dimethyl 1,2-dihydropyridine-2,3-dicarboxylate | 243868-66-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: dimethyl 1,2-dihydropyridine-2,3-dicarboxylate
• 英文别名: dimethyl 1,2-dihydro-2,3-pyridinedicarboxylate
• CAS: 243868-66-8
• 化学式: C₉H₁₁NO₄
• 分子量: 197.191
• InChiKey: MHKOEABLIGUWPQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dimethyl 1,2-dihydropyridine-2,3-dicarboxylate 在 sodium hydride 、 magnesium 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.67h， 生成 N-acetyl-4-triethylsilyl-2,3-dicarbomethoxy-1,2,3,4-tetrahydropyridine
  参考文献：
  名称：

  Highly selective and facile synthesis of dihydro- and tetrahydropyridine dicarboxylic acid derivatives using electroreduction as a key step

  摘要：

  Electroreduction of pyridinedicarboxylic acid derivatives la-g in methanol containing ammonium chloride using a divided cell brought about highly selective hydrogenation to give the corresponding dihydropyridines in good yields. From the electrolysis of dimethyl 2,3- and 2,5-pyridinedicarboxylates 1a,c, only the corresponding 1,2-dihydropyridine derivatives 2a,e were obtained in a regioselective manner while that of 2,4-, 2,6-, and 3,4- disubstituted pyridines 1b,d,e afforded the corresponding 1,4-dihydropyridine 2b,d,e selectively in good yields. Further hydrogenation of the resultant dihydropyridines by several methods led to the selective and facile formation of the corresponding tetrahydropyridines 6. Furthermore, Mg-promoted hydrosilylation of the N-acetylated product 5a gave C-silylated tetrahydropyridines in a stereoselective manner. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00058-8
• 作为产物：
  描述：

  2,3-吡啶二甲酸二甲酯 在 四乙基对甲苯磺酸铵 、 氯化铵 作用下， 以 甲醇 为溶剂， 以83%的产率得到dimethyl 1,2-dihydropyridine-2,3-dicarboxylate
  参考文献：
  名称：

  Selective and facile electroreductive synthesis of dihydro- and tetrahydropyridine dicarboxylic acid derivatives

  摘要：

  Electroreduction of pyridinedicarboxylic acid derivatives in methanol using a divided cell brought about highly selective hydrogenation to give efficiently the corresponding dihydropyridines in good yields. From the electrolysis of dimethyl 2,3- and 2,5-pyridinedicarboxylates, 1,2-dihydropyridine derivatives were obtained while that of 2,6-, 3,4- and 2,4-disubstituted pyridines afforded the corresponding 1,4-dihydropyridines selectively in good yields. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01789-x

文献信息

• Selective and facile electroreductive synthesis of dihydro- and tetrahydropyridine dicarboxylic acid derivatives
  作者：Yoshio Kita、Hirofumi Maekawa、Yasuhiro Yamasaki、Ikuzo Nishiguchi

  DOI：10.1016/s0040-4039(99)01789-x

  日期：1999.12

  Electroreduction of pyridinedicarboxylic acid derivatives in methanol using a divided cell brought about highly selective hydrogenation to give efficiently the corresponding dihydropyridines in good yields. From the electrolysis of dimethyl 2,3- and 2,5-pyridinedicarboxylates, 1,2-dihydropyridine derivatives were obtained while that of 2,6-, 3,4- and 2,4-disubstituted pyridines afforded the corresponding 1,4-dihydropyridines selectively in good yields. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Highly selective and facile synthesis of dihydro- and tetrahydropyridine dicarboxylic acid derivatives using electroreduction as a key step
  作者：Yoshio Kita、Hirofumi Maekawa、Yasuhiro Yamasaki、Ikuzo Nishiguchi

  DOI：10.1016/s0040-4020(01)00058-8

  日期：2001.3

  Electroreduction of pyridinedicarboxylic acid derivatives la-g in methanol containing ammonium chloride using a divided cell brought about highly selective hydrogenation to give the corresponding dihydropyridines in good yields. From the electrolysis of dimethyl 2,3- and 2,5-pyridinedicarboxylates 1a,c, only the corresponding 1,2-dihydropyridine derivatives 2a,e were obtained in a regioselective manner while that of 2,4-, 2,6-, and 3,4- disubstituted pyridines 1b,d,e afforded the corresponding 1,4-dihydropyridine 2b,d,e selectively in good yields. Further hydrogenation of the resultant dihydropyridines by several methods led to the selective and facile formation of the corresponding tetrahydropyridines 6. Furthermore, Mg-promoted hydrosilylation of the N-acetylated product 5a gave C-silylated tetrahydropyridines in a stereoselective manner. (C) 2001 Elsevier Science Ltd. All rights reserved.