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2-(menthyl)-2-methyl-4H-1,3-benzodioxin-4-one | 88354-00-1

中文名称
——
中文别名
——
英文名称
2-(menthyl)-2-methyl-4H-1,3-benzodioxin-4-one
英文别名
——
2-(menthyl)-2-methyl-4H-1,3-benzodioxin-4-one化学式
CAS
88354-00-1
化学式
C19H26O4
mdl
——
分子量
318.413
InChiKey
VWFDMPQHKFWVOE-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

物化性质

  • 沸点:
    444.4±45.0 °C(Predicted)
  • 密度:
    1.12±0.1 g/cm3(Predicted)

计算性质

  • 辛醇/水分配系数(LogP):
    4.39
  • 重原子数:
    23.0
  • 可旋转键数:
    3.0
  • 环数:
    3.0
  • sp3杂化的碳原子比例:
    0.63
  • 拓扑面积:
    44.76
  • 氢给体数:
    0.0
  • 氢受体数:
    4.0

SDS

SDS:81925ab509c8edbf77519d292d84ace7
查看

反应信息

  • 作为反应物:
    描述:
    2-(menthyl)-2-methyl-4H-1,3-benzodioxin-4-one 在 phosphate buffer 作用下, 以 1,4-二氧六环 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:
    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
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