octafluoro dipyridyl-(4,4') | 3511-91-9

• 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: octafluoro dipyridyl-(4,4')
• 英文别名: octafluoro-4,4'-bipyridine；perfluoro-4,4'-bipyridyl；perfluoro-4,4'-dipyridyl；2,3,5,6,2',3',5',6'-octafluoro-[4,4']bipyridinyl；Octafluor-4,4'-bipyridyl；Octafluor-4,4'-dipyridyl；2,3,5,6-tetrafluoro-4-(2,3,5,6-tetrafluoropyridin-4-yl)pyridine
• CAS: 3511-91-9
• 化学式: C₁₀F₈N₂
• 分子量: 300.111
• InChiKey: JOKKNKLCVFPMHP-UHFFFAOYSA-N

物化性质

• 熔点：
  81-82 °C
• 沸点：
  65-70 °C(Press: 0.4 Torr)
• 密度：
  1.716±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  二乙胺 、 octafluoro dipyridyl-(4,4') 以 乙醇 为溶剂， 反应 10.0h， 以50%的产率得到2,2'-di-N,N'-diethylamino-3,3',5,5',6,6'-hexafluoro-4,4'-bipyridine
  参考文献：
  名称：

  Octafluoro-4,4′-bipyridine and its derivatives: Synthesis, molecular and crystal structure

  摘要：

  The structure and chemical properties of perfluoro-4,4'-bipyridine have been studied. It was found that octafluoro-4,4'-bipyridine is a quite electron deficient system stable to the action of alkylating agents and sensitive to nucleophilic substitution of fluorine atoms. Depending on the reaction conditions and reagents used products could be obtained in which two and six fluorine atoms are substituted by nucleophiles. For all isolated compounds X-ray structure determination has been performed and the main peculiarities of the molecular and crystal structure of fluorine-containing bipyridines have been determined. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2009.11.022
• 作为产物：
  描述：

  2,3,5,6-四氟吡啶 在 iron(III) chloride 、 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex 、 氧气 作用下， 以 四氢呋喃 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 48.0h， 以54%的产率得到octafluoro dipyridyl-(4,4')
  参考文献：
  名称：

  Nickel, Manganese, Cobalt, and Iron-Catalyzed Deprotonative Arene Dimerization

  摘要：

  A number of first-row transition metal salts catalyze deprotonative dimerization of acidic arenes. Under the atmosphere of oxygen, nickel, manganese, cobalt, and Iron chlorides have been shown to dimerize five- and six-membered ring heterocycles as well as electron-poor arenes. Both tetramethylpiperidide and dicyclohexylamide bases can be employed; however, the former afford slightly higher yields.

  DOI：

  10.1021/ol902970z

文献信息

• Perfluorozinc aromatics by direct insertion of zinc into C–F or C–Cl bonds
  作者：Alexey O Miller、Vyacheslav I Krasnov、Dietmar Peters、Vyacheslav E Platonov、Ralf Miethchen

  DOI：10.1016/s0040-4039(00)00527-x

  日期：2000.5

  For the first time perfluoroaromatic organozinc compounds were obtained by direct action of zinc on C–F bonds in the presence of metal salts (SnCl2, CuCl2, ZnBr2). The reactions are accelerated by ultrasound. The scope of the method can be extended to polyfluoroaromatics which contain other halogen atoms (Cl) in the aromatic ring.

  首次通过在金属盐（SnCl 2，CuCl 2，ZnBr 2）存在下锌对C-F键的直接作用获得全氟芳族有机锌化合物。反应通过超声加速。该方法的范围可以扩展到在芳族环中包含其他卤素原子（Cl）的多氟芳族化合物。
• Chemistry of the metal carbonyls. Part LII. Complexes derived from 4,4′-octafluorobipyridyl and some 4-substituted tetrafluoropyridines
  作者：M. Green、Alison Taunton-Rigby、F. G. A. Stone

  DOI：10.1039/j19680002762

  日期：——

  4′-octafluorobipyridyl, 4-pentafluorophenyltetrafluoropyridine, 4-phenyltetrafluoropyridine, 4-aminotetrafluoropyridine, or 4-bromotetrafluoropyridine with the anions [Re(CO)5]– and [(π-C5H5)Fe(CO)2]– affords complexes containing polyfluoroheterocyclic rings σ-bonded to rhenium or iron. Treatment of tetrafluoro-pyridinemagnesium bromide with bis(triphenylphosphine)nickel dichloride yields [(C6H5)3P]2Ni(σ-C5F4N)2

