3-hydroxy-4,5(R)-dimethyl-2(5H)-furanone | 87068-70-0

• 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-4,5(R)-dimethyl-2(5H)-furanone
• 英文别名: (R)-(-)-Sotolon；4,5-Dimethyl-3-hydroxy-2,5-dihydro-2-furanone, (-)-；(2R)-4-hydroxy-2,3-dimethyl-2H-furan-5-one
• CAS: 87068-70-0
• 化学式: C₆H₈O₃
• 分子量: 128.128
• InChiKey: UNYNVICDCJHOPO-SCSAIBSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  3-hydroxy-4,5(R)-dimethyl-2(5H)-furanone 以 乙醇 为溶剂， 生成 葫芦巴内酯
  参考文献：
  名称：

  Distribution and Organoleptic Impact of Sotolon Enantiomers in Dry White Wines

  摘要：

  The enantiomers of sotolon, a flavor compound typical of oxidized white wines, were separated by preparative HPLC to determine their perception thresholds and distribution in wines. The enantiomeric ratios of chiral sotolon were evaluated in several dry white wines using gas chromatography and a chiral column (beta-cyclodextrin). connected to a 2 m precolumn (BP20). The perception threshold of (S)-sotolon (0.8 mu g/L) in model wine solution was 100 times lower than that of the (R) form (89 mu g/L), indicating that (S)-sotolon contributes to the characteristic aroma of prematurely aged dry white wines. Both enantiomers; are detected in white wines. Analysis of commercial dry white wines from various vintages and origins revealed three types of distribution patterns: the racemic form, an excess of R, and an excess of S. The proportions found in these wines may be partially explained by the slow racemization kinetics (20 months) of optically active sotolon.

  DOI：

  10.1021/jf072337r
• 作为产物：
  描述：

  2,3-dimethyl-4,5-dioxo-tetrahydro-furan-3-carboxylic acid ethyl ester 在 盐酸 、 jones' reagent 、 溶剂黄146 、 正丁醇 作用下， 以 环己烷 为溶剂， 反应 4.0h， 生成 3-hydroxy-4,5(R)-dimethyl-2(5H)-furanone
  参考文献：
  名称：

  Enzyme assisted synthesis of (S)-sotolon

  摘要：

  The preparation of enantiomerically enriched sotolon 1 has been studied starting from the racemic precursor 2. Yeast reduction of 2 is diastereoselective, giving access to the corresponding racemic alcohol 3 of anti relative configuration, the acetate of which is resolved into its enantiomers via a lipase catalyzed interesterification with n-butanol. Enantiomerically pure 4 affords (S)-1 of 0.75 ee.

  DOI：

  10.1016/s0040-4039(00)61164-4

文献信息

• A Vibrational Circular Dichroism Approach to the Determination of the Absolute Configurations of Flavorous 5-Substituted-2(5<i>H</i>)-furanones
  作者：Atsufumi Nakahashi、Yoshihiro Yaguchi、Nobuaki Miura、Makoto Emura、Kenji Monde

  DOI：10.1021/np1007763

  日期：2011.4.25

  (R)-(−)-1 and (S)-(+)-1 by adopting the vibrational circular dichroism (VCD) approach. The absolute configuration of 2, which has remained ambiguous since its discovery in 1957, was determined as (R)-(+)-2 and (S)-(−)-2 for the first time by the VCD technique. Surprisingly, the signs of the optical rotation of 2 are opposite of those of 1 regardless of their identical absolute configurations. This observation

  Sotolon（1）和枫木呋喃酮（2）是天然存在的手性呋喃酮。这些5-取代的2（5 H）-呋喃酮由于其特征的感官特性和极低的气味阈值而成为工业上重要的芳香化合物。通过制备对映选择性超临界流体色谱法成功获得了1和2的每个对映体。通过采用振动圆二色性（VCD）方法，将1的绝对构型确定为（R）-（-）- 1和（S）-（+）- 1。绝对配置2自1957年被发现以来，它一直是模棱两可的，通过VCD技术首次将其确定为（R）-（+）- 2和（S）-（-）- 2。出人意料的是，的旋光的符号2是相反的那些的1不论其相同绝对构型的。该观察结果基于对相似结构的旋光信号的比较，强调了绝对配置分配中的风险。2种对映异构体的气味评估显示出不同的气味强度。
• Okada, Katsuhide; Kobayashi, Akio; Mori, Kenji, Agricultural and Biological Chemistry, 1983, vol. 47, # 5, p. 1071 - 1074
  作者：Okada, Katsuhide、Kobayashi, Akio、Mori, Kenji

  DOI：——

  日期：——
• Funebrine, a structurally novel pyrrole alkaloid, and other .gamma.-hydroxyisoleucine-related metabolites of Quararibea funebris (Llave) Vischer (Bombacaceae)
  作者：Robert F. Raffauf、Thomas M. Zennie、Kay D. Onan、Philip W. Le Quesne

  DOI：10.1021/jo00189a013

  日期：1984.7
• Enzyme assisted synthesis of (S)-sotolon
  作者：Giovanni Fronza、Claudio Fuganti、Piero Grasselli、Giuseppe Pedrocchi-Fantoni、Stefano Servi

  DOI：10.1016/s0040-4039(00)61164-4

  日期：1992.9

  The preparation of enantiomerically enriched sotolon 1 has been studied starting from the racemic precursor 2. Yeast reduction of 2 is diastereoselective, giving access to the corresponding racemic alcohol 3 of anti relative configuration, the acetate of which is resolved into its enantiomers via a lipase catalyzed interesterification with n-butanol. Enantiomerically pure 4 affords (S)-1 of 0.75 ee.
• Distribution and Organoleptic Impact of Sotolon Enantiomers in Dry White Wines
  作者：Alexandre Pons、Valérie Lavigne、Yannick Landais、Philippe Darriet、Denis Dubourdieu

  DOI：10.1021/jf072337r

  日期：2008.3.1

  The enantiomers of sotolon, a flavor compound typical of oxidized white wines, were separated by preparative HPLC to determine their perception thresholds and distribution in wines. The enantiomeric ratios of chiral sotolon were evaluated in several dry white wines using gas chromatography and a chiral column (beta-cyclodextrin). connected to a 2 m precolumn (BP20). The perception threshold of (S)-sotolon (0.8 mu g/L) in model wine solution was 100 times lower than that of the (R) form (89 mu g/L), indicating that (S)-sotolon contributes to the characteristic aroma of prematurely aged dry white wines. Both enantiomers; are detected in white wines. Analysis of commercial dry white wines from various vintages and origins revealed three types of distribution patterns: the racemic form, an excess of R, and an excess of S. The proportions found in these wines may be partially explained by the slow racemization kinetics (20 months) of optically active sotolon.