4-acetyl-N-benzylbenzamide | 904078-20-2

• 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: 4-acetyl-N-benzylbenzamide
• CAS: 904078-20-2
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: QKGKFXKBBMVXRV-UHFFFAOYSA-N

物化性质

• 熔点：
  112-113 °C
• 沸点：
  478.0±38.0 °C(Predicted)
• 密度：
  1.140±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-3-(pyridin-4-yl)acrylaldehyde 、 4-acetyl-N-benzylbenzamide 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 12.25h， 以55%的产率得到N-benzyl-4-((2E,4E)-5-(pyridin-4-yl)penta-2,4-dienoyl)benzamide
  参考文献：
  名称：

  Anti-oligomerization sheet molecules: Design, synthesis and evaluation of inhibitory activities against α-synuclein aggregation

  摘要：

  Aggregation of alpha-synuclein (alpha-Syn) play a key role in the development of Parkinson Disease (PD). One of the effective approaches is to stabilize the native, monomeric protein with suitable molecule ligands. We have designed and synthesized a series of sheet-like conjugated compounds which possess different skeletons and various heteroatoms in the two blocks located at both ends of linker, which have good pi-electron delocalization and high ability of hydrogen-bond formation. They have shown anti-aggregation activities in vitro towards alpha-Syn with IC50 down to 1.09 mu M. The molecule is found binding in parallel to the NACore within NAC domain of alpha-Syn, interfering aggregation of NAC region within different alpha-Syn monomer, and further inhibiting or slowing down the formation of alpha-Syn oligomer nuclei at lag phase. The potential inhibitor obtained by our strategy is considered to be highly efficient to inhibit alpha-Syn aggregation.

  DOI：

  10.1016/j.bmc.2019.05.032
• 作为产物：
  描述：

  4-乙酰基苯甲酸 、 苄胺 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 4-acetyl-N-benzylbenzamide
  参考文献：
  名称：

  Anti-oligomerization sheet molecules: Design, synthesis and evaluation of inhibitory activities against α-synuclein aggregation

  摘要：

  Aggregation of alpha-synuclein (alpha-Syn) play a key role in the development of Parkinson Disease (PD). One of the effective approaches is to stabilize the native, monomeric protein with suitable molecule ligands. We have designed and synthesized a series of sheet-like conjugated compounds which possess different skeletons and various heteroatoms in the two blocks located at both ends of linker, which have good pi-electron delocalization and high ability of hydrogen-bond formation. They have shown anti-aggregation activities in vitro towards alpha-Syn with IC50 down to 1.09 mu M. The molecule is found binding in parallel to the NACore within NAC domain of alpha-Syn, interfering aggregation of NAC region within different alpha-Syn monomer, and further inhibiting or slowing down the formation of alpha-Syn oligomer nuclei at lag phase. The potential inhibitor obtained by our strategy is considered to be highly efficient to inhibit alpha-Syn aggregation.

  DOI：

  10.1016/j.bmc.2019.05.032

文献信息

• Mo(CO)₆-Mediated Carbamoylation of Aryl Halides
  作者：Wei Ren、Motoki Yamane

  DOI：10.1021/jo101611g

  日期：2010.12.17

  A simple method for the synthesis of amides has been developed by molybdenum-mediated carbamoylation of aryl halides. Whereas the conventional palladium-catalyzed three-component coupling reaction requires a large excess of gaseous carbon monoxide, the incorporation of carbon monoxide in this Mo-mediated carbamoylation reaction is so efficient that it requires only a slight excess amount of carbon monoxide

  通过钼介导的芳基卤化物的氨基甲酰化，已经开发出一种简单的酰胺合成方法。常规的钯催化三组分偶联反应需要大量过量的气态一氧化碳，而在Mo介导的氨基甲酰化反应中一氧化碳的掺入非常有效，以至于仅需少量过量的一氧化碳即可。其钼配合物Mo（CO）6。通过使用氨水，该反应不仅可用于合成各种仲酰胺和叔酰胺，而且还可用于伯酰胺的合成。
• Phosphine-Based Redox Catalysis in the Direct Traceless Staudinger Ligation of Carboxylic Acids and Azides
  作者：Andrew D. Kosal、Erin E. Wilson、Brandon L. Ashfeld

  DOI：10.1002/anie.201206533

  日期：2012.11.26

  Redox catalysis: Aryl amides, imides, lactams, and dipeptides are obtained through a direct Staudinger ligation mediated by phosphine‐based redox catalysis (see scheme). Mechanistic studies indicate the involvement of a phosphonium carboxylate intermediate that leads to a 1,3‐acyl migration and thus results in CN bond formation.

