1,4-bis(3,3,3-trifluoroprop-1-yn-1-yl)benzene | 130778-59-5

• 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: 1,4-bis(3,3,3-trifluoroprop-1-yn-1-yl)benzene
• 英文别名: 1,4-Bis(3,3,3-trifluoroprop-1-ynyl)benzene；1,4-bis(3,3,3-trifluoroprop-1-ynyl)benzene
• CAS: 130778-59-5
• 化学式: C₁₂H₄F₆
• 分子量: 262.154
• InChiKey: JNNDGNDPLJZNRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  1,4-bis(3,3,3-trifluoroprop-1-yn-1-yl)benzene 在 硫酸 作用下， 生成 3,3,3-Trifluoro-1-(4-trifluoroprop-1-ynyl-phenyl)-propan-1-one
  参考文献：
  名称：

  Cox, Robin A.; Grant, Ewart; Whitaker, Todd, Canadian Journal of Chemistry, 1990, vol. 68, # 10, p. 1876 - 1881

  摘要：

  DOI：
• 作为产物：
  描述：

  1,4-双[(三甲基硅基)乙炔基]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 25.5h， 生成 1,4-bis(3,3,3-trifluoroprop-1-yn-1-yl)benzene
  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

• Fluoroform-Derived CuCF₃ for Trifluoromethylation of Terminal and TMS-Protected Alkynes
  作者：Lisi He、Gavin Chit Tsui

  DOI：10.1021/acs.orglett.6b00999

  日期：2016.6.17

  An efficient trifluoromethylation reaction of alkynes using a fluoroform-derived CuCF3 reagent is described. The CF3 source is the inexpensive industrial waste fluoroform (CF3H). The air-stable CuCF3 reagent can be prepared in large quantities and is convenient to use. Synthetically useful trifluoromethylated alkynes containing a wide range of functional groups were successfully synthesized under mild conditions. Both terminal and TMS-protected alkynes gave the products in one step. The beneficial effect of a diamine ligand tetramethylethylenediamine (TMEDA) with the fluoroform-derived CuCF3 reagent was also demonstrated.
• 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.
• Cox, Robin A.; Grant, Ewart; Whitaker, Todd, Canadian Journal of Chemistry, 1990, vol. 68, # 10, p. 1876 - 1881
  作者：Cox, Robin A.、Grant, Ewart、Whitaker, Todd、Tidwell, Thomas T.

  DOI：——

  日期：——