methyl (1S,5R,7S)-5-methyl-2-oxo-6,8-dioxabicyclo[3.2.1]oct-3-ene-7-carboxylate | 1266556-03-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: methyl (1S,5R,7S)-5-methyl-2-oxo-6,8-dioxabicyclo[3.2.1]oct-3-ene-7-carboxylate
• CAS: 1266556-03-9
• 化学式: C₉H₁₀O₅
• 分子量: 198.175
• InChiKey: YOHLKXNMZZKPNC-BKPPORCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  methyl 3-(5-methyl-2-furyl)acrylate 在 甲基磺酰胺 、 AD-mix-β 、 氧气 、 rose bengal 作用下， 以 甲醇 、 水 、 叔丁醇 为溶剂， 反应 18.0h， 生成 methyl (1S,5R,7S)-5-methyl-2-oxo-6,8-dioxabicyclo[3.2.1]oct-3-ene-7-carboxylate
  参考文献：
  名称：

  Scope and Limitations of the Photooxidations of 2-(α-Hydroxyalkyl)furans: Synthesis of 2-Hydroxy-exo-brevicomin

  摘要：

  Photooxygenation of 2-(alpha-hydroxyalkyl)furans at 5 degrees C in MeOH followed by in situ reduction affords, in one synthetic operation, 6-hydroxy-3(2H)-pyranones and/or 5-hydroxy-2(5H)-furanones. The relative ratio of the final products is highly dependent on the substitution of the starting furan substrate. Photooxygenation of 2-(alpha,beta-dihydroxyalkyl)furans followed by in situ reduction and ketalization with acid rapidly provides the 6,8-dioxabicyclo[3.2.1]oct-3-en-2-one framework. This new methodology was successfully applied to the synthesis of 2-hydroxy-exo-brevicomin.

  DOI：

  10.1021/ol200027f

文献信息

• Scope and Limitations of the Photooxidations of 2-(α-Hydroxyalkyl)furans: Synthesis of 2-Hydroxy-<i>exo</i>-brevicomin
  作者：Dimitris Noutsias、Antonia Kouridaki、Georgios Vassilikogiannakis

  DOI：10.1021/ol200027f

  日期：2011.3.4

  Photooxygenation of 2-(alpha-hydroxyalkyl)furans at 5 degrees C in MeOH followed by in situ reduction affords, in one synthetic operation, 6-hydroxy-3(2H)-pyranones and/or 5-hydroxy-2(5H)-furanones. The relative ratio of the final products is highly dependent on the substitution of the starting furan substrate. Photooxygenation of 2-(alpha,beta-dihydroxyalkyl)furans followed by in situ reduction and ketalization with acid rapidly provides the 6,8-dioxabicyclo[3.2.1]oct-3-en-2-one framework. This new methodology was successfully applied to the synthesis of 2-hydroxy-exo-brevicomin.