3,4-二羟基-5-甲基-2-呋喃酮 | 3566-57-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 中文名称: 3,4-二羟基-5-甲基-2-呋喃酮
• 中文别名: 3,4-二羟基-5-甲基呋喃-2(5H)-酮
• 英文名称: 3,4-Dihydroxy-5-methyl-5H-furan-2-one
• 英文别名: 3,4-dihydroxy-5-methylfuran-2-on；3,4-dihydroxy-5-methyl-5H-furan-2-one；3,4-Dihydroxy-5-methyl-5H-furan-2-on；3,4-dihydroxy-5-methyl-2(5H)-furanone；γ-Methyl-α-hydroxy-tetronsaeure；3,4-Dihydroxy-5-methylfuran-2(5H)-one；3,4-dihydroxy-2-methyl-2H-furan-5-one
• CAS: 3566-57-2
• 化学式: C₅H₆O₄
• 分子量: 130.1
• InChiKey: ASEPVSZWYGTTAB-UHFFFAOYSA-N

物化性质

• 沸点：
  330.5±42.0 °C(Predicted)
• 密度：
  1.636±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  9
• 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：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2932209090

反应信息

• 作为反应物：
  描述：

  3,4-二羟基-5-甲基-2-呋喃酮 在 甲烷 氧气 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 24.0h， 生成 2-(2-aminophenylcarbamoyl)-3-(1-hydroxyethyl)quinoxaline
  参考文献：
  名称：

  Condensation of o-phenylenediamine with dehydro-l-ascorbic acid derivatives and analogs

  摘要：

  DOI：

  10.1016/0008-6215(85)85233-2
• 作为产物：
  描述：

  benzyl O^α-benzoylglycolate 在 D,L-α-Benzoyloxy-propionsaeure-aethylester 、 氢化钾 、 苯 作用下， 生成 3,4-二羟基-5-甲基-2-呋喃酮
  参考文献：
  名称：

  Micheel; Haarhoff, Justus Liebigs Annalen der Chemie, 1940, vol. 545, p. 28,32

  摘要：

  DOI：

文献信息

• Reaction of Superoxide with Ascorbic Acid Derivatives: Insight into the Superoxide-Mediated Oxidation of Dehydroascorbic Acid
  作者：Aryeh A. Frimer、Pessia Gilinsky-Sharon

  DOI：10.1021/jo00114a031

  日期：1995.5

  In order to gain greater insight into the mechanism of superoxide-mediated oxidation of ascorbic acid (1) in aprotic media, we reacted O-2(.-) (generated from KO2/18-crown-6 in toluene) with vitamin C derivatives 13a and 14a and the corresponding mono- and dimethoxy analogs 13b and 13c, respectively. Dihydroxyfuranones 13a and 14a underwent oxidative cleavage with O-2(.-) yielding, upon methyl iodide workup, the corresponding keto ester (15 or 17, respectively) and threonic acid analog (16 or 18, respectively). On the other hand, mono- and dimethoxy analogs 13b and 13c each react with superoxide to give a single isolable product, oxyester 16 and alkylidenefuranone 20, respectively. Finally, 13a reacts with tert-butoxide, again yielding 16 as the major product. The data are best resolved by suggesting that ascorbic acid analogs 13a and 14a (and presumably ascorbic acid as well) are oxidized by O-2(.-) to the corresponding triketone 21 which reacts in turn by attack at the highly electrophilic central carbonyl C-2. Cyclization of the resulting 2-peroxy 1,3-diketone 22 into the C-1 carbonyl, followed by oxidative cleavage, saponification, and methylation, yields the observed products. By contrast, O-2(.-) oxidation of 13b and tert-butoxide oxidation of 13a yield 3-peroxy-1,2-diketone 29 which cyclizes into the C-1 carbonyl ultimately yielding 16. Finally, 13c, which lacks enolic hydrogens, undergoes abstraction of the gamma-hydrogen followed by the elimination of acetone, yielding 20. Similarly, 5,6-dihydropyrone 33 undergoes superoxide-mediated elimination yielding dienone 34. The data presented herein are consistent with the mechanism suggested by Sawyer et al. (J. Am. Chem. Sec. 1982, 104, 6273-6278) for the superoxide-mediated oxidation of dehydroascorbic acid (2)-with the modification that the position of initial O-2(.-) attack is at the C-2 (rather than the C-3) carbonyl.
• Hasselquist, Arkiv foer Kemi, 1955, vol. 8, p. 381,386
  作者：Hasselquist

  DOI：——

  日期：——
• v. Euler; Hasselquist, Arkiv foer Kemi, 1955, vol. 8, p. 67,71
  作者：v. Euler、Hasselquist

  DOI：——

  日期：——
• Kamiya, Nippon Nogeikagaku Kaishi, 1959, vol. 33, p. 402
  作者：Kamiya

  DOI：——

  日期：——
• Micheel; Haarhoff, Justus Liebigs Annalen der Chemie, 1940, vol. 545, p. 28,32
  作者：Micheel、Haarhoff

  DOI：——

  日期：——