N-(4-chlorobenzyl) 2-bromobenzamide | 446855-40-9

• 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-(4-chlorobenzyl) 2-bromobenzamide
• 英文别名: 2-bromo-N-[(4-chlorophenyl)methyl]benzamide
• CAS: 446855-40-9
• 化学式: C₁₄H₁₁BrClNO
• mdl: MFCD02335762
• 分子量: 324.604
• InChiKey: GHEQDJFHCLKLEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 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-(4-chlorobenzyl) 2-bromobenzamide 在 palladium(II) trifluoroacetate 、 potassium carbonate 、 tricyclohexylphosphine tetrafluoroborate 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以61%的产率得到
  参考文献：
  名称：

  Rapid construction of C4-substituted phenanthridinones through palladium-catalyzed domino N-arylation/aryl-aryl coupling process

  摘要：

  DOI：

  10.1016/j.mcat.2021.111766
• 作为产物：
  描述：

  对氯苄胺 、 2-溴苯甲酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以51%的产率得到N-(4-chlorobenzyl) 2-bromobenzamide
  参考文献：
  名称：

  Rapid construction of C4-substituted phenanthridinones through palladium-catalyzed domino N-arylation/aryl-aryl coupling process

  摘要：

  DOI：

  10.1016/j.mcat.2021.111766

文献信息

• Efficient Synthesis of a (Z)-3-Methyleneisoindolin-1-one Library Using Cu(OAc)2•H2O/DBU under Microwave Irradiation
  作者：Li Zhang、Yongliang Zhang、Xin Wang、Jingkang Shen

  DOI：10.3390/molecules18010654

  日期：——

  Microwave-promoted efficient synthesis of a (Z)-3-methyleneisoindolin-1-one library from 2-bromobenzamides and terminal alkynes using Cu(OAc)2•H2O/DBU is described. Various benzamide substituents, ring substitutions, including heteroaryl, aryl acetylenes and aliphatic alkynes, could be applied to afford the desired products in good to moderate yield with high stereoselectivity. It is noteworthy that DBU maybe play a dual role as not only the base, but also as a ligand for copper. The reaction is catalyzed by the complex of Cu(OAc)2•H2O and DBU without other additives.

  介绍了利用 Cu(OAc)2-H2O/DBU 以 2-溴苯甲酰胺和端炔类化合物为原料，通过微波促进高效合成 (Z)-3 亚甲基异吲哚啉-1-酮库。应用各种苯甲酰胺取代基、环取代基（包括杂芳基、芳基乙炔基和脂肪族炔烃）可得到所需的产品，产率从良好到中等，且具有很高的立体选择性。值得注意的是，DBU 可能具有双重作用，它不仅是碱，还是铜的配体。该反应由 Cu(OAc)2-H2O 和 DBU 的络合物催化，无需其他添加剂。
• Construction of Phenanthridinone Skeletons through Palladium-Catalyzed Annulation
  作者：Xin Geng、Heng He、Andrey Shatskiy、Elena V. Stepanova、Gregory R. Alvey、Jian-Quan Liu、Markus D. Kärkäs、Xiang-Shan Wang

  DOI：10.1021/acs.joc.3c01429

  日期：2023.9.1

  Herein, a straightforward synthetic approach for the construction of phenanthridin-6(5H)-one skeletons is disclosed. The developed protocol relies on palladium catalysis, providing controlled access to a range of functionalized phenanthridin-6(5H)-ones in 59–88% yields. Furthermore, plausible reaction pathways are proposed based on mechanistic experiments.

  本文公开了构建菲啶-6(5 H )-酮骨架的简单合成方法。所开发的方案依赖于钯催化，以 59-88% 的产率提供一系列功能化菲啶-6(5 H )-酮的受控访问。此外，基于机械实验提出了合理的反应途径。
• 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.
• 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.
• Rapid construction of C4-substituted phenanthridinones through palladium-catalyzed domino N-arylation/aryl-aryl coupling process
  作者：Chao Liu、Liangliang Song、Luc Van Meervelt、Erik V. Van der Eycken

  DOI：10.1016/j.mcat.2021.111766

  日期：2021.8