1-(m-trifluoromethylphenyl)-3,3,3-trifluoropropyne

• 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: 1-(m-trifluoromethylphenyl)-3,3,3-trifluoropropyne
• 英文别名: 1-(trifluoromethyl)-3-(3,3,3-trifluoroprop1-yn-1-yl)benzene；2,5-Bis(trifluoromethyl)phenylacetylene；1-(trifluoromethyl)-3-(3,3,3-trifluoroprop-1-ynyl)benzene
• 化学式: C₁₀H₄F₆
• 分子量: 238.132
• InChiKey: VKBNZYKOLSOUJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(m-trifluoromethylphenyl)-3,3,3-trifluoropropyne 在 氯[2-(二叔丁基磷)二苯基]金 、 水 、 silver trifluoromethanesulfonate 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以75%的产率得到3,3,3-trifluoro-1-[3-(trifluoromethyl)phenyl]propan-1-one
  参考文献：
  名称：

  Regioselective Gold-Catalyzed Hydration of CF₃- and SF₅-alkynes

  摘要：

  The regioselective gold-catalyzed hydration of CF3- and SF5-alkynes is described. The corresponding trifluoromethylated and pentasulfanylated ketones are obtained in up to 91% yield as single regioisomers showcasing the use of CF3 and SF5 as highly efficient directing groups in this reaction. Notably, this transformation represents the first use of CF3- and SF5-alkynes in gold catalysis.

  DOI：

  10.1021/acs.orglett.9b01379
• 作为产物：
  描述：

  1-[(三甲基硅基)乙炔基]-3-(三氟甲基)苯 在 copper(l) iodide 、 四甲基乙二胺 、 四丁基氟化铵 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.5h， 生成 1-(m-trifluoromethylphenyl)-3,3,3-trifluoropropyne
  参考文献：
  名称：

  Regioselective Gold-Catalyzed Hydration of CF₃- and SF₅-alkynes

  摘要：

  The regioselective gold-catalyzed hydration of CF3- and SF5-alkynes is described. The corresponding trifluoromethylated and pentasulfanylated ketones are obtained in up to 91% yield as single regioisomers showcasing the use of CF3 and SF5 as highly efficient directing groups in this reaction. Notably, this transformation represents the first use of CF3- and SF5-alkynes in gold catalysis.

  DOI：

  10.1021/acs.orglett.9b01379

文献信息

• Iron-Catalyzed Intermolecular Hydrothiolation of Internal Alkynes with Thiosalicylic Acids, and Sequential Intramolecular Cyclization Reaction
  作者：Taro Sonehara、Shogo Murakami、Sae Yamazaki、Motoi Kawatsura

  DOI：10.1021/acs.orglett.7b01953

  日期：2017.8.18

  We demonstrate the iron-catalyzed intermolecular coupling of internal alkynes and thiosalicylic acid derivatives. The reaction was effectively catalyzed by the Fe(acac)2/1,10-phenanthroline catalyst in toluene/HFIP (hexafluoroisopropyl alcohol) as the reaction solvent and afforded several types of 1,3-oxathiine derivatives in moderate to high yields through the intermolecular hydrothiolation and sequential

  我们证明了内部炔烃和硫代水杨酸衍生物的铁催化的分子间偶联。Fe（acac）2 / 1,10-菲咯啉催化剂在甲苯/ HFIP（六氟异丙醇）中作为反应溶剂有效地催化了该反应，并通过分子间反应以中等至高收率提供了几种类型的1,3-氧代嘧啶衍生物氢硫基化和顺序分子内环化。
• Synthesis of trifluoromethyl-group-containing cyclopentadienones by the palladium-catalyzed [2 + 2 + 1] cycloaddition of aryl- and trifluoromethyl-group substituted internal alkynes and carbon monoxide
  作者：Shogo Murakami、Taro Sonehara、Kousuke Iwakami、Hiroaki Tsuji、Motoi Kawatsura

  DOI：10.1016/j.tetlet.2019.01.036

  日期：2019.2

  We investigated the palladium-catalyzed [2 + 2 + 1] cycloaddition of aryl- and trifluoromethyl-group-substituted internal alkynes and carbon monoxide, and revealed that the PdBr2 effectively catalyzed the intended reaction. The PdBr2-catalyzed reaction smoothly proceeded and provided aryl- and trifluoromethyl-group-containing cyclopentadienone derivatives in up to 92% yield.

  我们研究了钯催化的芳基和三氟甲基取代的内部炔烃和一氧化碳的[2 + 2 + 1]环加成反应，并揭示了PdBr 2有效催化了预期的反应。PdBr 2催化的反应顺利进行，并以高达92％的收率提供了含芳基和三氟甲基的环戊二烯酮衍生物。
• Regioselective Gold-Catalyzed Hydration of CF₃- and SF₅-alkynes
  作者：Mélissa Cloutier、Majdouline Roudias、Jean-François Paquin

  DOI：10.1021/acs.orglett.9b01379

  日期：2019.5.17

  The regioselective gold-catalyzed hydration of CF3- and SF5-alkynes is described. The corresponding trifluoromethylated and pentasulfanylated ketones are obtained in up to 91% yield as single regioisomers showcasing the use of CF3 and SF5 as highly efficient directing groups in this reaction. Notably, this transformation represents the first use of CF3- and SF5-alkynes in gold catalysis.