2-phenyl-4-(trifluoromethyl)-6-methoxyquinoline

• 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-methoxyquinoline
• 英文别名: 6-methoxy-2-phenyl-4-(trifluoromethyl)quinoline；6-methoxy-2-phenyl-4-trifluoromethylquinoline
• 化学式: C₁₇H₁₂F₃NO
• 分子量: 303.284
• InChiKey: GBAGYKNRWWPLLD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  22.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-(2-氨基-5-甲氧基苯基)-2,2,2-三氟乙烷酮 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-methoxyquinoline
  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

• Synthesis of fluorinated heterocycles
  作者：Joseph C. Sloop、Carl L. Bumgardner、W.David Loehle

  DOI：10.1016/s0022-1139(02)00221-x

  日期：2002.12

  Selected 1,3-diketones having a trifluoromethyl group and/or a fluorine in the 2-position were condensed with aromatic hydrazines, hydroxylamine, urea, thiourea, guanidine, and substituted anilines producing pyrazoles, isoxazoles, pyrimidines, and quinolines, respectively, in yields ranging from 27 to 87%.

  将选定的在2位具有三氟甲基和/或氟的1,3-二酮与芳族肼，羟胺，尿素，硫脲，胍和取代的苯胺缩合，分别生成吡唑，异恶唑，嘧啶和喹啉。产率从27％到87％。
• A Convenient Synthesis of 4‐CF ₃ ‐Quinolines from 1‐Trifluoromethyl‐prop‐2‐yne 1‐Iminium Salts and Arylamines
  作者：Thomas Schneider、Maximilian Fleischmann、Daniel Hergesell、Nicola Majstorović、Gerhard Maas

  DOI：10.1002/ejoc.202100378

  日期：2021.5.26

  1-CF3-substituted acetylenic iminium salts are excellent C3-building blocks for the regioselective and generally high-yielding synthesis of 4-trifluoromethyl-quinolines from a wide range of ring-substituted anilines and of 4-CF3-benzo[h]quinolines from 1-naphthylamine. With N-monosubstituted anilines, 4-CF3-quinolinium salts and pyrrolo[1,2-a;3.4-c’]diquinolines can be obtained.

  1-CF 3取代的炔基亚胺盐是出色的C 3砌块，可用于从多种环取代的苯胺和4-CF 3-苯并[h]区域选择性合成高产的四三氟甲基喹啉。1-萘胺的]喹啉。用N-单取代的苯胺，可以得到4-CF 3-喹啉鎓盐和吡咯并[1,2-a; 3.4-c']二喹啉。
• 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。
• One-Pot Synthesis of 3-Fluoro-4-(trifluoromethyl)quinolines from Pentafluoropropen-2-ol and Their Molecular Modification
  作者：Tsuyoshi Hosokawa、Akemi Matsumura、Toshimasa Katagiri、Kenji Uneyama

  DOI：10.1021/jo702568z

  日期：2008.2.1

  Pentafluoropropen-2-ol (PFP) was prepared by the reaction of hexafluoroacetone (HFA) with Mg/TMSCl. The one-pot tandem sequential reactions of PFP via Mannich addition with aldimines followed by Friedel-Crafts cyclization and aromatization afforded the title quinolines. A variety of corresponding 3-substituted quinolines were derived from the title quinoline by nucleophilic substitution of 3-fluorine with nucleophiles. A defluorinative transformation of the 4-trifluoromethyl group of the title quinoline with hydrazine afforded pyrazoloquinoline.
• 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.