N-benzyl-2-bromo-5-chlorobenzamide | 924660-37-7

• 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: N-benzyl-2-bromo-5-chlorobenzamide
• CAS: 924660-37-7
• 化学式: C₁₄H₁₁BrClNO
• 分子量: 324.604
• InChiKey: FDIVWJFAWHLRNS-UHFFFAOYSA-N

物化性质

• 沸点：
  426.7±45.0 °C(Predicted)
• 密度：
  1.484±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 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：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-benzyl-2-bromo-5-chlorobenzamide 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以43%的产率得到
  参考文献：
  名称：

  涉及高价钯物种的菲啶酮类化合物的选择性多米诺骨牌合成中的溶剂/碱效应：实验和理论研究

  摘要：

  邻溴苯甲酰胺1 a – m在K 2 CO 3和[PdCl 2（PPh 3）2 ]催化剂的存在下的多米诺反应允许选择性地利用菲啶酮2或新的1-羧酰胺菲啶酮3，具体取决于分别是DMF或1,4-二恶烷。对反应参数的研究为碱解离和溶剂极性与所观察到的选择性之间的直接相关提供了第一个例子。此外，机理研究（NMR光谱和ESI-MS监测）使我们能够表征Pd II palladacycle4和联芳基物质是这两个多米诺骨牌工艺的常见中间体。在此基础上，可以设想通过在Pd II palladacycle 4中氧化添加1后生成Pd IV络合物来形成C（sp 2）C（sp 2）键，这一原理得到DFT计算的支持。提出了一般的催化循环来解释这些观察结果。

  DOI：

  10.1002/chem.201101354
• 作为产物：
  描述：

  2-溴-5-氯苯甲酸 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 N-benzyl-2-bromo-5-chlorobenzamide
  参考文献：
  名称：

  Efficient Synthesis of Phenanthridinone Derivatives via a Palladium-Catalyzed Coupling Process

  摘要：

  A palladium-mediated domino reaction was developed to conveniently synthesize phenanthridinone derivatives. Phosphine ligand 1 strongly promotes the domino process, which includes aryl-aryl coupling and C-N bond formations concomitant with a deamidation reaction. The versatility and applicability to a broad range of substrates make this reaction useful for the development of bioactive derivatives.

  DOI：

  10.1021/ol062599z

文献信息

• Palladium-Catalyzed Annulation of Arynes by <i>o</i>-Halobenzamides: Synthesis of Phenanthridinones
  作者：Chun Lu、Anton V. Dubrovskiy、Richard C. Larock

  DOI：10.1021/jo3016192

  日期：2012.10.5

  The palladium-catalyzed annulation of arynes by substituted o-halobenzamides produces N-substituted phenanthridinones in good yields. This methodology provides this important heterocyclic ring system in a single step by simultaneous C–C and C–N bond formation, under relatively mild reaction conditions, and tolerates a variety of functional groups.

  通过取代的邻卤代苯甲酰胺钯催化的芳炔环化以良好的产率产生N-取代的菲啶酮。该方法通过在相对温和的反应条件下同时形成 C-C 和 C-N 键，一步提供了这种重要的杂环系统，并且可以耐受多种官能团。
• Assembly of Substituted 3-Methyleneisoindolin-1-ones via a CuI/<scp>l</scp>-Proline-Catalyzed Domino Reaction Process of 2-Bromobenzamides and Terminal Alkynes
  作者：Li Li、Miao Wang、Xiaojing Zhang、Yongwen Jiang、Dawei Ma

  DOI：10.1021/ol9000922

  日期：2009.3.19

  CuI/L-proline catalyzed coupling of 2-bromobenzamides and terminal alkynes in PrOH (or DMF and DMSO) at 85-110 degrees C and subsequent additive cyclization produces substituted 3-methyleneisoindolin-1-ones. Variation of N-substituents, aromatic ring, and methylene part is possible by using suitable starting materials.
• Efficient Synthesis of Phenanthridinone Derivatives via a Palladium-Catalyzed Coupling Process
  作者：Takumi Furuta、Yuki Kitamura、Ayano Hashimoto、Satoshi Fujii、Kiyoshi Tanaka、Toshiyuki Kan

  DOI：10.1021/ol062599z

  日期：2007.1.1

  A palladium-mediated domino reaction was developed to conveniently synthesize phenanthridinone derivatives. Phosphine ligand 1 strongly promotes the domino process, which includes aryl-aryl coupling and C-N bond formations concomitant with a deamidation reaction. The versatility and applicability to a broad range of substrates make this reaction useful for the development of bioactive derivatives.
• Selective Unusual Pd-Mediated Biaryl Coupling Reactions: Solvent Effects with Carbonate Bases
  作者：Ludovic Donati、Sylvie Michel、François Tillequin、François-Hugues Porée

  DOI：10.1021/ol902570s

  日期：2010.1.1

  A one-step Pd-catalyzed reaction performed on an o-bromobenzamide permitted the selective formation of either phenanthridinones 2 via an ipso substitution or new phenanthridinone-1-carboxamides 3 through a direct N-arylation. A direct correlation between the solvent polarity and the carbonate base on the selectivity has been observed. The proposed catalytic cycle involves the initial formation of a common Intermediate and depends on the base assistance.
• Assembly of Substituted Homophthalimides via CuI-Catalyzed Coupling of 2-Bromobenzamides with β-Keto Ester
  作者：Dawei Ma、Hexiang Wang、Kun Gao、Yongwen Jiang

  DOI：10.3987/com-08-s(d)36

  日期：——

  CuI catalyzed coupling of 2-bromobenzamides and beta-keto esters takes place at 90 degrees C in i-PrOH to afford substituted homophthalimides in good yields. This transformation undergoes a cascade coupling/intramolecular condensation process, which allows assembly of a wide range of substituted homophthalimides by varying 2-bromobenzamides and beta-keto esters.