(E)-4-chloro-2-(3,3,3-trifluoroprop-1-en-1-yl)aniline | 1440779-46-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-4-chloro-2-(3,3,3-trifluoroprop-1-en-1-yl)aniline
• 英文别名: 4-chloro-2-[(E)-3,3,3-trifluoroprop-1-enyl]aniline
• CAS: 1440779-46-3
• 化学式: C₉H₇ClF₃N
• 分子量: 221.609
• InChiKey: LTZJRVCTIKWUNJ-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-4-chloro-2-(3,3,3-trifluoroprop-1-en-1-yl)aniline 、 苯甲醛 在 copper(I) trifluoromethanesulfonate benzene 、 三氯苯 作用下， 反应 3.0h， 以82%的产率得到6-chloro-2-phenyl-3-(trifluoromethyl)quinoline
  参考文献：
  名称：

  Synthesis of 2-Aryl-3-trifluoromethylquinolines Using (E)-Trimethyl(3,3,3-trifluoroprop-1-enyl)silane

  摘要：

  The Hiyama cross-coupling reaction of (E)-trimethyl (3,3,3-trifluoroprop-1-enyl)silane (1) with 2-iodoaniline (2) proceeded without any protection of the amino group. The coordination of copper(II) fluoride to 2,2'-bipyridyl provided the fluoride source required to trigger this reaction, affording (E)-2-(3,3,3-trifluoroprop-1-enyl)aniline (3). In the presence of a stoichiometric amount of [Cu(OTf)](2)center dot C6H6, the treatment of 3 with an aryl aldehyde at 200 degrees C provided the 2-aryl-3-trifluoromethylquinoline (4) via the oxidative cyclization of an in situ-generated imine substructure.

  DOI：

  10.1021/jo400859s
• 作为产物：
  描述：

  2-碘-4-氯苯胺 、 三甲基(3,3,3-三氟丙-1-烯基)硅烷 在 2,2'-联吡啶 、 copper (II)-fluoride 、 bis[1,2-bis(diphenylphosphino)ethane]palladium(0) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 以54%的产率得到(E)-4-chloro-2-(3,3,3-trifluoroprop-1-en-1-yl)aniline
  参考文献：
  名称：

  Synthesis of 2-Aryl-3-trifluoromethylquinolines Using (E)-Trimethyl(3,3,3-trifluoroprop-1-enyl)silane

  摘要：

  The Hiyama cross-coupling reaction of (E)-trimethyl (3,3,3-trifluoroprop-1-enyl)silane (1) with 2-iodoaniline (2) proceeded without any protection of the amino group. The coordination of copper(II) fluoride to 2,2'-bipyridyl provided the fluoride source required to trigger this reaction, affording (E)-2-(3,3,3-trifluoroprop-1-enyl)aniline (3). In the presence of a stoichiometric amount of [Cu(OTf)](2)center dot C6H6, the treatment of 3 with an aryl aldehyde at 200 degrees C provided the 2-aryl-3-trifluoromethylquinoline (4) via the oxidative cyclization of an in situ-generated imine substructure.

  DOI：

  10.1021/jo400859s

文献信息

• Synthesis of 2-Aryl-3-trifluoromethylquinolines Using (<i>E</i>)-Trimethyl(3,3,3-trifluoroprop-1-enyl)silane
  作者：Masaaki Omote、Miyuu Tanaka、Miki Tanaka、Akari Ikeda、Atsushi Tarui、Kazuyuki Sato、Akira Ando

  DOI：10.1021/jo400859s

  日期：2013.6.21

  The Hiyama cross-coupling reaction of (E)-trimethyl (3,3,3-trifluoroprop-1-enyl)silane (1) with 2-iodoaniline (2) proceeded without any protection of the amino group. The coordination of copper(II) fluoride to 2,2'-bipyridyl provided the fluoride source required to trigger this reaction, affording (E)-2-(3,3,3-trifluoroprop-1-enyl)aniline (3). In the presence of a stoichiometric amount of [Cu(OTf)](2)center dot C6H6, the treatment of 3 with an aryl aldehyde at 200 degrees C provided the 2-aryl-3-trifluoromethylquinoline (4) via the oxidative cyclization of an in situ-generated imine substructure.