4-((4-methylbenzyl)amino)benzonitrile | 690247-92-8

• 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: 4-((4-methylbenzyl)amino)benzonitrile
• 英文别名: 4-[(4-Methylphenyl)methylamino]benzonitrile
• CAS: 690247-92-8
• 化学式: C₁₅H₁₄N₂
• mdl: MFCD11145718
• 分子量: 222.29
• InChiKey: CYGJKOPMAHQRCD-UHFFFAOYSA-N

物化性质

• 沸点：
  392.9±30.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.133
• 拓扑面积：
  35.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  对甲基苯甲醛 、 对氨基苯腈 在 5%-palladium/activated carbon 氢气 作用下， 以 乙醇 为溶剂， 以99%的产率得到4-((4-methylbenzyl)amino)benzonitrile
  参考文献：
  名称：

  1-N-phenylamino-1H-imidazole derivatives as aromatase inhibitors

  摘要：

  本发明涉及以下式子的咪唑衍生物：其中R1、R2、R3、R4、R5、R6和n的定义如规范中所述。本发明还涉及含有这些衍生物的药物组合物及其用途。

  公开号：

  EP1431292A1

文献信息

• Iron-Catalyzed Oxidative Amination of Benzylic C(sp³)–H Bonds with Anilines
  作者：Yan-Ling Song、Bei Li、Zhen-Biao Xie、Dan Wang、Hong-Mei Sun

  DOI：10.1021/acs.joc.1c02311

  日期：2021.12.17

  Iron-catalyzed oxidative amination of benzylic C(sp3)–H bonds with anilines bearing electron-withdrawing groups (EWGs) or electron-donating groups (EDGs) is realized based on simple variations of N-substituents on imidazolium cations in novel ionic Fe(III) complexes. The structural modification of the imidazolium cation resulted in regulation of the redox potential and the catalytic performance of

  基于新型离子 Fe 中咪唑鎓阳离子上 N 取代基的简单变化，实现了苄基 C(sp 3 )-H 键与带有吸电子基团 (EWG) 或供电子基团 (EDG) 的苯胺的铁催化氧化胺化（三）配合物。咪唑鎓阳离子的结构改性导致氧化还原电位和铁金属中心催化性能的调节。使用DTBP作为氧化剂，[HI t Bu][FeBr 4 ]对带有EWG的苯胺表现出最高的催化活性，而[HIPym][FeBr 4 ]对EDG取代的苯胺更有效。这项工作为苄胺提供了替代途径，同时具有广泛的底物范围和铁催化的优点。
• <i>N</i>-Alkylation of Amines with Alcohols Catalyzed by Manganese(II) Chloride or Bromopentacarbonylmanganese(I)
  作者：Dongyue Wei、Peng Yang、Chuanman Yu、Fengkai Zhao、Yilei Wang、Zhihua Peng

  DOI：10.1021/acs.joc.0c02407

  日期：2021.2.5

  manganese-catalyzed N-alkylation reaction of amines with alcohols via hydrogen autotransfer strategy has been demonstrated. The developed practical catalytic system including an inexpensive, nontoxic, commercially available MnCl2 or MnBr(CO)5 as the metal salt and triphenylphosphine as a ligand provides access to diverse aromatic, heteroaromatic, and aliphatic secondary amines in moderate-to-high yields

  已经证明了通过氢自动转移策略的锰与醇的锰催化的N-烷基化反应。已开发的实用催化系统包括廉价，无毒，可商购的MnCl 2或MnBr（CO）5作为金属盐，以及三苯基膦作为配体，可提供中等至高收率的多种芳族，杂芳族和脂族仲胺。另外，该操作简单的方案可扩展至克水平，并且适合于合成已知对阿尔茨海默氏病具有活性的杂环，例如吲哚和白藜芦醇衍生的胺。
• 1-N-phenylamino-1H-imidazole derivatives as aromatase inhibitors and pharmaceutical compositions containing them
  申请人：Laboratoire Theramex

  公开号：US06737433B1

  公开（公告）日：2004-05-18

  Imidazole derivatives of the formula: in which R1 and R2 are each independently hydrogen, (C1-C6)alkyl or (C3-C8)cycloalkyl; n is 0, 1 or 2; R3, R4, R5 and R6 are each independently hydrogen or a (C1-C6)alkyl, halogen, cyano, (C1-C6)alkoxy, trifluoromethyl, (C1-C6)alkylthio, (C1-C6)alkylsulfonyl, sulfonamido, acyl, (C1-C6)alkoxycarbonyl, or carboxamido group; R3 and R6 together with the phenyl ring bearing them can also form a benzofurane, or a N-methylbenzotriazole. The invention also relates to pharmaceutical compositions containing these derivatives, and to the uses thereof.

