(E)-4-(3,3,3-trifluoroprop-1-en-1-yl)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)-4-(3,3,3-trifluoroprop-1-en-1-yl)phenol
• 英文别名: 1-(4-Hydroxy-phenyl)-2-(trifluormethyl)-ethylen；4-[(E)-3,3,3-trifluoroprop-1-enyl]phenol
• 化学式: C₉H₇F₃O
• 分子量: 188.149
• InChiKey: NDBWVSWVNBQUAG-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：

  (E)-4-(3,3,3-trifluoroprop-1-enyl)benzenecarbonitrile 在 sodium hydroxide 、 双氧水 、 溴 作用下， 以 乙醇 为溶剂， 生成 (E)-4-(3,3,3-trifluoroprop-1-en-1-yl)phenol
  参考文献：
  名称：

  Yagupol'skii,L.M.; Fialkov,Yu.A., Journal of general chemistry of the USSR, 1961, vol. 31, p. 3343 - 3349

  摘要：

  DOI：

文献信息

• Copper- and Iron-Catalyzed Decarboxylative Tri- and Difluoromethylation of α,β-Unsaturated Carboxylic Acids with CF₃SO₂Na and (CF₂HSO₂)₂Zn via a Radical Process
  作者：Zejiang Li、Zili Cui、Zhong-Quan Liu

  DOI：10.1021/ol3034059

  日期：2013.1.18

  A copper-catalyzed decarboxylative trifluoromethylation of various α,β-unsaturated carboxylic acids by using a stable and inexpensive solid, sodium trifluoromethanesulfinate (CF3SO2Na, Langlois reagent), was developed. In addition, an iron-catalyzed difluoromethylation of aryl-substituted acrylic acids by using zinc difluoromethanesulfinate (DFMS, (CF2HSO2)2Zn, Baran reagent) via a similar radical

  通过使用稳定且廉价的固体三氟甲烷亚磺酸钠（CF 3 SO 2 Na，Langlois试剂），开发了铜催化的各种α，β-不饱和羧酸的脱羧三氟甲基化反应。另外，还通过类似的自由基方法，通过使用二氟甲亚磺酸锌（DFMS，（CF 2 HSO 2）2 Zn，Baran试剂），实现了铁催化的芳基取代的丙烯酸的二氟甲基化。
• Decarboxylative and Denitrative Trifluoromethylation for the Synthesis of C_vinylCF₃Compounds with Togni (II) Reagent
  作者：Jing-jing Ma、Wen-bin Yi、Guo-ping Lu、Chun Cai

  DOI：10.1002/adsc.201500631

  日期：2015.11.16

  A highly efficient dimethylformamide (DMF)-promoted decarboxylative trifluoromethylation of α,β-unsaturated carboxylic acids with Togni (II) reagent under metal-free conditions has been developed. The reactions showed good yields, high stereoselectivities and excellent functional group tolerance. Mechanistic studies confirmed that free-radical processes were involved in this system since the CF3 radical

  在无金属条件下，用Togni（II）试剂开发了高效的二甲基甲酰胺（DMF）促进的α，β-不饱和羧酸的脱羧三氟甲基化反应。反应显示出良好的产率，高的立体选择性和优异的官能团耐受性。机理研究证实，该自由基系统参与了该系统，因为CF 3自由基已被清除剂清楚地捕获。该方法已扩展到在铁（III）催化剂存在下β-硝基苯乙烯的反硝化三氟甲基化反应。
• Electrochemical Synthesis Strategy for C_vinyl-CF₃ Compounds through Decarboxylative Trifluoromethylation
  作者：Huanliang Hong、Yibiao Li、Lu Chen、Bin Li、Zhongzhi Zhu、Xiuwen Chen、Ling Chen、Yubing Huang

  DOI：10.1021/acs.joc.9b00766

  日期：2019.5.3

  An efficient decarboxylative trifluoromethylation of α,β-unsaturated carboxylic acids using the Langlois reagent as a trifluoromethyl precursor has been achieved by an electro-oxidative strategy. Under catalyst-free and external oxidant-free electrolysis conditions, a series of Cvinyl-CF3 compounds are obtained with a high regioselectivity in good yields. The successful trapping of the CF3 radical

  通过电氧化策略，已经使用Langlois试剂作为三氟甲基前体，对α，β-不饱和羧酸进行了有效的脱羧三氟甲基化。在无催化剂和无外部氧化剂的电解条件下，以高产率获得了具有高区域选择性的一系列C乙烯基-CF 3化合物。清除剂成功捕获CF 3自由基已证实该系统涉及自由基过程。
• Copper/Silver-Mediated Decarboxylative Trifluoromethylation of α,β-Unsaturated Carboxylic Acids with CF3SO2Na
  作者：Yaming Li、Chunying Duan、Jun Yin、Rong Zhang、Kun Jin

  DOI：10.1055/s-0033-1338578

  日期：——

  copper/silver-catalyzed decarboxylative trifluoromethylation of α,β-unsaturated carboxylic acids with CF3SO2Na was performed under relatively mild conditions. The reaction shows high E/Z selectivity and wide substrate tolerance. Ag2CO3 plays an important role in promoting the decarboxylation process. A copper/silver-catalyzed decarboxylative trifluoromethylation of α,β-unsaturated carboxylic acids with CF3SO2Na

  摘要 在相对温和的条件下，用CF 3 SO 2 Na进行铜/银催化的α，β-不饱和羧酸的脱羧三氟甲基化反应。该反应显示出高的E / Z选择性和宽的底物耐受性。Ag 2 CO 3在促进脱羧过程中起重要作用。 在相对温和的条件下，用CF 3 SO 2 Na进行铜/银催化的α，β-不饱和羧酸的脱羧三氟甲基化反应。该反应显示出高的E / Z选择性和宽的底物耐受性。Ag 2 CO 3在促进脱羧过程中起重要作用。
• 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.