1-(2-氨基苯基)-2-(2-溴苯基)乙酮 | 869668-73-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 1-(2-氨基苯基)-2-(2-溴苯基)乙酮
• 英文名称: 1-(2-aminophenyl)-2-(2-bromophenyll)ethanone
• 英文别名: 1-(2-aminophenyl)-2-(2-bromophenyl)ethanone
• CAS: 869668-73-5
• 化学式: C₁₄H₁₂BrNO
• 分子量: 290.159
• InChiKey: NTSBNIHFCWAGBK-UHFFFAOYSA-N

物化性质

• 熔点：
  84-86 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  425.3±25.0 °C(Predicted)
• 密度：
  1.449±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-氨基苯基)-2-(2-溴苯基)乙酮 在 palladium diacetate 、 potassium phosphate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 氯仿 、 水 、 甲苯 为溶剂， 反应 5.0h， 生成 奥卡西平
  参考文献：
  名称：

  An Advantageous Route to Oxcarbazepine (Trileptal) Based on Palladium-Catalyzed Arylations Free of Transmetallating Agents

  摘要：

  [GRAPHICS]A new route to oxcarbazepine (Trileptal), the most widely prescribed antiepileptic drug, starting from commercially available 2'-aminoacetophenone and 1,2-dibromobenzene, is reported. The sequentially accomplished key steps are palladium-catalyzed intermolecular alpha-arylation of ketone enolates and intramolecular N-arylation reactions. After several experiments to establish the best conditions for both arylation processes, the target oxcarbazepine is obtained in a satisfactory overall yield, minimizing the number of steps and employing scalable catalytic procedures developed in partially aqueous media.

  DOI：

  10.1021/ol051291p
• 作为产物：
  描述：

  N-(2-acetylphenyl)-4-methylbenzenesulfonamide 在 palladium diacetate 、 硫酸 、 caesium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 水 、 甲苯 为溶剂， 反应 48.17h， 生成 1-(2-氨基苯基)-2-(2-溴苯基)乙酮
  参考文献：
  名称：

  An Advantageous Route to Oxcarbazepine (Trileptal) Based on Palladium-Catalyzed Arylations Free of Transmetallating Agents

  摘要：

  [GRAPHICS]A new route to oxcarbazepine (Trileptal), the most widely prescribed antiepileptic drug, starting from commercially available 2'-aminoacetophenone and 1,2-dibromobenzene, is reported. The sequentially accomplished key steps are palladium-catalyzed intermolecular alpha-arylation of ketone enolates and intramolecular N-arylation reactions. After several experiments to establish the best conditions for both arylation processes, the target oxcarbazepine is obtained in a satisfactory overall yield, minimizing the number of steps and employing scalable catalytic procedures developed in partially aqueous media.

  DOI：

  10.1021/ol051291p

文献信息

• Application of nanoparticle mediated N-arylation of amines for the synthesis of pharmaceutical entities using vit-E analogues as amphiphiles in water
  作者：Atul Kumar、Ajay Kumar Bishnoi

  DOI：10.1039/c4ra15267k

  日期：——

  The first CuI-nanoparticle catalyzed inter and intramolecular N-arylation of amines using vitamin E analogues as amphiphiles was developed in water and is extended to azoles, substituted indoles, a bioactive natural product and intermediates of pharmaceutical entities.

  首次在水中开发了以维生素E类似物为两性分子的CuI纳米颗粒催化的胺的分子内和分子间N-芳基化反应，并扩展到唑类化合物、取代吲哚、生物活性天然产物和药物实体的中间体。
• Sequential palladium-catalysed C- and N-arylation reactions as a practical and general protocol for the synthesis of the first series of oxcarbazepine analogues
  作者：Mónica Carril、Raul SanMartin、Esther Domínguez、Imanol Tellitu

  DOI：10.1016/j.tet.2006.11.003

  日期：2007.1

  The first series of oxcarbazepine analogues, starting from readily-available materials and through a high-yielding five-step sequence based on palladium catalysis, is reported. The so-obtained compounds incorporate not only a variety of substituents in both of the aryl rings comprising the framework of an oxcarbazepine, but also involve the more challenging palladium-catalysed coupling of a number of heteroaromatic substrates. The addition of small amounts of water in some of the metal-catalysed processes showed a beneficial effect, highly increasing the selectivity of such reactions. (c) 2006 Elsevier Ltd. All rights reserved.
• On-Water Chemistry:  Copper-Catalyzed Straightforward Synthesis of Benzo[<i>b</i>]furan Derivatives in Neat Water
  作者：Mónica Carril、Raul SanMartin、Imanol Tellitu、Esther Domínguez

  DOI：10.1021/ol060274c

  日期：2006.3.1

  A more sustainable protocol leading to 2-alkyl- or 2-aryl-substituted benzo[b]furans is reported, involving a copper-TMEDA complex which catalyzes the transformation of readily available ketone derivatives into the corresponding benzofurans in good to excellent yields. The reaction is accomplished using water as the solvent without organic cosolvents, and one example of catalyst reutilization is also presented.
• An Advantageous Route to Oxcarbazepine (Trileptal) Based on Palladium-Catalyzed Arylations Free of Transmetallating Agents
  作者：Mónica Carril、Raul SanMartin、Fátima Churruca、Imanol Tellitu、Esther Domínguez

  DOI：10.1021/ol051291p

  日期：2005.10.1

  [GRAPHICS]A new route to oxcarbazepine (Trileptal), the most widely prescribed antiepileptic drug, starting from commercially available 2'-aminoacetophenone and 1,2-dibromobenzene, is reported. The sequentially accomplished key steps are palladium-catalyzed intermolecular alpha-arylation of ketone enolates and intramolecular N-arylation reactions. After several experiments to establish the best conditions for both arylation processes, the target oxcarbazepine is obtained in a satisfactory overall yield, minimizing the number of steps and employing scalable catalytic procedures developed in partially aqueous media.