tert-butyldimethylsilyl ether of 5-hydroxy-1,10-undecadien-6-one | 141019-66-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyldimethylsilyl ether of 5-hydroxy-1,10-undecadien-6-one
• 英文别名: 5-[tert-butyl(dimethyl)silyl]oxyundeca-1,10-dien-6-one
• CAS: 141019-66-1
• 化学式: C₁₇H₃₂O₂Si
• 分子量: 296.525
• InChiKey: GBFWCVMIYAOKIE-UHFFFAOYSA-N

物化性质

• 沸点：
  337.8±42.0 °C(Predicted)
• 密度：
  0.874±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.27
• 重原子数：
  20.0
• 可旋转键数：
  10.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  tert-butyldimethylsilyl ether of 5-hydroxy-1,10-undecadien-6-one 在 sodium hydroxide 、 sodium tetrahydroborate 、 高氯酸 、 氢氟酸 、 mercury(II) diacetate 、 苄基三乙基氯化铵 作用下， 以 乙腈 为溶剂， 反应 4.5h， 生成 (2R,5R,6S,8R)-2,8-dimethyl-1,7-dioxaspiro<5.5>undecan-5-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
• 作为产物：
  描述：

  rac-2-hydroxyhex-5-enenitrile 在 咪唑 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 tert-butyldimethylsilyl ether of 5-hydroxy-1,10-undecadien-6-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