(E)-2-(3,3,3-trifluoroprop-1-enyl)phenol

• 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)-2-(3,3,3-trifluoroprop-1-enyl)phenol
• 英文别名: (E)-2-(3,3,3-trifluoroprop-1-en-1-yl)phenol；(E)-1-(2-hydroxyphenyl)-3,3,3-trifluoropropene；β-trifluoromethyl-2-hydroxystyrene；2-[(E)-3,3,3-Trifluoro-1-propenyl]phenol；2-[(E)-3,3,3-trifluoroprop-1-enyl]phenol
• 化学式: C₉H₇F₃O
• 分子量: 188.149
• InChiKey: QXMMGWYYRDHBSR-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  13
• 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：
  20.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  水杨醛 在 copper(II) choride dihydrate 、 一水合肼 、 乙二胺 作用下， 以 乙二醇 为溶剂， 反应 1.17h， 生成 (E)-2-(3,3,3-trifluoroprop-1-enyl)phenol
  参考文献：
  名称：

  Facile synthesis of (E)-β-(trifluoromethyl)styrenes from halothane (HCFC-123B1)

  摘要：

  A practical and convenient synthesis of (E)-beta-(trifluoromethyl)styrenes has been achieved by the reaction of commercially available halothane (HCFC-123B1) and hydrazones prepared in advance in situ, in the presence of 1,2-ethylenediamine and a catalytic amount of CuCl2.2H(2)O at room temperature. The products showed acceptable to high yields and high to excellent stereoselectivity. This handy synthetic method provided easy access to a variety of (E)-beta-(trifluoromethyl)styrenes. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2014.07.018

文献信息

• Iron-Mediated Decarboxylative Trifluoromethylation of α,β-Unsaturated Carboxylic Acids with Trifluoromethanesulfinate
  作者：Tuhin Patra、Arghya Deb、Srimanta Manna、Upendra Sharma、Debabrata Maiti

  DOI：10.1002/ejoc.201300473

  日期：2013.8

  A sustainable FeCl3-mediated method has been developed for the decarboxylative trifluoromethylation of α,β-unsaturated carboxylic acids by using NaSO2CF3 as an economic and stable CF3 source. The reaction proceeds under mild condition and tolerates various functional groups. Advantageously, this method does not require an inert atmosphere and proceeds well in air at ambient temperature.

  通过使用 NaSO2CF3 作为经济且稳定的 CF3 源，开发了一种可持续的 FeCl3 介导的方法，用于 α,β-不饱和羧酸的脱羧三氟甲基化。该反应在温和的条件下进行并且可以耐受各种官能团。有利地，该方法不需要惰性气氛并且在环境温度下在空气中很好地进行。
• Oxy-trifluoromethylation of alkenes and its application to the synthesis of β-trifluoromethylstyrene derivatives
  作者：Hiromichi Egami、Ryo Shimizu、Yoshihiko Usui、Mikiko Sodeoka

  DOI：10.1016/j.jfluchem.2014.05.009

  日期：2014.11

  Oxy-trifluoromethylation of di-substituted styrenes and dienes was achieved by using Cu/Togni's reagent system. Not only gem-di-substituted styrenes, but also a beta-methylstyrene derivative were transformed to the corresponding oxy-trifluoromethylation products. 1,4-Addition products were obtained selectively in the reaction of mono-substituted dienes. These reactions provide a new approach for the synthesis of beta-trifluoromethyl styrene derivatives. (C) 2014 The Authors. Published by Elsevier B.V.
• Facile synthesis of (E)-β-(trifluoromethyl)styrenes from halothane (HCFC-123B1)
  作者：Kensuke Hirotaki、Genyu Kawazoe、Takeshi Hanamoto

  DOI：10.1016/j.jfluchem.2014.07.018

  日期：2015.3

  A practical and convenient synthesis of (E)-beta-(trifluoromethyl)styrenes has been achieved by the reaction of commercially available halothane (HCFC-123B1) and hydrazones prepared in advance in situ, in the presence of 1,2-ethylenediamine and a catalytic amount of CuCl2.2H(2)O at room temperature. The products showed acceptable to high yields and high to excellent stereoselectivity. This handy synthetic method provided easy access to a variety of (E)-beta-(trifluoromethyl)styrenes. (C) 2014 Elsevier B.V. All rights reserved.