N-(4-methoxyphenyl)-3,4-dimethylaniline | 198291-18-8

• 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)-3,4-dimethylaniline
• 英文别名: 3,4-dimethylphenyl-4'-methoxyphenylamine；N-(3,4-dimethylphenyl)-4-anisidine
• CAS: 198291-18-8
• 化学式: C₁₅H₁₇NO
• 分子量: 227.306
• InChiKey: XBFIDTFTKRNRRR-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

• 作为反应物：
  描述：

  N-(4-methoxyphenyl)-3,4-dimethylaniline 在 三叔丁基膦 、 三(五氟苯基)硼烷 、 palladium diacetate 、 sodium t-butanolate 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 N-[4-[4-[N-(3,4-dimethylphenyl)-4-[dimethyl(trimethylsilyloxy)silyl]oxyanilino]phenyl]phenyl]-N-[4-[dimethyl(trimethylsilyloxy)silyl]oxyphenyl]-3,4-dimethylaniline
  参考文献：
  名称：

  Liquid Triarylamines: The Scope and Limitations of Piers–Rubinsztajn Conditions for Obtaining Triarylamine–Siloxane Hybrid Materials

  摘要：

  New liquid triarylamine-siloxane hybrid materials are produced using the Piers-Rubinsztajn reaction. Under mild conditions, liquid analogues of conventional and commonly crystalline triarylamines are easily synthesized from readily available or accessible intermediates. Using a diverse selection of triarylamines, we explored the effects of siloxane group and substitution pattern on the physical properties of these materials, and we have demonstrated that relatively large molecular liquids with desirable electrochemical properties can be produced. The interactions between the strongly Lewis acidic catalyst used for this transformation, tris(pentafluorophenyl)borane (BCF), and the Lewis basic triarylamine substrates were studied. Through UV-vis-NIR and F-19 NMR spectroscopy, we have proposed that the catalyst undergoes a reversible redox reaction with the substrates to produce a charge transfer complex. The formation of this charge transfer complex is sensitive to the oxidation potential of the triarylamine and can greatly affect the kinetics of the Piers-Rubinsztajn reaction.

  DOI：

  10.1021/jo2020906
• 作为产物：
  描述：

  在 三氟乙酸 、 锌 作用下， 以 甲醇 为溶剂， 生成 N-(4-methoxyphenyl)-3,4-dimethylaniline
  参考文献：
  名称：

  通过氧化脱芳香化反应-氨基交换-还原芳香化反应由两个芳香胺一锅法合成二芳基胺

  摘要：

  已经开发了仅使用芳族胺作为起始原料的二芳基胺的一锅合成策略。该方法涉及PhI（OAc）2诱导的N-磺酰基保护的对位取代苯胺的氧化脱芳香化作用，Bi（OTf）3催化的N-磺酰基环己二亚胺和芳香胺之间的亚氨基交换反应，以及CF 3 COOH / Zn介导的所得N-芳基环己二亚胺的还原芳构化。

  DOI：

  10.1021/ol4007162

文献信息

• Benzyloxycalix[8]arene supported Pd–NHC cinnamyl complexes for Buchwald–Hartwig C–N cross-couplings
  作者：Sandra Abi Fayssal、Timothée Naret、Vincent Huc、Julien Buendia、Cyril Martini、Emmanuelle Schulz

  DOI：10.1039/d1cy00669j

  日期：——

  and in one case, promoted the synthesis of an unprecedented Pd-catalyzed C–H activation product. Thanks to the calixarenic support, the target products could be isolated with low levels of residual palladium, and in some cases, even below the restrictive toxic metal standards applied by the pharmaceutical industry. Through an easy to implement procedure, these perfectly characterised catalysts thus

  报道了在苄氧基杯[8]芳烃上负载的 Pd-NHC 肉桂基配合物的可扩展合成。这些催化剂对 Buchwald-Hartwig 交叉偶联反应非常活跃，允许使用低催化负载将芳基氯和芳基溴与各种烷基和芳基胺偶联。负载的配合物还成功地提供了有吸引力的不对称三芳基胺，并且在一种情况下，促进了前所未有的 Pd 催化的 C-H 活化产物的合成。由于杯芳烃支持，目标产品可以分离出低水平的残留钯，在某些情况下，甚至低于制药行业应用的限制性有毒金属标准。通过一个易于实施的程序，
• Triarylbismuthane - iodobenzene diacetate: One-pot system for copper-catalysed N-arylation under neutral conditions
  作者：Sébastien Combes、Jean-Pierre Finet

