N-(4-methoxyphenyl)-3-methylaniline | 85614-82-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-(4-methoxyphenyl)-3-methylaniline
• CAS: 85614-82-0
• 化学式: C₁₄H₁₅NO
• 分子量: 213.279
• InChiKey: CICOSBZONFODGX-UHFFFAOYSA-N

物化性质

• 熔点：
  72-75 °C
• 沸点：
  345.7±25.0 °C(Predicted)
• 密度：
  1.089±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  N-(4-methoxyphenyl)-3-methylaniline 在 1,1'-双(二苯基膦)二茂铁 、 四(三苯基膦)钯 、 tris(dibenzylideneacetone)dipalladium (0) 、 2,6-二叔丁基-4-甲基苯酚 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 生成 (4-Methoxy-phenyl)-m-tolyl-(4-vinyl-phenyl)-amine
  参考文献：
  名称：

  Designing Interfaces That Function to Facilitate Charge Injection in Organic Light-Emitting Diodes

  摘要：

  Layer-by-layer (LbL) assembly of triarylamine (TAA)-containing polymers has been applied for anode functionalizations in organic light-emitting diodes (OLEDs). Surface work function of the ITO electrodes was significantly altered with the functionalizations, and the values changed depending on electron affinity of the substituents (X) on the TAA units. When the functionalized ITO electrodes were utilized for the conventional TPD/Alq OLED, the multilayers of P1 (X = 4-OMe) and P2 (X = none) were found to promote better energy matching at the ITO/TPD interface to reduce the hole injection barrier. Furthermore, the multilayers having heterodeposited structure of several TAA polymers provided stepped and graded electronic profiles to facilitate hole mobility from ITO to TPD, so that the resulting OLED devices can exhibit appreciably reduced turn-on voltage and higher luminous intensities.

  DOI：

  10.1021/ja052170n
• 作为产物：
  描述：

  间甲酚 在 苯乙烯 、 palladium on activated charcoal 、 10 wt% Pd(OH)2 on carbon 、 氢气 作用下， 以 甲苯 为溶剂， 140.0 ℃ 、500.01 kPa 条件下， 反应 13.5h， 生成 N-(4-methoxyphenyl)-3-methylaniline
  参考文献：
  名称：

  利用集成床流系统从苯酚连续合成芳胺。

  摘要：

  芳胺是其他众多应用中的重要药物中间体。在此，开发了在连续流动条件下使用苯酚与胺和苯乙烯的脱水胺化反应合成芳胺的环境友好途径和新方法。廉价且易于获得的苯酚在多相连续流反应器中，在多相钯催化剂的存在下，可与少量易除去的副产物（即H 2 O和烷烃）有效地转化为相应的芳基胺。这种方法的高产物选择性和官能团耐受性允许在一周的连续操作时间内以高收率选择性地获得具有各种官能团的芳基胺。

  DOI：

  10.1002/anie.202005109

文献信息

• Cu-Catalyzed Cross-Coupling of Nitroarenes with Aryl Boronic Acids to Construct Diarylamines
  作者：Xinyu Guan、Haoran Zhu、Tom G. Driver

  DOI：10.1021/acscatal.1c03113

  日期：2021.10.15

  copper-catalyzed reaction of nitroarenes with aryl boronic acids to form diarylamines that uses phenyl silane as the stoichiometric terminal reductant is described. This cross-coupling reaction requires as little as 2 mol % of CuX and 4 mol % of diphosphine for success and tolerates a broad range of functional groups on either the nitroarene or the aryl boronic acid to afford the amine in good yield. Mechanistic

  描述了使用苯基硅烷作为化学计量末端还原剂的硝基芳烃与芳基硼酸形成二芳基胺的简单铜催化反应的开发和研究。这种交叉偶联反应只需要 2 mol% 的 CuX 和 4 mol% 的二膦即可成功，并且可以容忍硝基芳烃或芳基硼酸上的多种官能团，从而以良好的收率提供胺。机理研究表明，交叉偶联反应通过亚硝基芳烃中间体进行，并且铜需要催化硝基芳烃的脱氧以提供亚硝基芳烃和亚硝基芳烃与芳基硼酸的 C-NAr 键形成。
• Visible-Light-Induced Multicomponent Synthesis of γ-Amino Esters with Diazo Compounds
  作者：Na Ma、Lin Guo、Dan Qi、Fei Gao、Chao Yang、Wujiong Xia

  DOI：10.1021/acs.orglett.1c02071

  日期：2021.8.20

  ethyl diazoacetate, diarylamines, and styrene-type alkenes is described. This novel 1,2-difunctionalization of alkenes can be readily achieved under a simple operation and mild conditions, affording γ-amino esters as major products. The reaction proceeds through the generation of carbon-centered radicals from diazo compounds by a visible-light-promoted proton-coupled electron transfer (PCET) process.

