N-Methyl-4-aminotetrafluoropyridine | 65171-12-2

• 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-Methyl-4-aminotetrafluoropyridine
• 英文别名: 2,3,5,6-tetrafluoro-N-methylpyridin-4-amine
• CAS: 65171-12-2
• 化学式: C₆H₄F₄N₂
• 分子量: 180.105
• InChiKey: XXVKPBPMLKVSRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.17
• 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-Methyl-4-aminotetrafluoropyridine 在 过氧化双月桂酰 、 sodium hydride 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 3.25h， 生成 4-(ethoxycarbonothioylthio)-5-(N-(3,5,6-trifluoro-4-(N-methylmethylsulfonamido)pyridin-2-yl)acetamido)pentanoate
  参考文献：
  名称：

  自由基ipso-取代导致氟7-氮杂吲哚和氟7-氮杂吲哚的碳-氟键

  摘要：

  报道了碳-氟键在合成上有用的自由基ipso取代的罕见例子，导致高度官能化的5,6-二氟-7-氮杂二氢吲哚。在N-苄基-四唑衍生物的情况下，观察到了意外的氢原子易位和断裂，并损失了分子氮并形成了腈。

  DOI：

  10.1021/ol500985f
• 作为产物：
  描述：

  五氟吡啶 、 甲胺 以 乙醇 为溶剂， 反应 0.5h， 生成 N-Methyl-4-aminotetrafluoropyridine
  参考文献：
  名称：

  自由基ipso-取代导致氟7-氮杂吲哚和氟7-氮杂吲哚的碳-氟键

  摘要：

  报道了碳-氟键在合成上有用的自由基ipso取代的罕见例子，导致高度官能化的5,6-二氟-7-氮杂二氢吲哚。在N-苄基-四唑衍生物的情况下，观察到了意外的氢原子易位和断裂，并损失了分子氮并形成了腈。

  DOI：

  10.1021/ol500985f

文献信息

• Fluoroazaindolines by an Uncommon Radical ipso-Substitution of a C-F Bond
  作者：Yann Laot、Laurent Petit、Ngoc Diem My Tran、Samir Z. Zard

  DOI：10.1071/ch10422

  日期：——

  Trifluoroazaindoline derivatives are prepared using the first synthetically useful radical ipso-substitution of a fluorine atom. The initial procedure has been improved to allow the gram scale synthesis of these building blocks, which can be regioselectively substituted by nucleophiles under mild conditions to rapidly access a library of new molecules. Oxidation to the corresponding fluoroazaindole core has also been accomplished.

  三氟氮杂吲哚啉衍生物的制备首次使用了对合成有用的氟原子同位取代基。对最初的程序进行了改进，从而可以在克级规模上合成这些构筑基块，这些基块可以在温和的条件下被亲核物进行区域选择性取代，从而快速获得新分子库。氧化成相应的氟氮杂环吲哚核心的过程也已经完成。
• 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.
• Identification of orally bioavailable, non-amidine inhibitors of Urokinase Plasminogen Activator (uPA)
  作者：Christopher W. West、Marc Adler、Danny Arnaiz、Deborah Chen、Kieu Chu、Giovanna Gualtieri、Elena Ho、Christoph Huwe、David Light、Gary Phillips、Rebecca Pulk、Drew Sukovich、Marc Whitlow、Shendong Yuan、Judi Bryant

  DOI：10.1016/j.bmcl.2009.08.008

  日期：2009.10

  In this Letter we report the synthesis and evaluation of a series of non-amidine inhibitors of Urokinase Plasminogen Activator (uPA). Starting from compound 1, a significant change provided compounds in which the amidine, binding in the S1 pocket, was replaced with a primary amine. Further modifications led to the identification of potent, selective, and orally bioavailable uPA inhibitors. (C) 2009 Elsevier Ltd. All rights reserved.
• Polyfluorinated arylnitrosamines
  作者：Vyacheslav E. Platonov、Alois Haas、Meinolf Schelvis、Max Lieb、Kira V. Dvornikova、Olga I. Osina、Tatyana V. Rybalova、Yuri V. Gatilov

  DOI：10.1016/s0022-1139(01)00567-x

  日期：2002.3

  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.
• SALEN COMPLEXES WITH DIANIONIC COUNTERIONS
  申请人：Novomer, Inc

  公开号：US20140336354A1

  公开（公告）日：2014-11-13

  The present invention describes metal salen complexes having dianionic counterions. Such complexes can be readily precipitated and provide an economical method for the purification and isolation of the complexes, and are useful to prepare novel polymer compositions.