2-(2-Acetoxybenzoyloxy)acetophenone | 53278-17-4

• 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: 2-(2-Acetoxybenzoyloxy)acetophenone
• 英文别名: (2-Acetylphenyl) 2-acetyloxybenzoate
• CAS: 53278-17-4
• 化学式: C₁₇H₁₄O₅
• 分子量: 298.295
• InChiKey: GNKYLAHPCNUZDO-UHFFFAOYSA-N

物化性质

• 沸点：
  490.6±30.0 °C(Predicted)
• 密度：
  1.232±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 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：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(2-Acetoxybenzoyloxy)acetophenone 在 水 作用下， 以 1,4-二氧六环 为溶剂， 生成 2'-羟基苯乙酮 、 2-(2-Hydroxybenzoyloxy)acetophenone 、 阿司匹林
  参考文献：
  名称：

  Prodrugs Part 31. 2-Formylphenyl esters of indomethacin, ketoprofen and ibuprofen and 6-substituted 2-formyl and 2-acylphenyl esters of aspirin

  摘要：

  The synthesis and study of a novel series of potential prodrugs of indomethacin, ketoprofen, ibuprofen and aspirin are reported. 2-Formylphenyl esters of the NSAIDs, together with two 6-substituted 2-formyl and two 2-acylphenyl aspirins and 4-formylphenylindomethacin, have been prepared. A study of their alkaline and neutral hydrolysis shows that these compounds, with the exception of 2-acetylphenyl aspirin, act as true prodrugs of the NSAIDs, giving the NSAID and acylphenol. The rates of hydrolysis and activation parameters indicate that the 2-acylphenyl esters employ an intramolecular catalytic route. The 2-formylphenyl testers were more potent as anti-inflammatory agents than the parent compounds in the carragheenan-induced paw oedema test. (C) 1998 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(97)00014-1
• 作为产物：
  描述：

  阿司匹林 在 氯化亚砜 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 10.17h， 生成 2-(2-Acetoxybenzoyloxy)acetophenone
  参考文献：
  名称：

  Prodrugs Part 31. 2-Formylphenyl esters of indomethacin, ketoprofen and ibuprofen and 6-substituted 2-formyl and 2-acylphenyl esters of aspirin

  摘要：

  The synthesis and study of a novel series of potential prodrugs of indomethacin, ketoprofen, ibuprofen and aspirin are reported. 2-Formylphenyl esters of the NSAIDs, together with two 6-substituted 2-formyl and two 2-acylphenyl aspirins and 4-formylphenylindomethacin, have been prepared. A study of their alkaline and neutral hydrolysis shows that these compounds, with the exception of 2-acetylphenyl aspirin, act as true prodrugs of the NSAIDs, giving the NSAID and acylphenol. The rates of hydrolysis and activation parameters indicate that the 2-acylphenyl esters employ an intramolecular catalytic route. The 2-formylphenyl testers were more potent as anti-inflammatory agents than the parent compounds in the carragheenan-induced paw oedema test. (C) 1998 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(97)00014-1

文献信息

• Adam, Waldemar; Schulz, Manfred H., Chemische Berichte, 1992, vol. 125, # 11, p. 2455 - 2462
  作者：Adam, Waldemar、Schulz, Manfred H.

  DOI：——

  日期：——
• Prodrugs Part 31. 2-Formylphenyl esters of indomethacin, ketoprofen and ibuprofen and 6-substituted 2-formyl and 2-acylphenyl esters of aspirin
  作者：Evelyn A. Abordo、Keith Bowden、Anthony P. Huntington、Sarah L. Powell

  DOI：10.1016/s0014-827x(97)00014-1

  日期：1998.2

  The synthesis and study of a novel series of potential prodrugs of indomethacin, ketoprofen, ibuprofen and aspirin are reported. 2-Formylphenyl esters of the NSAIDs, together with two 6-substituted 2-formyl and two 2-acylphenyl aspirins and 4-formylphenylindomethacin, have been prepared. A study of their alkaline and neutral hydrolysis shows that these compounds, with the exception of 2-acetylphenyl aspirin, act as true prodrugs of the NSAIDs, giving the NSAID and acylphenol. The rates of hydrolysis and activation parameters indicate that the 2-acylphenyl esters employ an intramolecular catalytic route. The 2-formylphenyl testers were more potent as anti-inflammatory agents than the parent compounds in the carragheenan-induced paw oedema test. (C) 1998 Elsevier Science S.A. All rights reserved.