4,4'-bis[1H,1H,2H,2H,3H,3H-perfluorononyl]-2,2'-bipyridine | 241481-85-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4,4'-bis[1H,1H,2H,2H,3H,3H-perfluorononyl]-2,2'-bipyridine
• 英文别名: 4,4'-bis(perfluoro-1H,1H,2H,2H,3H,3H-nonyl)-2,2'-bipyridine；4,4'-(C6F13CH2CH2CH2)2-2,2'-bipyridine；4-(4,4,5,5,6,6,7,7,8,8,9,9,9-Tridecafluorononyl)-2-[4-(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononyl)pyridin-2-yl]pyridine；4-(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononyl)-2-[4-(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononyl)pyridin-2-yl]pyridine
• CAS: 241481-85-6
• 化学式: C₂₈H₁₈F₂₆N₂
• 分子量: 876.423
• InChiKey: GQJRYJOMAUEVHZ-UHFFFAOYSA-N

物化性质

• 沸点：
  477.6±45.0 °C(Predicted)
• 密度：
  1.510±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12.4
• 重原子数：
  56
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  28

反应信息

• 作为反应物：
  描述：

  五羰基氯铼(I) 、 4,4'-bis[1H,1H,2H,2H,3H,3H-perfluorononyl]-2,2'-bipyridine 以 甲苯 为溶剂， 生成 fac-ReCl(4,4'-(C₆F₁₃CH₂CH₂CH₂)2-2,2'-bipyridine)(CO)3
  参考文献：
  名称：

  氟化ReCl（4,4'-R 2 -2,2'-联吡啶）（CO）3配合物的合成及其在CH 3 CN和超临界CO 2中的光物理特性

  摘要：

  带有氟化烷基配体4,4'-（C 6 F 13 CH 2 CH 2 CH 2）2 -2,2'-联吡啶（1a）和4,4的两个新的可溶于CO 2的可溶于I 2的bi（I）联吡啶配合物制备了'-（C 8 F 17 CH 2 CH 2 CH 2）2 -2,2'-联吡啶（1b），并在CH 3 CN和超临界CO 2中研究了它们的光物理性质。这些络合物在CH 3中的电化学和光谱表征CN表明，三个亚甲基单元有效地使联吡啶环和the中心与氟化烷基链的吸电子作用隔离。用三乙胺对金属到配体的电荷转移激发态进行还原淬灭，发现超临界CO 2中的淬灭速率常数仅比CH 3 CN中的淬灭速率慢6倍。

  DOI：

  10.1021/ic8019556
• 作为产物：
  描述：

  4,4'-二甲基-2,2'-联吡啶 、 1-碘-1H,1H,2H,2H-全氟辛烷 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以40%的产率得到4,4'-bis[1H,1H,2H,2H,3H,3H-perfluorononyl]-2,2'-bipyridine
  参考文献：
  名称：

  新型甲基三氧or /（马尾氟）2,2'-联吡啶催化剂对烯烃的高效选择性环氧化

  摘要：

  合成了甲基三氧methyl（MTO）和双（氟马尾）2,2'-联吡啶（bpy-F n）之间的新型配合物，并在氟催化下用过氧化氢氧化烯烃。获得了高转化率和相应环氧化物的产率。

  DOI：

  10.1002/adsc.201000032
• 作为试剂：
  描述：

  咪唑 、 4-甲氧基苯硼酸 在 4,4'-bis[1H,1H,2H,2H,3H,3H-perfluorononyl]-2,2'-bipyridine 、 氧气 、 copper diacetate 作用下， 以 水 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 以78%的产率得到1-(4-甲氧基苯基)-1H-咪唑
  参考文献：
  名称：

  Efficient use of a surfactant for copper-catalyzed coupling reaction of arylboronic acids with imidazoles in water

  摘要：

  Copper-catalyzed oxidative coupling of arylboronic acids with imidazoles in water was realized by using an amphiphilic surfactant. By choosing an appropriate surfactant, reactions of a variety of arylboronic acids proceeded smoothly under mild and base-free conditions, providing an efficient, practical, and greener method for the synthesis of N-arylimidazoles. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.07.042

文献信息

• An Efficient and Selective Epoxidation of Olefins with Novel Methyltrioxorhenium/(Fluorous Ponytailed) 2,2′-Bipyridine Catalysts
  作者：Raffaele Saladino、Maria Cristina Ginnasi、Daniela Collalto、Roberta Bernini、Claudia Crestini

  DOI：10.1002/adsc.201000032

  日期：——

  Novel complexes between methyltrioxorhenium (MTO) and bis(fluorous‐ponytailed) 2,2′‐bipyridines (bpy‐Fn) were synthesized and used for the oxidation of alkenes with hydrogen peroxide under fluorous catalysis. High conversions and yields of the corresponding epoxides were obtained.

