoline Derivatives
  作者：Biao Jiang、Yu-Gui Si

  DOI：10.1021/jo0204606

  日期：2002.12.1

  A novel efficient route to 4-trifluoromethyl-substituted quinoline derivatives through the Zn(II)-mediated alkynylation-cyclization of o-trifluoroacetyl anilines is described.