2-acetoxymethyl-2-methyl-2,3-dihydroquinazolin-4(1H)-one | 1239347-30-8

• 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-acetoxymethyl-2-methyl-2,3-dihydroquinazolin-4(1H)-one
• CAS: 1239347-30-8
• 化学式: C₁₂H₁₄N₂O₃
• 分子量: 234.255
• InChiKey: BDPHGCAHRSGRAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.12
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  67.43
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  过氧化乙酰丙酮 、 2-氨基苯甲酰胺 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以80%的产率得到2-acetoxymethyl-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