(ethoxycarbonyl)methyl 1-(tert-butyloxycarbonyl)-1,2,3,6-tetrahydropyridine-4-carboxylate | 76309-81-4

• 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: (ethoxycarbonyl)methyl 1-(tert-butyloxycarbonyl)-1,2,3,6-tetrahydropyridine-4-carboxylate
• CAS: 76309-81-4
• 化学式: C₁₅H₂₃NO₆
• 分子量: 313.351
• InChiKey: GDHBSERVAOSEKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.66
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  82.14
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (ethoxycarbonyl)methyl 1-(tert-butyloxycarbonyl)-1,2,3,6-tetrahydropyridine-4-carboxylate 在 氢溴酸 、 溶剂黄146 作用下， 以 乙酸乙酯 为溶剂， 反应 0.25h， 以62%的产率得到(ethoxycarbonyl)methyl 1,2,3,6-tetrahydropyridine-4-carboxylate hydrobromide
  参考文献：
  名称：

  Esters of isoguvacine as potential prodrugs

  摘要：

  The syntheses of the methyl ester, butyl ester, (ethoxycarbonyl)methyl ester, and 11 (acyloxy)methyl esters of the potent gamma-aminobutyric acid agonist isoguvacine (1,2,3,6-tetrahydropyridine-4-carboxylic acid) and described. The chemical stability of the esters and their in vitro rates of hydrolysis under approximately physiological conditions by nonspecific esterases from human serum were examined. A selected number of the esters were tested for antagonism of convulsions induced by bicuculline, isoniazide, and by electroschock. While in the compounds showed only weak activities in the bicuculline and isoniazide tests, a good correlation between in vitro rates of enzymatic hydrolysis and the time of onset of the antagonism of the electroschock-induced convulsions could be found.

  DOI：

  10.1021/jm00135a009
• 作为产物：
  描述：

  1,2,3,6-四氢-4-吡啶甲酸盐酸盐 在 potassium carbonate 、 三乙胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 42.5h， 生成 (ethoxycarbonyl)methyl 1-(tert-butyloxycarbonyl)-1,2,3,6-tetrahydropyridine-4-carboxylate
  参考文献：
  名称：

  Esters of isoguvacine as potential prodrugs

  摘要：

  The syntheses of the methyl ester, butyl ester, (ethoxycarbonyl)methyl ester, and 11 (acyloxy)methyl esters of the potent gamma-aminobutyric acid agonist isoguvacine (1,2,3,6-tetrahydropyridine-4-carboxylic acid) and described. The chemical stability of the esters and their in vitro rates of hydrolysis under approximately physiological conditions by nonspecific esterases from human serum were examined. A selected number of the esters were tested for antagonism of convulsions induced by bicuculline, isoniazide, and by electroschock. While in the compounds showed only weak activities in the bicuculline and isoniazide tests, a good correlation between in vitro rates of enzymatic hydrolysis and the time of onset of the antagonism of the electroschock-induced convulsions could be found.

  DOI：

  10.1021/jm00135a009