N-butyl-2,3,5,6-tetrafluoropyridin-4-amine | 370556-61-9

• 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: N-butyl-2,3,5,6-tetrafluoropyridin-4-amine
• 英文别名: N-n-Butyl-4-aminotetrafluoropyridine
• CAS: 370556-61-9
• 化学式: C₉H₁₀F₄N₂
• 分子量: 222.185
• InChiKey: QKXWSEBTWLNNQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  24.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-butyl-2,3,5,6-tetrafluoropyridin-4-amine 在 盐酸 、 sodium nitrite 作用下， 反应 3.0h， 以85%的产率得到N-nitroso-N-n-butyl-4-aminotetrafluoropyridine
  参考文献：
  名称：

  Polyfluorinated arylnitrosamines

  摘要：

  N-Methyl-, N-n-butyl-, N-t-butylperfluoroarylamines undergo nitrosation with nitrous acid to give the corresponding N-nitroso derivatives. Perfluoroaryl groups were selected from the benzene, indane, biphenyl, naphthalene and pyridine series. According to H-1 and F-19 NMR spectra, N-nitroso-N-methyl derivatives of polyfluoroarenes, consist of E and Z isomers with the former prevailing. The more bulky n-butyl group promotes an increase in the formation of Z isomers. Only Z isomers have been obtained from N-t-butyl derivatives of perfluorinated 4-toluidine and 4-aminopyridine. The structure of the Z isomer of N-nitroso-N-methylperfluoro-4-toluidine is confirmed by X-ray data. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-1139(01)00567-x
• 作为产物：
  描述：

  2,3,5,6-四氟吡啶 、 O-benzoyl-N-butylhydroxylamine 在 1,10-菲罗啉 、 copper diacetate 、 lithium tert-butoxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 以46%的产率得到N-butyl-2,3,5,6-tetrafluoropyridin-4-amine
  参考文献：
  名称：

  Copper-Catalyzed Direct Amination of Polyfluoroarenes and Azoles with Hydroxylamines and Its Application to the Synthesis of 3-Aminobenzoheteroles

  摘要：

  开发了一种铜催化的亲电性乌姆堡胺化策略，用于直接实现多氟芳烃和1,3-唑的C-H胺化。基于铜的胺化反应具有鲁棒性，可以轻松地在克规模上扩大规模。还描述了其在邻炔基苯酚和苯胺的累积亲电胺化反应中的应用，用于合成3-氨基苯并呋喃和吲哚。

  DOI：

  10.1055/s-0031-1289715

文献信息

• Copper-Catalyzed Direct Amination of Electron-Deficient Arenes with Hydroxylamines
  作者：Naoki Matsuda、Koji Hirano、Tetsuya Satoh、Masahiro Miura

  DOI：10.1021/ol200855t

  日期：2011.6.3

  The C–H amination of electron-deficient arenes such as polyfluoroarenes and azole compounds with O-acylated hydroxylamines effectively proceeds in the presence of a copper catalyst even at room temperature to provide the corresponding anilines and aminoazoles in good yields.

  在铜催化剂的存在下，即使在室温下，缺电子芳烃（如多氟芳烃和唑化合物）的C–H胺化也能在O酰化的羟胺下有效地进行，从而以高收率提供相应的苯胺和氨基唑。
• Continuous flow glassware reactors for the laboratory
  作者：Richard D. Chambers、Graham Sandford、Jelena Trmcic

  DOI：10.1016/j.jfluchem.2007.07.010

  日期：2007.12

  Simple, general use continuous flow glassware reactors that are constructed by standard glass blowing techniques have been designed and used for various nucleophilic aromatic substitution reactions. The glassware flow reactors, consisting of a reaction channel that is 0.5 mm in diameter and may possess a range of inlet and outlet ports, provide the opportunity for research scientists to use inexpensive

  已经设计了通过标准的玻璃吹制技术构造的简单，通用的连续流玻璃器皿反应器，并将其用于各种亲核芳族取代反应。玻璃器皿流动反应器由直径为0.5毫米的反应通道组成，并可能具有一定范围的入口和出口，这为研究科学家提供了在实验室环境中使用廉价，操作简便的连续流方法的机会。由五氟吡啶通过连续的亲核芳族取代，在单个连续流动过程中制备了短系列的2-烷氧基-4-氨基三氟吡啶衍生物。
• Cyclising peptides
  申请人：The University of Durham

  公开号：US10906932B2

  公开（公告）日：2021-02-02

  A method for preparing a cyclic peptide, derivative or analogue thereof is described. The method comprises contacting a peptide, derivative or analogue thereof with a fluoro-heteroaromatic compound to cyclise the peptide, derivative or analogue thereof.

  本发明描述了一种制备环肽、其衍生物或类似物的方法。该方法包括将多肽、衍生物或其类似物与氟代芳香族化合物接触，使多肽、衍生物或其类似物环化。
• Polyfluorinated arylnitramines
  作者：V.E Platonov、A Haas、M Schelvis、M Lieb、K.V Dvornikova、O.I Osina、Yu.V Gatilov

  DOI：10.1016/s0022-1139(01)00367-0

  日期：2001.7

  N-methyl- and N-butylperfluoroarylamines are transformed by HNO3 into N-nitro-N-methyl- and N-nitro-N-butylperfluoroarylamines. These reactions were used to synthesise N-nitro-N-methylpentafluoroaniline and its p-CF3. -CN, -C6F5 substituted derivatives, N-nitro-N-methylperfluoro-2,4-xylidine, N-nitro-N-methyl-4-aminotetrafluoropyridine N-nitro-N-methyl 5-aminoperfluoroindane, N-nitro-N-methyl-2- aminoheptafluoronaphthalene. 4,4 ' -bis(N-nitro-N- merhylamino)octafluorobiphenyl from 4,4 ' -bis(N-methylamino)octafluorobiphenyl, N-nitro-N-n-butylpentafluoroaniline, N-nitro-N-n-butylperfluoro-p-toluidine, N-nitro-N-n-butyl-4-aminotetrafluoropyridine and N-nitro-bis( perfluoro-p-tolyl)amine. Tetrafluoro-p-benzoquinone and heptafluoro-p-toluquinol were obtained from N-methylpentafluoroanilinz and N-methylperfluoro-p-toluidine, respectively, under the action of a mixture of HNO3 and H2SO4 The X-ray crystal structure of N-nitro-N-methylperfluoro-p-toluidine was determined. (C) 2001 Elsevier Science B.V. All rights reserved.
• Cyclising Peptides
  申请人：The University of Durham

  公开号：US20170204134A1

  公开（公告）日：2017-07-20

  A method for preparing a cyclic peptide, derivative or analogue thereof is described. The method comprises contacting a peptide, derivative or analogue thereof with a fluoro-heteroaromatic compound to cyclise the peptide, derivative or analogue thereof.