1-(2,3,5,6-四氟-4-碘苯基)哌啶 | 15368-92-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 中文名称: 1-(2,3,5,6-四氟-4-碘苯基)哌啶
• 英文名称: 4-Piperidino-1-iodotetrafluorobenzene
• 英文别名: 1-(2,3,5,6-tetrafluoro-4-iodophenyl)piperidine
• CAS: 15368-92-0
• 化学式: C₁₁H₁₀F₄IN
• 分子量: 359.105
• InChiKey: VRHIZVGNGXCUTP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (Z)-1-methoxybut-1-en-3-yne 、 1-(2,3,5,6-四氟-4-碘苯基)哌啶 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 二异丙胺 作用下， 以66%的产率得到(Z)-1-Methoxy-4-(4-piperidino-2,3,5,6-tetrafluorophenyl)-1-buten-3-yne
  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
• 作为产物：
  描述：

  以 环己烷 为溶剂， 生成 三正丁基氧化磷 、 1-(2,3,5,6-四氟-4-碘苯基)哌啶
  参考文献：
  名称：

  溶液中卤素键合的热力学：取代基、结构和溶剂效应

  摘要：

  详细研究了有机溶液中卤素键相互作用的热力学。(19)F NMR 滴定用于确定各种路易斯碱与氟化碘代烷烃和碘代芳烃相互作用的缔合常数。描述了取代碘全氟芳烃 XC(6)F(4)I 的卤素键供体能力的线性自由能关系，表明取代基常数 (sigma) 和计算的分子静电势表面可用于构建此类关系。然而，静电模型在提供与更全面的数据集相关的能力方面受到限制，其中卤键供体和受体能力都不同：阐明了计算得出的结合能对此类数据进行准确建模的能力。

  DOI：

  10.1021/ja9086352

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。
• Thermodynamics of Halogen Bonding in Solution: Substituent, Structural, and Solvent Effects
  作者：Mohammed G. Sarwar、Bojan Dragisic、Lee J. Salsberg、Christina Gouliaras、Mark S. Taylor

  DOI：10.1021/ja9086352

  日期：2010.2.10

  demonstrating that both substituent constants (sigma) and calculated molecular electrostatic potential surfaces are useful for constructing such relationships. An electrostatic model is, however, limited in its ability to provide correlation with a more comprehensive data set in which both halogen bond donor and acceptor abilities are varied: the ability of computationally derived binding energies to accurately

  详细研究了有机溶液中卤素键相互作用的热力学。(19)F NMR 滴定用于确定各种路易斯碱与氟化碘代烷烃和碘代芳烃相互作用的缔合常数。描述了取代碘全氟芳烃 XC(6)F(4)I 的卤素键供体能力的线性自由能关系，表明取代基常数 (sigma) 和计算的分子静电势表面可用于构建此类关系。然而，静电模型在提供与更全面的数据集相关的能力方面受到限制，其中卤键供体和受体能力都不同：阐明了计算得出的结合能对此类数据进行准确建模的能力。
• 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.