2-Phenyl-4-pyridin-2-yl-6,7-bis-p-tolylamino-4,5-dihydro-pyrrolo[3,4-c]pyridine-1,3-dione | 181311-14-8

• 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: 2-Phenyl-4-pyridin-2-yl-6,7-bis-p-tolylamino-4,5-dihydro-pyrrolo[3,4-c]pyridine-1,3-dione
• CAS: 181311-14-8
• 化学式: C₃₂H₂₇N₅O₂
• 分子量: 513.599
• InChiKey: ARAFIBBPYQFHLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.61
• 重原子数：
  39.0
• 可旋转键数：
  6.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  86.36
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-乙基马来酰亚胺 、 2-Phenyl-4-pyridin-2-yl-6,7-bis-p-tolylamino-4,5-dihydro-pyrrolo[3,4-c]pyridine-1,3-dione 在 N-苯基马来酰亚胺 作用下， 以 xylene 为溶剂， 反应 4.0h， 以10%的产率得到2-Ethyl-7-phenyl-4,5-bis-p-tolylamino-pyrrolo[3,4-e]isoindole-1,3,6,8-tetraone
  参考文献：
  名称：

  Bicyclische Oxalamidine - Bausteine f�r hochsubstituierte 2,2?-Bipyridine und Benzolderivate

  摘要：

  The bis-imidoylchlorides 1 derived from oxalic acid exhibit a high regio- and chemoselectivity. As in the case of 2-picolylamine 2 the acylation with oxalyl chloride furnished the expected open chained oxalic diamides 3a while the imidoylchlorides 1 yield exclusively the new pyrido[1,2-a]-pyrazines 4. These heterocycles represent readily crystallisable and orange-red coloured compounds with a mesomeric dipolar aromatic substructure. The synthetic value of 4 is based on their easy transformation into highly substituted arenes and hetarenes. Thus, electron deficient dienophiles as dimethyl acetylenedicarboxylate lead to the bipyridines 6 via Hetero-Diels-Alder-Reaction and subsequent 1,5-hydrogen shift. In a complex reaction the derivatives of maleic acid 7a-c yield the bipyridines of type 9 while the new hexasubstituted arenes 10 can be isolated under anaerobic conditions and with an excess of dienophilic component. A x-ray structural determination of 10b shows an alternation of bond lenghts in the benzene ring. This can be considered as a distinct disturbance of aromaticity caused by the arrangement of substituents.

  DOI：

  10.1002/prac.19963380184
• 作为产物：
  描述：

  2-氨甲基吡啶 在 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 28.0h， 生成 2-Phenyl-4-pyridin-2-yl-6,7-bis-p-tolylamino-4,5-dihydro-pyrrolo[3,4-c]pyridine-1,3-dione
  参考文献：
  名称：

  Bicyclische Oxalamidine - Bausteine f�r hochsubstituierte 2,2?-Bipyridine und Benzolderivate

  摘要：

  The bis-imidoylchlorides 1 derived from oxalic acid exhibit a high regio- and chemoselectivity. As in the case of 2-picolylamine 2 the acylation with oxalyl chloride furnished the expected open chained oxalic diamides 3a while the imidoylchlorides 1 yield exclusively the new pyrido[1,2-a]-pyrazines 4. These heterocycles represent readily crystallisable and orange-red coloured compounds with a mesomeric dipolar aromatic substructure. The synthetic value of 4 is based on their easy transformation into highly substituted arenes and hetarenes. Thus, electron deficient dienophiles as dimethyl acetylenedicarboxylate lead to the bipyridines 6 via Hetero-Diels-Alder-Reaction and subsequent 1,5-hydrogen shift. In a complex reaction the derivatives of maleic acid 7a-c yield the bipyridines of type 9 while the new hexasubstituted arenes 10 can be isolated under anaerobic conditions and with an excess of dienophilic component. A x-ray structural determination of 10b shows an alternation of bond lenghts in the benzene ring. This can be considered as a distinct disturbance of aromaticity caused by the arrangement of substituents.

  DOI：

  10.1002/prac.19963380184