phenyl(4-(p-tolylamino)phenyl)methanone | 42872-23-1

• 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: phenyl(4-(p-tolylamino)phenyl)methanone
• 英文别名: [4-[(4-methylphenyl)amino]phenyl](phenyl)methanone；[4-(4-methylanilino)phenyl]-phenylmethanone
• CAS: 42872-23-1
• 化学式: C₂₀H₁₇NO
• 分子量: 287.361
• InChiKey: QCUZVCYLUPIQSC-UHFFFAOYSA-N

物化性质

• 熔点：
  128-130 °C
• 沸点：
  465.4±28.0 °C(Predicted)
• 密度：
  1.150±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  对苄基三氟甲磺酸 、 4-氨基二苯甲酮 在 palladium diacetate Celite 、 caesium carbonate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 甲苯 、 叔丁醇 为溶剂， 反应 0.25h， 以91%的产率得到phenyl(4-(p-tolylamino)phenyl)methanone
  参考文献：
  名称：

  Rapid and Efficient Microwave-Assisted Synthesis of Aryl Aminobenzophenones Using Pd-Catalyzed Amination

  摘要：

  Substituted aryl aminobenzophenone p38 MAP kinase inhibitors were synthesized in good to excellent yields using palladium-catalyzed aryl amination under conditions of microwave irradiation. Various ligands have been screened, and the reaction conditions were optimized. These coupling reactions are suitable for various anilines and aryl bromides that bear a variety of functional groups. Some leaving groups (iodides, chlorides, triflates, and tosylates) other than bromides have also been investigated. By this method, a large number of aryl aminobenzophenone p38 MAP kinase inhibitors were prepared in short order.

  DOI：

  10.1021/jo049572i

文献信息

• Aminations of Aryl Bromides in Water at Room Temperature
  作者：Bruce H. Lipshutz、David W. Chung、Brian Rich

  DOI：10.1002/adsc.200900323

  日期：2009.8

  Unsymmetrical di- and triarylamines can be formed under green chemistry conditions, taking advantage of micellar catalysis leading to palladium-catalyzed aminations at ambient temperatures in water as the only medium.

  不对称的二芳基胺和三芳基胺可以在绿色化学条件下形成，利用胶束催化导致钯催化胺化在环境温度下在水中作为唯一介质。
• Sodium Butylated Hydroxytoluene: A Functional Group Tolerant, Eco‐Friendly Base for Solvent‐Free, Pd‐Catalysed Amination
  作者：Volodymyr Semeniuchenko、Wilfried M. Braje、Michael G. Organ

  DOI：10.1002/chem.202101617

  日期：2021.9

  NaBHT (sodium 2,6-di-tert-butyl-4-methylphenolate), a strong, but hindered and lipophilic base, has been effectively paired with similarly lipophilic, high-reactivity Pd-NHC (N-heterocyclic carbene) catalysts to produce an ideal combination for performing solvent-free (melt) cross-coupling amination. The mild nucleophilicity of NaBHT, coupled with the anti-oxidant properties of its conjugate acid byproduct

  NaBHT（2,6-二叔丁基-4-甲基苯酚钠）是一种强但受阻且亲脂的碱，已与类似的亲脂性、高反应性 Pd-NHC（N-杂环卡宾）催化剂有效配对以生产进行无溶剂（熔融）交叉偶联胺化的理想组合。NaBHT 温和的亲核性，加上其共轭酸副产物的抗氧化特性，BHT 意味着该过程似乎没有官能团不相容性。在所有情况下，仅使用 0.1-0.2 mol% 的催化剂就观察到碱敏感和氧化还原活性官能团的高效偶联。使用该反应的标准碱 KOtBu 进行比较，导致大多数应用中偶联不良或完全降解 - 只有 NaBHT 有效。
• Stable Nickel(0) Phosphites as Catalysts for CN Cross-Coupling Reactions
  作者：Sven S. Kampmann、Alexandre N. Sobolev、George A. Koutsantonis、Scott G. Stewart

  DOI：10.1002/adsc.201400201

  日期：2014.6.16

  phosphite‐based catalysts for use in the CN cross‐coupling reaction. The combination of nickel tetrakis(triphenyl phosphite) Ni[P(OPh)3]4} and 1,1′‐bis(diphenylphosphino)ferrocene (dppf), and in particular a newly developed catalyst (dppf)Ni[P(OPh)3]2, were found to be extremely effective in catalyzing a range of amination reactions of anilines and amines with aryl chlorides. This new catalyst system offers

  本文中，我们描述了用于CN交叉偶联反应的廉价，空气稳定的亚磷酸镍基催化剂的设计和制备。四（三亚磷酸三苯酯）镍Ni [P（OPh）3 ] 4 }和1,1'-双（二苯基膦基）二茂铁（dppf）的组合，尤其是新开发的催化剂（dppf）Ni [P（OPh） ）3 ] 2，被发现在催化一系列苯胺和胺与芳基氯化物的胺化反应中极为有效。这种新的催化剂体系提供了通常用于CN键形成的双（环辛二烯基）镍[Ni（COD）2 ]和钯（0）催化剂的替代品。
• Selective Monoarylation of Primary Anilines Catalyzed by Pd(dippf) and its Application in OLED Component Synthesis
  作者：Matthias F. Grünberg、Fan Jia、Andreas Rivas-Nass、Lukas J. Gooßen

  DOI：10.1002/adsc.201501160

  日期：2016.5.19

  Palladium 1,1′‐bis(diisopropylphosphino)‐ferrocene [Pd(dippf)] complexes were found to promote the monoarylation of primary anilines with unprecedented selectivities. They also allow the sequential arylation of primary anilines with two different aryl bromides in one pot. The reactions can be performed at low catalyst loadings (0.2 mol%) and high substrate concentrations. The synthetic utility of the

  发现钯1,1'-双（二异丙基膦基）-二茂铁[Pd（dippf）]配合物以前所未有的选择性促进伯苯胺的单芳基化。它们还允许在一个罐中用两种不同的芳基溴将芳基苯胺依次芳基化。该反应可以在低催化剂负载量（0.2mol％）和高底物浓度下进行。各种二-和三芳基胺的合成证明了最佳催化剂的合成效用。特别关注的是最先进的小分子有机发光二极管（OLED）中使用的具有咔唑和芴部分的化合物。
• Synthesis and properties of phenylogous amides
  作者：Ryu Yamasaki、Hirokazu Ikeda、Hyuma Masu、Isao Azumaya、Shinichi Saito

  DOI：10.1016/j.tet.2012.07.084

  日期：2012.10

  which involves the connection of two substituents through a benzene ring, is rarely recognized as a related idea. In this article, we present synthesis and physical properties, including their structure and reactivity of phenylogous amides. This amide mimetic unit is relatively stable and easily prepared by the Hartwig–Buchwald amination reaction. The effect of the resonance was examined by means

  Vinyology是一个广泛接受的原理，涉及通过双键转移电子化学特征，并且通过应用该概念已开发出许多反应。相反，涉及通过苯环连接两个取代基的苯甲醛很少被认为是相关的想法。在本文中，我们介绍了合成和物理性质，包括其结构和苯酚酰胺的反应性。该酰胺模拟单元相对稳定，可通过Hartwig-Buchwald胺化反应轻松制备。通过晶体学，反应性和紫外可见光谱检查了共振的影响。