4-(cyclohex-2-enylmethoxy)-3-methoxycarbonyl-5,5-dimethylfuran-2-(5H)-one | 1274896-74-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 4-(cyclohex-2-enylmethoxy)-3-methoxycarbonyl-5,5-dimethylfuran-2-(5H)-one
• 英文别名: methyl-4-(cyclohex-2-enylmethoxy)-5,5-dimethylfuran-2-(5H)-one-3-carboxylate；Methyl 4-(cyclohex-2-en-1-ylmethoxy)-5,5-dimethyl-2-oxofuran-3-carboxylate；methyl 4-(cyclohex-2-en-1-ylmethoxy)-5,5-dimethyl-2-oxofuran-3-carboxylate
• CAS: 1274896-74-0
• 化学式: C₁₅H₂₀O₅
• 分子量: 280.321
• InChiKey: VHAPXWIQRYEASE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(cyclohex-2-enylmethoxy)-3-methoxycarbonyl-5,5-dimethylfuran-2-(5H)-one 以 叔丁醇 为溶剂， 反应 0.5h， 以65%的产率得到3,3-dimethyl-6-methoxycarbonyl-2,8-oxaethano-4-oxatricyclo[5.4.0.0(2,6)]undecan-5-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：

  2-环己烯-1-甲醇 、 5,5-dimethyl-3-methoxycarbonyl tetronic acid 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90%的产率得到4-(cyclohex-2-enylmethoxy)-3-methoxycarbonyl-5,5-dimethylfuran-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

文献信息

• 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).