N-benzylidene-2,3-dimethylaniline | 194875-08-6

• 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-benzylidene-2,3-dimethylaniline
• 英文别名: Dimethyl benzalaniline；N-(2,3-dimethylphenyl)-1-phenylmethanimine
• CAS: 194875-08-6
• 化学式: C₁₅H₁₅N
• 分子量: 209.291
• InChiKey: PCWRTXYUOHUXQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-benzylidene-2,3-dimethylaniline 在 sodium tetrahydroborate 、 NiLa₂O₄ 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.17h， 以86%的产率得到N-benzyl-2,3-dimethylaniline
  参考文献：
  名称：

  Nano-sized NiLa2O4 spinel–NaBH4-mediated reduction of imines to secondary amines

  摘要：

  Nano-sized NiLa2O4 spinel was produced by thermal decomposition of Ni-La compounds via a sol-gel method. The well-crystallized spinel structure was formed after calcination at 750 degrees C. The physicochemical properties of the spinel were investigated using differential thermal analysis, X-ray diffraction, transmission electron microscopy, scanning electron microscopy, and particle size distribution analysis. The results show that the nanoparticles have regular shapes with well-defined crystal faces and consist of uniform quasi-spherical crystallites of average size 40 nm. The refined unit cell parameters are a = 3.861205 angstrom and c = 12.6793 angstrom. This new nano-sized NiLa2O4 spinel is an efficient heterogeneous catalyst for the selective conversion of imines to the corresponding secondary amines in the presence of NaBH4 as a reducing agent, in good to excellent yields. All the reactions were completely chemoselective at room temperature and had relatively short reaction times. Secondary amines with different aryl groups, including those bearing electron-withdrawing or electron-donating groups, were obtained under the optimum reaction conditions. The catalyst was readily recovered and was recycled four times with no significant loss of catalytic activity. (C) 2015, Dalian Institute of Chemical Physics, Chinese Academy of Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/s1872-2067(15)60921-4
• 作为产物：
  描述：

  2,3-二甲基苯胺 、 苯甲醇 在 (phthalocyaninato)iron(II) 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以69%的产率得到N-benzylidene-2,3-dimethylaniline
  参考文献：
  名称：

  Highly efficient iron phthalocyanine catalyzed oxidative synthesis of imines from alcohols and amines

  摘要：

  开发了一种高效的铁酞菁催化方法，用于直接氧化偶联醇和胺，生成相应的亚胺。该方法适用于各种取代芳香族和脂肪族醇和胺。该反应被认为通过铁酞菁对醇的活化，通过路易斯酸碱相互作用形成醛，然后通过胺的亲核攻击转化为相应的亚胺。

  DOI：

  10.1139/cjc-2012-0399

文献信息

• Transition Metal-Free Oxidative Coupling of Primary Amines in Polyethylene Glycol at Room Temperature: Synthesis of Imines, Azobenzenes, Benzothiazoles, and Disulfides
  作者：Abhinandan D. Hudwekar、Praveen K. Verma、Jaspreet Kour、Shilpi Balgotra、Sanghapal D. Sawant

  DOI：10.1002/ejoc.201801610

  日期：2019.2.14

  A transition metal‐free protocol has been developed for the oxidative coupling of primary amines to imines and azobenzenes, thiols to disulfides, and 2‐aminothiophenols to benzothiazoles, offering excellent yields. The advantageous features of the present environmentally benign methodology include the usage of biocompatable and green reaction conditions such as solvent, room temperature reactions,

  已开发出一种无过渡金属的方案，用于伯胺与亚胺和偶氮苯的氧化偶联，巯基与二硫化物的氧化偶联以及2-氨基硫酚与苯并噻唑的氧化偶联，具有优异的收率。当前环境友好方法的优势包括使用可生物相容的绿色反应条件，例如溶剂，室温反应，无过渡金属的方法。此外，它提供了更广阔的基板范围。
• Highly efficient iron phthalocyanine catalyzed oxidative synthesis of imines from alcohols and amines
  作者：Manju Bala、Praveen Kumar Verma、Neeraj Kumar、Upendra Sharma、Bikram Singh

  DOI：10.1139/cjc-2012-0399

  日期：2013.8

  An efficient iron phthalocyanine catalyzed method was developed for direct oxidative coupling of alcohols with amines to afford corresponding imines. The present protocol is applicable to various substituted aromatic and aliphatic alcohols and amines. The reaction is believed to proceed via activation of alcohols by iron phthalocyanines through Lewis acid–base interaction to form aldehydes, which by nucleophilic attack of amines are converted into the corresponding imines.

  开发了一种高效的铁酞菁催化方法，用于直接氧化偶联醇和胺，生成相应的亚胺。该方法适用于各种取代芳香族和脂肪族醇和胺。该反应被认为通过铁酞菁对醇的活化，通过路易斯酸碱相互作用形成醛，然后通过胺的亲核攻击转化为相应的亚胺。
• Nano-sized NiLa2O4 spinel–NaBH4-mediated reduction of imines to secondary amines
  作者：Ali Shiri、Faezehy Soleymanpour、Hossein Eshghi、Iman Khosravi

  DOI：10.1016/s1872-2067(15)60921-4

  日期：2015.8

  Nano-sized NiLa2O4 spinel was produced by thermal decomposition of Ni-La compounds via a sol-gel method. The well-crystallized spinel structure was formed after calcination at 750 degrees C. The physicochemical properties of the spinel were investigated using differential thermal analysis, X-ray diffraction, transmission electron microscopy, scanning electron microscopy, and particle size distribution analysis. The results show that the nanoparticles have regular shapes with well-defined crystal faces and consist of uniform quasi-spherical crystallites of average size 40 nm. The refined unit cell parameters are a = 3.861205 angstrom and c = 12.6793 angstrom. This new nano-sized NiLa2O4 spinel is an efficient heterogeneous catalyst for the selective conversion of imines to the corresponding secondary amines in the presence of NaBH4 as a reducing agent, in good to excellent yields. All the reactions were completely chemoselective at room temperature and had relatively short reaction times. Secondary amines with different aryl groups, including those bearing electron-withdrawing or electron-donating groups, were obtained under the optimum reaction conditions. The catalyst was readily recovered and was recycled four times with no significant loss of catalytic activity. (C) 2015, Dalian Institute of Chemical Physics, Chinese Academy of Sciences. Published by Elsevier B.V. All rights reserved.