N-benzyl-5-acetyl-3,4-dihydropyridin-2-one | 23645-88-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-benzyl-5-acetyl-3,4-dihydropyridin-2-one
• 英文别名: 5-acetyl-1-benzyl-3,4-dihydro-1H-pyridin-2-one；5-Acetyl-1-benzyl-3,4-dihydro-1H-pyridin-2-on；5-Acetyl-1-benzyl-3,4-dihydropyridin-2-one
• CAS: 23645-88-7
• 化学式: C₁₄H₁₅NO₂
• 分子量: 229.279
• InChiKey: HKRBWBOABNUCTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-benzyl-5-acetyl-3,4-dihydropyridin-2-one 在 palladium on activated charcoal 氢气 、 sodium carbonate 作用下， 以 乙醇 为溶剂， 以62%的产率得到5-Acetyl-1-benzyl-piperidin-2-one
  参考文献：
  名称：

  Construction of Hydroxylated Alkaloids (.+-.)-Mannonolactam, (.+-.)-Deoxymannojirimycin, and (.+-.)-Prosopinine through Aza-Annulation

  摘要：

  The aza-annulation of beta enamino carbonyl substrates with acrylate derivatives provides an efficient and convenient route for the regioselective construction of delta-lactams. This two-step ring-forming sequence involved initial generation of the benzyl enamine through either a condensation or conjugate addition reaction with BnNH(2), followed by aza-annulation with acryloyl chloride or acrylic anhydride. Controlled by the rigid framework of the intermediate lactam, introduction of ring substituents was accomplished with high relative stereoselectivity. The carbonyl functionality, which was necessary to direct the regioselectivity of the aza-annulation reaction, was then transformed into a protected hydroxyl substituent through Baeyer-Villiger oxidation. The resultant delta-lactam product was used as a valuable intermediate in the synthesis of three natural products. Subsequent modification of this delta-lactam gave the naturally occurring alpha-mannosidase inhibitors (+/-)-mannonolactam and (+/-)deoxymannojirimycin, while synthesis of the alkaloid (+/-)-prosopinine was accomplished through homologation of the lactam carbonyl.

  DOI：

  10.1021/jo00092a015
• 作为产物：
  描述：

  3-acetyl-N-benzylpyridinium chloride 在 吡啶 、 chromium(VI) oxide 、 盐酸 、 sodium dithionite 、 水 、 碳酸氢钠 作用下， 生成 N-benzyl-5-acetyl-3,4-dihydropyridin-2-one
  参考文献：
  名称：

  A Study of the Primary Acid Reaction on Model Compounds of Reduced Diphosphopyridine Nucleotide^1,2

  摘要：

  DOI：

  10.1021/ja01537a063

文献信息

• Diels-Alder reactions of methyl N-p-methoxybenzensulfonylindole-2-(2-propenoate), a convenient dienophile towards the synthesis of andranginine
  作者：Bruno Danieli、Giordano Lesma、Marcello Luzzani、Daniele Passarella、Alessandra Silvani

  DOI：10.1016/0040-4020(96)00655-2

  日期：1996.8

  Methyl N-p-methoxybenzensulfonylindole-2-(2-propenoate) (2) undergoes Diels-Alder reactions with silyloxybutadienes and 5-ethenylpyridinones to afford advanced intermediates for the total synthesis of (±)-andranginine (1).

  甲基ñ - p -methoxybenzensulfonylindole -2-（2-丙烯酸甲酯）（2）经历与silyloxybutadienes和5- ethenylpyridinones狄尔斯-阿尔德反应，得到高级中间体的全合成（±）-andranginine（1）。