2,3,6-trihydroxy-4-oxo-2-hexen-5-olide | 132030-82-1

• 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: 2,3,6-trihydroxy-4-oxo-2-hexen-5-olide
• CAS: 132030-82-1
• 化学式: C₆H₅O₆*Na
• 分子量: 196.092
• InChiKey: GZRSNEHWDWJVLD-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -5.39
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  106.89
• 氢给体数：
  2.0
• 氢受体数：
  6.0

文献信息

• Preparation and Characterization of a 345 nm Absorbing Reductant Derived from Dehydro-L-Ascorbic Acid
  作者：Hidehiko Tanaka、Eiji Kimoto

  DOI：10.1246/bcsj.63.2569

  日期：1990.9

  The addition of sodium hydroxide to an ethanolic dehydro-l-ascorbic acid solution produced a yellowish precipitate which was enriched by a reductant possessing absorption maxima at 345 and 225 nm. This reductant was purified by DEAE-Sepharose column chromatography and Cellulofine-gel chromatography; on the basis of physicochemical analyses it was deduced to be the 2,3-enediol form of 2,3-diketo-l-gulono-δ-lactone (2,3,6-trihydroxy-4-oxo-2-hexen-5-olide). The process, derived from dehydro-l-ascorbic acid, involved a hydrolytic cleavage of a 5-membered γ-lactone ring, conversion to the 2,3-enediol form and rearrangement to 6-membered δ-lactone. The marked bathochromic shift of the absorption maximum of this reductant from that of ascorbic acid (265 nm) could be due to an extended conjugation among the enediol group and two carbonyl groups on both sides.

  将氢氧化钠加入乙醇脱氢抗坏血酸溶液中，生成了一种黄色沉淀物，该沉淀物经具有345和225 nm吸收峰的还原剂富集。该还原剂通过DEAE-Sepharose柱色谱和Cellulofine-gel色谱法纯化；基于物理化学分析，推断其为2,3-二酮-L-古洛糖酸-δ-内酯的2,3-烯二醇形式（2,3,6-三羟基-4-氧代-2-己烯-5-内酯）。该过程源自脱氢抗坏血酸，涉及一个五元γ-内酯环的水解断裂，转化为2,3-烯二醇形式，并重排为六元δ-内酯。该还原剂的最大吸收峰与抗坏血酸（265 nm）相比显著红移，可能是由于烯二醇基团与两侧的两个羰基之间的共轭延伸所致。
• Detection of oxidation radicals of 2,3-enediol form of 2,3-dioxoguluno-δ-lactone by pulse radiolysis
  作者：Kunihiko Nakata、Hideo Horii、Naofumi Morita

  DOI：10.1039/c39930001172

  日期：——

  The OH adduct radicals of the 2,3-enediol form of 2,3-dioxoguluno-δ-lactone (2,3-End.DKGL) have been observed in aqueous solution by puise radiolysis (the adduct radicals were converted into the one-electron oxidation radical in alkaline solutions by dehydration); the oxidation radical has also been produced by oxidation of 2,3-End.DKGL by the azide radical (N3˙).

  通过脉冲辐解技术，在水中观察到了2,3-二氧古洛糖酸δ-内酯（2,3-End.DKGL）的2,3-烯二醇形式的OH加合物自由基（在碱性溶液中，这些加合物自由基通过脱水转化为单电子氧化自由基）；此外，叠氮自由基（N3·）也能将2,3-End.DKGL氧化生成该氧化自由基。