ethyl 1-(ethoxycarbonyl)-4-(benzylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate | 82817-57-0

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: ethyl 1-(ethoxycarbonyl)-4-(benzylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate
• 英文别名: diethyl 4-(benzylamino)-3,6-dihydro-2H-pyridine-1,5-dicarboxylate
• CAS: 82817-57-0
• 化学式: C₁₈H₂₄N₂O₄
• 分子量: 332.4
• InChiKey: NODBGQCLVKXCSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.46
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  67.87
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl 1-(ethoxycarbonyl)-4-(benzylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate 以77%的产率得到
  参考文献：
  名称：

  JACOBSEN, P.;LABOUTA, I. M.;SCHAUMBURG, K.;FALCH, E.;KROGSGAARD-LARSEN, P+, J. MED. CHEM., 1982, 25, N 10, 1157-1162

  摘要：

  DOI：
• 作为产物：
  描述：

  4-oxo-piperidine-1,3-dicarboxylic acid diethyl ester 、 苄胺 在 molecular sieve 作用下， 以 甲苯 为溶剂， 反应 20.0h， 以68%的产率得到ethyl 1-(ethoxycarbonyl)-4-(benzylamino)-1,2,5,6-tetrahydropyridine-3-carboxylate
  参考文献：
  名称：

  Hydroxy- and amino-substituted piperidinecarboxylic acids as .gamma.-aminobutyric acid agonists and uptake inhibitors

  摘要：

  The syntheses of (3RS,4RS)-4-hydroxypiperidine-3-carboxylic acid (4), (3RS,5SR)-5-hydroxypiperidine-3-carboxylic acid (20), (3RS,4SR)-4-acetamidopiperidine-3-carboxylic acid (10), and (3RS,5SR)-5-acetamidopiperidine-3-carboxylic acid (18), related to the specific gamma-aminobutyric acid (GABA) uptake inhibitors (RS)-piperidine-3-carboxylic acid (nipecotic acid) and (3RS,4SR)-4-hydroxypiperidine-3-carboxylic acid (21), are described. Furthermore, (3RS,4SR)-3-hydroxypiperidine-4-carboxylic acid (14), related to the specific GABA agonist piperidine-4-carboxylic acid (isonipecotic acid), has been synthesized. The structures of 4, 10, 14, 18, and 20 have been established by 270-MHz 1H NMR spectroscopic analyses. The affinity of the compounds for the GABA receptors and for the neuronal (synaptosomal) GABA uptake system in vitro has been measured. Compound 14 interacts selectively with the GABA receptors but less effectively than isonipecotic acid and the cis-isomer 22. Compounds 4, 18, and 20 are inhibitors of the GABA uptake system, although much weaker than nipecotic acid and (3RS,4SR)-4-hydroxypiperidine-3-carboxylic acid (21). Compound 10 is inactive in both test systems.

  DOI：

  10.1021/jm00352a012