dimethyl 1,4-dihydro-2,6-pyridinedicarboxylate | 243868-68-0

• 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 1,4-dihydro-2,6-pyridinedicarboxylate
• 英文别名: dimethyl 1,4-dihydropyridine-2,6-dicarboxylate
• CAS: 243868-68-0
• 化学式: C₉H₁₁NO₄
• 分子量: 197.191
• InChiKey: DIBIQUSMXLTGMG-UHFFFAOYSA-N

物化性质

• 沸点：
  331.6±42.0 °C(Predicted)
• 密度：
  1.230±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 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 1,4-dihydro-2,6-pyridinedicarboxylate 在 双氧水 、 水 、 sodium hydroxide 作用下， 反应 8.0h， 以91.6%的产率得到吡啶-2,6-二甲酸
  参考文献：
  名称：

  一种2,6-吡啶二羧酸的制备方法

  摘要：

  本发明提供一种2,6‑吡啶二羧酸的制备方法，利用1,7‑庚二酸或1,7‑庚二酸二酯(I)为原料，经卤代反应得到2,2,6,6‑四卤代物(II)，然后和氨经环化反应制得二氢吡啶衍生物(III)，再经氧化剂氧化或经氧化‑水解得到2,6‑吡啶二羧酸。本发明的方法原料价廉易得，制备方法简单、易于实现、安全环保，废水量小，成本低，产率和选择性高，副产物少，适于工业化生产。

  公开号：

  CN110229096B
• 作为产物：
  描述：

  吡啶-2.6-二羧酸二甲酯 以 甲醇 为溶剂， 以92%的产率得到dimethyl 1,4-dihydro-2,6-pyridinedicarboxylate
  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

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.