(E)-1-fluoro-3-(3,3,3-trifluoroprop-1-en-1-yl)benzene | 2226-36-0

• 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-fluoro-3-(3,3,3-trifluoroprop-1-en-1-yl)benzene
• 英文别名: (E)-3-fluorophenethenyltrifluoromethane；1-fluoro-3-[(E)-3,3,3-trifluoroprop-1-enyl]benzene
• CAS: 2226-36-0
• 化学式: C₉H₆F₄
• 分子量: 190.14
• InChiKey: PCNZGBFOGVFSQG-SNAWJCMRSA-N

物化性质

• 沸点：
  68 °C(Press: 18 Torr)
• 密度：
  1.259±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 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：
  0
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-碘-3,3,3-三氟丙烷 、 间氟碘苯 在 palladium diacetate 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 以41%的产率得到(E)-1-fluoro-3-(3,3,3-trifluoroprop-1-en-1-yl)benzene
  参考文献：
  名称：

  Rapid Syntheses of [¹¹C]Arylvinyltrifluoromethanes through Treatment of (E)-Arylvinyl(phenyl)iodonium Tosylates with [¹¹C]Trifluoromethylcopper(I)

  摘要：

  We report a method for labeling arylvinyltrifluoromethanes with carbon-11 (t(1/2) = 20.4 min) as representatives of a new radiolabeled chemotype that has potential for developing radiotracers for biomedical imaging with positron emission tomography. Treatment of (E)-arylvinyl(phenyl)iodonium tosylates (1a - 1k) with [C-11]CuCF3 gave the corresponding [C-11]arylvinyltrifluoromethanes ([C-11]2a-[C-11]2k) in high radiochemical yields (90-97%) under rapid (2 min) and mild (60 degrees C) conditions.

  DOI：

  10.1021/acs.orglett.0c01705

文献信息

• Copper-catalyzed trifluoromethylation of alkenes with an electrophilic trifluoromethylating reagent
  作者：Xiao-Ping Wang、Jin-Hong Lin、Cheng-Pan Zhang、Ji-Chang Xiao、Xing Zheng

  DOI：10.3762/bjoc.9.299

  日期：——

  An efficient method for the copper-catalyzed trifluoromethylation of terminal alkenes with an electrophilic trifluoromethylating reagent has been developed. The reactions proceeded smoothly to give trifluoromethylated alkenes in good to excellent yields. The results provided a versatile approach for the construction of Cvinyl-CF3 bonds without using prefunctionalized substrates.

  已经开发了一种使用亲电三氟甲基化试剂对末端烯烃进行铜催化三氟甲基化的有效方法。反应顺利进行，以良好到极好的产率得到三氟甲基化烯烃。结果提供了一种无需使用预官能化底物即可构建 Cvinyl-CF3 键的通用方法。
• A Facile Synthesis of<i>trans</i>-β-Trifluoromethylstyrene,<i>trans</i>-2,3,4,5,6-Pentafluorostilbene and their Derivatives
  作者：Takamasa Fuchikami、Momoko Yatabe、Iwao Ojima

  DOI：10.1055/s-1981-29449

  日期：——
• FUCHIKAMI TAKAMASSA; YATABE MOMOKO; OJIMA IWAO, SYNTHESIS, 1981, NO 5, 365-366
  作者：FUCHIKAMI TAKAMASSA、 YATABE MOMOKO、 OJIMA IWAO

  DOI：——

  日期：——
• Hydroxylamine‐Mediated C(sp2)−H Trifluoromethylation of Terminal Alkenes
  作者：Xiao Zhao、Bing Zhong、Likun Dong、Yu‐Shan Zhang、Hai‐Tian Luo、Jin‐Dong Yang、Jin‐Pei Cheng

  DOI：10.1002/chem.202400995

  日期：2024.6.12

  Introduction of the trifluoromethyl (CF3) group into organic compounds has garnered substantial interest because of its significant role in pharmaceuticals and agrochemicals. Here, we report a hydroxylamine‐mediated radical process for C(sp2)−H trifluoromethylation of terminal alkenes. The reaction shows good reactivity, impressive E/Z selectivity (up to >20 : 1), and broad functional group compatibility. Expansion of this approach to perfluoroalkylation and late‐stage trifluoromethylation of bioactive molecules demonstrates its promising application potential. Mechanistic studies suggest that the reaction follows a radical addition and subsequent elimination pathway.