1,5-Dioxonane-3,6,9-trione | 219485-80-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,5-Dioxonane-3,6,9-trione
• CAS: 219485-80-0
• 化学式: C₇H₈O₅
• 分子量: 172.138
• InChiKey: SLKNNTSLDRFSHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  丁二酸酐 、 1,3-二羟基丙酮 在 三乙胺 、 氯甲酸异丁酯 作用下， 生成 1,5-Dioxonane-3,6,9-trione
  参考文献：
  名称：

  Novel Cyclic Ketones for Catalytic Oxidation Reactions

  摘要：

  In our effort to search for Ca symmetric and conformationally rigid chiral ketones as catalysts for asymmetric epoxidation, a series of cyclic ketones 4-10 were prepared from the corresponding diacids. Compared with acyclic ketones for epoxidation of trans-stilbene, those 9-, 10-, and 11-membered-ring cyclic ketones were found to have much higher catalytic activities, which were attributed to steric effects, electronic effects, and ring strains. By using the homogeneous acetonitrile-water solvent system, unfunctionalized olefins with various substitution patterns (with 5 mol % of ketone 9) and strongly electron-deficient olefins (with a 1:1 ketone 9:substrate ratio) were epoxidized with Oxone as terminal oxidant in 75-96% yield at room temperature and neutral pH. In addition, oxidation of alcohols (with 20 mol % of ketone 9) was carried out successfully with good isolated yields of aldehydes or ketones (75-88%).

  DOI：

  10.1021/jo981659e

文献信息

• Novel Cyclic Ketones for Catalytic Oxidation Reactions
  作者：Dan Yang、Yiu-Chung Yip、Man-Wai Tang、Man-Kin Wong、Kung-Kai Cheung

  DOI：10.1021/jo981659e

  日期：1998.12.1

  In our effort to search for Ca symmetric and conformationally rigid chiral ketones as catalysts for asymmetric epoxidation, a series of cyclic ketones 4-10 were prepared from the corresponding diacids. Compared with acyclic ketones for epoxidation of trans-stilbene, those 9-, 10-, and 11-membered-ring cyclic ketones were found to have much higher catalytic activities, which were attributed to steric effects, electronic effects, and ring strains. By using the homogeneous acetonitrile-water solvent system, unfunctionalized olefins with various substitution patterns (with 5 mol % of ketone 9) and strongly electron-deficient olefins (with a 1:1 ketone 9:substrate ratio) were epoxidized with Oxone as terminal oxidant in 75-96% yield at room temperature and neutral pH. In addition, oxidation of alcohols (with 20 mol % of ketone 9) was carried out successfully with good isolated yields of aldehydes or ketones (75-88%).