(E)-5-butylidene-3,4-diethoxy-2(5H)-furanone

• 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: (E)-5-butylidene-3,4-diethoxy-2(5H)-furanone
• 化学式: C₁₂H₁₈O₄
• 分子量: 226.273
• InChiKey: AAPFSEPBFAHJOX-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.51
• 重原子数：
  16.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  4-n-butyl-2,3-diethoxy-4-hydroxy-2-cyclobuten-1-one 在 lead(IV) acetate 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以60%的产率得到5-acetoxy-5-butyl-3,4-diethoxy-2(5H)-furanone
  参考文献：
  名称：

  Oxidative Rearrangement of 4-Hydroxy-2-cyclobutenone. A New Route to Highly Substituted Furanones from Squaric Acid

  摘要：

  4-Hydroxy-2-cyclobutenones, which were obtained by the reaction of diethyl squarate with an organolithium, reacted with lead tetraacetate (to generate an oxy radical) affording 5-acetoxy-2(5H)-furanones and 5-alkylidene-2(5H)-furanones. This type of rearrangement was realized in a simple four-membered cyclic alpha-ketol but not in the corresponding five-membered ring.

  DOI：

  10.1021/jo00096a001

文献信息

• Oxidative Rearrangement of 4-Hydroxy-2-cyclobutenone. A New Route to Highly Substituted Furanones from Squaric Acid
  作者：Yoshihiko Yamamoto、Masatomi Ohno、Shoji Eguchi

  DOI：10.1021/jo00096a001

  日期：1994.8

  4-Hydroxy-2-cyclobutenones, which were obtained by the reaction of diethyl squarate with an organolithium, reacted with lead tetraacetate (to generate an oxy radical) affording 5-acetoxy-2(5H)-furanones and 5-alkylidene-2(5H)-furanones. This type of rearrangement was realized in a simple four-membered cyclic alpha-ketol but not in the corresponding five-membered ring.