1-(4-Methoxytetrafluorophenyl)-1-hexyne | 132162-66-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-(4-Methoxytetrafluorophenyl)-1-hexyne
• 英文别名: 1-(4-Methoxy-2,3,5,6-tetrafluorophenyl)-1-hexyne；1,2,4,5-Tetrafluoro-3-(1-hexynyl)-6-methoxybenzene；1,2,4,5-tetrafluoro-3-hex-1-ynyl-6-methoxybenzene
• CAS: 132162-66-4
• 化学式: C₁₃H₁₂F₄O
• 分子量: 260.231
• InChiKey: IHEYLLLFVDZZRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-Methoxy-1-iodotetrafluorobenzene 、 1-己炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 二异丙胺 作用下， 反应 2.0h， 以81%的产率得到1-(4-Methoxytetrafluorophenyl)-1-hexyne
  参考文献：
  名称：

  钯/碘化亚铜催化四氟苯基卤化物与1-炔烃的偶联反应

  摘要：

  在碘化亚铜的存在下，取代的四氟苯基卤化物与1-炔烃的钯催化偶联反应在温和条件下以良好或优异的收率得到相应的氟芳基炔烃。4-取代的（甲氧基，N，N-二甲基氨基，吗啉代）四氟苯基碘和溴离子均能很好地起作用，并且在反应条件下，炔烃部分中的烷基，三甲基甲硅烷基，苯基，羟基和醚官能团是可容忍的。该方法提供了取代的氟化芳基炔烃的实用合成。

  DOI：

  10.1016/s0022-1139(00)80502-3

文献信息

• Palladium/Cuprous Iodide Catalyzed Coupling of Substituted Tetrafluorophenyl Halides With 1-Alkynes
  作者：Ba V. Nguyen、Zhen-yu Yang、Donald J. Burton

  DOI：10.1016/s0022-1139(00)80502-3

  日期：1990.11

  In the presence of cuprous iodide, the palladium catalyzed coupling reaction of substituted tetrafluorophenyl halides with 1- alkynes gives the corresponding fluoroaryl alkynes in good to excellent yields under mild conditions. Both 4-substituted (methoxy, N,N-dimethylamino, morpholino) tetrafluorophenyl iodides and bromides work well, and alkyl, trimethylsilyl, phenyl, hydroxy, and ether functionalities

  在碘化亚铜的存在下，取代的四氟苯基卤化物与1-炔烃的钯催化偶联反应在温和条件下以良好或优异的收率得到相应的氟芳基炔烃。4-取代的（甲氧基，N，N-二甲基氨基，吗啉代）四氟苯基碘和溴离子均能很好地起作用，并且在反应条件下，炔烃部分中的烷基，三甲基甲硅烷基，苯基，羟基和醚官能团是可容忍的。该方法提供了取代的氟化芳基炔烃的实用合成。
• 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.