o-(N,N-dimethylamino)phenyl benzoate | 57999-23-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: o-(N,N-dimethylamino)phenyl benzoate
• 英文别名: 2-(dimethylamino)phenyl benzoate；benzoic acid-(2-dimethylamino-phenyl ester)；Benzoesaeure-(2-dimethylamino-phenylester)；[2-(Dimethylamino)phenyl] benzoate；[2-(dimethylamino)phenyl] benzoate
• CAS: 57999-23-2
• 化学式: C₁₅H₁₅NO₂
• 分子量: 241.29
• InChiKey: LLYCKPQPNCNFRO-UHFFFAOYSA-N

物化性质

• 熔点：
  54 °C
• 沸点：
  405.5±28.0 °C(Predicted)
• 密度：
  1.144±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N,N-二甲基苯胺 、 过氧化苯甲酰 在 iron(III) chloride hexahydrate 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以52%的产率得到o-(N,N-dimethylamino)phenyl benzoate
  参考文献：
  名称：

  铁 (III)-催化的 CH 官能化：N,N-二烷基苯胺的邻苯甲酰氧基化及其在 1,4-苯并恶氮中的应用

  摘要：

  介绍了通过邻位 N,N-二烷基苯胺的 C-H 官能化进行的 AC-O 键形成反应。铁催化的选择性邻苯甲酰氧基化遵循极性 Friedel-Crafts 机制，对苯胺的亲核性敏感。各种 N,N-二取代苯胺和 N-苯基杂环的苯甲酰氧基化是在极其温和的条件下进行的。此外，该方法已成功用于生成 1,4-苯并氧氮杂和 o-氨基苯酚。

  DOI：

  10.1002/ejoc.201402751

文献信息

• Zinner; Herbig, Chemische Berichte, 1957, vol. 90, p. 1548,1550
  作者：Zinner、Herbig

  DOI：——

  日期：——
• Mechanism of Polyphosphoric Acid and Phosphorus Pentoxide−Methanesulfonic Acid as Synthetic Reagents for Benzoxazole Formation
  作者：Ying-Hung So、Jerry P. Heeschen

  DOI：10.1021/jo960441u

  日期：1997.5.1

  The mechanism of 2-phenylbenzoxazole formation from benzoic acid and o-aminophenol in polyphosphoric acid (PPA) is studied by NMR spectroscopy and chemical analysis. Benzoic acid reacts with PPA to form benzoic-phosphoric anhydride and benzoic-polyphosphoric anhydride. The ratio of mixed anhydride to free carboxylic acid increases dramatically as the P2O5 content of PPA increases, but this ratio is independent of reaction temperature and time. When o-aminophenol dissolves in PPA, part of the hydroxyl group is converted to phosphate ester, and only protonated amine is detected. Benzoic acid, mixed anhydride, and PPA are in dynamic equilibrium, and so are PPA, o-aminophenol, and its phosphate ester. The mixed anhydride and o-aminophenol react to form 8-aminophenyl benzoate as the first reaction intermediate which undergoes rapid acyl migration to generate 2-hydroxybenzanilide. Ring closure of 2-hydroxybenzanilide to form 8-phenylbenzoxazole is acid catalyzed. The reactive components in phosphorus pentoxide-methanesulfonic acid (P2O5-MSA) which is a convenient alternative to PPA are very similar to those present in PPA. Benzoic acid is also converted into mixed anhydride in P2O5-MSA.