1,6-dimethyl-4-phenyl-2,2-di-p-tolyl-1H-pyrrolo[3,4-b]pyridine-5,7(2H,6H)-dione | 1451000-01-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 1,6-dimethyl-4-phenyl-2,2-di-p-tolyl-1H-pyrrolo[3,4-b]pyridine-5,7(2H,6H)-dione
• 英文别名: 1,6-Dimethyl-2,2-bis(4-methylphenyl)-4-phenylpyrrolo[3,4-b]pyridine-5,7-dione
• CAS: 1451000-01-3
• 化学式: C₂₉H₂₆N₂O₂
• 分子量: 434.538
• InChiKey: UAEKNYDPYUWPAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  33
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-甲基-3-(甲基氨基)-1H-吡咯-2,5-二酮 、 3-phenyl-1,1-di-p-tolylprop-2-yn-1-ol 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以74%的产率得到1,6-dimethyl-4-phenyl-2,2-di-p-tolyl-1H-pyrrolo[3,4-b]pyridine-5,7(2H,6H)-dione
  参考文献：
  名称：

  Lewis acid-promoted cascade reaction of primary amine, 2-butynedioate, and propargylic alcohol: a convenient approach to 1,2-dihydropyridines and 1H-pyrrolo[3,4-b]pyridine-5,7(2H,6H)-diones

  摘要：

  1,2-Dihydropyridine-5,6-dicarboxylates were efficiently constructed through a cascade reaction of primary amine, 2-butynedioate and propargylic alcohol in the presence of Lewis acid under mild conditions. As exceptional, 1H-pyrrolo[3,4-b]pyridine-5,7(2H,6H)-diones were approached when the primary amine was methylamine. Possible mechanism for the formation of 1,2-dihydropyridine skeleton is proposed. The process involves 1,3,4-pentatrien-1-amine as a key intermediate that formed in situ by trapping allenic carbocations with enamines. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.07.076