3,5,5-trimethyltetronic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 3,5,5-trimethyltetronic acid
• 英文别名: 3,5,5-trimethyl-furan-2,4-dione；3,5,5-Trimethyl-furan-2,4-dion；3,5,5-trimethyloxolane-2,4-dione
• 化学式: C₇H₁₀O₃
• 分子量: 142.155
• InChiKey: PWMYMYHXXBGTSG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.53
• 重原子数：
  10.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3,5,5-trimethyltetronic acid 、 2-环己烯-1-甲醇 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以75%的产率得到4-(cyclohex-2-enylmethoxy)-3,5,5-trimethylfuran-2-(5H)-one
  参考文献：
  名称：

  A Photocycloaddition/Fragmentation Approach toward the 3,12-Dioxatricyclo[8.2.1.0^6,13]tridecane Skeleton of Terpenoid Natural Products

  摘要：

  Starting from tetronate 1 (R = CH2OH), a short photochemical access to the 3,12-dioxatricyclo[8.2.1.0(6,13)]tridecane-skeleton 2 of briarellin and asbestinin diterpenes has been explored. In the course of these studies, a number of surprising observations were made. For example, a two-step reaction pathway to the bicyclic ketolactone 3 was discovered, which is based on tetronate 1 (R = COOMe).

  DOI：

  10.1021/ol2004462
• 作为产物：
  描述：

  4-bromo-2,4-dimethyl-3-oxo-valeric acid ethyl ester 在 barium dihydroxide 、 水 作用下， 生成 3,5,5-trimethyltetronic acid
  参考文献：
  名称：

  THE OXIDATION OF TETRONIC ACIDS. I. STRUCTURAL CRITERIA FOR THE FORMATION OF 1,2-DIKETONES

  摘要：

  DOI：

  10.1021/jo01149a021

文献信息

• THE OXIDATION OF TETRONIC ACIDS. I. STRUCTURAL CRITERIA FOR THE FORMATION OF 1,2-DIKETONES
  作者：EVANS B. REID、ROBERT B. FORTENBAUGH、HELEN R. PATTERSON

  DOI：10.1021/jo01149a021

  日期：1950.5
• A Photocycloaddition/Fragmentation Approach toward the 3,12-Dioxatricyclo[8.2.1.0^6,13]tridecane Skeleton of Terpenoid Natural Products
  作者：Jörg P. Hehn、Eberhardt Herdtweck、Thorsten Bach

  DOI：10.1021/ol2004462

  日期：2011.4.1

  Starting from tetronate 1 (R = CH2OH), a short photochemical access to the 3,12-dioxatricyclo[8.2.1.0(6,13)]tridecane-skeleton 2 of briarellin and asbestinin diterpenes has been explored. In the course of these studies, a number of surprising observations were made. For example, a two-step reaction pathway to the bicyclic ketolactone 3 was discovered, which is based on tetronate 1 (R = COOMe).