E,E-1,4-bis[2-(2,3,4,5,6-pentafluorophenyl)ethenyl]benzene | 128207-26-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: E,E-1,4-bis[2-(2,3,4,5,6-pentafluorophenyl)ethenyl]benzene
• 英文别名: trans,trans-1,4-bis(2-pentafluorophenyl-ethenyl)-benzene；1,4-bis(2,3,4,5,6-pentafluorostyryl)benzene；trans,trans-1,4-bis(2-pentafluorophenylethenyl)benzene；1,2,3,4,5-pentafluoro-6-[(E)-2-[4-[(E)-2-(2,3,4,5,6-pentafluorophenyl)ethenyl]phenyl]ethenyl]benzene
• CAS: 128207-26-1
• 化学式: C₂₂H₈F₁₀
• 分子量: 462.29
• InChiKey: GMFARDGUQMIGES-KQQUZDAGSA-N

物化性质

• 沸点：
  408.5±45.0 °C(Predicted)
• 密度：
  1.551±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  E,E-1,4-bis[2-(2,3,4,5,6-pentafluorophenyl)ethenyl]benzene 在 palladium on activated charcoal 氢气 作用下， 生成 1,4-bis(2,3,4,5,6-pentamethylphenethyl)benzene
  参考文献：
  名称：

  四氟[2.2]环芳烷中的环过环失活。开放链模拟物的亲电反应性

  摘要：

  制备了最相似于4,5,7,8-四氟[2.2]对环环烷（1）的结构的开链类似物（3）。与（1）相反，（3）经历苯环的乙酰化。该观察结果提供了进一步的证据，证明（1）不能进行亲电取代主要归因于四氟苯基环对苯的跨环失活，而归因于通过sigma键网络的感应作用。

  DOI：

  10.1016/s0022-1139(00)80461-3
• 作为产物：
  描述：

  五氟苯甲醛 在 dirhodium tetraacetate 氢氧化钾 、 二正丁基碲 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 52.07h， 生成 E,E-1,4-bis[2-(2,3,4,5,6-pentafluorophenyl)ethenyl]benzene
  参考文献：
  名称：

  醛与全氟苯基重氮甲烷通过碲化钇反应，由Rh 2（OAc）4催化形成反式烯烃

  摘要：

  Rh 2（OAc）4可通过全氟苯基重氮甲烷与活化的芳基醛通过硫代叶立德中间体的反应催化含全氟苯基的反式环氧化物的形成。相反，在相同的反应条件下，通过碲化碲中间体以优异的产率获得了反式烯烃。

  DOI：

  10.1016/j.tetlet.2006.06.065

文献信息

• Transition-Metal-Catalyzed Formation of <i>trans </i>Alkenes via Coupling of Aldehydes
  作者：Shifa Zhu、Yuanxi Liao、Shizheng Zhu

  DOI：10.1021/ol036197s

  日期：2004.2.1

  [reaction: see text] Rh(2)(OAc)(4) catalyzed the formation of exclusively trans fluorinated alkenes from aldehydes and pentafluorobenzaldehyde tosylhydrazone salts, which were readily prepared from pentafluorobenzaldehyde using the Bamford-Stevens reaction. A series of pentafluorophenyl-containing alkenes were synthesized from aldehydes in moderate to good yields under mild reaction conditions in a

  [反应：见正文] Rh（2）（OAc）（4）催化了醛和五氟苯甲醛甲苯磺酰salts盐的完全反式氟化烯烃的形成，它们很容易使用Bamford-Stevens反应由五氟苯甲醛制备。在温和的反应条件下，通过一锅反应，由醛以中等至良好的收率合成了一系列含五氟苯基的烯烃。这是首次报道将两种不同的醛偶合以仅形成反式烯烃。
• Phenyl−Perfluorophenyl Stacking Interactions:  Topochemical [2+2] Photodimerization and Photopolymerization of Olefinic Compounds
  作者：Geoffrey W. Coates、Alex R. Dunn、Lawrence M. Henling、Joseph W. Ziller、Emil B. Lobkovsky、Robert H. Grubbs

  DOI：10.1021/ja974072a

  日期：1998.4.1

  The face-to-face stacking interaction between phenyl and perfluorophenyl groups is emerging as a common noncovalent interaction. To explore the generality of this supramolecular synthon, the solid-state packing structure and reactivity of several monoolefins and diolefins substituted with phenyl and perfluorophenyl groups was investigated. Of the seven crystalline or cocrystalline materials investigated, six were found to undergo a photochemically induced [2+2] reaction in the solid state. By determining the stereochemistry of the photoproduct and/or X-ray structural analysis of the olefinic precursors, the stacked interaction between phenyl and perfluorophenyl groups in the photoactive crystals were revealed.
• Fluorinated Distyrylbenzene Chromophores:  Effect of Fluorine Regiochemistry on Molecular Properties and Solid-State Organization
  作者：Michelle L. Renak、Glenn P. Bartholomew、Shujun Wang、Pascal J. Ricatto、Rene J. Lachicotte、Guillermo C. Bazan

  DOI：10.1021/ja984440q

  日期：1999.9.1
• Rh2(OAc)4-catalyzed formation of trans-alkenes from the reaction of aldehydes with perfluorophenyl diazomethane through tellurium ylide
  作者：Shifa Zhu、Chunhui Xing、Wan Pang、Shizheng Zhu

  DOI：10.1016/j.tetlet.2006.06.065

  日期：2006.8

  Rh2(OAc)4 can catalyze the formation of perfluorophenyl-containing trans-epoxides from the reactions of perfluorophenyl diazomethane with activated aryl aldehydes through sulfur ylide intermediate. In contrast, under the same reaction conditions, trans-alkenes were obtained in excellent yield through tellurium ylide intermediates.

  Rh 2（OAc）4可通过全氟苯基重氮甲烷与活化的芳基醛通过硫代叶立德中间体的反应催化含全氟苯基的反式环氧化物的形成。相反，在相同的反应条件下，通过碲化碲中间体以优异的产率获得了反式烯烃。
• Transannular Deactivation in Tetrafluoro[2.2]Paracyclophane. Electrophilic Reactivity of its Open-Chain Analog
  作者：Robert Filler、Joseph E. Gadomski

  DOI：10.1016/s0022-1139(00)80461-3

  日期：1990.4

  resembles the structure of 4,5,7,8-tetrafluoro[2.2]paracyclophane (1) has been prepared. In contrast to (1), (3) undergoes acetylation of the phenyl ring. This observation provides further evidence that the failure of (1) to undergo electrophilic substitution can be attributed primarily to transannular deactivation of the phenyl by the tetrafluorophenyl ring and much less to an inductive effect through

  制备了最相似于4,5,7,8-四氟[2.2]对环环烷（1）的结构的开链类似物（3）。与（1）相反，（3）经历苯环的乙酰化。该观察结果提供了进一步的证据，证明（1）不能进行亲电取代主要归因于四氟苯基环对苯的跨环失活，而归因于通过sigma键网络的感应作用。