1-(4-diethylaminophenyl)-7,7-dimethyl-2,5-dioxo-1,2,5,6,7,8-hexahydro-3-quinolinecarboxamide | 1029690-85-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-(4-diethylaminophenyl)-7,7-dimethyl-2,5-dioxo-1,2,5,6,7,8-hexahydro-3-quinolinecarboxamide
• 英文别名: 1-[4-(Diethylamino)phenyl]-7,7-dimethyl-2,5-dioxo-6,8-dihydroquinoline-3-carboxamide；1-[4-(diethylamino)phenyl]-7,7-dimethyl-2,5-dioxo-6,8-dihydroquinoline-3-carboxamide
• CAS: 1029690-85-4
• 化学式: C₂₂H₂₇N₃O₃
• 分子量: 381.475
• InChiKey: QUDYPQMVRKKJRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  83.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  dimethylammonium 2-(2-carbamoyl-2-cyano-1-ethenyl)-5,5-dimethyl-3-oxo-1-cyclohexen-1-olate 、 N,N-二乙基对苯二胺 在 溶剂黄146 作用下， 以73%的产率得到1-(4-diethylaminophenyl)-7,7-dimethyl-2,5-dioxo-1,2,5,6,7,8-hexahydro-3-quinolinecarboxamide
  参考文献：
  名称：

  An efficient synthesis of N1-substituted 2,5-dioxo-1,2,5,6,7,8-hexahydro-3-quinolinecarboxamide via enolate salts

  摘要：

  Various 2-(2-cyano-2-carbamoyl-1-ethenyl)-5,5-dimethyl-3-oxo-1-cyclohexen-1-olates substituted in the amide group with dialkylammonium or sodium cations were prepared via reactions of N-substituted cyanoacetamides with dimedone-DMFDMA adduct by a one-pot, two-step protocol. The salts obtained were used in reactions with N-nucleophiles for further synthesis of the N1-substituted 2,5-dioxo- 1,2,5,6,7,8-hexahydro-3-quinolinecarboxamides that are analogues of well-known pharmaceuticals. The structure of the salts and the N1-substituted 2,5-dioxo-1,2,5,6,7,8-hexahydro-3-quinolinecarboxamides was established by means of spectroscopic and X-ray diffraction studies. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.02.095

文献信息

• An efficient synthesis of N1-substituted 2,5-dioxo-1,2,5,6,7,8-hexahydro-3-quinolinecarboxamide via enolate salts
  作者：Sergey A. Yermolayev、Nikolay Yu. Gorobets、Elena V. Lukinova、Oleg V. Shishkin、Svetlana V. Shishkina、Sergey M. Desenko

  DOI：10.1016/j.tet.2008.02.095

  日期：2008.5

  Various 2-(2-cyano-2-carbamoyl-1-ethenyl)-5,5-dimethyl-3-oxo-1-cyclohexen-1-olates substituted in the amide group with dialkylammonium or sodium cations were prepared via reactions of N-substituted cyanoacetamides with dimedone-DMFDMA adduct by a one-pot, two-step protocol. The salts obtained were used in reactions with N-nucleophiles for further synthesis of the N1-substituted 2,5-dioxo- 1,2,5,6,7,8-hexahydro-3-quinolinecarboxamides that are analogues of well-known pharmaceuticals. The structure of the salts and the N1-substituted 2,5-dioxo-1,2,5,6,7,8-hexahydro-3-quinolinecarboxamides was established by means of spectroscopic and X-ray diffraction studies. (C) 2008 Elsevier Ltd. All rights reserved.