2-Methyl-2-m-tolylsulfanyl-benzo[1,3]dioxin-4-one | 88354-07-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: 2-Methyl-2-m-tolylsulfanyl-benzo[1,3]dioxin-4-one
• 英文别名: 2-Methyl-2-[(3-methylphenyl)sulfanyl]-2H,4H-1,3-benzodioxin-4-one；2-methyl-2-(3-methylphenyl)sulfanyl-1,3-benzodioxin-4-one
• CAS: 88354-07-8
• 化学式: C₁₆H₁₄O₃S
• 分子量: 286.351
• InChiKey: DRMGIHHKDIMSQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  60.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  邻乙酰水杨酰氯 、 3-甲基苯硫酚 以27%的产率得到
  参考文献：
  名称：

  HANSEN, A. B.;SENNING, A., ACTA CHEM. SCAND., 1983, 37, N 4, 351-359

  摘要：

  DOI：

文献信息

• Chemical Feasibility Studies Concerning Potential Prodrugs of Acetylsalicylic Acid.
  作者：Asger B. Hansen、Alexander Senning、Xu Jie-Cheng、Ulla Björkroth、Lu Yi-An、Liu Yin-Zeng

  DOI：10.3891/acta.chem.scand.37b-0351

  日期：——

  A rationale is developed for aspirin prodrugs based on non-acidic latentiated derivatives. Knowledge of the gastro-intestinal liabilities and pharmacological profile is required for this approach whereby aspirin is built into a common ortho ester function of the type 2-substituted 2-methyl-4H-1,3-benzodioxin-4-one with latentiated carboxyl and acetoxy groups. Twelve compounds of this type, ten substituted with various alkoxy and aryloxy groups and two with arylthio groups, have been isolated and characterized. A new synthetic route, comprising the reaction of 2-acetoxybenzoyl chloride with TMS derivatives of the corresponding alcohols and phenols, has been devised for the preparation of some of the compounds while others were prepared according to known methods. Subsequently, the prodrug candidates have been subjected to non-enzymatic hydrolysis for a first rapid screening in vitro. Only 2-tert-butoxy-2-methyl-4H-1,3-benzodioxin-4-one is observed to act as a true proaspirin, releasing aspirin, under these conditions, but analogous compounds with tertiary substituents may display the same behavior, and this chemical approach to aspirin modification may offer a viable rationale for aspirin prodrugs with reduced gastric irritancy or for making "superaspirins".
• HANSEN, A. B.;SENNING, A., ACTA CHEM. SCAND., 1983, 37, N 4, 351-359
  作者：HANSEN, A. B.、SENNING, A.

  DOI：——

  日期：——