N-benzyl-2-bromo-3-methylbenzamide | 924660-38-8

• 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-3-methylbenzamide
• CAS: 924660-38-8
• 化学式: C₁₅H₁₄BrNO
• 分子量: 304.186
• InChiKey: RMZCOCPILJGRHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 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-3-methylbenzamide 在 palladium diacetate [2-(8-methoxynaphthalen-1-yl)phenyl]diphenylphosphane 、 caesium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以81%的产率得到5-benzyl-1,10-dimethylphenanthridin-6(5H)-one
  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
• 作为产物：
  描述：

  2-溴-3-甲基苯甲酸 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-3-methylbenzamide
  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。
• Preparation of benzisothiazolones from 2-bromobenzamides and sulfur under copper catalysis conditions
  作者：V. Krasikova、M. Katkevics

  DOI：10.1007/s10593-013-1193-5

  日期：2013.2

  A convenient two-stage method has been developed for preparing benz[d]isothiazol-3(2H)-ones from 2-bromobenzamides and sulfur in a one-pot process under copper catalysis conditions. The method is suitable for the synthesis of N-aryl-, benzyl-, and alkyl-substituted benzisothiazolones. The yields of the benzisothiazolones depend on the nature of the starting amide and can reach 91%.

  已经开发了一种方便的两步法，用于在铜催化条件下通过一锅法从2-溴苯甲酰胺和硫制备苯并[ d ]异噻唑-3（2 H）-一。该方法适合于合成N-芳基-，苄基-和烷基取代的苯并异噻唑酮。苯并异噻唑酮的产率取决于起始酰胺的性质，可以达到91％。
• 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.