4-methylbenzo[1,3]dioxole-5,6-diol | 607351-69-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 4-methylbenzo[1,3]dioxole-5,6-diol
• 英文别名: 4-Methyl-1,3-benzodioxole-5,6-diol
• CAS: 607351-69-9
• 化学式: C₈H₈O₄
• 分子量: 168.149
• InChiKey: UTBDWTGVYDEPOK-UHFFFAOYSA-N

物化性质

• 沸点：
  351.2±42.0 °C(Predicted)
• 密度：
  1.478±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,3-苯并二噁唑,5-(甲氧基甲氧基)-4-甲基- 在 盐酸 、 potassium dihydrogenphosphate 、 sodium dithionite 、 potassium nitrososulfonate 作用下， 以 甲醇 、 水 、 乙酸乙酯 为溶剂， 反应 1.58h， 生成 4-methylbenzo[1,3]dioxole-5,6-diol
  参考文献：
  名称：

  Development of Novel Antioxidants:  Design, Synthesis, and Reactivity

  摘要：

  We are attempting to develop novel synthetic antioxidants aimed at retarding the effects of free-radical induced cell damage. In this paper we discuss the design strategy and report the synthesis of seven novel antioxidants, including six catechols and a benzylic phenol. The bond dissociation enthalpy (BDE) for the most active (weakest) OH bond in each molecule was calculated by theoretical methods, as well as the BDE for the semiquinone radical. Reaction rates with the nitrogen-centered free radical DPPH. were measured in ethyl acetate. The log of k(DPPH) for bimolecular reaction correlated well with the primary BDE. The correlation between rate constants and calculated BDEs shows that the BDE is a good predictor of antioxidant activity with DPPH., suggesting that our design criteria are useful and that these compounds should undergo further testing in cell cultures and in animal models.

  DOI：

  10.1021/jo0301090

文献信息

• Development of Novel Antioxidants:  Design, Synthesis, and Reactivity
  作者：Helmi H. Hussain、Gordana Babic、Tony Durst、James S. Wright、Mihaela Flueraru、Alexandru Chichirau、Leonid L. Chepelev

  DOI：10.1021/jo0301090

  日期：2003.9.1

  We are attempting to develop novel synthetic antioxidants aimed at retarding the effects of free-radical induced cell damage. In this paper we discuss the design strategy and report the synthesis of seven novel antioxidants, including six catechols and a benzylic phenol. The bond dissociation enthalpy (BDE) for the most active (weakest) OH bond in each molecule was calculated by theoretical methods, as well as the BDE for the semiquinone radical. Reaction rates with the nitrogen-centered free radical DPPH. were measured in ethyl acetate. The log of k(DPPH) for bimolecular reaction correlated well with the primary BDE. The correlation between rate constants and calculated BDEs shows that the BDE is a good predictor of antioxidant activity with DPPH., suggesting that our design criteria are useful and that these compounds should undergo further testing in cell cultures and in animal models.