6-hydroxy-2,2,6-trimethyl-2,3-dihydro-6H-pyran-3-one | 154840-00-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 6-hydroxy-2,2,6-trimethyl-2,3-dihydro-6H-pyran-3-one
• 英文别名: 2,2,6-trimethyl-6-hydroxy-(2H)-pyran-3(6H)-one；6-Hydroxy-2,2,6-trimethyl-2H-pyran-3(6H)-one；6-hydroxy-2,2,6-trimethylpyran-3-one
• CAS: 154840-00-3
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: NFLUURBUYXJHRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  6-hydroxy-2,2,6-trimethyl-2,3-dihydro-6H-pyran-3-one 在 盐酸 、 sodium hydroxide 、 双氧水 、 二异丁基氢化铝 作用下， 以 甲醇 为溶剂， 反应 4.5h， 生成 (1R,2R,6R)-2-methoxy-2,4,4-trimethyl-3,7-dioxabicyclo[4.1.0]heptan-5-ol
  参考文献：
  名称：

  硬化菌素A原始结构类似物的合成方法。

  摘要：

  描述了硬化菌素A的原始结构的类似物的途径。将双脱氧核糖基腈10a，b的β-端基异构体（由谷氨酸制备）转化为甲基酮11。在乙醚/三甲胺中将甲硅烷基化的乙炔化物加到11上，主要得到22a。用甲基烯丙基卤化物烷基化并进行臭氧分解，得到酮24，然后通过氢化和第二次臭氧分解将其转化为酮醛26。两步的醇醛缩醛工艺以良好的总产率提供了所需的3-吡喃酮27。然而，几种将该烯酮27转化为所需的菌藻素类似物2的方法失败了。

  DOI：

  10.1021/jo016246j
• 作为产物：
  描述：

  2-(1'-hydroxy-1'-methylethyl)-5-methylfuran 在 氧气 作用下， 以 水 为溶剂， 反应 0.5h， 以74%的产率得到6-hydroxy-2,2,6-trimethyl-2,3-dihydro-6H-pyran-3-one
  参考文献：
  名称：

  Using water, light, air and spirulina to access a wide variety of polyoxygenated compounds

  摘要：

  本文介绍了一套全新的绿色方法，利用空气、光、水和螺旋藻将易获得的呋喃底物转化为在天然产物中常见的多种合成上有用的多氧官能团结构单元。

  DOI：

  10.1039/c2gc16397g

文献信息

• The first enzymatic Achmatowicz reaction: selective laccase-catalyzed synthesis of 6-hydroxy-(2H)-pyran-3(6H)-ones and (2H)-pyran-2,5(6H)-diones
  作者：Chimène Asta、Dietmar Schmidt、Jürgen Conrad、Bernhard Förster-Fromme、Till Tolasch、Uwe Beifuss

  DOI：10.1039/c3ra44107e

  日期：——

  laccase-catalyzed oxidation of (5-alkylfuran-2-yl)carbinols using aerial oxygen as an oxidant selectively affords 6-hydroxy-(2H)-pyran-3(6H)-ones with yields up to 90%. With suitable substituted furan-2-yl carbinols as substrates the procedure allows the efficient preparation of (2H)-pyran-2,5(6H)-diones in a single step.

  使用空气中的氧气作为氧化剂的漆酶催化的（5-烷基呋喃-2-基）甲醇的氧化选择性生成6-羟基-（2 H）-吡喃-3（6 H）-一，收率高达90％。以合适的取代的呋喃-2-基甲醇为底物，该方法允许在一个步骤中高效制备（2 H）-吡喃-2,5（6 H）-二酮。
• The intramolecular enyne diels-alder reaction. Stereoselective construction of tricyclic dioxadienones and mechanistic outline
  作者：H.M.R. Hoffmann、D. Krumwiede、B. Mucha、H.H. Oehlerking、G.W. Prahst

  DOI：10.1016/s0040-4020(01)91218-9

  日期：1993.1

  4-Methylpent-4-en-2-yn-1-ols and 6-hydroxy-2,3-dihydro-6H pyran 3-ones are condensed in different ways to a series of tricyclic dioxadienones which contain the basic framework of the cadlinolides. A mechanism of the intramolecular enyne-ene cycloisomerization and the origin of the resulting type I and type II dienes is proposed.
• New procedures for the enantioselective oxidation of sulfides under stoichiometric and catalytic conditions
  作者：Antonio Massa、Francesca R Siniscalchi、Valeria Bugatti、Alessandra Lattanzi、Arrigo Scettri

  DOI：10.1016/s0957-4166(02)00326-9

  日期：2002.7

  Acid-catalyzed oxidation of 2-furylcarbinols with hydrogen peroxide affords alternatively 2-(1-hydroperoxyalkyl)furans 2 or 6-hydroperoxy-2H-pyran-3(6H)-ones 3. Compounds of the type 2 and 3 have been used Lis oxygen donors in efficient stoichiometric or catalytic procedures for the asymmetric sulfoxidation of prochiral sulfides in the presence of Ti(O-i-Pr)(4)/L-DET or Ti(O-i-Pr)(4)/(R)-BINOL/H2O systems. Positive non linear effects, (+)-NLE, were observed in the enantioselective oxidation of methyl p-tolyl sulfide, promoted by enantiomierically enriched Ti(IV)/BINOL/H2O complexes. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Scope and Limitations of the Photooxidations of 2-(α-Hydroxyalkyl)furans: Synthesis of 2-Hydroxy-<i>exo</i>-brevicomin
  作者：Dimitris Noutsias、Antonia Kouridaki、Georgios Vassilikogiannakis

  DOI：10.1021/ol200027f

  日期：2011.3.4

  Photooxygenation of 2-(alpha-hydroxyalkyl)furans at 5 degrees C in MeOH followed by in situ reduction affords, in one synthetic operation, 6-hydroxy-3(2H)-pyranones and/or 5-hydroxy-2(5H)-furanones. The relative ratio of the final products is highly dependent on the substitution of the starting furan substrate. Photooxygenation of 2-(alpha,beta-dihydroxyalkyl)furans followed by in situ reduction and ketalization with acid rapidly provides the 6,8-dioxabicyclo[3.2.1]oct-3-en-2-one framework. This new methodology was successfully applied to the synthesis of 2-hydroxy-exo-brevicomin.