N-(4-fluorophenyl)pyridin-4-amine | 72358-71-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(4-fluorophenyl)pyridin-4-amine
• CAS: 72358-71-5
• 化学式: C₁₁H₉FN₂
• mdl: MFCD22083761
• 分子量: 188.204
• InChiKey: KJPKOBPONMSVCR-UHFFFAOYSA-N

物化性质

• 熔点：
  199-200 °C
• 沸点：
  317.0±22.0 °C(Predicted)
• 密度：
  1.230±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  24.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-fluorophenyl)pyridin-4-amine 在 palladium on activated charcoal N-甲基吡咯烷酮 、 sodium tetrahydroborate 、 氢气 、 溴甲苯 、 sodium carbonate 、 potassium carbonate 、 potassium iodide 、 copper(I) bromide 作用下， 以 various solvent(s) 为溶剂， 反应 48.0h， 生成 4-1-<4-(4-fluorophenyl)-4-oxobutyl>piperidine
  参考文献：
  名称：

  Neuroleptic activity of chiral trans-hexahydro-.gamma.-carbolines

  摘要：

  A series of trans-8-fluoro-5-(4-fluorophenyl)-2,3,4,4a,5, 9b-hexahydro-1H-pyrido[4,3-b]indoles with various N-2 substituents has been prepared and tested for neuroleptic activity [( 3H]spiroperidol binding and amphetamine antagonism). Several members of this series showed exceptional in vivo potency, especially the hydantoin derivatives 27-30. Resolution into the enantiomers showed that neuroleptic activity is associated with the 4aS,9bS absolute configuration. These rigid neuroleptics have been correlated with other rigid neuroleptics [(+)-dexclamol, Ro 22-1319] and can serve to further define the topography of the dopamine receptor.

  DOI：

  10.1021/jm00151a002
• 作为产物：
  描述：

  4-氨基吡啶 在 盐酸 作用下， 以 1,4-二氧六环 、 乙醇 、 二甲基亚砜 为溶剂， 反应 31.17h， 生成 N-(4-fluorophenyl)pyridin-4-amine
  参考文献：
  名称：

  吡咯盐对氨基杂环的选择性功能化

  摘要：

  提出了使用四氟硼酸吡啶鎓试剂（Pyry-BF 4）对氨基杂环进行官能化的方法。该试剂可与多种杂环胺有效地缩合，并为亲核芳香族取代反应准备C-N键。本文公开了用于形成CO，CN，CS或CS 2 R键的60多个例子。与通过重氮化和多烷基化进行CN活化相反，该方法的特点是条件温和且对官能团的耐受力强。除小分子衍生化外，Pyry-BF 4还允许以后期方式引入官能团，以提供高度官能化的结构。

  DOI：

  10.1002/anie.201806271

文献信息

• Antimicrobial bis-[4-(substituted-amino)-1-pyridinium]alkanes
  申请人：Sterling Drug Inc.

  公开号：US04206215A1

  公开（公告）日：1980-06-03

  Bis-[4-(R-amino)-1-pyridinium]alkanes are prepared by reacting a 4-(R-amino)pyridine with an appropriate disubstituted alkane. The compounds are useful as antimicrobial agents. Certain species are also useful as dental plaque-preventive agents.

  双[4-(R-氨基)-1-吡啶烷]脂肪烃是通过将4-(R-氨基)吡啶与适当的二取代脂肪烃反应来制备的。这些化合物作为抗菌剂很有用。某些物种作为牙齿菌斑预防剂也很有用。
• New Stable Cu(I) Catalyst Supported on Weakly Acidic Polyacrylate Resin for Green C-N Coupling: Synthesis of N-(Pyridin-4-yl)benzene Amines and N,N-Bis(pyridine-4-yl)benzene Amines
  作者：Nitin Kore、Pavel Pazdera

  DOI：10.3390/molecules22010002

  日期：——

  A method for preparation of a new stable Cu(I) catalyst supported on weakly acidic polyacrylate resin without additional stabilizing ligands is described. A simple and efficient methodology for Ullmann Cu(I) catalyzed C-N cross coupling reactions using this original catalyst is reported. Coupling reactions of 4-chloropyridinium chloride with anilines containing electron donating (EDG) or electron withdrawing

