2,3,4,5,6-pentafluoro-N-methylaniline | 1201-02-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2,3,4,5,6-pentafluoro-N-methylaniline
• 英文别名: N-Methylpentafluoroaniline；methyl(pentafluorophenyl)amine；Benzenamine, 2,3,4,5,6-pentafluoro-N-methyl-
• CAS: 1201-02-1
• 化学式: C₇H₄F₅N
• mdl: MFCD08061543
• 分子量: 197.107
• InChiKey: ZWWAUEAPYBCUMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3,4,5,6-pentafluoro-N-methylaniline 在 sodium nitrite 作用下， 以 溶剂黄146 为溶剂， 反应 20.0h， 以80%的产率得到N-亚硝基-N-甲基五氟苯胺
  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：

  N-Methyl-N-p-toluolsulfonyl-pentafluor-anilin 在 硫酸 作用下， 以 溶剂黄146 为溶剂， 生成 2,3,4,5,6-pentafluoro-N-methylaniline
  参考文献：
  名称：

  水溶液中伯胺、仲胺和叔胺的闪光光解生成及其在该介质中的碳质子化反应研究

  摘要：

  一组九种苯胺（PhC⋮CNH2、PhC⋮CNHCH(CH3)2、PhC⋮CNHC6H11、PhC⋮CNHC6H5、PhC⋮CNHC6F5、PhC⋮CN(CH2)5、PhC⋮CN(CH2CH2)2O、PhC⋮CNHC6H5 CH2CH2CN)2 和PhC⋮CN(CH3)C6F5) 是在水溶液中通过相应苯基氨基环丙烯酮的闪光光解脱羰产生的，并研究了它们在该介质中容易衰变的动力学。这种衰变由所有ynaminesprimary、secondary和叔的酸以及伯和仲ynamines的碱催化。溶剂同位素效应和酸碱催化的形式表明，酸催化路径涉及通过决定质子转移到 ynamines 的 β-碳原子的速率来形成 keteniminium 离子。由一级和二级 ynamines 产生的离子然后失去与氮结合的质子，得到 ketenimines，由仲ynamines得到的烯酮亚胺水合为苯乙酰胺，而从primary

  DOI：

  10.1021/ja9601797

文献信息

• Polyfluoroarylcarbonimidoyl dichlorides and chlorides. A new method of obtaining such compounds from polyfluoroaromatic amines and compounds of the CCl3R-type in the presence of AlCl3
  作者：T.I. Savchenko、I.V. Kolesnikova、T.D. Petrova、V.E. Platonov

  DOI：10.1016/s0022-1139(00)81166-5

  日期：1983.5

  polyfluorinated amines of the benzene, diphenyl, naphthalene and pyridine series with CCl4 in the presence of AlCl3 have been Investigated. A new method is proposed for producing polyfluoroarylcarbonimidoyl dichlorides ArfNCCl2. The reaction is shown to be sufficiently general and applicable in the series of polychlorinated anilines and low-base anilines of the hydrocarbon series as well. The possibility

  研究了在AlCl 3存在下苯，联苯，萘和吡啶系列的一些多氟胺与CCl 4的反应。提出了一种新的制备聚氟芳基碳亚氨基二氯化物Ar f N = CCl 2的方法。该反应显示出足够普遍，并且适用于烃系列的多氯苯胺和低碱苯胺系列。已经研究了反应中可能包含其他类型的CCl 3 R化合物和其他路易斯酸的可能性。讨论了影响反应过程的因素以及多氟芳基碳亚氨基二氯化物的形成机理。
• 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。
• Anilinic N-Oxides Support Cytochrome P450-Mediated N-Dealkylation through Hydrogen-Atom Transfer
  作者：Kenneth M. Roberts、Jeffery P. Jones

  DOI：10.1002/chem.201000185

  日期：2010.7.19

  formation of CPA argues against a SET mechanism in favor of a P450‐like HAT mechanism. We suggest that the similarity of KIEs, in addition to the formation of the ring‐intact CPA, argues for a similar mechanism of Compound I (Cpd I) formation followed by HAT for N‐dealkylation by the native and N‐oxide‐supported systems and demonstrate the ability of the N‐oxide‐generated oxidant to act as an accurate

  由细胞色素 P450 (P450) 介导的 N-脱烷基化机制长期以来一直被研究并争论为单电子转移 (SET) 或氢原子转移 (HAT) 从胺到 P450 的氧化剂，即著名的铁 -牛。在我们的研究中，叔苯胺 N 氧化物被用作氧替代物，以直接生成 P450 介导的氧化剂，该氧化剂能够对来自供氧的二甲基苯胺进行 N 脱烷基化。这些替代物被用来探测产生的活性氧和随后的 N-脱烷基化机制，以区分 HAT 和 SET 机制。除了预期的产物苯胺的 N-去甲基化，2,3,4,5,6-五氟-N，N-二甲基苯胺 N氧化物（PFDMAO）被发现能够的N-脱烷基化两者Ñ，Ñ二甲基苯胺（DMA）和ñ -环丙基- Ñ甲基苯胺（CPMA）。PFDMAO 支持的 DMA 的 N-去甲基化的速率比较显示比N , N-二甲基苯胺 N-氧化物 (DMAO)支持的速率快 27 倍。虽然分子间动力学同位素效应被掩盖了，但分子内测量显示的值反映了先前在
• [EN] 2,3-DIHYDRO-6-NITROIMIDAZO (2,1-B) OXAZOLE COMPOUNDS FOR THE TREATMENT OF TUBERCULOSIS<br/>[FR] COMPOSES 2,3-DIHYDRO-6-NITROIMIDAZO (2,1-B) OXAZOLE POUR LE TRAITEMENT DE LA TUBERCULOSE
  申请人：OTSUKA PHARMA CO LTD

