4-(4-Methoxy-2,3,5,6-tetrafluorophenyl)-3-butyn-2-ol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(4-Methoxy-2,3,5,6-tetrafluorophenyl)-3-butyn-2-ol
• 英文别名: 4-(2,3,5,6-Tetrafluoro-4-methoxyphenyl)but-3-yn-2-ol
• 化学式: C₁₁H₈F₄O₂
• 分子量: 248.177
• InChiKey: ACCHXFXZQRPFFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-Methoxy-1-iodotetrafluorobenzene 、 3-丁炔-2-醇 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 二异丙胺 作用下， 以80%的产率得到4-(4-Methoxy-2,3,5,6-tetrafluorophenyl)-3-butyn-2-ol
  参考文献：
  名称：

  General method for the preparation of functionalized fluorinated phenyl alkynes

  摘要：

  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.

  DOI：

  10.1021/jo00078a013

文献信息

• 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.