2-(2-bromophenyl)-1-[2-N-(4-methylbenzenesulfonamido)phenyl]ethanone | 869668-71-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-(2-bromophenyl)-1-[2-N-(4-methylbenzenesulfonamido)phenyl]ethanone
• 英文别名: N-(2-(2-(2-bromophenyl)acetyl)phenyl)-4-methylbenzenesulfonamide；N-[2-[2-(2-bromophenyl)acetyl]phenyl]-4-methylbenzenesulfonamide
• CAS: 869668-71-3
• 化学式: C₂₁H₁₈BrNO₃S
• 分子量: 444.349
• InChiKey: WFXAVPAYVJCEMG-UHFFFAOYSA-N

物化性质

• 熔点：
  125-126 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  579.9±60.0 °C(Predicted)
• 密度：
  1.465±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-bromophenyl)-1-[2-N-(4-methylbenzenesulfonamido)phenyl]ethanone 在 palladium diacetate 、 potassium phosphate 、 硫酸 、 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 5.17h， 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：

  邻氨基苯乙酮 在 吡啶 、 palladium diacetate 、 caesium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 48.0h， 生成 2-(2-bromophenyl)-1-[2-N-(4-methylbenzenesulfonamido)phenyl]ethanone
  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

• [EN] PROCESS FOR MAKING TETRACYCLIC HETEROCYCLE COMPOUNDS<br/>[FR] PROCÉDÉ DE PRÉPARATION DE COMPOSÉS HÉTÉROCYCLIQUES TÉTRACYCLIQUES
  申请人：MERCK SHARP & DOHME

  公开号：WO2016004899A1

  公开（公告）日：2016-01-14

  The present invention is directed to a process for making Tetracyclic Heterocycle Compounds of Formula (I) and pharmaceutically acceptable salts thereof, wherein X1, X2, R1, R2 and R3 are defined above herein. The present invention is also directed to compounds that are useful as synthetic intermediates in the process of the invention.

  本发明涉及一种制备式(I)四环杂环化合物及其药用可接受盐的方法，其中X1、X2、R1、R2和R3如上所定义。本发明还涉及在该方法中作为合成中间体有用的化合物。
• Broad Synthesis of Disubstituted Dihydrofuran-Fused [60]Fullerene Derivatives via Cu(I)/Ag(I)-Mediated Synergistic Annulation Reaction
  作者：Shilu Xia、Tong-Xin Liu、Pengling Zhang、Jinliang Ma、Qingfeng Liu、Nana Ma、Zhiguo Zhang、Guisheng Zhang

  DOI：10.1021/acs.joc.7b02848

  日期：2018.1.19

  annulation reaction of [60]fullerene with diarylethanones, benzoylacetonitriles, and β-dicarbonyl compounds has been developed for the direct construction of diverse disubstituted dihydrofuran-fused [60]fullerene derivatives. This transformation exhibits a remarkably broad substrate scope and functional group tolerance and provides a useful method to a scarce class of fullerene derivatives.

  已开发出新颖且有效的Cu（I）/ Ag（I）介导的[60]富勒烯与二芳烃酮，苯甲酰基乙腈和β-二羰基化合物的协同环化反应，用于直接构建不同的二取代的二取代二氢呋喃稠合的[60]富勒烯衍生品。该转化表现出非常宽的底物范围和官能团耐受性，并为稀有种类的富勒烯衍生物提供了一种有用的方法。
• Process for making tetracyclic heterocycle compounds
  申请人：Merck Sharp & Dohme. Corp.

  公开号：US10202401B2

  公开（公告）日：2019-02-12

  The present invention is directed to a process for making Tetracyclic Heterocycle Compounds of Formula (I): and pharmaceutically acceptable salts thereof, wherein X1, X2, R1, R2 and R3 are defined above herein. The present invention is also directed to compounds that may be useful as synthetic intermediates in the process of the invention.

  本发明涉及一种制造式（I）四环杂环化合物的工艺： 及其药学上可接受的盐类，其中 X1、X2、R1、R2 和 R3 的定义如上。本发明还涉及在本发明工艺中可用作合成中间体的化合物。
• 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.
• Enantioselective Synthesis of Hemiaminals via Pd-Catalyzed C–N Coupling with Chiral Bisphosphine Mono-oxides
  作者：Hongming Li、Kevin M. Belyk、Jingjun Yin、Qinghao Chen、Alan Hyde、Yining Ji、Steven Oliver、Matthew T. Tudge、Louis-Charles Campeau、Kevin R. Campos

  DOI：10.1021/jacs.5b05934

  日期：2015.11.4

  A novel approach to hemiaminal synthesis via palladium-catalyzed C-N coupling with chiral bisphosphine mono-oxides is described. This efficient new method exhibits a broad scope, provides a highly efficient synthesis of HCV drug candidate elbasvir, and has been applied to the synthesis of chiral N,N-acetals.