N-(2-isopropyl-4-oxo-4H-quinazolin-3-yl)-2-phenylpropionamide | 178422-75-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: N-(2-isopropyl-4-oxo-4H-quinazolin-3-yl)-2-phenylpropionamide
• 英文别名: N-(4-oxo-2-propan-2-ylquinazolin-3-yl)-2-phenylpropanamide
• CAS: 178422-75-8
• 化学式: C₂₀H₂₁N₃O₂
• 分子量: 335.406
• InChiKey: OROKJPUPTSURJR-UHFFFAOYSA-N

物化性质

• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  61.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酰氯 、 N-(2-isopropyl-4-oxo-4H-quinazolin-3-yl)-2-phenylpropionamide 在 吡啶 作用下， 反应 5.0h， 生成 N-(2-Isopropyl-4-oxo-4H-quinazolin-3-yl)-N-(2-phenyl-propionyl)-acetamide
  参考文献：
  名称：

  The N–N bond as a chiral axis: 3-diacylaminoquinazolinones as chiral acylating agents

  摘要：

  3-Diacylaminoquinazolinones 10 and 15 have high enough barriers to rotation around their N-N bonds to allow separation of each into diastereoisomers. Interconversion of diastereoisomers 10a and 10b occurs on heating in boiling toluene and thermodynamic parameters for this process have been measured, The barriers to rotation around the N-N bonds in analogous monoacylaminoquinazolinones are not sufficient to permit isolation of stereoisomers at room temperature unless the exocyclic nitrogen is additionally substituted e.g. by an alkyl group as in 28, X-Ray crystal structure determinations carried out on 10a, 10b, 15a and 28b confirm the presence of chiral axes, Reaction of both diastereoisomers 15a and 15b with 1-phenylethylamine takes place with exclusive reaction at the 1-acetoxypropionyl carbonyl group and with partial kinetic resolution: the preferred sense of enantioselectivity obtained is dominated by the N-N axis.

  DOI：

  10.1039/p19960001047
• 作为产物：
  描述：

  3-氨基-2-异丙基-4(3H)-喹唑啉酮 在 草酰氯 、 N,N-二甲基甲酰胺 、 吡啶 、 碳酸氢钠 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以85%的产率得到N-(2-isopropyl-4-oxo-4H-quinazolin-3-yl)-2-phenylpropionamide
  参考文献：
  名称：

  WO2007/57447

  摘要：

  公开号：

文献信息

• Novel Quinazoline Derivatives and Their Medical Use
  申请人：Brown William Dalby

  公开号：US20090291973A1

  公开（公告）日：2009-11-26

  This invention relates to novel quinazoline derivatives having medical utility, to use of the quinazoline derivatives of the invention for the manufacture of a medicament, to pharmaceutical compositions comprising the quinazoline derivatives of the invention, and to methods of treating a disorder, disease or a condition of a subject, which disorder, disease or condition is responsive to activation of K v 7 channels.

  本发明涉及具有医学用途的新型喹唑啉衍生物，涉及使用本发明的喹唑啉衍生物制造药物，涉及含有本发明的喹唑啉衍生物的药物组合物，以及涉及治疗响应于Kv7通道激活的主体的紊乱、疾病或状况的方法。
• The N–N bond as a chiral axis: 3-diacylaminoquinazolinones as chiral acylating agents
  作者：Robert S. Atkinson、Emma Barker、Paul J. Edwards、Gordon A. Thomson

  DOI：10.1039/p19960001047

  日期：——

  3-Diacylaminoquinazolinones 10 and 15 have high enough barriers to rotation around their N-N bonds to allow separation of each into diastereoisomers. Interconversion of diastereoisomers 10a and 10b occurs on heating in boiling toluene and thermodynamic parameters for this process have been measured, The barriers to rotation around the N-N bonds in analogous monoacylaminoquinazolinones are not sufficient to permit isolation of stereoisomers at room temperature unless the exocyclic nitrogen is additionally substituted e.g. by an alkyl group as in 28, X-Ray crystal structure determinations carried out on 10a, 10b, 15a and 28b confirm the presence of chiral axes, Reaction of both diastereoisomers 15a and 15b with 1-phenylethylamine takes place with exclusive reaction at the 1-acetoxypropionyl carbonyl group and with partial kinetic resolution: the preferred sense of enantioselectivity obtained is dominated by the N-N axis.
• WO2007/57447
  申请人：——

  公开号：——

  公开（公告）日：——