  描述了一种可见光诱导的重氮乙酸乙酯、二芳基胺和苯乙烯型烯烃的多组分反应。这种烯烃的新型 1,2-双官能化可以在简单的操作和温和的条件下轻松实现，主要产物为 γ-氨基酯。该反应通过可见光促进的质子耦合电子转移 (PCET) 过程从重氮化合物生成以碳为中心的自由基进行。然后碳自由基添加到不同的烯烃中，提供新的碳自由基物种，最终产物通过自由基 - 自由基偶联与以N 为中心的自由基形成。
• Smiles rearrangement for the synthesis of diarylamines
  作者：Xiao Tian、Ren-Min Wu、Gang Liu、Zhu-Bo Li、He-Lin Wei、Hao Yang、Dong-Soo Shin、Li-Ying Wang、Hua Zuo

  DOI：10.3998/ark.5550190.0012.a10

  日期：——

  A protocol for the one-pot synthesis of diarylamines via Smiles rearrangement under microwave irradiation has been developed. Various diarylamines were effectively synthesized starting from readily available substituted phenols, arylamines and chloroacetyl chloride in moderate to good yields (58–92%).

  已经开发了一种在微波辐射下通过 Smiles 重排一锅合成二芳胺的协议。从容易获得的取代酚、芳胺和氯乙酰氯开始，以中等至良好的产率（58-92%）有效合成了各种二芳胺。
• Acid-Free Synthesis of Carbazoles and Carbazolequinones by Intramolecular Pd-Catalyzed, Microwave-Assisted Oxidative Biaryl Coupling Reactions - Efficient Syntheses of Murrayafoline A, 2-Methoxy-3-methylcarbazole, and Glycozolidine
  作者：Vellaisamy Sridharan、M. Antonia Martín、J. Carlos Menéndez

  DOI：10.1002/ejoc.200900537

  日期：2009.9

  A mild and efficient methodology for the synthesis of oxygenated carbazoles from diarylamines under non-acidic conditions was developed, based on a palladium-catalyzed, microwave-assisted double C–H bond activation process. This new protocol was successfully applied to the synthesis of three naturally occurring carbazoles, namely murrayafoline A, 2-methoxy-3-methylcarbazole, and glycozolidine. The

  基于钯催化的微波辅助双 C-H 键活化过程，开发了一种在非酸性条件下由二芳基胺合成氧化咔唑的温和有效的方法。这一新协议已成功应用于三种天然咔唑的合成，即 murrayafoline A、2-甲氧基-3-甲基咔唑和糖唑烷。反应范围也扩大到包括苯并稠合咔唑醌的合成。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Cu-ACP-Am-Fe3O4@SiO2: an efficient and recyclable heterogeneous catalyst for the Chan–Lam coupling reaction of boronic acids and amines
  作者：Sandip P. Vibhute、Pradeep M. Mhaldar、Dipak S. Gaikwad、Rajendra V. Shejwal、Dattaprasad M. Pore

  DOI：10.1007/s00706-019-02529-w

  日期：2020.1

  AbstractWe have developed an efficient method for Cu-ACP-Am-Fe3O4@SiO2 catalyzed Chan–Lam coupling of phenylboronic acid with primary amine furnished secondary amines. The catalyst offered virtues like mild reaction conditions, magnetically separable, and reusable and exhibits excellent performance in terms of good product yield and high turnover number. Graphic abstract

  摘要我们已经开发出一种有效的方法，用于Cu-ACP-Am-Fe 3 O 4 @SiO 2催化苯基硼酸与伯胺提供的仲胺的Chan-Lam偶联。该催化剂具有温和的反应条件，可磁分离和可重复使用的优点，并在良好的产物收率和高周转率方面表现出优异的性能。 图形摘要