1-benzyl-6-oxopiperidine-3-carboxylic acid | 32749-55-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-benzyl-6-oxopiperidine-3-carboxylic acid
• 英文别名: 1-Benzyl-2-oxo-5-pyridincarbonsaeure；1-benzyl-6-oxo-3-piperidinecarboxylic acid
• CAS: 32749-55-6
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: QQVADMMBTIQOOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-benzyl-6-oxopiperidine-3-carboxylic acid 在 盐酸 、 sodium hydroxide 、 二苯基磷酸 、 三乙胺 作用下， 生成 5-amino-1-benzylpiperidin-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：

  diethyl 2-methyleneglutarate 在 sodium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 145.0h， 生成 1-benzyl-6-oxopiperidine-3-carboxylic acid
  参考文献：
  名称：

  EP1180513

  摘要：

  公开号：

文献信息

• CYCLIC AMIDE COMPOUNDS, PROCESS FOR THE PREPARATION OF THE SAME AND USES THEREOF
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP1180513A1

  公开（公告）日：2002-02-20

  A compound of the formula: wherein R1 is a hydrocarbon group, R2 is a hydrocarbon group having 2 or more carbon atoms, where R1 and R2 may in combination form, together with an adjacent nitrogen atom, a ring optionally having a substituent or substituents, R3 is a hydrocarbon group optionally having a substituent or substituents or a heterocyclic group optionally having a substituent or substituents, R4 is a hydrogen atom, a hydrocarbon group, a heterocyclic group and the like, E is a divalent chain hydrocarbon group and the like, G is CO or SO2, J is a nitrogen atom, a methine group and the like, and Q and R are each a divalent chain C1-3 hydrocarbon group and the like, and a salt thereof show a superior CCR5 antagonistic activity and are useful as agents for the prophylaxis or treatment of HIV infection of human peripheral blood mononuclear cells, particularly AIDS.

  以下式子的化合物 其中 R1 是烃基；R2 是具有 2 个或 2 个以上碳原子的烃基；其中 R1 和 R2 可与相邻的氮原子结合形成任选具有一个或多个取代基的环；R3 是任选具有一个或多个取代基的烃基或任选具有一个或多个取代基的杂环基；R4 是氢原子、烃基、杂环基等；E 是二价链烃基等；G 是 CO 或 SO2；J 是氮原子、甲基等、E是二价链烃基等，G是CO或SO2，J是氮原子、甲基等，Q和R各自是二价链C1-3烃基等，它们及其盐具有优异的CCR5拮抗活性，可作为预防或治疗人类外周血单核细胞HIV感染，特别是艾滋病的药物。
• Synthesis and reduction reactions of pyridones and 5-acyl-2-methoxypyridines
  作者：Alexander A. Bisset、Allan Dishington、Teyrnon Jones、Guy J. Clarkson、Martin Wills

  DOI：10.1016/j.tet.2014.06.046

  日期：2014.10

  The synthesis of a series of pyridones, from their 2-hydroxypyridine or 2-methoxypyridine precursors, is described, along with studies into their reductions to saturated heterocycles. A number of 5-acylpyridones were prepared and were evaluated as substrates for asymmetric transfer hydrogenation prior to conversion to saturated heterocycles. The enantioselective reduction of 5-acetyl-1-benzylpyrimidine-2,4(1H,3H)-dione is also described. (C) 2014 Elsevier Ltd. All rights reserved.
• Construction of Hydroxylated Alkaloids (.+-.)-Mannonolactam, (.+-.)-Deoxymannojirimycin, and (.+-.)-Prosopinine through Aza-Annulation
  作者：Gregory R. Cook、Lars G. Beholz、John R. Stille

  DOI：10.1021/jo00092a015

  日期：1994.7

  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.
• EP1180513
  申请人：——

  公开号：——

  公开（公告）日：——