4-lithium 2,3,5,6-tetrafluoro pyridine | 30697-78-0

• 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-lithium 2,3,5,6-tetrafluoro pyridine
• 英文别名: 2,3,5,6-tetrafluoropyrid-4-yllithium
• CAS: 30697-78-0
• 化学式: C₅F₄LiN
• 分子量: 156.996
• InChiKey: OYSLUEYQZXJVBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.43
• 重原子数：
  11.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.89
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  4-lithium 2,3,5,6-tetrafluoro pyridine 在 五氟化砷 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 20.5h， 生成 2,3,5,6-tetrafluoropyrid-4-yldifluoroborane
  参考文献：
  名称：

  Polyfluoroorganotrifluoroborates and -difluoroboranes: interesting materials in fluoroorgano and fluoroorgano-element chemistry

  摘要：

  The aimed introduction of the polyfluoroorgano groups (4-C5F4N), C6F13C2H4, and C2F5 into methoxy group-containing boron electrophiles is reported. The new compounds obtained after transformations K[(4-C5F4N)BF3], (4-C5F4N)BF2, K[C6F13C2H4BF3], C6F13C2H4BF2, K[(C2F5)(2)B(OMe)(2)], and K[(C2F5)(2)BF2] were isolated and characterised. Additionally some of their precursors as there are Li(4-C5F4N), Li[(4-C5F4N)B(OMe)(3)], (4-C5F4N)B(OH)(2) and the by-products Li[(4-C5F4N)(2)B(OMe)(2)], (4-C5F4NOOH, and K[(4-C5F4N)(2)BF2] are described. The usefulness of polyfluoroorganodifluoroboranes for introducing polyfluoroorgano groups into hypervalent FE-F bonds is demonstrated by the synthesis of [C6F5(4-C5F4N)I][BF4] and [p-FC6H4(trans-CF3CF=CF)I][BF4]. (C) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2004.09.011
• 作为产物：
  描述：

  2,3,5,6-四氟吡啶 在 正丁基锂 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 1.5h， 生成 4-lithium 2,3,5,6-tetrafluoro pyridine
  参考文献：
  名称：

  Polyfluoroorganotrifluoroborates and -difluoroboranes: interesting materials in fluoroorgano and fluoroorgano-element chemistry

  摘要：

  The aimed introduction of the polyfluoroorgano groups (4-C5F4N), C6F13C2H4, and C2F5 into methoxy group-containing boron electrophiles is reported. The new compounds obtained after transformations K[(4-C5F4N)BF3], (4-C5F4N)BF2, K[C6F13C2H4BF3], C6F13C2H4BF2, K[(C2F5)(2)B(OMe)(2)], and K[(C2F5)(2)BF2] were isolated and characterised. Additionally some of their precursors as there are Li(4-C5F4N), Li[(4-C5F4N)B(OMe)(3)], (4-C5F4N)B(OH)(2) and the by-products Li[(4-C5F4N)(2)B(OMe)(2)], (4-C5F4NOOH, and K[(4-C5F4N)(2)BF2] are described. The usefulness of polyfluoroorganodifluoroboranes for introducing polyfluoroorgano groups into hypervalent FE-F bonds is demonstrated by the synthesis of [C6F5(4-C5F4N)I][BF4] and [p-FC6H4(trans-CF3CF=CF)I][BF4]. (C) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2004.09.011

文献信息

• 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。
• 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
• Polyfluoroheterocyclic compounds. Part XVI. Tetrafluoropyridine-3- and -4-carbaldehydes and some derivatives of the latter
  作者：R. D. Chambers、C. A. Heaton、W. K. R. Musgrave、L. Chadwick

  DOI：10.1039/j39690001700

  日期：——

  Tetrafluoro-3- and -4-lithiopyridines behave normally in reacting with N-methylformanilide to give tetrafluoropyridine-3- and -4-carbaldehydes. The 4-carbaldehyde can be oxidised and reduced to the corresponding acid and carbinol respectively. It also reacts with pentafluorophenyl-lithium and tetrafluoro-4-lithiopyridine to give the corresponding secondary alcohols, which can be oxidised to pentafluorophenyl

  四氟-3-和-4-硫代吡啶与N-甲基甲酰苯胺反应生成四氟吡啶-3-和-4-甲醛。4-甲醛可以被氧化并还原为相应的酸和甲醇。它还与五氟苯基锂和四氟-4-锂硫代吡啶反应，得到相应的仲醇，可以将其氧化为五氟苯基四氟-4-吡啶基和双（四氟-4-吡啶基）酮。后者将与更多的四氟-4-锂硫代吡啶反应，得到三（四氟-4-吡啶基）甲醇，也可以由四氟异烟酸乙酯和四氟-4-硫代吡啶制备。
• Polyfluoroheterocyclic compounds. Part XIV. Some reactions of tetrafluoroisonicotinic acid and pentafluorobenzoic acid
  作者：R. D. Chambers、C. A. Heaton、W. K. R. Musgrave

  DOI：10.1039/j39680001933

  日期：——

  The anhydride and acid chloride of tetrafluoroisonicotinic acid have been made and used to prepare substituted amides and hydrazines. NN′-Di(tetrafluoroisonicotinoyl)hydrazine undergoes cyclodehydration when treated with phosphoryl chloride or phosphorus pentasulphide, to give 2,5-di(tetrafluoro-4-pyridyl)-1,3,4-oxadiazole and -thiadiazole respectively. Tetrafluoroisonicotinoyl fluoride reacts with

  已经制备了四氟异烟酸的酸酐和酰氯，并用于制备取代的酰胺和肼。神经网络当用磷酰氯或五硫化二磷处理时，'-二（四氟异烟酰基）肼经历环脱水作用，分别得到2,5-二（四氟-4-吡啶基）-1,3,4-恶二唑和-噻二唑。四氟异二十二碳酰氟与由六氟丙烯和氟离子制备的七氟异丙基阴离子反应，得到全氟（异丙基4-吡啶基酮）。其中一些反应已与五氟苯甲酰氯和五氟苯甲酰氟重复进行。除了与七氟异丙基阴离子形成酮外，后者还在环中进行亲核取代，从而得到全氟（异丙基4-异丙基苯基酮）。
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: F: PerFHalOrg.4, 1.3.3.8, page 33 - 59
  作者：

  DOI：——

  日期：——