  通过用五氟吡啶处理三甲基锡锂，可以高收率制备4,4'-八氟联吡啶。4,4'-八氟联吡啶，4-五氟苯基四氟吡啶，4-苯基四氟吡啶，4-氨基四氟吡啶或4-溴四氟吡啶与阴离子[Re（CO）5 ] –和[（π- C 5 H 5）Fe（CO）2 ] –提供含有结合到rh或铁上的σ的多氟杂环的配合物。用双（三苯基膦）二氯化镍处理四氟吡啶溴化镁，可制得[（C 6 H 5）3 P] 2 Ni（σ- C 5 F 4 N）2。
• Polyhalogenoheterocyclic compounds—321
  作者：R.D. Chambers、W.K.R. Musgrave、C.R. Sargent、F.G. Drakesmith

  DOI：10.1016/s0040-4020(01)92434-2

  日期：1981.1

  Electrochemical reduction of pentafluoropyridine and other polyhalopyridines gives bipyridyl derivatives etc. and it is inferred from the structures of the products that, in the intermediate radical-anion, charge- and spin-density is concentrated at the 1- and 4-positions. This is further supported by measurement of Ep12 values. Trapping experiments with hydroquinone and carbon dioxide are described

  五氟吡啶和其他聚卤吡啶的电化学还原反应生成联吡啶衍生物等，从产物的结构推断，在中间体自由基阴离子中，电荷和自旋密度集中在1和4位。Ep 12值的测量进一步支持了这一点。描述了对苯二酚和二氧化碳的捕集实验。
• Heterocyclic polyfluoro-compounds. Part XII. Synthesis and some reactions of 2,3,5,6-tetrafluoro-4-iodopyridine
  作者：R. E. Banks、R. N. Haszeldine、E. Phillips、I. M. Young

  DOI：10.1039/j39670002091

  日期：——

  oxidation of 2,3,5,6-tetrafluoro-4-hydrazinopyridine in the presence of methyl iodide or, preferably, by reaction of pentafluoropyridine with sodium iodide in dimethylformamide, is readily converted into 2,3,5,6-tetrafluoropyridylmagnesium iodide or 2,3,5,6-tetrafluoropyridyllithium; some reactions of these organometallic compounds are described. Hydroxide ion, methoxide ion, and ammonia attack 2,3,5

  2,3,5,6-四氟-4-碘吡啶，是通过在甲基碘存在下氧化2,3,5,6-四氟-4-肼基吡啶制备的，或最好是使五氟吡啶与碘化钠在二甲基甲酰胺中反应制得容易地转化为2,3,5,6-四氟吡啶基碘化镁或2,3,5,6-四氟吡啶基锂; 描述了这些有机金属化合物的一些反应。氢氧根离子，甲醇根离子和氨在2位上攻击2,3,5,6-四氟-4-碘吡啶，生成相应的2-取代的三氟-4-碘吡啶，但碘离子似乎在4位上进攻。与碘取代形成2,3,5,6-四氟吡啶基阴离子。通过乌尔曼技术将四氟-4-碘吡啶偶联，得到全氟-4,4'-联吡啶基。3-氯-2,4,5的反应
• From hypervalent xenon difluoride and aryliodine(III) difluorides to onium salts: Scope and limitation of acidic fluoroorganic reagents in the synthesis of fluoroorgano xenon(II) and iodine(III) onium salts
  作者：Anwar Abo-Amer、Hermann-Josef Frohn、Christoph Steinberg、Ulrich Westphal

  DOI：10.1016/j.jfluchem.2006.05.008

  日期：2006.10

  RfBF2 are in general suitable reagents to transform XeF2 and RIF2 into the corresponding onium tetrafluoroborate salts [RfXe][BF4] and [R(Rf)I][BF4], respectively. (4-C5F4N)BF2 and trans-CF3CFCFBF2 which represent boranes of high acidity form no Xe–C onium salts in reactions with XeF2 but give the desired iodonium salts with RIF2 (R = C6F5, o-, m-, p-C6FH4). The reaction of (4-C5F4N)BF2 with XeF2 ends with

  通常，氟化有机二氟硼烷R f BF 2是将XeF 2和RIF 2分别转化为相应的四氟硼酸盐[R f Xe] [BF 4 ]和[R（R f）I] [BF 4 ]的试剂。（4-C 5 F 4 N）BF 2和反式-CF 3 CFCFBF 2代表高酸性硼烷，在与XeF 2反应时不形成Xe-C鎓盐，但与RIF 2形成所需的碘鎓盐（R = C 6 ˚F 5，o-，m-，p -C 6 FH 4）。（4-C 5 F 4 N）BF 2与XeF 2的反应以XeF 2-硼烷加合物终止。当C 6 F 5 XeF与Cd（4-C 5 F 4 N ）反应时，获得第一个Xe-（4-C 5 F 4 N）化合物C 6 F 5 Xe（4-C 5 F 4 N）。）2。我们描述了（4-C 5 F 4 N）IF 2的合成和（4-C 5 F 4 N）IF 2和C 6 F 5 IF 2与（4-C 5 F 4 N）BF 2的反应。类似于[（4-C