(E)-1,1,1-trifluoro-4,4-diphenylbut-2-ene

• 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)-1,1,1-trifluoro-4,4-diphenylbut-2-ene
• 英文别名: (E)-1,1,1-Trifluoro-4,4-diphenyl-2-butene；[(E)-4,4,4-trifluoro-1-phenylbut-2-enyl]benzene
• 化学式: C₁₆H₁₃F₃
• 分子量: 262.274
• InChiKey: ONFBLTSYDIXOFS-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (+/-)-E-1,1,1-trifluoro-4-phenylbut-3-en-2-ol 、 苯 在 iron(III) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以65%的产率得到(E)-1,1,1-trifluoro-4,4-diphenylbut-2-ene
  参考文献：
  名称：

  Trifluoromethylated allyl alcohols: acid-promoted reactions with arenes and unusual ‘dimerization’

  摘要：

  An unusual 'dimerization' of CF3-allyl alcohols [ArCH=CHCH(OH)CF3] under the action of anhydrous FeCl3 was found to give fluorinated indanes in 62-90% yields via the formation of intermediate allyl cations. Reactions of CF3-allyl alcohols with arenes (Ar'H) led to CF3-alkenes [Ar(Ar')CHCH=CHCF3] in 48-75% yields. The mechanisms of the transformations are discussed. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.10.083

文献信息

• Acid-Promoted Reaction of Trifluoromethylated Allyl Alcohols with Arenes. Stereoselective Synthesis of CF₃-Alkenes and CF₃-Indanes
  作者：Anna N. Kazakova、Roman O. Iakovenko、Irina A. Boyarskaya、Valentine G. Nenajdenko、Aleksander V. Vasilyev

  DOI：10.1021/acs.joc.5b01398

  日期：2015.10.2

  Reaction of 4-aryl-1,1,1-trifluorobut-3-en-2-ols [CF3-allyl alcohols, ArCH=CHCH(OH)CF3] with arenes under activation activation with anhydrous FeCl3 or FSO3H was studied. We found that the transformation led to trifluoromethylated alkenes [Ar(Ar')CHCH=CHCF3] or 1-trifluoromethylated indanes (CF3-indanes). The formation of these two types of reaction products strongly depends on the nudeophilicity of the starting arene and the electrophilicity of cationic intermediates generated from CF3-allyl alcohols under reaction conditions. Benzene, anisole, veratrole, and ortho-xylene lead exclusively to CF3-alkenes with an E-configuration. More pi-donating polyrnethylated arenes (pseudocumene, mesitylene) afford only CF3-indanes with a predominantly cis-orientation of substituents at positions 1 and 3 of the indane ring. Meta- and para-xylenes show an intermediate behavior; they may form both CF3-alkenes and/or CF3-indanes. The mechanisms of the investigated transformations are discussed.
• Trifluoromethylated allyl alcohols: acid-promoted reactions with arenes and unusual ‘dimerization’
  作者：Anna N. Kazakova、Roman O. Iakovenko、Vasiliy M. Muzalevskiy、Irina A. Boyarskaya、Margarita S. Avdontceva、Galina L. Starova、Aleksander V. Vasilyev、Valentine G. Nenajdenko

  DOI：10.1016/j.tetlet.2014.10.083

  日期：2014.12

  An unusual 'dimerization' of CF3-allyl alcohols [ArCH=CHCH(OH)CF3] under the action of anhydrous FeCl3 was found to give fluorinated indanes in 62-90% yields via the formation of intermediate allyl cations. Reactions of CF3-allyl alcohols with arenes (Ar'H) led to CF3-alkenes [Ar(Ar')CHCH=CHCF3] in 48-75% yields. The mechanisms of the transformations are discussed. (C) 2014 Elsevier Ltd. All rights reserved.