dimethyl N-methyl-1,4-dihydro-3,4-pyridinedicarboxylate | 87386-57-0

• 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: dimethyl N-methyl-1,4-dihydro-3,4-pyridinedicarboxylate
• 英文别名: dimethyl 1-methyl-4H-pyridine-3,4-dicarboxylate
• CAS: 87386-57-0
• 化学式: C₁₀H₁₃NO₄
• 分子量: 211.218
• InChiKey: JVAKMZHBXZNNDQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,4-bis-methoxycarbonyl-1-methyl-pyridinium; iodide 在 四乙基对甲苯磺酸铵 、 氯化铵 作用下， 以 甲醇 为溶剂， 以87%的产率得到dimethyl N-methyl-1,4-dihydro-3,4-pyridinedicarboxylate
  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

• Regioselective photochemical cycloaddition of enamine-carbaldehydes and alkenes; synthesis of 1,4-Dihydropyridines and 2-hydroxy-1,2,3,4-tetrahydropyridines
  作者：Lutz F. Tietz、Andreas Bergmann、Klaus Brüggemann

  DOI：10.1016/s0040-4039(00)88173-3

  日期：1983.1
• 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.
• TIETZE, L. F.;BERGMANN, A.;BRUEGGEMANN, K., TETRAHEDRON LETT., 1983, 24, N 34, 3579-3582
  作者：TIETZE, L. F.、BERGMANN, A.、BRUEGGEMANN, K.

  DOI：——

  日期：——
• 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.