7-chloro-3-furfurylquinazoline-2,4-dione

• 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: 7-chloro-3-furfurylquinazoline-2,4-dione
• 英文别名: 7-chloro-3-[(furan-2-yl)methyl]quinazoline-2,4-dione；7-chloro-3-(furan-2-ylmethyl)-1H-quinazoline-2,4-dione
• 化学式: C₁₃H₉ClN₂O₃
• 分子量: 276.679
• InChiKey: IHYSXGFMXSDTFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (4-{tris[2-(perfluorohexyl)ethyl]silyl}benzyl) 4-chloro-2-{[(furfuryl)amino]carbonyl}phenylcarbamate 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以90%的产率得到7-chloro-3-furfurylquinazoline-2,4-dione
  参考文献：
  名称：

  Perfluoro-Tagged Benzyloxycarbonyl Protecting Group and Its Application in Fluorous Biphasic Systems

  摘要：

  The synthesis of a new perfluoro-tagged benzyloxycarbonyl protecting group is reported, as well as its application in the parallel protection of amines. Isolation of the protected amines was performed by simple liquid-liquid extraction between perfluorinated and organic solvents, Deprotection was achieved by standard hydrogenolysis. The novel protecting group was also applied to cyclization protocols leading to quinazoline-2,4-diones. These products were isolated by simple extraction procedures.

  DOI：

  10.1002/1522-2675(200201)85:1<255::aid-hlca255>3.0.co;2-5

文献信息

• Multistep Parallel Synthesis of Quinazoline-2,4-diones by a Fluorous Biphasic Concept without Perfluorinated Solvents
  作者：Dominik Schwinn、Heiko Glatz、Willi Bannwarth

  DOI：10.1002/hlca.200390010

  日期：2003.1

  benzyl alcohol adsorbed via fluorous–fluorous interactions on fluorous reversed-phase silica gel (FRPSG), we have performed a multistep synthesis leading finally to a small library of quinazoline-2,4-diones. The whole reaction sequence runs without isolation of intermediates and most importantly, without the need of perfluorinated solvents.

  基于通过氟反相硅胶（FRPSG）上的氟-氟相互作用吸附的全氟标签苄醇，我们进行了多步合成，最终形成了一个小的喹唑啉-2,4-二酮文库。整个反应过程无需分离中间体，最重要的是，不需要全氟化溶剂。