1-Pentafluorophenyl-2-p-nitro-phenylacetylene | 129177-96-4

• 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-Pentafluorophenyl-2-p-nitro-phenylacetylene
• 英文别名: 4-[(pentafluorophenyl)ethynyl]nitrobenzene；1,2,3,4,5-pentafluoro-6-[2-(4-nitrophenyl)ethynyl]benzene
• CAS: 129177-96-4
• 化学式: C₁₄H₄F₅NO₂
• 分子量: 313.183
• InChiKey: XZDDBRTUCFHYKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.69
• 重原子数：
  22.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-Pentafluorophenyl-2-p-nitro-phenylacetylene 在 lithium bromide 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 4.5h， 以1%的产率得到4-[(4-nitrophenyl)ethynyl]-2,3,5,6-tetrafluorobromobenzene
  参考文献：
  名称：

  Specific interaction modes in the crystal structures of oligofluorinated tolanes featuring additional electron donor and acceptor groups

  摘要：

  A series of partially fluorinated and specifically para-substituted tolanes (1-4) have been synthesized via palladium-catalyzed Sonogashira cross-coupling reaction. The single-crystal structures have been determined by X-ray diffraction. The molecules adopt a geometry being more or less disturbed from planarity due to crystal packing effects. The packing structures are characterized by the formation of molecular stacks achieved through different modes of pi center dot center dot center dot pi interaction and being accomplished by other types of weak interactions including hydrogen bonds as well as bromo and in particular fluoro involved contacts. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2011.11.009
• 作为产物：
  描述：

  4-硝基碘苯 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 氨 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 16.0h， 生成 1-Pentafluorophenyl-2-p-nitro-phenylacetylene
  参考文献：
  名称：

  Specific interaction modes in the crystal structures of oligofluorinated tolanes featuring additional electron donor and acceptor groups

  摘要：

  A series of partially fluorinated and specifically para-substituted tolanes (1-4) have been synthesized via palladium-catalyzed Sonogashira cross-coupling reaction. The single-crystal structures have been determined by X-ray diffraction. The molecules adopt a geometry being more or less disturbed from planarity due to crystal packing effects. The packing structures are characterized by the formation of molecular stacks achieved through different modes of pi center dot center dot center dot pi interaction and being accomplished by other types of weak interactions including hydrogen bonds as well as bromo and in particular fluoro involved contacts. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2011.11.009

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。
• Synthesis of substituted polyfluoro-aromatic acetylenes
  作者：Yadong Zhang、Jianxun Wen

  DOI：10.1016/s0022-1139(00)80347-4

  日期：1991.5

  Reaction of pentafluoro-aromatic acetylene compounds with large excesses of nucleophilic agents using K2CO3 as base gave polysubstituted and monosubstituted polyfluoro-aromatic acetylenes.

  以K 2 CO 3为碱，使五氟-芳族乙炔化合物与大量过量的亲核试剂反应，得到多取代和单取代的多氟-芳族乙炔。