  氧化还原催化：芳基酰胺，酰亚胺，内酰胺和二肽是通过基于膦的氧化还原催化（见方案）介导的Staudinger直接连接获得的。机理研究表明，羧酸intermediate中间体的参与会导致1,3-酰基迁移，从而导致形成CN键。
• Carbamoylation of Aryl Halides by Molybdenum or Tungsten Carbonyl Amine Complexes
  作者：Wei Ren、Motoki Yamane

  DOI：10.1021/jo1002592

  日期：2010.5.7

  When aryl halide is treated with molybdenum carbonyl amine complex in the presence of base, carbamoylation proceeds to give amide in good yield. The proposed mechanism involves oxidative addition of aryl halide to molybdenum(0) complex, migratory insertion to carbon monoxide giving acyl(amino)molybdenum(II) or aryl(carbamoyl)molybdenum(II) intermediate, and reductive elimination of the amide. This

  当在碱的存在下用羰基钼胺络合物处理芳基卤化物时，进行氨基甲酰化反应，得到酰胺，收率很高。拟议的机制包括将芳基卤化物氧化加成到钼（0）络合物上，迁移插入一氧化碳，得到酰基（氨基）钼（II）或芳基（氨基甲酰基）钼（II）中间体，并还原消除酰胺。该方法是简单的，并且为使用气态一氧化碳的常规钯催化的酰胺形成提供了替代方法。
• Supported Palladium Nanoparticles that Catalyze Aminocarbonylation of Aryl Halides with Amines using Oxalic Acid as a Sustainable CO Source
  作者：C. Bal Reddy、Shankar Ram、Ajay Kumar、Richa Bharti、Pralay Das

  DOI：10.1002/chem.201900271

  日期：2019.3.15

  Polystyrene‐supported palladium (Pd@PS) nanoparticles (NPs) have been used to catalyze the aminocarbonylation of aryl halides with amines using oxalic acid as a CO source for the first‐time for the synthesis of amides. Furthermore, o‐iodoacetophenones participated in amidation and cyclization reactions to give isoindolinones in a single step following a concerted approach. Oxalic acid has been used

  首次使用草酸作为一氧化碳源，使用聚苯乙烯负载的钯（Pd @ PS）纳米颗粒（NPs）催化胺与胺的芳基卤化物的氨基羰基化反应，这是首次用于酰胺的合成。此外，o碘苯乙酮通过协同方法一步一步参与酰胺化和环化反应，得到异吲哚啉酮。在双层瓶（DLV）系统下，草酸已被用作安全，环境友好和操作简单的易地易位可持续CO源，用于不同的氨基羰基化反应。在CO环境下，催化剂的稳定性是一项艰巨的任务，但是，发现Pd @ PS具有可回收性，并且可用于广泛的基材范围，避免了再生步骤。草酸的易于处理，添加剂和无碱一氧化碳的产生，催化剂的稳定性以及通过过滤和引入DLV轻松从反应混合物中分离出催化剂的优点是使整个过程成为可持续的方法。
• Palladium-Catalyzed Carbamoylation of Aryl Halides by Tungsten Carbonyl Amine Complex
  作者：Wei Ren、Motoki Yamane

  DOI：10.1021/jo901486z

  日期：2009.11.6

  In the presence of aminepentacarbonyltungsten, base, and a catalytic amount of palladium(0) complex, carbamoylation of aryl halide proceeds to afford amide. The reaction may involve transmetalation between palladium(II) intermediate and carbamoyltungstenate that is generated in situ. This catalytic cross-coupling reaction provides an alternative method to the conventional palladium-catalyzed amidation

  在胺五碳羰基钨，碱和催化量的钯（0）络合物的存在下，芳基卤化物的氨基甲酰化继续进行，得到酰胺。该反应可能涉及钯（II）中间体与原位生成的氨基甲酸酯钨酸酯之间的金属转移。通过使用气态一氧化碳，这种催化的交叉偶联反应为常规的钯催化的酰胺化提供了另一种方法。