(E)-1-phenyl-3-(p-tolyl)-2-(trifluoromethyl)prop-2-en-1-one | 1568112-36-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-1-phenyl-3-(p-tolyl)-2-(trifluoromethyl)prop-2-en-1-one
• 英文别名: (E)-3-(4-methylphenyl)-1-phenyl-2-(trifluoromethyl)prop-2-en-1-one
• CAS: 1568112-36-6
• 化学式: C₁₇H₁₃F₃O
• 分子量: 290.285
• InChiKey: FJIALYRQIIVWAZ-RVDMUPIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  21
• 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：
  17.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-(4-甲基苯基)-1-苯基-丙-2-烯-1-酮 、 1-(三氟甲基)-1,2-苯碘酰-3(1H)-酮 在 copper(l) iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 以82%的产率得到(E)-1-phenyl-3-(p-tolyl)-2-(trifluoromethyl)prop-2-en-1-one
  参考文献：
  名称：

  Catalytic C–H α-Trifluoromethylation of α,β-Unsaturated Carbonyl Compounds

  摘要：

  A copper(I)-catalyzed, regioselective C-H alpha-trifluoromethylation of alpha,beta-unsaturated carbonyl compounds using Togni's reagent was developed. Diverse substrates, including enones as well as alpha,beta-unsaturated esters, thioesters, and amides, stereospecifically afforded the corresponding (E)-alpha-trifluoromethylated products in moderate to high yields. Further, this method was applied to the C-H trifluoromethylation of drugs.

  DOI：

  10.1021/ol5004498

文献信息

• Stereoselective Synthesis of α-Trifluoromethyl Enones by Au^I/Cu^I-Co-Catalyzed Tandem 1,3-Acyloxy Migration/Trifluoromethylation Reaction of Propargyl Acetates
  作者：Yun-Long Ji、Jin-Hong Lin、Ji-Chang Xiao、Yu-Cheng Gu

  DOI：10.1002/ejoc.201403115

  日期：2014.12

  AuI/CuI-co-catalyzed tandem 1,3-acyloxy migration/trifluoromethylation reaction of propargyl esters to give α-trifluoromethyl enones in moderate yields and with excellent stereoselectivity is described. It is proposed that the reaction proceeds through the 1,3-acyloxy migration of the propargyl esters catalyzed by AuI to produce an allenic intermediate, followed by its trifluoromethylation to give

  描述了 AuI/CuI 共催化的炔丙酯串联 1,3-酰氧基迁移/三氟甲基化反应，以中等产率和优异的立体选择性得到 α-三氟甲基烯酮。提出该反应通过由 AuI 催化的炔丙酯的 1,3-酰氧基迁移进行以产生丙二烯中间体，然后通过其三氟甲基化得到最终产物。