3-hydroxy-4-methyl-2(5H)-furanone | 22438-62-6

• 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: 3-hydroxy-4-methyl-2(5H)-furanone
• 英文别名: 3-Hydroxy-4-methylfuran-2(5H)-one；4-hydroxy-3-methyl-2H-furan-5-one
• CAS: 22438-62-6
• 化学式: C₅H₆O₃
• mdl: MFCD15145816
• 分子量: 114.101
• InChiKey: WXXOVRUZZHZUNY-UHFFFAOYSA-N

物化性质

• 沸点：
  331.1±42.0 °C(Predicted)
• 密度：
  1.382±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 3-hydroxy-4-methyl-2(5H)-furanone 以 乙醚 为溶剂， 生成 3-Methoxy-4-methyl-furan-2(5H)-on
  参考文献：
  名称：

  The fragmentation of isotetronic acidO-methyl ethers under electron impact

  摘要：

  AbstractThe mass spectra of a series of methyl ethers of isotetronic acids have been examined and the modes of fragmentation rationalized on the basis of two general schemes.

  DOI：

  10.1002/oms.1210160204
• 作为产物：
  描述：

  α-Keto-β-methyl-β-allyloxycarbonyl-γ-butyrolactone 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 三苯基膦 甲酸铵 作用下， 以 四氢呋喃 为溶剂， 以88%的产率得到3-hydroxy-4-methyl-2(5H)-furanone
  参考文献：
  名称：

  α-羟基丁烯内酯和α-酮-β-烯丙基-γ-丁内酯的简便合成

  摘要：

  在钯催化剂存在下，α-酮基-β-烷基-β-烯丙氧基羰基-γ-丁内酯与甲酸铵反应以良好的收率得到α-羟基丁烯内酯。当反应在没有甲酸铵的情况下进行时，发生脱羧-烯丙基化，得到 α-羟基丁烯内酯的烯丙醇醚，通过热克莱森重排将其转化为 α-酮基-β-烯丙基-γ-丁内酯。

  DOI：

  10.1246/cl.1991.1349

文献信息

• 一种3-羟基-4-甲基-2（5氢）-呋喃酮的制备方 法
  申请人：郑州轻工业学院

  公开号：CN105669612B

  公开（公告）日：2017-09-01

  本发明涉及一种3‑羟基‑4‑甲基‑2（5氢）‑呋喃酮的简便制备方法，其将木糖和赖氨酸与水混合后，在60－100℃加热反应0.5－4h，反应结束后用乙酸乙酯萃取反应液，有机相经纯化得到3‑羟基‑4‑甲基‑2（5氢）‑呋喃酮。本发明方法中以安全且廉价易得的木糖和赖氨酸为原料，大大节约了成本；不需要额外添加催化剂，且合成步骤简便，仅经过一步反应即得到目标产品3‑羟基‑4‑甲基‑2（5氢）‑呋喃酮，避免了现有技术的不足，为3‑羟基‑4‑甲基‑2（5氢）‑呋喃酮的制备提供了一条新的途径。
• Systematic Studies on Structure and Physiological Activity of Cyclic α-Keto Enamines, a Novel Class of “Cooling” Compounds
  作者：Harald Ottinger、Tomislav Soldo、Thomas Hofmann

  DOI：10.1021/jf010857v

  日期：2001.11.1

  3-methyl- and 5-methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one were recently identified as intense cooling compounds in roasted dark malt. To gain more insights into the molecular requirements of these compounds for imparting a cooling sensation, 26 cyclic alpha -keto enamine derivatives were synthesized, and their physiological cooling activities were evaluated. Any modification of the amino moiety, the carbocyclic ring size, or incorporation of additional methyl groups led to a significant increase of the cooling threshold. Insertion of an oxygen atom into the 2-cyclopenten-1-one ring, however, increased the cooling activity, e.g., the cooling threshold of the 5-methyl-4-(1-pyrrolidinyl)3(2H)-furanone was found to be 16-fold below the threshold concentration determined for the 3-methyl-2-(1-pyrrolidinyl)-2-cyclopenten-1-one. Shifting the oxygen atom from the 4- into the 5-position of the cyclopentenone ring resulted in a even more drastic increase in cooling activity, e.g., the 4-methyl-3-(1-pyrrolidinyl)-2(5H)-furanone exhibited the strongest cooling effect at the low oral threshold concentration of 0.02-0.06 mmol/L, which is 35-fold below the value determined for H-menthol. In contrast to the minty smelling (-)-menthol, most of the alpha -keto enamines were found to be virtually odorless but impart a sensation of "cooling" to the oral cavity as well as to the skin, thus illustrating that there is no physiological link between cooling activity and mint-like odors.