5-acetoxy-3,4-diethoxy-5-phenyl-2(5H)-furanone

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-acetoxy-3,4-diethoxy-5-phenyl-2(5H)-furanone
• 英文别名: (3,4-Diethoxy-5-oxo-2-phenylfuran-2-yl) acetate
• 化学式: C₁₆H₁₈O₆
• 分子量: 306.315
• InChiKey: IFGHTYQHQNIEPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-acetoxy-3,4-diethoxy-5-phenyl-2(5H)-furanone 在 水 、 溶剂黄146 作用下， 生成 3,4-diethoxy-5-hydroxy-5-phenylfuran-2(5H)-one
  参考文献：
  名称：

  使用方酸衍生物的 Mn(III) 基氧化自由基扩环反应：双（丁烯内酯）和乙酸酯单体的选择性合成

  摘要：

  DOI：

  10.3987/com-18-s(f)62
• 作为产物：
  描述：

  方酸二乙酯 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.0h， 生成 5-acetoxy-3,4-diethoxy-5-phenyl-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

• Radical-mediated ring enlargement of cyclobutenones: new synthetic potential of squaric acid.
  作者：Yoshihiko Yamamoto、Masatomi Ohno、Shoji Eguchi

  DOI：10.1021/ja00143a006

  日期：1995.9

  4-Hydroxy-2-cyclobutenones, which are readily obtainable from diethyl squarate, reacted with lead tetraacetate to give 5-acetoxy-2(5H)-furanones and 5-alkylidene-2(5H)-furanones via oxy-radical-triggered ring opening (beta-scission) and subsequent 5-endo reclosure. This method was extended to saturated four-membered alpha-ketol and applied to the synthesis of a natural product (Z-isomer of multicolanate). A carbon-centered radical-triggered reaction was also performed in which photolysis of a mixed anhydride of thiohydroxamic acid and (4-oxo-2-cyclobutenyl)acetic acid afforded a 4-cyclopentene-1,3-dione rather than the furanone as a rearranged product. The similarity of these rearrangements is discussed using a PM3 calculation in terms of pentadienoyl radical to cyclopentenone radical cyclization and its oxa version.
• PhI(OAc)₂-Promoted Rearrangement of the Hydroxyl Group:  Ring Expansion of 4-Hydroxy-2-cyclobutenone to 2(5<i>H</i>)-Furanone in Comparison with Ring Cleavage of the α-Hydroxycycloalkanone to the ω-Formyl Ester
  作者：Masatomi Ohno、Isamu Oguri、Shoji Eguchi

  DOI：10.1021/jo990704v

  日期：1999.12.1

  Reaction of 4-hydroxy-2-cyclobutenones with PhI(OAc)(2) in 1,2-dichloroethane at reflux temperature gave rise to 5-acetoxy-2(5H)-furanones as a rearranged product, formation of which is explained by ring cleavage of the once formed hypervalent iodine intermediate and following recyclization of the resulting acyl cation with a carbonyl oxygen. Likewise, 5-methoxy-2(5H)-furanones were obtained in better yields by using methanol as both a solvent and a nucleophile. Extension of this reaction to simple 2-hydroxycycloalkanones resulted in ring cleavage to methyl omega-formylalkanoates under milder conditions. In this case, the mechanism is explained by known glycol cleavage with PhI(OAc)(2).
• Mn(III)-Based Oxidative Radical Ring-Expansion Reaction Using Squarate Derivatives: Selective Synthesis of Bis(butenolide)s and the Acetate Monomers
  作者：Hiroshi Nishino、Jun-ichi Sasaki、Makoto Kobayashi、Yûsuke Ibe

  DOI：10.3987/com-18-s(f)62

  日期：——
• 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.