3-(4-pyridinyl)-5,6,7,8-tetrahydroindolizine-1,2-dicarboxylic acid dimethyl ester | 1199939-84-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3-(4-pyridinyl)-5,6,7,8-tetrahydroindolizine-1,2-dicarboxylic acid dimethyl ester
• 英文别名: Dimethyl 3-pyridin-4-yl-5,6,7,8-tetrahydroindolizine-1,2-dicarboxylate；dimethyl 3-pyridin-4-yl-5,6,7,8-tetrahydroindolizine-1,2-dicarboxylate
• CAS: 1199939-84-8
• 化学式: C₁₇H₁₈N₂O₄
• 分子量: 314.341
• InChiKey: SWBQCVIERQNLBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  70.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-(4-pyridinylcarbonyl)-2-piperidinecarboxylic acid 、 丁炔二酸二甲酯 在 乙酸酐 作用下， 反应 0.08h， 以63%的产率得到3-(4-pyridinyl)-5,6,7,8-tetrahydroindolizine-1,2-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Microwave-assisted synthesis of pyridylpyrroles from N-acylated amino acids

  摘要：

  A small library of 3- and 4-pyridyl-substituted pyrroles was prepared from N-acylated amino acids. Nicotinoyl or isonicotinoyl chloride was used for the N-acylation of benzyl esters of amino acids. Debenzylation by palladium-catalyzed hydrogenation gave N-acylated amino acids. Dehydration of the acylated amino acids gave cyclic intermediates, manchnones or aziactones, which were treated in situ with alkynes in 1,3-dipolar cycloadditions. The starting materials were prepared in a parallel fashion, and microwave irradiation was used to facilitate the cycloaddition reactions. The regiochemistry of the cycloaddition was studied. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.09.094

文献信息

• Microwave-assisted synthesis of pyridylpyrroles from N-acylated amino acids
  作者：Kirsi Harju、Nenad Manevski、Jari Yli-Kauhaluoma

  DOI：10.1016/j.tet.2009.09.094

  日期：2009.11

  A small library of 3- and 4-pyridyl-substituted pyrroles was prepared from N-acylated amino acids. Nicotinoyl or isonicotinoyl chloride was used for the N-acylation of benzyl esters of amino acids. Debenzylation by palladium-catalyzed hydrogenation gave N-acylated amino acids. Dehydration of the acylated amino acids gave cyclic intermediates, manchnones or aziactones, which were treated in situ with alkynes in 1,3-dipolar cycloadditions. The starting materials were prepared in a parallel fashion, and microwave irradiation was used to facilitate the cycloaddition reactions. The regiochemistry of the cycloaddition was studied. (C) 2009 Elsevier Ltd. All rights reserved.