(3R,S,7R,S)-octane-1,3,7-triol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (3R,S,7R,S)-octane-1,3,7-triol
• 化学式: C₈H₁₈O₃
• 分子量: 162.229
• InChiKey: NGACGNKKNNNNHK-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.28
• 重原子数：
  11.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  60.69
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  5-己烯-1-醇 在 palladium dichloride 吡啶 、 lithium aluminium tetrahydride 、 氧气 、 phosphorus pentoxide 、 二甲基亚砜 、 三乙胺 、 copper(l) chloride 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 (3R,S,7R,S)-octane-1,3,7-triol
  参考文献：
  名称：

  Isolation, Identification, and Enantioselective Synthesis of Octane-1,3,7-triol:  Determination of Its Absolute Configuration

  摘要：

  Extracts obtained by solid-phase extraction from apples were separated by multilayer countercurrent chromatography. In the most polar fractions, the novel octane-1,3,7-triol was identified by H-1 and C-13 NMR as well as LC-MS and by comparison with the synthesized racemic reference compound. Resolution of the enantiomers was achieved after acetylation of the triol followed by GC separation. The enantioselective synthesis of the stereoisomers of octane-1,3,7-triol was performed using the building blocks (R)- and (R,S)-butane-1,3-diol and (S)- and (R,S)-butane-1,2,4-triol, Comparison with the isolated products indicated that the natural compound consisted of a mixture of (3R,7S)- and (SR,7R)-octane-1,3,7-triol in a ratio of 2:3. Since the C3 chiral center is enantiomerically pure, the triol might be biogenetically related to the known antimicrobial (R)-(+)-octane-1,3 -diol, the major volatile compound of some apple cultivars.

  DOI：

  10.1021/np980094e

文献信息

• Isolation, Identification, and Enantioselective Synthesis of Octane-1,3,7-triol:  Determination of Its Absolute Configuration
  作者：Till Beuerle、Sonja Engelhard、Carlo Bicchi、Wilfried Schwab

  DOI：10.1021/np980094e

  日期：1999.1.1

  Extracts obtained by solid-phase extraction from apples were separated by multilayer countercurrent chromatography. In the most polar fractions, the novel octane-1,3,7-triol was identified by H-1 and C-13 NMR as well as LC-MS and by comparison with the synthesized racemic reference compound. Resolution of the enantiomers was achieved after acetylation of the triol followed by GC separation. The enantioselective synthesis of the stereoisomers of octane-1,3,7-triol was performed using the building blocks (R)- and (R,S)-butane-1,3-diol and (S)- and (R,S)-butane-1,2,4-triol, Comparison with the isolated products indicated that the natural compound consisted of a mixture of (3R,7S)- and (SR,7R)-octane-1,3,7-triol in a ratio of 2:3. Since the C3 chiral center is enantiomerically pure, the triol might be biogenetically related to the known antimicrobial (R)-(+)-octane-1,3 -diol, the major volatile compound of some apple cultivars.