(+)-didehydro-5,6-O-isopropylidene-L-ascorbic acid | 64344-03-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+)-didehydro-5,6-O-isopropylidene-L-ascorbic acid
• 英文别名: 5,6-isopropylidene-L-dehydroascorbic acid；(5R)-5-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]oxolane-2,3,4-trione
• CAS: 64344-03-2；63247-03-0
• 化学式: C₉H₁₀O₆
• 分子量: 214.175
• InChiKey: XTXAVJYXLXJPPA-MHTLYPKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+)-didehydro-5,6-O-isopropylidene-L-ascorbic acid 在 iron(III) sulfate 、 水 作用下， 生成 草酸 、 (2R)-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl](hydroxy)ethanoic acid
  参考文献：
  名称：

  的C铁介导的裂解？水中三羰基化合物中的C键

  摘要：

  一种三邻位三羰基化合物经历C： Ç裂解通过三价铁离子（参见方案）介导的。观察到的茚三酮和脱氢抗坏血酸的裂解与氨基酸检测和维生素C的代谢有关。

  DOI：

  10.1002/anie.200806296
• 作为产物：
  描述：

  5,6-O-Isopropyliden-2,3-O-bis(trimethylsilyl)-L-ascorbicsaeure 在 磺酰氯 作用下， 以 乙腈 为溶剂， 生成 (+)-didehydro-5,6-O-isopropylidene-L-ascorbic acid
  参考文献：
  名称：

  Chemie freier cyclischer vicinaler Tricarbonyl-Verbindungen (‘1,2,3-Trione') Teil 2. Redox-Reaktionen von 1,2,3-Trionen mit En-1,2-diolen (‘Reduktonen'), 2-Alkoxy-en-1-olen, En-1,2-diaminen und verwandten Spezies Für Teil 1, s. [1].

  摘要：

  Chemistry of Free Cyclic Vicinal Tricarbonyl Compounds ('1,2,3-Triones'). Part 2. Redox Reactions of 1,2,3-Triones with Ene-1,2-diols ('Reductones'), 2-Alkoxy-en-1-ols, Ene-1,2-diamines, and Related SpeciesMidstanding carbonyl groups of cyclic 1,2,3-triones 4 possess outstanding electrophilic (elcctron-pair accepting) as well as oxidizing (one-electron accepting) properties. Their reactions with selected electron-rich C C bonds as efficient nucleophiles (AN reactions) and as efficient reducing agents (SET (single electron transfer) reactions) are studied. In a few cases, short-lived charge-transfer colors could be observed. Particularly, free didehydro-5,6-0-isopropyliden-L-ascorbic acid (4g), its 0,C-adduct 8g to 5,6-O-isopropylidene-(L)-ascorbic acid (1g), and - via an independent pathway - the ostensible C,C-dimer 10a of mono-dehydrodimedone reductone were prepared. Intermediate radical anions 4- can be considered to be ideal representatives of dicapto-dative radicals. Novel large-scale syntheses of 3,4-dihydroxyfuran-2(5H)-one (1e) and of its vicinal trione 4e are presented.

  DOI：

  10.1002/1522-2675(200205)85:5<1295::aid-hlca1295>3.0.co;2-k

文献信息

• Condensation of o-phenylenediamine with dehydro-l-ascorbic acid derivatives and analogs
  作者：Yuji Tsujimoto、Mitsuaki Ohmori、Masanosuke Takagi

  DOI：10.1016/0008-6215(85)85233-2

  日期：1985.4
• Chemie freier cyclischer vicinaler Tricarbonyl-Verbindungen (‘1,2,3-Trione') Teil 2. Redox-Reaktionen von 1,2,3-Trionen mit En-1,2-diolen (‘Reduktonen'), 2-Alkoxy-en-1-olen, En-1,2-diaminen und verwandten Spezies Für Teil 1, s. [1].
  作者：Kurt Schank、Günter Bouillon、Michael Fünfrocken、Carlo Lick、Robert Lieder

  DOI：10.1002/1522-2675(200205)85:5<1295::aid-hlca1295>3.0.co;2-k

  日期：2002.5

  Chemistry of Free Cyclic Vicinal Tricarbonyl Compounds (‘1,2,3-Triones'). Part 2. Redox Reactions of 1,2,3-Triones with Ene-1,2-diols (‘Reductones'), 2-Alkoxy-en-1-ols, Ene-1,2-diamines, and Related Species. Midstanding carbonyl groups of cyclic 1,2,3-triones 4 possess outstanding electrophilic (electron-pair accepting) as well as oxidizing (one-electron accepting) properties. Their reactions with
• Iron-Mediated Cleavage of CC Bonds in Vicinal Tricarbonyl Compounds in Water
  作者：Jasmin Mecinović、Refaat B. Hamed、Christopher J. Schofield

  DOI：10.1002/anie.200806296

  日期：2009.3.30

  Three of a kind: Vicinal tricarbonyl compounds undergo CC cleavage mediated by ferric ions (see scheme). The observed cleavage of ninhydrin and dehydroascorbic acid has relevance for amino acid detection and the metabolism of vitamin C.

  一种三邻位三羰基化合物经历C： Ç裂解通过三价铁离子（参见方案）介导的。观察到的茚三酮和脱氢抗坏血酸的裂解与氨基酸检测和维生素C的代谢有关。