5-Methyl-2-(but-1-enyl)furan | 14313-21-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 5-Methyl-2-(but-1-enyl)furan
• 英文别名: 1-<5-Methyl-<2>furyl>-but-1-en；2-But-1-enyl-5-methylfuran
• CAS: 14313-21-4
• 化学式: C₉H₁₂O
• 分子量: 136.194
• InChiKey: QVVFSGWAESJAFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-Methyl-2-(but-1-enyl)furan 在 甲基磺酰胺 、 AD-mix-β 、 水 作用下， 以 叔丁醇 为溶剂， 反应 12.0h， 以70%的产率得到1-(5-Methyl-furan-2-yl)-butane-1,2-diol
  参考文献：
  名称：

  An expedient preparation of chiral building blocks having levoglucosenone chromophore: a new enanticontrolled route to (–)-β-multistriatin and (+)-exo-brevicomin

  摘要：

  2-Alkenylfurans are transformed enantioselectively into the bicyclic enones having the levoglucosenone chromophore, whose synthetic utility is demonstrated by a stereocontrolled synthesis of two insect pheromones (-)-beta-multistriatin and (+)-exo-brevicomin.

  DOI：

  10.1039/cc9960001477
• 作为产物：
  描述：

  5-甲基呋喃醛 以76%的产率得到5-Methyl-2-(but-1-enyl)furan
  参考文献：
  名称：

  An expedient preparation of chiral building blocks having levoglucosenone chromophore: a new enanticontrolled route to (–)-β-multistriatin and (+)-exo-brevicomin

  摘要：

  2-Alkenylfurans are transformed enantioselectively into the bicyclic enones having the levoglucosenone chromophore, whose synthetic utility is demonstrated by a stereocontrolled synthesis of two insect pheromones (-)-beta-multistriatin and (+)-exo-brevicomin.

  DOI：

  10.1039/cc9960001477

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.