  DOI：10.1016/s0040-4020(98)00126-4

  日期：1998.4

  Triarylbismuthanes react with iodobenzene diacetate in dichloromethane under mild, neutral conditions to afford triarylbismuth diacetates, which can be isolated in good yields. The reagents can also be directly used in a one-pot copper-catalysed N-arylation of anilines to give near quantitative yields of the corresponding diarylamines, except in the case of the 2-methoxyphenylbismuth derivative. N-arylation with tris(2-methoxyphenyl)bismuth diacetate was quantitative only when the reaction was performed with the pure isolated reagent. (C) 1998 Elsevier Science Ltd. All rights reserved.
• The Use of Piers–Rubinsztajn Conditions for the Placement of Triarylamines Pendant to Silicone Polymers
  作者：Michael J. Gretton、Brett A. Kamino、Michael A. Brook、Timothy P. Bender

  DOI：10.1021/ma202041u

  日期：2012.1.24

  The use of Piers-Rubinsztajn conditions was explored for the synthesis of silicone polymers bearing pendant triarylamine functionality. We have found that up to 60% of the hydride groups of a silicone copolymer can be successfully substituted with a triarylamine moiety, without metathesis or redistribution of the silicone. The resulting polymers are hydrolytically stable. The functionalization procedure is straightforward, conducted under ambient conditions with a simple one-step work-up, and avoids the use of a metal-based catalyst. The resulting phenylated triarylamine-silicone hybrid polymer was characterized by optical absorption and fluorescence spectroscopy, CV, and differential scanning calorimetry. The hybrids maintain the physical appearance of a silicone polymer while adopting the photophysical and electrochemical characteristics of the triarylamine.
• Liquid Triarylamines: The Scope and Limitations of Piers–Rubinsztajn Conditions for Obtaining Triarylamine–Siloxane Hybrid Materials
  作者：Brett A. Kamino、Bridget Mills、Christopher Reali、Michael J. Gretton、Michael A. Brook、Timothy P. Bender

  DOI：10.1021/jo2020906

  日期：2012.2.17

  New liquid triarylamine-siloxane hybrid materials are produced using the Piers-Rubinsztajn reaction. Under mild conditions, liquid analogues of conventional and commonly crystalline triarylamines are easily synthesized from readily available or accessible intermediates. Using a diverse selection of triarylamines, we explored the effects of siloxane group and substitution pattern on the physical properties of these materials, and we have demonstrated that relatively large molecular liquids with desirable electrochemical properties can be produced. The interactions between the strongly Lewis acidic catalyst used for this transformation, tris(pentafluorophenyl)borane (BCF), and the Lewis basic triarylamine substrates were studied. Through UV-vis-NIR and F-19 NMR spectroscopy, we have proposed that the catalyst undergoes a reversible redox reaction with the substrates to produce a charge transfer complex. The formation of this charge transfer complex is sensitive to the oxidation potential of the triarylamine and can greatly affect the kinetics of the Piers-Rubinsztajn reaction.
• One-Pot Synthesis of Diarylamines from Two Aromatic Amines via Oxidative Dearomatization–Imino Exchange–Reductive Aromatization
  作者：Li Zhang、Weibin Wang、Renhua Fan

  DOI：10.1021/ol4007162

  日期：2013.4.19

  A one-pot synthetic strategy for diarylamines using only aromatic amines as starting materials has been developed. This method involved a PhI(OAc)2-induced oxidative dearomatization of N-sulfonyl protected para-substituted anilines, a Bi(OTf)3-catalyzed imino exchange reaction between N-sulfonyl cyclohexadienimines and aromatic amines, and a CF3COOH/Zn mediated reductive aromatization of the resulting

  已经开发了仅使用芳族胺作为起始原料的二芳基胺的一锅合成策略。该方法涉及PhI（OAc）2诱导的N-磺酰基保护的对位取代苯胺的氧化脱芳香化作用，Bi（OTf）3催化的N-磺酰基环己二亚胺和芳香胺之间的亚氨基交换反应，以及CF 3 COOH / Zn介导的所得N-芳基环己二亚胺的还原芳构化。