1-(4-Piperidino-2,3,5,6-tetrafluorophenyl)-2-phenylethyne | 129177-97-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-(4-Piperidino-2,3,5,6-tetrafluorophenyl)-2-phenylethyne
• 英文别名: 1-[2,3,5,6-Tetrafluoro-4-(2-phenylethynyl)phenyl]piperidine
• CAS: 129177-97-5
• 化学式: C₁₉H₁₅F₄N
• 分子量: 333.328
• InChiKey: YESRHQQEFUZHCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-(2,3,5,6-四氟-4-碘苯基)哌啶 、 苯乙炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 三乙胺 作用下， 反应 12.0h， 以95.2%的产率得到1-(4-Piperidino-2,3,5,6-tetrafluorophenyl)-2-phenylethyne
  参考文献：
  名称：

  氟-芳族乙炔衍生物的便捷合成

  摘要：

  在三乙胺中双（三苯基膦）钯二氯化物和碘化铜（I）的催化下，多氟碘代苯与末端乙炔的偶合反应为合成氟-芳族乙炔衍生物提供了一种简单有效的方法。

  DOI：

  10.1016/s0022-1139(00)82405-7

文献信息

• A convenient synthesis of fluoro-aromatic acetylene derivatives
  作者：Zhang Yadong、Wen Jianxun

  DOI：10.1016/s0022-1139(00)82405-7

  日期：1990.5

  The coupling reaction between polyfluoroiodobenzenes and terminal acetylenes under the catalysis of bis(triphenylphosphine)palladium dichloride and copper(I) iodide in triethylamine afforded a simple and effective method for the synthesis of fluoro-aromatic acetylene derivatives.

  在三乙胺中双（三苯基膦）钯二氯化物和碘化铜（I）的催化下，多氟碘代苯与末端乙炔的偶合反应为合成氟-芳族乙炔衍生物提供了一种简单有效的方法。
• General method for the preparation of functionalized fluorinated phenyl alkynes
  作者：Ba V. Nguyen、Zhen Yu Yang、Donald J. Burton

  DOI：10.1021/jo00078a013

  日期：1993.12

  In the presence of cuprous iodide, the palladium-catalyzed coupling reaction of 4-substituted tetrafluorophenyl iodides 1 with terminal alkynes proceeds readily in diisopropylamine or triethylamine to afford the corresponding fluorinated phenylalkynes in excellent yields under mild conditions. A variety of substituents on F-benzenes such as methoxy, dimethylamino, hydro, acyl, piperidino, and morpholino do not interfere with the coupling reaction. The reaction works well with 1-alkynes containing functional groups, including alkyl, alkenyl, phenyl, vinyl ether, alkoxy, phenoxy, hydroxy, amino, trimethylsilyl, and cyano, to give the corresponding (fluorophenyl)alkynes. With dialkynes, 2 equiv of the fluorinated phenyl iodide give bis(fluorophenyl)dialkynes in good yields. When 1,4-dibromotetrafluorobenzene reacts with an excess of alkyne in diisopropylamine, the bis-alkynylated tetrafluorobenzenes are obtained in good yields. However, in triethylamine the reaction gives a mixture of mono- and bis-alkynylated products. This method provides a practical approach to fluorinated phenyl functionalized alkynes.