  公开号：WO2005042542A1

  公开（公告）日：2005-05-12

  The present invention provides a 2,3-dihydro-6-nitroimidazo[2,1-b]oxazole compound represented by the following general formula: (1)in the above formula (1), R1 represents a hydrogen atom or C1-C6 alkyl group, n represents an integer of 0 to 6, R1 and -(CH2)nR2 may form a spiro ring represented by the formula (30) below, together with the adjacent carbon atom (in the formula below, RRR represents a piperidyl group which may have substituents on the piperidine ring), (30)and R2 represents a benzothiazolyloxy group, quinolyloxy group, pyridyloxy group or the like. The present compound has an excellent bactericidal action against Mycobacterium tuberculosis, multi-drug-resistant Mycobacterium tuberculosis, and atypical acid-fast bacteria.

  本发明提供了一种由以下一般式表示的2,3-二氢-6-硝基咪唑[2,1-b]噁唑化合物：(1)在上述式(1)中，R1代表氢原子或C1-C6烷基，n代表0至6的整数，R1和-(CH2)nR2可以与下面的式(30)一起形成一个螺环，与相邻的碳原子一起（在下面的式中，RRR代表可能在哌啶环上具有取代基的哌啶基），(30)和R2代表苯并噻唑氧基、喹啉氧基、吡啶氧基或类似物。该化合物对结核分枝杆菌、多药耐药结核分枝杆菌和非典型耐酸细菌具有出色的杀菌作用。
• [¹⁸F]/¹⁹F exchange in fluorine containing compounds for potential use in¹⁸F-labelling strategies
  作者：Elisabeth Blom、Farhad Karimi、Bengt Långström

  DOI：10.1002/jlcr.1670

  日期：2009.9.30

  Exchange of [18F]fluoride with 19F in various organofluorine compounds in concentrations ranging from 0.06 to 56 mM was explored. We aimed to explore whether exchange reactions can be a potential useful labelling strategy, when there are no requirement of high specific radioactivity. Parameters such as solvents, temperature, conventional vs microwave heating, and the degree of fluorine load in some aromatic and alkyl compounds were investigated with regard to radiochemical yield and specific radioactivity. A series of fluorobenzophenones (1–6), 1-(4-fluorophenyl)ethanone (7), various activated and deactivated fluoro benzenes (8–16), N-(pentafluorophenyl)benzamide (17), (pentafluorophenyl)formamide (18), (tridecafluorohexyl)benzene (19) and tetradecafluorohexane (20) were subjected to [18F]/19F exchange. To test this strategy to label biologically active molecules containing fluorine atoms in an aryl group, two analogues of WAY-100635 (21–22), Lapatinib (23), 2,5,6,7,8-pentafluoro-3-methylnaphthoquinone (24) and 1-(2,4-difluorophenyl)-3-(4-fluorophenyl)propan-1-one (25) were investigated. The multi-fluorinated molecules containing an electron-withdrawing group were successfully labelled at room temperature, whereas the monofluorinated, as well as those containing an electron-donating group, required heating for the exchange reaction to take place. Copyright © 2009 John Wiley & Sons, Ltd.

  在浓度范围为0.06至56 mM的各种有机氟化合物中探索了[18F]氟化物与19F的交换。我们的目标是探讨当不需要高特定放射性时，交换反应是否可以成为一种潜在有用的标记策略。我们研究了溶剂、温度、传统加热与微波加热、以及某些芳香和烷基化合物的氟负载程度对放射化学产率和特定放射性的影响。 一系列氟苯酮（1–6）、1-(4-氟苯基)乙酮（7）、各种活化和去活化的氟苯（8–16）、N-(五氟苯基)苯酰胺（17）、(五氟苯基)甲酰胺（18）、(三十四氟十六烷)苯（19）和十四氟十六烷（20）参与了[18F]/19F交换。为了测试这种策略在含有芳基氟原子的生物活性分子中的标记效果，我们研究了WAY-100635的两个类似物（21–22）、拉帕替尼（23）、2,5,6,7,8-五氟-3-甲基萘醌（24）和1-(2,4-二氟苯基)-3-(4-氟苯基)丙酮（25）。含有电子吸引基团的多氟化分子在室温下成功标记，而单氟化分子以及含有电子供给基团的分子则需要加热才能进行交换反应。版权 © 2009 John Wiley & Sons, Ltd.