N-(4-chlorobenzyl)-2,4,6-trimethylaniline | 356532-15-5

• 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-chlorobenzyl)-2,4,6-trimethylaniline
• 英文别名: N-[(4-chlorophenyl)methyl]-2,4,6-trimethylaniline
• CAS: 356532-15-5
• 化学式: C₁₆H₁₈ClN
• 分子量: 259.779
• InChiKey: AVBFLNSFMNVMNA-UHFFFAOYSA-N

物化性质

• 沸点：
  376.3±37.0 °C(Predicted)
• 密度：
  1.127±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为产物：
  描述：

  在 silica gel 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 N-(4-chlorobenzyl)-2,4,6-trimethylaniline
  参考文献：
  名称：

  HBpin使用锌促进剂催化羰基化合物的硼氢化和还原胺化

  摘要：

  报道了在环境条件下由亚氨基吡啶负载的锌 (II) 络合物催化的醛和酮与 HBpin 的化学选择性硼氢化反应。

  DOI：

  10.1002/asia.202200013

文献信息

• Catalyst‐Free and Solvent‐Free Facile Hydroboration of Imines
  作者：Vipin K. Pandey、Siva Nagendra Reddy Donthireddy、Arnab Rit

  DOI：10.1002/asia.201901016

  日期：2019.10

  A facile process for the catalyst-free and solvent-free hydroboration of aromatic as well as heteroaromatic imines is reported. This atom-economic methodology is scalable, compatible with sterically and electronically diverse imines, displaying excellent tolerance towards various functional groups, and works efficiently at ambient temperature in most of the cases, affording secondary amines in good

  据报道，一种简便的方法可用于芳族和杂芳族亚胺的无催化剂和无溶剂的硼氢化反应。这种原子经济的方法具有可扩展性，可与空间和电子形式的亚胺兼容，对各种官能团均表现出优异的耐受性，并且在大多数情况下可在环境温度下有效发挥作用，水解后得到的仲胺的收率良好。
• Catalytic Hydroboration and Reductive Amination of Carbonyl Compounds by HBpin using a Zinc Promoter
  作者：Ravi Kumar、Parveen Rawal、Indrani Banerjee、Hari Pada Nayek、Puneet Gupta、Tarun K. Panda

  DOI：10.1002/asia.202200013

  日期：2022.3

  Chemoselective hydroboration of aldehydes and ketones with HBpin catalyzed by iminopyridine supported zinc(II) complex under ambient conditions is reported.

  报道了在环境条件下由亚氨基吡啶负载的锌 (II) 络合物催化的醛和酮与 HBpin 的化学选择性硼氢化反应。
• 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.
• Highly chemoselective reductive amination by one pot reaction of aldehydes, amines and Dihydropyridine Catalyzed by TMSCl
  作者：N. Azizi、A. R. Khajeh Amiri、H. Ghafuri、M. R. Saidi、M. Bolourtchian

  DOI：10.1007/bf03246028

  日期：2010.6

  More efficient, cost effective and metal free DHP/TMSCl system for one pot reductive amination of aldehydes was developed. The method allows the efficient one pot synthesis of structurally diverse amines with Hantzsch ester as the hydrogen source in the presence of trimethylsilyl chloride as a catalyst in high to quantitative yields under mild conditions.
• Hydroboration and reductive amination of ketones and aldehydes with HBpin by a bench stable Pd(<scp>ii</scp>)-catalyst
  作者：Shreya Mahato、Parveen Rawal、Ajitrao Kisan Devadkar、Mayank Joshi、Angshuman Roy Choudhury、Bhaskar Biswas、Puneet Gupta、Tarun K. Panda

  DOI：10.1039/d1ob02339j

  日期：——

  palladium(II) complex [(κ4-1,2-C6H4(NCH–C6H4O)2}Pd] (1) supported by a dianionic salen ligand [1,2-C6H4(NCH–C6H4O)2]2− (L) was synthesised and used as a molecular pre-catalyst in the hydroboration of aldehydes and ketones. The molecular structure of Pd(II) complex 1 was established by single-crystal X-ray diffraction analysis. Complex 1 was tested as a competent pre-catalyst in the hydroboration of aldehydes

  由双阴离子salen配体[1,2-C 6支持的钯( II )配合物[(κ 4 -1,2-C 6 H 4 (N CH–C 6 H 4 O) 2 }Pd] ( 1 ) H 4 (N CH–C 6 H 4 O) 2 ] 2- ( L )被合成并用作醛酮硼氢化的分子预催化剂。单晶 X 射线衍射分析 配合物1在无溶剂条件下在环境温度下以优异的收率对醛和酮与频哪醇硼烷 (HBpin) 的硼氢化反应中作为有效的预催化剂进行测试，以生产相应的硼酸酯。此外，复杂的1被证明是在温和和无溶剂条件下用 HBpin 和伯胺还原胺化醛的有效催化剂，可提供高产率（高达 97%）的相应仲胺。两种协议都提供了高转化率、卓越的选择性和广泛的底物范围，从吸电子到给电子和杂环取代。基于密度泛函理论 (DFT) 的计算研究揭示了在 HBpin 存在下 Pd 催化羰基物质硼氢化的反应机制。该协议还揭示了 HBpin 在实现硼氢化反应中的双重作用。