(E)-ethyl 2-(8-chloro-4-oxo-9b-(trifluoromethyl)-5-(2,4,6-trimethylbenzyl)-4,5-dihydro-1H-azeto[1,2-c]quinazolin-2(9bH)-ylidene)acetate | 1593480-19-3

• 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: (E)-ethyl 2-(8-chloro-4-oxo-9b-(trifluoromethyl)-5-(2,4,6-trimethylbenzyl)-4,5-dihydro-1H-azeto[1,2-c]quinazolin-2(9bH)-ylidene)acetate
• CAS: 1593480-19-3
• 化学式: C₂₅H₂₄ClF₃N₂O₃
• 分子量: 492.925
• InChiKey: JMWKOQXWPHLPHK-WOJGMQOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.32
• 重原子数：
  34.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  49.85
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2,3-丁二烯酸乙酯 、 6-chloro-4-(trifluoromethyl)-1-(2,4,6-trimethylbenzyl)quinazolin-2(1H)-one 在 三乙烯二胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以79%的产率得到(E)-ethyl 2-(8-chloro-4-oxo-9b-(trifluoromethyl)-5-(2,4,6-trimethylbenzyl)-4,5-dihydro-1H-azeto[1,2-c]quinazolin-2(9bH)-ylidene)acetate
  参考文献：
  名称：

  Nucleophilic Lewis Base Dependent Addition Reactions of Allenoates with Trifluoromethylated Cyclic Ketimines

  摘要：

  A detailed investigation on the different reactivity patterns shown by phosphorus- and nitrogen-containing Lewis base catalysts in the reactions of allenoates with cyclic trifluoromethyl ketimines was accomplished. With PPh3, [3 + 2] annulations proceeded smoothly to afford dihydropyrrole derivatives in excellent yields. Under the catalysis of DABCO, [2 + 2] annulations occurred, producing azetidine derivatives in good to high yields. However, in the presence of pyridine, alpha,alpha'-disubstituted allenoates were obtained in very high yields via aza-Morita-Baylis-Hillman reactions. These studies provide an opportunity for diverse synthesis of a variety of N-heterocyclic compounds from the same starting materials.

  DOI：

  10.1021/jo500356t