N-(2-甲氧基苯基)-2,6-二甲基苯胺 | 58656-24-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: N-(2-甲氧基苯基)-2,6-二甲基苯胺
• 英文名称: N-(2,6-dimethylphenyl)-2-methoxyaniline
• 英文别名: N-(2-methoxyphenyl)-2,6-dimethylaniline；N-(2-methoxyphenyl)-2,6-xylidine；2-Methoxy-2',6'-dimethyldiphenylamin
• CAS: 58656-24-9
• 化学式: C₁₅H₁₇NO
• 分子量: 227.306
• InChiKey: SNHZCMQKWIMSSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  2,6-二甲基苯酚 在 氢氧化钾 作用下， 以 二甲基亚砜 为溶剂， 生成 N-(2-甲氧基苯基)-2,6-二甲基苯胺
  参考文献：
  名称：

  用三价磷试剂还原亚硝基化合物。第十二部分。芳基2-硝基芳基醚转化为新型3-芳基-2,3-二氢-1,3,2-苯并恶唑磷（V）oles（氧杂氮膦）及其2-氧代衍生物

  摘要：

  芳基2-硝基芳基醚（2-NO 2 ·C 6 H 4 ·O·C 6 H 2 R 3 2 R 4：在异丙苯中的反应：R 3＝ Me，R 4＝ H； R 3＝ R 4＝ Me； R 3 = OMe，R 4 = H； R 3 = H，R 4 = OMe； R 3 = R 4 = H； R 3 = H，R 4 = Me； R 3 = Me，R 4 = CO 2 Me）与三价磷试剂（4摩尔当量）（R 2 R1 2 P：R 1 = R 2 = MeO，EtO或Pr i O；R 1＝ EtO，R 2＝ Me；R 1＝ MeO，R 2＝ Ph；R 1＝ Ph，R 2＝ MeO；R 1 2 = –O·CH 2 ·CH 2 ·O–，R 2 = Ph）得到新颖的五配位磷化合物，3-芳基-2,3-二氢-1,3,2-苯并氮杂磷（ V）oles（8）（12–95％）。它们在水中迅速水解，得到四配位磷化合物，2-烷氧基-

  DOI：

  10.1039/p19750002376

文献信息

• Effect of Aryl Ligand Identity on Catalytic Performance of Trineopentylphosphine Arylpalladium Complexes in <i>N</i>-Arylation Reactions
  作者：Huaiyuan Hu、Corrie E. Burlas、Sabrina J. Curley、Tomasz Gruchala、Fengrui Qu、Kevin H. Shaughnessy

  DOI：10.1021/acs.organomet.0c00140

  日期：2020.10.26

  A series of air-stable [(Np3P)Pd(Ar)Br]2 (Np = neopentyl) and (Np3P)Pd(Ar)(amine)Br complexes (amine = morpholine and isobutylamine) have been prepared and tested as precatalysts for the coupling of sterically demanding aryl bromides and aniline derivatives. The complexes are more active than the catalyst generated in situ from Pd2(dba)3 and PNp3. Increasing steric demand of the aryl group on palladium

  制备了一系列空气稳定的[（Np 3 P）Pd（Ar）Br] 2（Np =新戊基）和（Np 3 P）Pd（Ar）（胺）Br配合物（胺=吗啉和异丁胺），并且经测试可作为位阻芳基溴化物和苯胺衍生物偶联的前催化剂。该络合物比由Pd 2（dba）3和PNp 3原位产生的催化剂更具活性。钯上芳基空间需求的增加与催化剂活性的提高有关。[（Np 3 P）Pd（2,6-Me 2 C 6 H 3）Br] 2催化的反应与使用Pd 2（dba）3 / PNp 3的那些相比，在更低的温度下以更高的收率有效地发生。与[（Np 3 P）Pd（Ar）Br] 2络合物相比，胺加合物的反应速率和转化率更低。胺加合物的较低活性似乎是由缓慢的碱促进的还原消除产生的，从而产生催化活性的LPd（0）物质。
• Trineopentylphosphine: A Conformationally Flexible Ligand for the Coupling of Sterically Demanding Substrates in the Buchwald–Hartwig Amination and Suzuki–Miyaura Reaction
  作者：Steven M. Raders、Jane N. Moore、Jacquelynn K. Parks、Ashley D. Miller、Thomas M. Leißing、Steven P. Kelley、Robin D. Rogers、Kevin H. Shaughnessy

