N-(4-methoxyphenyl)-2-isopropylaniline | 1368252-21-4

• 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-methoxyphenyl)-2-isopropylaniline
• 英文别名: 2-isopropyl-N-(4-methoxyphenyl)aniline；N-(4-methoxyphenyl)-2-propan-2-ylaniline
• CAS: 1368252-21-4
• 化学式: C₁₆H₁₉NO
• 分子量: 241.333
• InChiKey: HUYNFRPTFNZZTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-溴苯甲醚 、 2-异丙基苯胺 在 copper(l) iodide 、 potassium carbonate 、 N'-carbazolyl-1H-pyrrole-2-carbohydrazide 作用下， 以 二乙二醇 为溶剂， 以86 %的产率得到N-(4-methoxyphenyl)-2-isopropylaniline
  参考文献：
  名称：

  室温 CuI 催化环丙胺的 N-芳基化

  摘要：

  开发了一种通用且高效的 CuI/ N-咔唑基-1H-吡咯-2-碳酰肼催化剂体系，用于在室温下使用芳基溴进行环丙胺的N-芳基化。在此，使用 5 mol% CuI 和 5 mol% 配体以中等至优异的产率合成N-芳基环丙胺。该方案被放大以生产克级的所需产物，并已推广到室温下芳基溴和胺之间的 C-N 偶联。

  DOI：

  10.1021/acs.joc.3c01357

文献信息

• Efficient catalytic aryl amination of bromoarenes using 3-iminophosphine palladium(II) chloride
  作者：Danielle C. Samblanet、Joseph A.R. Schmidt

  DOI：10.1016/j.jorganchem.2012.08.027

  日期：2012.12

  While pursuing the development of new hydroamination catalysts, a 3-iminophosphine palladium(II) chloride complex [(3IP)PdCl2] was synthesized that has subsequently proven to be an effective precatalyst for the aryl amination of bromoarenes. This (3IP)PdCl2 complex has been utilized in the catalytic aryl amination of both bromobenzene and bromopyridine derivatives, specifically yielding excellent activity in coupling reactions involving bromobenzene, 4-bromotoluene, and 2-bromopyridine. Using a standard set of catalytic conditions, many alkyl and aryl amines have been investigated as coupling partners in the aryl amination of bromoarenes. In general, secondary alkyl amines and ortho-substituted anilines proved to be the best substrates for this reaction, commonly giving quantitative conversion to products, while primary amines and other anilines gave only poor to moderate results. Catalytic screening data, product yields, and full characterization of isolated products are included. (C) 2012 Elsevier B.V. All rights reserved.
• Palladate Precatalysts for the Formation of C–N and C–C Bonds
  作者：Caroline M. Zinser、Katie G. Warren、Fady Nahra、Abdullah Al-Majid、Assem Barakat、Mohammad Shahidul Islam、Steven P. Nolan、Catherine S. J. Cazin

  DOI：10.1021/acs.organomet.9b00326

  日期：2019.7.22

  A series of imidazolium-based palladate precatalysts has been synthesized and the catalytic activity of these air- and moisture-stable complexes evaluated as a function of the nature of the imidazolium counterion. These precatalysts can be converted under catalytic conditions to Pd-NHC species capable of enabling the Buchwald-Hartwig aryl amination and the alpha-arylation of ketones. Both reactions can be carried out efficiently under very mild operating conditions. The effectiveness of the protocol was tested on functionality-laden substrates.
• Room-Temperature CuI-Catalyzed <i>N</i>-Arylation of Cyclopropylamine
  作者：Peng Hong、Xinhai Zhu、Xin Lai、Zinan Gong、Manna Huang、Yiqian Wan

  DOI：10.1021/acs.joc.3c01357

  日期：2024.1.5

  A general and efficient CuI/N-carbazolyl-1H-pyrrole-2-carbohydrazide catalyst system was developed for the N-arylation of cyclopropylamine using aryl bromides at room temperature. Herein, 5 mol % CuI and 5 mol % of the ligand were used to synthesize N-aryl cyclopropylamines in moderate to excellent yields. This protocol was scaled up to produce the desired product at gram levels and has been generalized

  开发了一种通用且高效的 CuI/ N-咔唑基-1H-吡咯-2-碳酰肼催化剂体系，用于在室温下使用芳基溴进行环丙胺的N-芳基化。在此，使用 5 mol% CuI 和 5 mol% 配体以中等至优异的产率合成N-芳基环丙胺。该方案被放大以生产克级的所需产物，并已推广到室温下芳基溴和胺之间的 C-N 偶联。