Ethyl 3-hydroxy-5,5-dimethylhexanoate | 149650-14-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: Ethyl 3-hydroxy-5,5-dimethylhexanoate
• CAS: 149650-14-6
• 化学式: C₁₀H₂₀O₃
• 分子量: 188.267
• InChiKey: PVMKNDORHFROCY-UHFFFAOYSA-N

物化性质

• 沸点：
  265.6±13.0 °C(Predicted)
• 密度：
  0.965±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Ethyl 3-hydroxy-5,5-dimethylhexanoate 在 咪唑 、 正丁基锂 、 三氟化硼乙醚 、 氢氟酸 作用下， 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Stereoselective synthesis of syn-1,3-diols

  摘要：

  beta-Hydroxyalkynones 1, readily available from the corresponding beta-hydroxyesters, are reduced by DIBAL-H in THF at -78-degrees with good selectivity to syn-diols 2.

  DOI：

  10.1016/s0040-4039(00)79685-7
• 作为产物：
  描述：

  3,3-二甲基丁醛 、 乙酸乙酯 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 生成 Ethyl 3-hydroxy-5,5-dimethylhexanoate
  参考文献：
  名称：

  Stereoselective acetalization of 1,3-alkanediols by l-menthone: application to the resolution of racemic 1,3-alkanediols and to the determination of the absolute configuration of enantiomeric 1,3-alkanediols

  摘要：

  A general and reliable method for the resolution of racemic 1,3-alkanediols, which involves their conversion into diastereomeric spiroacetals derived from l-menthone, is described. Thus, the reaction of the bis-O-trimethylsilyl derivatives of racemic 1,3-alkanediols with l-menthone in the presence of a catalytic amount of trimethylsilyl trifluoromethanesulfonate affords the diastereomeric spiroacetals 3 and 4. The two can be readily separated by silica gel column chromatography. Hydrolysis of each diastereomer under acidic conditions liberates the corresponding enantiomerically pure diol. An empirically derived correlation of configuration and H-1 NMR chemical shifts for spiroacetals 3 and 4 has been developed which is rationalized based on long-range effects due to the magnetic anisotropy inherent to the menthane ring in a rigid spiroacetal conformation. The method described here should be widely applicable to the determination of the absolute configuration of various 1,3-alkanediols.

  DOI：

  10.1021/jo00031a019

文献信息

• Stereoselective acetalization of 1,3-alkanediols by l-menthone: application to the resolution of racemic 1,3-alkanediols and to the determination of the absolute configuration of enantiomeric 1,3-alkanediols
  作者：Toshiro Harada、Hideaki Kurokawa、Yasuhiro Kagamihara、Sachi Tanaka、Atsushi Inoue、Akira Oku

  DOI：10.1021/jo00031a019

  日期：1992.2

  A general and reliable method for the resolution of racemic 1,3-alkanediols, which involves their conversion into diastereomeric spiroacetals derived from l-menthone, is described. Thus, the reaction of the bis-O-trimethylsilyl derivatives of racemic 1,3-alkanediols with l-menthone in the presence of a catalytic amount of trimethylsilyl trifluoromethanesulfonate affords the diastereomeric spiroacetals 3 and 4. The two can be readily separated by silica gel column chromatography. Hydrolysis of each diastereomer under acidic conditions liberates the corresponding enantiomerically pure diol. An empirically derived correlation of configuration and H-1 NMR chemical shifts for spiroacetals 3 and 4 has been developed which is rationalized based on long-range effects due to the magnetic anisotropy inherent to the menthane ring in a rigid spiroacetal conformation. The method described here should be widely applicable to the determination of the absolute configuration of various 1,3-alkanediols.
• Stereoselective synthesis of syn-1,3-diols
  作者：Peter Mohr

  DOI：10.1016/s0040-4039(00)79685-7

  日期：1991.5

  beta-Hydroxyalkynones 1, readily available from the corresponding beta-hydroxyesters, are reduced by DIBAL-H in THF at -78-degrees with good selectivity to syn-diols 2.