(2R,4R)-2-methyl-4-pentyl-1,3-dioxane | 193292-87-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: (2R,4R)-2-methyl-4-pentyl-1,3-dioxane
• 英文别名: (2R,4R)-2-Methyl-4-pentyl-1,3-dioxane
• CAS: 193292-87-4
• 化学式: C₁₀H₂₀O₂
• 分子量: 172.268
• InChiKey: NZTUUEJEMACERX-NXEZZACHSA-N

物化性质

• 沸点：
  206.9±8.0 °C(Predicted)
• 密度：
  0.880±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,4R)-2-methyl-4-pentyl-1,3-dioxane 生成 (2S,4S)-2-methyl-4-pentyl-1,3-dioxane
  参考文献：
  名称：

  Absolute Configuration and Conformation of 1,3-Dioxanes from Cider

  摘要：

  In extracts obtained by Liquid-liquid extraction from French cider (2S,4R)-and (2R,4R)-2-methyl-4-pentyl-1,3-dioxane, 1a and 1b as well as (2S,4R)-and (2R,4R)-2-methyl-4-(2'(Z)-pentenyl)-1,3-dioxane, 2a and 2b, were identified by capillary gas chromatography (HRGC) and capillary gas chromatography-mass spectrometry (HRGC-MS). Absolute configuration and conformation of the 1,3-dioxanes was determined by nuclear magnetic resonance (NMR) spectrometry techniques [C-13, H-1, nuclear Overhauser enhancement (NOE), and WH homonuclear decoupling], multidimensional gas chromatography (MDGC), and by comparison with synthesized reference compounds. A nonenzymatic formation of la and Ib and 2a and 2b during fermentation of apple juice was proposed leading to 22, 8, 2, and < 1 mg/L of la, 2a, 1b, and 2b, respectively in cider.

  DOI：

  10.1021/jf970162n
• 作为产物：
  描述：

  1,3-辛二醇 在 2-甲基苯磺酸 作用下， 以 乙醚 为溶剂， 反应 24.0h， 生成 (2R,4R)-2-methyl-4-pentyl-1,3-dioxane
  参考文献：
  名称：

  Absolute Configuration and Conformation of 1,3-Dioxanes from Cider

  摘要：

  In extracts obtained by Liquid-liquid extraction from French cider (2S,4R)-and (2R,4R)-2-methyl-4-pentyl-1,3-dioxane, 1a and 1b as well as (2S,4R)-and (2R,4R)-2-methyl-4-(2'(Z)-pentenyl)-1,3-dioxane, 2a and 2b, were identified by capillary gas chromatography (HRGC) and capillary gas chromatography-mass spectrometry (HRGC-MS). Absolute configuration and conformation of the 1,3-dioxanes was determined by nuclear magnetic resonance (NMR) spectrometry techniques [C-13, H-1, nuclear Overhauser enhancement (NOE), and WH homonuclear decoupling], multidimensional gas chromatography (MDGC), and by comparison with synthesized reference compounds. A nonenzymatic formation of la and Ib and 2a and 2b during fermentation of apple juice was proposed leading to 22, 8, 2, and < 1 mg/L of la, 2a, 1b, and 2b, respectively in cider.

  DOI：

  10.1021/jf970162n

文献信息

• Novel 1,3-Dioxanes from Apple Juice and Cider
  作者：Dominique Kavvadias、Till Beuerle、Martina Wein、Barbara Boss、Thorsten König、Wilfried Schwab

  DOI：10.1021/jf990714x

  日期：1999.12.1

  Extracts obtained by XAD solid-phase extraction of apple juice and cider were separated by liquid chromatography on silica gel. Several new 1,3-dioxanes including the known 2-methyl-4-pentyl-1,3-dioxane and 2-methyl-4-[2'(Z)-pentenyl]-1,3-dioxane, were identified in the nonpolar fractions by GC/MS analysis and confirmed by chemical synthesis. The enantioselective synthesis of the stereoisomers of the 1,3-dioxanes was performed using (R)- and (R,S)-actane-1,3-diol and (R)- and (R,S)-5(Z)-octene-1,3-diol as starting material. Comparison with the isolated products indicated that the natural products consisted of a mixture of (2S,4R) and (2R,4R) stereoisomers in the ratio of approximately 10:1, except for 1,3-dioxanes generated from acetone and 2-butanone. It is assumed that the 1,3-dioxanes are chemically formed in the apples and cider from the natural apple ingredients (R)-octane-1,3-diol, (R)-5(Z)-octene-1,3-diol, (3R,7R)- and (3R,7S)-octane-1,3,7-triol, and the appropriate aldehydes and ketones, which are produced either by the apples or by yeast during fermentation of the apple juice.
• Absolute Configuration and Conformation of 1,3-Dioxanes from Cider
  作者：Claudia Dietrich、Till Beuerle、Barbara Withopf、Peter Schreier、Pascal Brunerie、Carlo Bicchi、Wilfried Schwab

  DOI：10.1021/jf970162n

  日期：1997.8.1

  In extracts obtained by Liquid-liquid extraction from French cider (2S,4R)-and (2R,4R)-2-methyl-4-pentyl-1,3-dioxane, 1a and 1b as well as (2S,4R)-and (2R,4R)-2-methyl-4-(2'(Z)-pentenyl)-1,3-dioxane, 2a and 2b, were identified by capillary gas chromatography (HRGC) and capillary gas chromatography-mass spectrometry (HRGC-MS). Absolute configuration and conformation of the 1,3-dioxanes was determined by nuclear magnetic resonance (NMR) spectrometry techniques [C-13, H-1, nuclear Overhauser enhancement (NOE), and WH homonuclear decoupling], multidimensional gas chromatography (MDGC), and by comparison with synthesized reference compounds. A nonenzymatic formation of la and Ib and 2a and 2b during fermentation of apple juice was proposed leading to 22, 8, 2, and < 1 mg/L of la, 2a, 1b, and 2b, respectively in cider.