2-oxopropyl 2-anilinobenzoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-oxopropyl 2-anilinobenzoate
• 化学式: C₁₆H₁₅NO₃
• 分子量: 269.3
• InChiKey: ZCXPPKZTPVIFNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-oxopropyl 2-anilinobenzoate 在 ammonium acetate 、 溶剂黄146 作用下， 反应 0.83h， 以52%的产率得到2-methyl-1-phenyl-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
• 作为产物：
  描述：

  N-苯基邻氨基苯甲酸 、 一氯丙酮 在 potassium carbonate 作用下， 生成 2-oxopropyl 2-anilinobenzoate
  参考文献：
  名称：

  1,2-二取代-3-羟基-4（1 H）-喹啉酮的制备及其取代对环化过程的影响

  摘要：

  描述了通过N-取代的苯甲酰基或乙酰基邻氨基苯甲酸酯的环化合成1，2-二取代的-3-羟基-4（1 H）-喹啉酮。两种方法被用于邻氨基苯甲酸酯的环化。在多磷酸中加热具有广泛的适用性。沸腾的N-甲基吡咯烷酮中的热环化受空间效应的限制。

  DOI：

  10.1002/jhet.5570360121

文献信息

• Study of anthranilates cyclization to 2-hydroxymethyl-2,3-dihydroquinazolin-4(1H)-one derivatives and alternative way of their synthesis
  作者：Miroslav Soural、Petr Funk、Lubomir Kvapil、Pavel Hradil、Jan Hlavac、Valerio Bertolasi

  DOI：10.3998/ark.5550190.0011.a21

  日期：——

  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.
• Preparation of 1,2-disubstituted-3-hydroxy-4(1<i>H</i>)-quinolinones and the influence of substitution on the course of cyclization
  作者：Pavel Hradil、Jan Hlaváč、Karel Lemr

  DOI：10.1002/jhet.5570360121

  日期：1999.1

  Synthesis of 1,2-disubstituted-3-hydroxy-4(1H)-quinolinones by the cyclization of N-substituted phenacyl or acetonyl anthranilates is described. Two methods were employed for cyclization of anthranilates. Heating in polyphosphoric acid has a wide scope of applicability. The thermal cyclization in boiling N-methylpyrrolidone is limited by steric effect.

  描述了通过N-取代的苯甲酰基或乙酰基邻氨基苯甲酸酯的环化合成1，2-二取代的-3-羟基-4（1 H）-喹啉酮。两种方法被用于邻氨基苯甲酸酯的环化。在多磷酸中加热具有广泛的适用性。沸腾的N-甲基吡咯烷酮中的热环化受空间效应的限制。