N-(4-chlorobenzyl)-4-methoxyaniline | 20357-42-0

• 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)-4-methoxyaniline
• 英文别名: N-[(4-chlorophenyl)methyl]-4-methoxyaniline
• CAS: 20357-42-0
• 化学式: C₁₄H₁₄ClNO
• mdl: MFCD01427007
• 分子量: 247.724
• InChiKey: GQRCXKTWRYIKBP-UHFFFAOYSA-N

物化性质

• 熔点：
  69-70 °C
• 沸点：
  376.9±27.0 °C(Predicted)
• 密度：
  1.205±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  反丁烯二酰氯 、 N-(4-chlorobenzyl)-4-methoxyaniline 在 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 反应 12.0h， 生成 but-2-enedioic acid bis[(4-chlorobenzyl)(4-methoxyphenyl)amide]
  参考文献：
  名称：

  Preparation, anticholinesterase activity, and docking study of new 2-butenediamide and oxalamide derivatives

  摘要：

  Several new oxalamide and 2-butenediamide derivatives have been designed, synthesized and evaluated as the acetyl- and butyryl-cholinesterase inhibitors for Alzheimer's disease. The enzyme inhibitory activity of the synthesized compounds was measured using Ellman's colorimetric method. It was revealed that compound 1a (N, N'-bis-(4-chloro-benzyl)-N, N'-diphenyl-oxalamide) showed maximum activity against BuChE with a half maximal inhibitory concentration (IC50) = 1.86 mu M and compound 2a (but-2-enedioic acid bis-[(4-chloro-benzyl)-phenyl-amide]) exhibited optimum AChE (IC50 = 1.51 mu M) inhibition with a high-selectivity index. To better understand the enzyme-inhibitor interaction of the most active compounds towards cholinesterase, molecular modelling studies were carried out. Docking simulations revealed that inhibitors 1a and 2a targeted both the catalytic active site and the peripheral anionic site of 1ACJ and 1P0I.

  DOI：

  10.3109/14756366.2014.959947
• 作为产物：
  描述：

  (E)-1-(4-chlorophenyl)-N-(4-methoxyphenyl)methanimine 在 甲酸铵 、 锌 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以80%的产率得到N-(4-chlorobenzyl)-4-methoxyaniline
  参考文献：
  名称：

  Abiraj; Dinesh; Srinivasa, Journal of Chemical Research, 2006, # 8, p. 534 - 535

  摘要：

  DOI：

文献信息

• Iron-Catalyzed Nitrene Transfer Reaction of 4-Hydroxystilbenes with Aryl Azides: Synthesis of Imines via C═C Bond Cleavage
  作者：Yi Peng、Yan-Hui Fan、Si-Yuan Li、Bin Li、Jing Xue、Qing-Hai Deng

  DOI：10.1021/acs.orglett.9b03160

  日期：2019.10.18

  C═C bond breaking to access the C═N bond remains an underdeveloped area. A new protocol for C═C bond cleavage of alkenes under nonoxidative conditions to produce imines via an iron-catalyzed nitrene transfer reaction of 4-hydroxystilbenes with aryl azides is reported. The success of various sequential one-pot reactions reveals that the good compatibility of this method makes it very attractive for

  打破C bondC债券以获取C═N债券的领域仍然不发达。报道了一种在非氧化条件下通过4-羟基苯乙烯与芳基叠氮化物的铁催化的腈转移反应产生亚胺的烯烃的C═C键裂解的新方案。各种顺序一锅法反应的成功表明，该方法的良好兼容性使其对于合成应用非常有吸引力。在实验观察的基础上，还提出了合理的反应机理。
• Fast Reductive Amination by Transfer Hydrogenation “on Water”
  作者：Qian Lei、Yawen Wei、Dinesh Talwar、Chao Wang、Dong Xue、Jianliang Xiao

  DOI：10.1002/chem.201204194

  日期：2013.3.18

  Reductive amination of various ketones and aldehydes by transfer hydrogenation under aqueous conditions has been developed, by using cyclometallated iridium complexes as catalysts and formate as hydrogen source. The pH value of the solution is shown to be critical for a high catalytic chemoselectivity and activity, with the best pH value being 4.8. In comparison with that in organic solvents, the reductive