  合成了甲基三氧methyl（MTO）和双（氟马尾）2,2'-联吡啶（bpy-F n）之间的新型配合物，并在氟催化下用过氧化氢氧化烯烃。获得了高转化率和相应环氧化物的产率。
• [EN] NOVEL FLUORINATED METAL COMPLEXES<br/>[FR] NOUVEAUX COMPLEXES MÉTALLIQUES FLUORÉS
  申请人：TOZZI GREEN S P A

  公开号：WO2019029789A1

  公开（公告）日：2019-02-14

  New improved fluorinated metal complexes based on bi pyridine ligands are disclosed. The complexes are characterized by a balance of fluorination among specific substituents attached to the pyridine rings, i.e. the overall number of fluorine atoms throughout said substituents ranges from 7 to 26 and, at the same time, the difference in number of fluorine atoms between said substituents is equal or less than 13. The new complexes advantageously combine a good solubility in polar solvents, in particular alcoholic ones, to an efficient photovoltaic performance.

  基于双吡啶配体的新改进的氟化金属配合物已经公开。这些配合物的特点是在连接到吡啶环的特定取代基之间实现氟化平衡，即整体氟原子数量在这些取代基中的范围为7至26，并且同时，这些取代基之间的氟原子数量差异等于或小于13。这些新配合物有利地将良好的溶解性与极高的光伏性能结合在一起，特别是在极性溶剂，尤其是醇类溶剂中。
• Fluorous modification of 2,2′-bipyridine
  作者：Byron L. Bennett、Kathleen A. Robins、Ryan Tennant、Kyler Elwell、Felice Ferri、Inna Bashta、Grant Aguinaldo

  DOI：10.1016/j.jfluchem.2005.09.019

  日期：2006.1

  A series of 2,2'-bipyridines featuring fluorinated alkyl groups [(CH2)(3)(CF2)(x)CF3: X = 0, (1); 5, (2); 7, (3); 9 (4)] appended in the 4 and 4' positions have been prepared. 1-4 were characterized by spectroscopy and physical methods including partition coefficient (biphase: perfluoromethylcyclohexane/toluene) and cyclic voltammetry (THF). Ab-initio calculations of vertical ionization potentials (VIPs) for 1-4 confirm the insulating role of the methylene spacers as the electrochemical reduction potentials of 1-4 are almost identical to that of 2,2'-bipyridine. Calculations for (CH2)(n)CF3 derivatives (n = 0-10) describe a limit for impact of the CF3 group through 9-10 methylenes. From both physical and theoretical data fluorinated alkyl groups of the formula -(CH2)(3)(CF2)(x)CF3 [x = 0-9] are inductively equivalent to a hydrogen substituent when appended to the bipyridine moiety. (C) 2005 Elsevier B.V. All rights reserved.
• Efficient use of a surfactant for copper-catalyzed coupling reaction of arylboronic acids with imidazoles in water
  作者：Kiyofumi Inamoto、Kanako Nozawa、Jun Kadokawa、Yoshinori Kondo

  DOI：10.1016/j.tet.2012.07.042

  日期：2012.9

  Copper-catalyzed oxidative coupling of arylboronic acids with imidazoles in water was realized by using an amphiphilic surfactant. By choosing an appropriate surfactant, reactions of a variety of arylboronic acids proceeded smoothly under mild and base-free conditions, providing an efficient, practical, and greener method for the synthesis of N-arylimidazoles. (C) 2012 Elsevier Ltd. All rights reserved.
• Synthesis of Fluorinated ReCl(4,4′-R₂-2,2′-bipyridine)(CO)₃Complexes and Their Photophysical Characterization in CH₃CN and Supercritical CO₂
  作者：Mark D. Doherty、David C. Grills、Etsuko Fujita

  DOI：10.1021/ic8019556

  日期：2009.3.2

  bearing the fluorinated alkyl ligands 4,4′-(C6F13CH2CH2CH2)2-2,2′-bipyridine (1a), and 4,4′-(C8F17CH2CH2CH2)2-2,2′-bipyridine (1b) have been prepared and their photophysical properties investigated in CH3CN and supercritical CO2. Electrochemical and spectroscopic characterization of these complexes in CH3CN suggests that the three methylene units effectively insulate the bipyridyl rings and the rhenium center

  带有氟化烷基配体4,4'-（C 6 F 13 CH 2 CH 2 CH 2）2 -2,2'-联吡啶（1a）和4,4的两个新的可溶于CO 2的可溶于I 2的bi（I）联吡啶配合物制备了'-（C 8 F 17 CH 2 CH 2 CH 2）2 -2,2'-联吡啶（1b），并在CH 3 CN和超临界CO 2中研究了它们的光物理性质。这些络合物在CH 3中的电化学和光谱表征CN表明，三个亚甲基单元有效地使联吡啶环和the中心与氟化烷基链的吸电子作用隔离。用三乙胺对金属到配体的电荷转移激发态进行还原淬灭，发现超临界CO 2中的淬灭速率常数仅比CH 3 CN中的淬灭速率慢6倍。