1,2-dimethyl-2-hydroxymethyl-2,3-dihydroquinazolin-4(1H)-one | 1239347-23-9

• 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: 1,2-dimethyl-2-hydroxymethyl-2,3-dihydroquinazolin-4(1H)-one
• 英文别名: 2-(hydroxymethyl)-1,2-dimethyl-3H-quinazolin-4-one
• CAS: 1239347-23-9
• 化学式: C₁₁H₁₄N₂O₂
• 分子量: 206.244
• InChiKey: WNFYHISCUCQXPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  52.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-oxopropyl 2-(methylamino)benzoate 在 ammonium acetate 、 溶剂黄146 作用下， 反应 3.0h， 以19%的产率得到1,2-dimethyl-2-hydroxymethyl-2,3-dihydroquinazolin-4(1H)-one
  参考文献：
  名称：

  Study of anthranilates cyclization to 2-hydroxymethyl-2,3-dihydroquinazolin-4(1H)-one derivatives and alternative way of their synthesis

  摘要：

  Applicability of the previously described rearrangement of 2-oxo-2-phenylethyl 2-amino-benzoate leading to 2-phenyl-2-hydroxymethyl-2,3-dihydroquinazolin-4(1H)-one has been studied. To test the limits of the reaction, various starting compounds such as 2-oxopropyl 2-aminobenzoate, 2-oxo-2-phenylethyl 2-aminobenzoate and 3,3-dimethyl-2-oxobutyl 2-aminobenzoate as well as some of their corresponding N-methyl and N-phenyl analogues were used. The structure-reactivity dependence was observed giving the expected products only in specific cases and in limited yields. Structure of the dihydroquinazolin-4(1H)-one skeleton was unambiguously confirmed with use of X-ray analysis of two selected compounds. Finally, an alternative way for the preparation of the desired derivatives was developed.

  DOI：

  10.3998/ark.5550190.0011.a21