2-(4'-(tetrahydropyranyloxy)pentyl)furan | 141019-50-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 2-(4'-(tetrahydropyranyloxy)pentyl)furan
• 英文别名: 2-[5-(furan-2-yl)pentan-2-yloxy]oxane
• CAS: 141019-50-3；141019-51-4
• 化学式: C₁₄H₂₂O₃
• 分子量: 238.327
• InChiKey: QWDWTYFNWAIURQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.53
• 重原子数：
  17.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  31.6
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(4'-(tetrahydropyranyloxy)pentyl)furan 在 正丁基锂 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 生成 6-hydroxy-2-methyl-6-[4-(oxan-2-yloxy)pentyl]pyran-3-one
  参考文献：
  名称：

  Diastereo- and enantioselective routes to some 2,8-dimethyl-1,7-dioxaspiro[5.5]undecanols. Absolute stereochemistry of (E,E,E)-2,8-dimethyl-1,7-dioxaspiro[5.5]undecan-3-ol and of (E,E)-8-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)methanol present in Bactrocera cucumis

  摘要：

  Routes to the four regioisomeric 2,8-dimethyl-1,7-dioxaspiro[5.5]undecanols have been developed, and in the racemic series, mercury(II)-mediated reactions of appropriate dienone, hydroxy enone, dienedione, and hydroxy dienone systems have been exploited. Most of the epimeric pairs of alcohols (i.e. axial or equatorial) in the E,E, E,Z, or Z,E spiroacetal ring systems have been characterized by detailed H-1, C-13, and correlated NMR spectroscopy and mass spectrometry. Key enantiomers of these alcohols have been obtained by elaborating chiral starting materials such as D-mannitol, L-arabinose, poly(hydroxybutyrate), and in the case of the 5-hydroxy derivative, mandelonitrile lyase mediated formation of a key chiral cyanohydrin was employed. Most of the alcohols, as their trifluoroacetates, are resolved (into enantiomers) on a Lipodex A GC column, thus facilitating their identification from natural sources. In this way, the absolute configurations of a number of 2,8-dimethyl-1,7-dioxaspiro[5.5]undecanols present in the rectal gland secretion of Bactrocera cucumis (cucumber fly) have been determined.

  DOI：

  10.1021/jo00038a027
• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 、 alkaline earth salt of/the/ methylsulfuric acid 在 正丁基锂 、 三甲基氯硅烷 、 氢气 、 sodium iodide 作用下， 反应 3.5h， 生成 2-(4'-(tetrahydropyranyloxy)pentyl)furan
  参考文献：
  名称：

  Diastereo- and enantioselective routes to some 2,8-dimethyl-1,7-dioxaspiro[5.5]undecanols. Absolute stereochemistry of (E,E,E)-2,8-dimethyl-1,7-dioxaspiro[5.5]undecan-3-ol and of (E,E)-8-methyl-1,7-dioxaspiro[5.5]undecan-2-yl)methanol present in Bactrocera cucumis

  摘要：

  Routes to the four regioisomeric 2,8-dimethyl-1,7-dioxaspiro[5.5]undecanols have been developed, and in the racemic series, mercury(II)-mediated reactions of appropriate dienone, hydroxy enone, dienedione, and hydroxy dienone systems have been exploited. Most of the epimeric pairs of alcohols (i.e. axial or equatorial) in the E,E, E,Z, or Z,E spiroacetal ring systems have been characterized by detailed H-1, C-13, and correlated NMR spectroscopy and mass spectrometry. Key enantiomers of these alcohols have been obtained by elaborating chiral starting materials such as D-mannitol, L-arabinose, poly(hydroxybutyrate), and in the case of the 5-hydroxy derivative, mandelonitrile lyase mediated formation of a key chiral cyanohydrin was employed. Most of the alcohols, as their trifluoroacetates, are resolved (into enantiomers) on a Lipodex A GC column, thus facilitating their identification from natural sources. In this way, the absolute configurations of a number of 2,8-dimethyl-1,7-dioxaspiro[5.5]undecanols present in the rectal gland secretion of Bactrocera cucumis (cucumber fly) have been determined.

  DOI：

  10.1021/jo00038a027