(2S,4S,6R,8S)-2,8-Dimethyl-1,7-dioxa-spiro[5.5]undecan-4-ol | 141115-54-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,4S,6R,8S)-2,8-Dimethyl-1,7-dioxa-spiro[5.5]undecan-4-ol
• 英文别名: (2S,4S,6R,8S)-2,8-dimethyl-1,7-dioxaspiro[5.5]undecan-4-ol
• CAS: 141115-54-0
• 化学式: C₁₁H₂₀O₃
• 分子量: 200.278
• InChiKey: UGQSSMAXOUSHAY-XWLWVQCSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (E,E)-(2R,6S,8R)-4-oxo-2,8-dimethyl-1,7-dioxaspiro<5.5>undecane 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 (2R,4S,6S,8R)-2,8-Dimethyl-1,7-dioxaspiro<5.5>undecan-4-ol 、 (2S,4R,6R,8S)-2,8-Dimethyl-1,7-dioxaspiro<5.5>undecan-4-ol 、 (2R,4R,6S,8R)-2,8-Dimethyl-1,7-dioxa-spiro[5.5]undecan-4-ol 、 (2S,4S,6R,8S)-2,8-Dimethyl-1,7-dioxa-spiro[5.5]undecan-4-ol
  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

文献信息

• 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
  作者：Michael V. Perkins、Mark F. Jacobs、William Kitching、Peter J. Cassidy、Judith A. Lewis、Richard A. I. Drew

  DOI：10.1021/jo00038a027

  日期：1992.6

  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.