1,3-Dioxane, 2,2-dimethyl-4-pentyl, 4R

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3-Dioxane, 2,2-dimethyl-4-pentyl, 4R
• 英文别名: (4R)-2,2-dimethyl-4-pentyl-1,3-dioxane
• 化学式: C₁₁H₂₂O₂
• 分子量: 186.294
• InChiKey: ADNZCWQGZVIHRC-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 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

• 作为产物：
  描述：

  丙酮 、 (R)-octane-1,3-diol 在 对甲苯磺酸 、 sodium sulfate 作用下， 以 乙醚 为溶剂， 生成 1,3-Dioxane, 2,2-dimethyl-4-pentyl, 4R
  参考文献：
  名称：

  Novel 1,3-Dioxanes from Apple Juice and Cider

  摘要：

  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.

  DOI：

  10.1021/jf990714x

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.