  配方为imidazole衍生物的公式： 其中， R1和R2各自独立地为氢、(C1-C6)烷基或(C3-C8)环烷基； n为0、1或2； R3、R4、R5和R6各自独立地为氢或(C1-C6)烷基、卤素、氰基、(C1-C6)烷氧基、三氟甲基、(C1-C6)烷基硫醇基、(C1-C6)烷基磺酰基、磺酰胺基、酰基、(C1-C6)烷氧羰基或羧酰胺基； R3和R6与它们所承载的苯环也可以形成苯并呋喃或N-甲基苯并三唑。 本发明还涉及含有这些衍生物的药物组合物以及它们的用途。
• One‐Pot <i>N</i>‐Alkylation of Amines over Ni(II) Embedded Reusable Porous Organic Polymer <i>via</i> Borrowing Hydrogen Strategy
  作者：Debabrat Pathak、Bikash Kumar Kalita、Himanshu Sharma、Nishant Biswakarma、Ramesh Ch. Deka、Bipul Sarma

  DOI：10.1002/cctc.202301399

  日期：2024.4.22

  The first‐of‐its‐kind, one‐pot N‐alkylation reaction of amines over Ni(II) impregnated porous organic polymer of highly dense N‐rich skeleton is reported. The primeval Ni(II) decorated hollow spherical porous polymer is synthesized and employed in a series of catalytic reactions involving C−N bond formation. The catalytic reactions are optimised to yield the desired product highlighting the role of different substituents present on the reactants towards the overall selectivity and efficiency. The detailed reaction mechanism is corroborated with computation validating a three‐step arrow formalism viz. dehydrogenation of the alcohol, condensation with amines to generate the imine as intermediate followed by hydrogenation by a borrowing strategy to yield the final product. The role of the bare support material in the first step and that of the Ni(II) centres of the support material in the third step is marked as pivotal for the forward reaction to proceed with enriching sustainability and feasibility.

  摘要 首次报道了在富含高密度 N 骨架的浸渍镍（II）多孔有机聚合物上进行胺的单锅 N- 烷基化反应。原始的 Ni(II) 装饰空心球形多孔聚合物是在一系列涉及 C-N 键形成的催化反应中合成和使用的。对催化反应进行了优化，以获得所需的产物，突出了反应物上不同取代基对整体选择性和效率的作用。详细的反应机理通过计算得到了证实，即醇的脱氢、与胺缩合生成亚胺作为中间体，然后通过借用策略进行氢化以生成最终产物的三步箭头形式主义。裸支持材料在第一步中的作用以及支持材料中的 Ni(II) 中心在第三步中的作用，对于正向反应的进行具有关键性的作用，从而提高了可持续性和可行性。
• Ruthenium(II) bis(hydrazone) complexes derived from 1,3,4-oxadiazoles: Synthesis, crystal structure and catalytic application in N-alkylation reactions
  作者：Govindan Prakash、Rangasamy Ramachandran、Muthukumaran Nirmala、Periasamy Viswanathamurthi、Jesus Sanmartin

  DOI：10.1016/j.ica.2015.01.002

  日期：2015.3

  1,3,4-Oxadiazoles (A-C) were derived via a series of reactions between isoniazid and salicylaldehydes. While reacting the oxadiazoles with [RuHCl(CO)(PPh3)(3)] in the presence of NaOH, mononuclear ruthenium(II) complexes bearing 'salen' type N,N'-bis(salicylidene) hydrazone ligands (1-3) were obtained. The oxadiazoles and ruthenium(II) complexes were characterized by analytical and spectral methods. The single crystal XRD analyses of complexes 1 and 2 suggested an octahedral geometry around ruthenium(II) ions in which the bis(hydrazone) act as mononegative bidentate ligands. It was also observed that the presence of an intramolecular hydrogen bonding between the hydroxyl proton and one of the azomethine nitrogens in all the complexes. Further, the complexes were proved as versatile catalysts for the N-alkylation of amines with alcohols under optimized reaction conditions. (C) 2015 Elsevier B.V. All rights reserved.