N-[4-(dimethylamino)phenyl]-N-methyl-N-phenylamine | 15016-99-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-[4-(dimethylamino)phenyl]-N-methyl-N-phenylamine
• 英文别名: N,N,N'-trimethyl-N'-phenyl-1,4-benzenediamine；N-phenyl-N,N',N'-trimethyl-p-phenylenediamine；4-dimethylaminodiphenyl-methylamine；N,N,N'-trimethyl-N'-phenyl-p-phenylenediamine；N,N,N'-Trimethyl-N'-phenyl-p-phenylendiamin；4-Dimethylamino-N-methyldiphenylamin；1-N,1-N,4-N-trimethyl-4-N-phenylbenzene-1,4-diamine
• CAS: 15016-99-6
• 化学式: C₁₅H₁₈N₂
• 分子量: 226.321
• InChiKey: BDVGVAYKSGFIAL-UHFFFAOYSA-N

物化性质

• 熔点：
  44-45 °C
• 沸点：
  369.4±25.0 °C(Predicted)
• 密度：
  1.067±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：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-[4-(dimethylamino)phenyl]-N-methyl-N-phenylamine 、 硫酸二甲酯 在 potassium carbonate 作用下， 生成 tri-N-methyl-4-(N-methyl-anilino)-anilinium; iodide
  参考文献：
  名称：

  Fichter; Rothenberger, Helvetica Chimica Acta, 1922, vol. 5, p. 169

  摘要：

  DOI：
• 作为产物：
  描述：

  N,N-二甲基苯胺 在 硫酸 作用下， 生成 N-[4-(dimethylamino)phenyl]-N-methyl-N-phenylamine
  参考文献：
  名称：

  Fichter; Rothenberger, Helvetica Chimica Acta, 1922, vol. 5, p. 169

  摘要：

  DOI：

文献信息

• (<i>t</i>-Bu)₂PNP(<i>i</i>-BuNCH₂CH₂)₃N:  New Efficient Ligand for Palladium-Catalyzed C−N Couplings of Aryl and Heteroaryl Bromides and Chlorides and for Vinyl Bromides at Room Temperature
  作者：Ch. Venkat Reddy、Jesudoss V. Kingston、John G. Verkade

  DOI：10.1021/jo702367k

  日期：2008.4.1

  chlorides possessing base-sensitive substituents (nitro, ester, and keto) provide coupling products with bulky aryl amines in good to excellent yields. Aryl halides possessing other functional groups including cyano, amino, trifluoromethyl, and phenol, coupled with equal ease, producing highly functionalized amines in good to excellent yields. Moreover, an aryl chloro group can be preserved in the presence

  通过使用Pd（OAc）2，Cs 2 CO 3或NaOH，以及新的配体（t -Bu）2 PN P（i-BuNCH 2 CH 2）3 N（3a），具有碱敏感取代基（硝基，酯和酮）的电子形式多样的芳基溴化物和氯化物阵列，可提供丰满的芳基胺类化合物，并具有良好的收率和优异的收率。具有其他官能团（包括氰基，氨基，三氟甲基和苯酚）的芳基卤化物同等容易地偶联，从而以良好或优异的收率生产出高度官能化的胺。此外，在我们的反应条件下，在溴取代基的存在下可以保留芳基氯基。中银保护的胺类也有效参与。杂环溴化物和氯化物与胺进行干净的偶联，收率很高。我们协议的一个重要优势是使用了比以前报道的钯含量更低的钯含量，同时又不影响产量。空气稳定的钯络合物（η3-肉桂基）PdCl·（3a）（5）也成功地用于C-N偶联反应中，而巴豆基类似物的疗效较差。在图3a /钯（OAC）2催化剂体系促进，对于第一次，与各种胺，以产生亚胺和烯胺的乙烯基溴化物的有效耦合室温。
• Bulky Alkylphosphines with Neopentyl Substituents as Ligands in the Amination of Aryl Bromides and Chlorides
  作者：Lensey L. Hill、Lucas R. Moore、Rongcai Huang、Raluca Craciun、Andrew J. Vincent、David A. Dixon、Joe Chou、Christopher J. Woltermann、Kevin H. Shaughnessy

