4-hydroperoxy-2-methoxy-4-(prop-2-en-1-yl)cyclohexa-2,5-dien-1-one | 1128087-06-8

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机氢过氧化物
• 英文名称: 4-hydroperoxy-2-methoxy-4-(prop-2-en-1-yl)cyclohexa-2,5-dien-1-one
• 英文别名: 4-hydroperoxy-2-methoxy-4-prop-2-enylcyclohexa-2,5-dien-1-one
• CAS: 1128087-06-8
• 化学式: C₁₀H₁₂O₄
• 分子量: 196.203
• InChiKey: SOTQJJGQCIVVOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  丁香酚 在 氧气 、 Chlorophyll 作用下， 以 氯仿 为溶剂， 反应 16.0h， 以42%的产率得到4-hydroperoxy-2-methoxy-4-(prop-2-en-1-yl)cyclohexa-2,5-dien-1-one
  参考文献：
  名称：

  Oxidation reactions of some natural volatile aromatic compounds: anethole and eugenol

  摘要：

  trans-Anethole [1-methoxy-4-(trans-prop-1-en-1-yl)benzene] was isolated from anise seed oil (Pimpinella anisum). Its photochemical oxidation with hydrogen peroxide gave the corresponding epoxy derivative together with 4-methoxybenzaldehyde. The thermal oxidation of trans-anethole with 3-chloroperoxybenzoic acid at room temperature resulted in the formation of dimeric epoxide, 2,5-bis(4-methoxyphenyl)-3,6-dimethyl-1,4-dioxane, as the only product. Photochemical oxygenation of trans-anethole in the presence of tetraphenylporphyrin, Rose Bengal, or chlorophyll as sensitizer led to a mixture of 1-(4-methoxyphenyl)prop-2-en-1-yl hydroperoxide and 4-methoxybenzaldehyde. Eugenol was isolated from clove oil [Eugenia caryophyllus (Spreng.)]. It was converted into 2-methoxy-4-(prop-2-en-1-yl)phenyl hydroperoxide by oxidation with hydrogen peroxide under irradiation. Thermal oxidation of eugenol with 3-chloroperoxypenzoic acid at room temperature produced 2-methoxy-4-(oxiran-2-ylmethyl)phenol, while sensitized photochemical oxygenation (in the presence of Rose Bengal or chlorophyll) gave 4-hydroperoxy-2-methoxy-4-(prop-2-en-1-yl)cyclohexa-2,5-dien-1-one.

  DOI：

  10.1134/s1070428008060079