  通过使用环金属化的铱络合物作为催化剂，甲酸盐作为氢源，开发了在水性条件下通过转移氢化进行各种酮和醛的还原胺化反应。溶液的pH值对于高催化化学选择性和活性至关重要，最佳pH值为4.8。与有机溶剂相比，水相中的还原胺化速度更快，并且底物与催化剂的摩尔比（S / C）可设置为高达1×10 5。，是还原胺化反应中报道的最高S / C值。该催化剂易于获得，反应操作简单，可以使各种酮和醛与各种胺高产率地反应。该方案为合成胺化合物提供了一种实用且环保的新方法。
• Alkyl formates as reagents for reductive amination of carbonyl compounds
  作者：Oleg I. Afanasyev、Ilia Cherkashchenko、Anton Kuznetsov、Fedor Kliuev、Sergey Semenov、Olga Chusova、Gleb Denisov、Denis Chusov

  DOI：10.1016/j.mencom.2020.01.037

  日期：2020.1

  Alkyl formates in the presence of basic additives can serve as a reagent in the direct reductive amination of carbonyl compounds. The developed procedure can be applied to various aldehydes and ketones with electron donating and electron withdrawing groups.

  在碱性添加剂存在下，烷基甲酸酯可以用作羰基化合物直接还原胺化反应的试剂。所开发的方法可以用于具有给电子和吸电子基团的各种醛和酮。
• Designed pincer ligand supported Co(<scp>ii</scp>)-based catalysts for dehydrogenative activation of alcohols: Studies on <i>N</i>-alkylation of amines, α-alkylation of ketones and synthesis of quinolines
  作者：Anshu Singh、Ankur Maji、Mayank Joshi、Angshuman R. Choudhury、Kaushik Ghosh

  DOI：10.1039/d0dt03748f

  日期：——

  Base-metal catalysts Co1, Co2 and Co3 were synthesized from designed pincer ligands L1, L2 and L3 having NNN donor atoms respectively. Co1, Co2 and Co3 were characterized by IR, UV–Vis. and ESI-MS spectroscopic studies. Single crystal X-ray diffraction studies were investigated to authenticate the molecular structures of Co1 and Co3. Catalysts Co1, Co2 and Co3 were utilized to study the dehydrogenative

  贱金属催化剂Co1、Co2和Co3由分别具有NNN供体原子的设计的钳状配体L 1、L 2和L 3合成。Co1、Co2和Co3通过 IR、UV-Vis 进行表征。和 ESI-MS 光谱研究。研究了单晶 X 射线衍射研究以验证Co1和Co3的分子结构。催化剂Co1 , Co2和Co3用于研究醇的脱氢活化胺的N-烷基化、酮的 α-烷基化和喹啉的合成。在优化的反应条件下，开发了广泛的底物，包括醇类、苯胺类和酮类。对胺的N-烷基化、酮的 α-烷基化和喹啉合成的一系列控制实验进行了检查，以了解反应途径。研究了 ESI-MS 光谱研究以表征钴-醇盐和钴-氢化物中间体。研究了反应过程中放出的氢气对苯乙烯的还原，以验证催化剂的脱氢性质。为N提出了可能的反应途径-胺类烷基化、酮类α-烷基化和喹啉的合成基于对照实验和反应中间体的检测。
• Boron-Catalyzed <i>N</i>-Alkylation of Arylamines and Arylamides with Benzylic Alcohols
  作者：Murali Mohan Guru、Pradip Ramdas Thorve、Biplab Maji

  DOI：10.1021/acs.joc.9b02816

  日期：2020.1.17

  A sustainable boron-based catalytic approach for chemoselective N-alkylation of primary and secondary aromatic amines and amides with primary, secondary, and tertiary benzylic alcohols has been presented. The metal-free protocol operates at low catalyst loading, tolerates several functional groups, and generates H2O as the sole byproduct. Preliminary mechanistic studies were performed to demonstrate

  提出了一种可持续的基于硼的催化方法，用于伯，仲和叔苄醇对伯和仲芳族胺和酰胺的化学选择性N-烷基化。不含金属的方案在低催化剂负载下运行，可耐受多个官能团，并生成H2O作为唯一的副产物。进行了初步的机理研究，以证明硼催化剂在中间体二苄基醚的活化中的关键作用，并确定了决定速率的步骤。