  DOI：10.1021/jo060303x

  日期：2006.7.1

  than tri(tert-butyl)phosphine (TTBP) under mild conditions. DTBNpP also provided effective catalysts for amination reactions of aryl chlorides at elevated temperatures. Further replacement of tert-butyl groups with neopentyl substituents resulted in less effective ligands for amination reactions. Computationally derived cone angles showed that replacement of a tert-butyl group with a neopentyl group

  在温和条件下，二（叔丁基）新戊基膦（DTBNpP）与钯源的结合为芳基溴的Hartwig-Buchwald胺化提供了与三（叔丁基）膦（TTBP）相当或更好的活性。DTBNpP还为芳基氯在高温下的胺化反应提供了有效的催化剂。用新戊基取代基进一步取代叔丁基会导致胺化反应的配体效率降低。计算得出的锥角表明，更换的叔具有新戊基的叔丁基显着增加了膦的锥角。与TTBP相比，DTBNpP的锥角更大似乎与衍生自DTBNpP的催化剂在芳基溴化胺化反应中的较高活性相关。TTBP是一种比DTBNpP更强的电子供体，这可以解释TTBP衍生的催化剂对芳基氯具有更高的活性。
• Polycationic States of Oligoanilines Based on Wurster's Blue
  作者：Akihiro Ito、Daisuke Sakamaki、Haruhiro Ino、Aya Taniguchi、Yasukazu Hirao、Kazuyoshi Tanaka、Katsuichi Kanemoto、Tatsuhisa Kato

  DOI：10.1002/ejoc.200900403

  日期：2009.9

  multiplicities of the dominant polycationic species of 2 and 3 formed by 3 equiv. of oxidant can be assigned to quartet and doublet states, respectively on the basis of pulsed EPR spectroscopy. These results demonstrate that the intramolecular connectivity between the spin-containing units decisively influences the spin preference of the multispin systems based on oligoanilines.(© Wiley-VCH Verlag GmbH &

  基于 Wurster's blue,N,N',N"-tris[4-(二甲氨基)苯基]-N,N',N"-trimethyl-1,3,5-benzotriamine (2) 和 N 的两种低聚苯胺的聚阳离子， N'-双(3-N-[4-(二甲氨基)苯基]-N-甲氨基}苯基)-N，N'-二甲基-对苯二胺(3)，已通过逐步氧化程序有效地产生。它们的氧化还原行为的特征在于嵌入的对苯二胺 (PD) 单元及其分子内连接性。氧化的 2 和 3 物种的 EPR 分析揭示了溶液中存在高自旋物种。发现2和3的主要聚阳离子物质的自旋多重性由3当量形成。在脉冲 EPR 光谱的基础上，氧化剂的 4 可分别分配为四重态和双重态。
• On the ESR identification of paramagnetic species observed during set oxidation of N,N-dimethyl-p-anisidine
  作者：F. Ciminale、R. Curci、M. Portacci、L. Troisi

  DOI：10.1016/s0040-4039(00)87908-3

  日期：——
• Oxidative Activation in Aromatic Substitutions. Reactions of <i>N</i>,<i>N</i>-Dimethylanilines with Secondary Anilines Promoted by Thallium Triacetate
  作者：Francesco Ciminale、Antonella Ciardo、Salvatore Francioso、Angelo Nacci

  DOI：10.1021/jo982276j

  日期：1999.4.1

  The reactions of N,N-dimethyl-p-anisidine (1a), N,N-dimethylaniline (1b), and N,N-dimethyl-p-fluoroaniline (1c) toward secondary anilines 2(a-d)-H in the presence of thallium triacetate sesquihydrate have been studied as representative of a novel oxidatively activated aromatic substitution affording 1,4-benzenediamine derivatives 3a-d. All of the substrates considered gave substitution with diphenylamine (2d-H). However, with anilines 2b,c-H, only 1a underwent substitution, and substrates 1b,c were practically unreactive. The observed differences in reactivity are well accounted for within a mechanistic framework wherein oxidative activation of both the substrate and the secondary aniline is regarded as alternatively (or simultaneously) possible, depending on the redox characteristics of the reactants. For instance, it can be stated, beyond any reasonable doubt, that reactions of 1a with 2b,c-H proceed via nucleophilic attack of the latter on 1a(+), and that the reaction of 1a-c with 2d-H must involve the diphenylamino radical 2d.