2-hydroxymethyl-2-methyl-2,3-dihydroquinazolin-4(1H)-one | 1239347-22-8

• 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: 2-hydroxymethyl-2-methyl-2,3-dihydroquinazolin-4(1H)-one
• 英文别名: 2-(Hydroxymethyl)-2-methyl-1,3-dihydroquinazolin-4-one
• CAS: 1239347-22-8
• 化学式: C₁₀H₁₂N₂O₂
• 分子量: 192.217
• InChiKey: JMCGZMPZGRFBFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  61.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氧代丙基2-氨基苯甲酸酯 在 ammonium acetate 、 溶剂黄146 作用下， 反应 1.5h， 以27%的产率得到2-hydroxymethyl-2-methyl-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