2,6-di-tert-butyl-4-(2-hydroxyethylidene)cyclohexa-2,5-dien-1-one

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2,6-di-tert-butyl-4-(2-hydroxyethylidene)cyclohexa-2,5-dien-1-one
• 英文别名: 2,6-Ditert-butyl-4-tert-butylperoxy-4-(2-hydroxyethyl)cyclohexa-2,5-dien-1-one；2,6-ditert-butyl-4-tert-butylperoxy-4-(2-hydroxyethyl)cyclohexa-2,5-dien-1-one
• 化学式: C₂₀H₃₄O₄
• 分子量: 338.488
• InChiKey: RMSFGLMCSTYNJI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  叔丁基过氧化氢 、 2-(3,5-di-t-butyl-4-hydroxyphenyl)ethanol 在 四丁基碘化铵 作用下， 以 正壬烷 、 1,2-二氯乙烷 为溶剂， 反应 36.0h， 以96%的产率得到2,6-di-tert-butyl-4-(2-hydroxyethylidene)cyclohexa-2,5-dien-1-one
  参考文献：
  名称：

  Ammonium Hypoiodite-Catalyzed Peroxidative Dearomatization of Phenols

  摘要：

  Here, we report the first transition metal-free peroxidative dearomatization of phenols using hypoiodite catalysis with TBHP. Hypoiodite salts are generated in situ from the corresponding quaternary ammonium iodides in the presence of TBHP, and the oxidative coupling reaction proceeds efficiently under mild conditions. The dearomatized products are versatile synthetic intermediates for further synthetic transformations to various complex structures including heterocycles. As a demonstration, the further oxidation of the unsaturated peroxide with TBHP afforded the corresponding peroxy epoxide in good yield.

  DOI：

  10.3987/com-16-s(s)84

文献信息

• Ammonium Hypoiodite-Catalyzed Peroxidative Dearomatization of Phenols
  作者：Kazuaki Ishihara、Muhammet Uyanik、Kohei Nishioka

  DOI：10.3987/com-16-s(s)84

  日期：——

  Here, we report the first transition metal-free peroxidative dearomatization of phenols using hypoiodite catalysis with TBHP. Hypoiodite salts are generated in situ from the corresponding quaternary ammonium iodides in the presence of TBHP, and the oxidative coupling reaction proceeds efficiently under mild conditions. The dearomatized products are versatile synthetic intermediates for further synthetic transformations to various complex structures including heterocycles. As a demonstration, the further oxidation of the unsaturated peroxide with TBHP afforded the corresponding peroxy epoxide in good yield.