3-Methyl-2-(1,3-butadienyl)furan | 52559-03-2

• 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: 3-Methyl-2-(1,3-butadienyl)furan
• 英文别名: 2-buta-1,3-dienyl-3-methylfuran
• CAS: 52559-03-2
• 化学式: C₉H₁₀O
• 分子量: 134.178
• InChiKey: ZJBYEBXMBBVOLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (Z)-6-Methoxymethoxy-3-methyl-oct-2-en-4-yne-1,8-diol 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以9%的产率得到3-Methyl-2-(1,3-butadienyl)furan
  参考文献：
  名称：

  Synthesis of the pseudopterane 2,5-furanocyclic ring system by [2,3] Wittig ring contraction of bridged furan and dihydrofuran propargylic ethers

  摘要：

  Two routes to the 2,5-furanocyclic ring system of the pseudopterane family of natural products are described. Both employ [2,3] Wittig ring contraction of a 15-membered allylic propargylic ether as the key step. The first route utilizes the bridged 2,5-dihydro furanocyclic ether 24 as the immediate precursor. Treatment with BuLi in THF-pentanes at -78 degrees C affords a 70:30 mixture of trans,anti and trans,syn diastereomers 29 and 31 in 68% yield. The acetate derivatives 30 and 32 are dehydrogenated to furan 33 by MnO2 in ether. In the second route, the furano bridged (Z)-allylic propargylic ether 40Z rearranges to furanocycle 41 in 73% yield upon treatment with LiTMP in; THF-pentane at -78 degrees C.

  DOI：

  10.1021/jo00081a009