  描述了一种在没有额外稳定配体的情况下制备负载在弱酸性聚丙烯酸酯树脂上的新型稳定 Cu (I) 催化剂的方法。报道了使用这种原始催化剂的 Ullmann Cu (I) 催化 CN 交叉偶联反应的简单有效方法。4-氯吡啶鎓与分别含有给电子 (EDG) 或吸电子 (EWG) 基团、萘-2-胺和哌嗪的苯胺的偶联反应得到了成功证明。
• Iodine-mediated oxidative N–N coupling of secondary amines to hydrazines
  作者：Linning Ren、Manman Wang、Benyao Fang、Wenquan Yu、Junbiao Chang

  DOI：10.1039/c9ob00279k

  日期：——

  An I2-mediated N–N coupling reaction has been established for oxidative dimerization of N-aryl aminopyridines to a variety of novel hydrazine derivatives under mild conditions. This synthetic method does not require use of transition metals and can be conveniently carried out on a gram scale. It is also applicable to diphenylamine and N-alkyl aniline substrates.

  已经建立了I 2介导的N–N偶联反应，用于在温和条件下将N-芳基氨基吡啶氧化成二种新的肼衍生物。该合成方法不需要使用过渡金属，并且可以方便地以克为单位进行。它也适用于二苯胺和N-烷基苯胺底物。
• Direct <i>N</i> −H Activation to Generate Nitrogen Radical for Arylamine Synthesis via Quantum Dots Photocatalysis
  作者：Qi‐Chao Gan、Jia Qiao、Chao Zhou、Rui‐Nan Ci、Jia‐Dong Guo、Bin Chen、Chen‐Ho Tung、Li‐Zhu Wu

  DOI：10.1002/anie.202218391

  日期：——

  Direct activation of amine N−H bonds is realized to provide N-radicals in a redox-neutral and site-selective manner. Under visible-light irradiation of quantum dots, the N-radicals are successfully applied to the synthesis of aromatic amines. The high efficiency and broad functional-group tolerance demonstrate the potential of photocatalytic N-radicals in the construction of valuable arylamines.

  实现了胺 N-H 键的直接激活，以氧化还原中性和位点选择性方式提供 N-自由基。在量子点的可见光照射下，N-自由基成功地应用于芳香胺的合成。高效率和广泛的官能团耐受性证明了光催化N-自由基在构建有价值的芳基胺方面的潜力。
• Chain Transfer Kinetics of Acid/Base Switchable <i>N</i>-Aryl-<i>N</i>-Pyridyl Dithiocarbamate RAFT Agents in Methyl Acrylate, <i>N</i>-Vinylcarbazole and Vinyl Acetate Polymerization
  作者：Daniel J. Keddie、Carlos Guerrero-Sanchez、Graeme Moad、Roger J. Mulder、Ezio Rizzardo、San H. Thang

  DOI：10.1021/ma300616g

  日期：2012.5.22

  The structures of the "Z" and "R" substituents of a RAFT agent (Z-C(S)S R) determine a RAFT agent's ability to control radical polymerization. In this paper we report new acid/base switchable N-aryl-N-pyridyl dithiocarbamates (R = -CH2CN, Z = -N(Py)(Ar)) which vary in substituent at the 4-position of the aryl ring and the use of these to control molecular weight and dispersity. In their protonated form, the new RAFT agents are more effective in controlling polymerization of the more activated monomer, methyl acrylate (MA), whereas in their neutral form they provide more effective control of the polymerization of less activated monomers, N-vinyl carbazole (NVC) and vinyl acetate (VAc). For each polymerization, the apparent chain transfer coefficient (C-tr(aPP)) shows a good correlation with Hammett parameters. Dithiocarbamates with more electron-withdrawing aryl ring substituents have the higher C-tr(aPP). This demonstrates the influence of polar effects on C-tr(aPP) and supports the hypothesis that the activity of these RAFT agents is determined by the availability of the lone pair of the dithiocarbamate nitrogen.