ethyl 2-(6-chloro-5-fluoro-1-(4-methoxybenzyl)-2-oxo-4-(trifluoromethyl)-1,2,3,4-tetrahydroquinazolin-4-yl)buta-2,3-dienoate | 1593480-26-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2-(6-chloro-5-fluoro-1-(4-methoxybenzyl)-2-oxo-4-(trifluoromethyl)-1,2,3,4-tetrahydroquinazolin-4-yl)buta-2,3-dienoate
• CAS: 1593480-26-2
• 化学式: C₂₃H₁₉ClF₄N₂O₄
• 分子量: 498.861
• InChiKey: FDHOGLGXDNWXPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.25
• 重原子数：
  34.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  67.87
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2,3-丁二烯酸乙酯 、 6-Chloro-5-fluoro-1-[(4-methoxyphenyl)methyl]-4-(trifluoromethyl)quinazolin-2-one 在 吡啶 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以96%的产率得到ethyl 2-(6-chloro-5-fluoro-1-(4-methoxybenzyl)-2-oxo-4-(trifluoromethyl)-1,2,3,4-tetrahydroquinazolin-4-yl)buta-2,3-dienoate
  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