2-(2-naphthyloxy)-2-methyl-4H-1,3-benzodioxin-4-one | 52602-13-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(2-naphthyloxy)-2-methyl-4H-1,3-benzodioxin-4-one
• 英文别名: 2-methyl-2-(2-naphthyloxy)-4H-1,3-benzodioxin-4-one；2-methyl-2-naphthalen-2-yloxy-benzo[1,3]dioxin-4-one；4H-1,3-Benzodioxin-4-one, 2-methyl-2-(2-naphthalenyloxy)-；2-methyl-2-naphthalen-2-yloxy-1,3-benzodioxin-4-one
• CAS: 52602-13-8
• 化学式: C₁₉H₁₄O₄
• 分子量: 306.318
• InChiKey: YCYBZZVHZKGYHH-UHFFFAOYSA-N

物化性质

• 沸点：
  524.6±50.0 °C(Predicted)
• 密度：
  1.293±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-naphthyloxy)-2-methyl-4H-1,3-benzodioxin-4-one 在 phosphate buffer 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 水杨酸
  参考文献：
  名称：

  Chemical Feasibility Studies Concerning Potential Prodrugs of Acetylsalicylic Acid.

  摘要：

  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".

  DOI：

  10.3891/acta.chem.scand.37b-0351
• 作为产物：
  描述：

  2-萘酚 、 邻乙酰水杨酰氯 以 乙腈 为溶剂， 生成 2-(2-naphthyloxy)-2-methyl-4H-1,3-benzodioxin-4-one
  参考文献：
  名称：

  Structure and conformation of 2-methyl-2-(2-naphthyloxy)-4H-1,3-benzodioxin-4-one

  摘要：

  DOI：

  10.1107/s0567740882004713

文献信息

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

  DOI：——

  日期：——