2-(1-methylethyl)-5-(4-pyridinyl)-1H-pyrrole-3,4-dicarboxylic acid dimethyl ester | 1199939-82-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-(1-methylethyl)-5-(4-pyridinyl)-1H-pyrrole-3,4-dicarboxylic acid dimethyl ester
• CAS: 1199939-82-6
• 化学式: C₁₆H₁₈N₂O₄
• 分子量: 302.33
• InChiKey: QUJBYFBSLAFZGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.77
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  81.28
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  丁炔二酸二甲酯 、 isonicotinoyl-L-Val 在 乙酸酐 作用下， 反应 0.08h， 以28%的产率得到2-(1-methylethyl)-5-(4-pyridinyl)-1H-pyrrole-3,4-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