  DOI：10.1021/jo400435z

  日期：2013.5.17

  palladium provides a highly effective catalyst for the Buchwald–Hartwig coupling of sterically demanding aryl bromides and chlorides with sterically hindered aniline derivatives. Excellent yields are obtained even when both substrates include 2,6-diisopropyl substituents. Notably, the reaction rate is inversely related to the steric demand of the substrates. X-ray crystallographic structures of Pd(TNpP)2,

  三叔戊基膦（TNpP）与钯的结合为空间受限的芳族溴化物和氯化物与空间受阻的苯胺衍生物的布赫瓦尔德-哈特维格偶联提供了一种高效的催化剂。即使两个底物都包含2，6-二异丙基取代基，也可获得优异的产率。值得注意的是，反应速率与底物的空间需求成反比。Pd（TNpP）2，[Pd（4- t -Bu-C 6 H 4）（TNpP）（μ-Br）] 2和[Pd（2-Me-​​C 6 H 4）的X射线晶体结构（TNpP）（μ-Br）] 2被报道。这些结构表明，TNpP配体的构象柔韧性在允许催化剂偶联受阻底物方面起着关键作用。Pd / TNpP系统对受阻芳基溴化物的Suzuki偶联也显示出良好的活性。
• Solvent-free aryl amination catalysed by [Pd(NHC)] complexes
  作者：Anthony Chartoire、Arnaud Boreux、Anthony R. Martin、Steven P. Nolan

  DOI：10.1039/c3ra40386f

  日期：——

  A highly effective solvent-free protocol for the Buchwald–Hartwig amination of unactivated aryl chlorides is described. The effect of various [Pd(NHC)] pre-catalyst systems on the reactivity has been studied. [Pd(IPr*)(cin)Cl] is reported as the complex of choice for the transformation.

  描述了一种用于未活化的芳基氯的布赫瓦尔德-哈特维格胺胺化的高效无溶剂方案。研究了各种[Pd（NHC）]预催化剂体系对反应活性的影响。据报道[Pd（IPr *）（cin）Cl]是转化的选择复合物。
• N‐Heterocyclic Carbene Palladium(II) Amine Complexes: The Role of Primary Aryl‐ or Alkylamine Binding and Applications in the Buchwald‐Hartwig Amination Reaction
  作者：Yu‐Cheng Hsu、Ming‐Tsz Chen

  DOI：10.1002/ejic.202100828

  日期：2022.1.11

  The family of N-heterocyclic carbene-palladium(II) complexes bearing primary aryl- or alkylamines were synthesized as well as characterized by single crystal X-ray diffraction and NMR spectroscopy. 21 expected coupling arylated anilines were obtained in moderate to high yields under mild conditions. All reactions were carried out in air and all starting materials were used as supplied without purification

  合成了带有伯芳基或烷基胺的 N-杂环卡宾-钯 (II) 配合物家族，并通过单晶 X 射线衍射和核磁共振光谱进行了表征。在温和条件下以中等至高产率获得了 21 种预期的偶联芳基化苯胺。所有反应均在空气中进行，所有原料均未经纯化直接使用。
• Carbene adduct of cyclopalladated ferrocenylimine as an efficient catalyst for the amination of aryl chlorides
  作者：Jingya Li、Mengjun Cui、Ajuan Yu、Yangjie Wu

  DOI：10.1016/j.jorganchem.2007.05.022

  日期：2007.8

  A novel air- and moisture-stable carbene adduct of cyclopalladated ferrocenylimine has been synthesized and characterized. The structure of this compound was determined by X-ray crystal structure analysis. This adduct has been applied as an efficient catalyst for the amination of aryl chlorides.

  合成并表征了一种新型的对空气和水分稳定的环palpalated二茂铁亚胺卡宾加合物。通过X射线晶体结构分析确定该化合物的结构。该加合物已被用作胺化芳基氯的有效催化剂。