6-Chloro-3-hydroxy-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one | 919512-05-3

• 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: 6-Chloro-3-hydroxy-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one
• 英文别名: 6-chloro-3-hydroxy-2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one
• CAS: 919512-05-3
• 化学式: C₁₁H₉ClN₂O₂
• 分子量: 236.658
• InChiKey: MJQNIBOSPHEHBF-UHFFFAOYSA-N

物化性质

• 沸点：
  455.0±55.0 °C(Predicted)
• 密度：
  1?+-.0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-溴-2-吡咯啉酮 、 2-氨基-4-氯苯甲酸 、 alkaline earth salt of/the/ methylsulfuric acid 以88%的产率得到6-Chloro-3-hydroxy-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one
  参考文献：
  名称：

  Solid-phase synthesis of fused [2,1-b]quinazolinone alkaloids

  摘要：

  Solid-phase synthesis of fused [2,1-b]quinazolinone alkaloids has been developed for the preparation of vasicinone and deoxyvasicinone by two approaches. The derivative of polymer-supported p-nitrophenyl carbonate was attached to anthranilic acid and then coupled with various bromo-lactams. This resin-linked bromo intermediate upon acetylation, hydrolysis and resin cleavage gave the cyclized [2,1-b]quinazolmones (vasicinone). Alternatively, resin-linked azido-benzoic acids were coupled with bromo-substituted lactams followed by cyclization in an aza-Wittig reductive cyclization process giving the bromo-substituted quinazolinone intermediates, with subsequent acetylation, hydrolysis and resin cleavage affording the fused [2,1-b]quinazolinones. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.10.123

文献信息

• Solid-phase synthesis of fused [2,1-b]quinazolinone alkaloids
  作者：Ahmed Kamal、N. Shankaraiah、V. Devaiah、K. Laxma Reddy

  DOI：10.1016/j.tetlet.2006.10.123

  日期：2006.12

  Solid-phase synthesis of fused [2,1-b]quinazolinone alkaloids has been developed for the preparation of vasicinone and deoxyvasicinone by two approaches. The derivative of polymer-supported p-nitrophenyl carbonate was attached to anthranilic acid and then coupled with various bromo-lactams. This resin-linked bromo intermediate upon acetylation, hydrolysis and resin cleavage gave the cyclized [2,1-b]quinazolmones (vasicinone). Alternatively, resin-linked azido-benzoic acids were coupled with bromo-substituted lactams followed by cyclization in an aza-Wittig reductive cyclization process giving the bromo-substituted quinazolinone intermediates, with subsequent acetylation, hydrolysis and resin cleavage affording the fused [2,1-b]quinazolinones. (c) 2006 Elsevier Ltd. All rights reserved.