(2R,2'S,5'R)-2-[(5'-methyl-5'-vinyl)tetrahydrofuran-2'-yl]propanol | 525598-07-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: (2R,2'S,5'R)-2-[(5'-methyl-5'-vinyl)tetrahydrofuran-2'-yl]propanol
• 英文别名: (2R,2'S,5'R)-lilac alcohol；(2R)-2-[(2S,5R)-5-ethenyl-5-methyloxolan-2-yl]propan-1-ol
• CAS: 525598-07-6
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: VUEGXHXUMOZKKN-UTLUCORTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,2'S,5'R)-2-[(5'-methyl-5'-vinyl)tetrahydrofuran-2'-yl]propanol 在 pyridinium chlorochromate 作用下， 以11.8 mg的产率得到(2S,2'S,5'R)-2-[(5'-methyl-5'-vinyl)tetrahydrofuran-2'-yl]propanal
  参考文献：
  名称：

  Synthesis, Structure Elucidation, and Olfactometric Analysis of Lilac Aldehyde and Lilac Alcohol Stereoisomers

  摘要：

  Structure elucidation of the lilac aldehyde and lilac alcohol stereoisomers was ascertained by H-1 nuclear magnetic resonance (NMR) spectroscopy, including intramolecular nuclear Overhauser effects of the separated diastereoisomers and anisotropic effects of the diastereomeric 2-phenylpropionyl ester, and H-1, H-1 COSY NMR spectroscopy of synthesized (5'R)-configured stereoisomers, synthesized from (R)-linalool. Direct stereodifferentiation of the eight stereoisomers of lilac aldehyde and lilac alcohol, respectively, has been achieved, using enantioselective capillary GC. The elution order of the isomers was deduced from the chromatographic behavior of the (5'R)-configured diastereoisomers. Additionally, the odor thresholds of lilac aldehyde and lilac alcohol stereoisomers are reported.

  DOI：

  10.1021/jf021140q
• 作为产物：
  描述：

  (1''S,4''R)-camphanic acid (2R,2'S,5'R)-2-[(5'-methyl-5'-vinyl)tetrahydrofuran-2'-yl]propyl ester 在 lithium aluminium tetrahydride 作用下， 以18.1 mg的产率得到(2R,2'S,5'R)-2-[(5'-methyl-5'-vinyl)tetrahydrofuran-2'-yl]propanol
  参考文献：
  名称：

  Synthesis, Structure Elucidation, and Olfactometric Analysis of Lilac Aldehyde and Lilac Alcohol Stereoisomers

  摘要：

  Structure elucidation of the lilac aldehyde and lilac alcohol stereoisomers was ascertained by H-1 nuclear magnetic resonance (NMR) spectroscopy, including intramolecular nuclear Overhauser effects of the separated diastereoisomers and anisotropic effects of the diastereomeric 2-phenylpropionyl ester, and H-1, H-1 COSY NMR spectroscopy of synthesized (5'R)-configured stereoisomers, synthesized from (R)-linalool. Direct stereodifferentiation of the eight stereoisomers of lilac aldehyde and lilac alcohol, respectively, has been achieved, using enantioselective capillary GC. The elution order of the isomers was deduced from the chromatographic behavior of the (5'R)-configured diastereoisomers. Additionally, the odor thresholds of lilac aldehyde and lilac alcohol stereoisomers are reported.

  DOI：

  10.1021/jf021140q

文献信息

• Synthesis, Structure Elucidation, and Olfactometric Analysis of Lilac Aldehyde and Lilac Alcohol Stereoisomers
  作者：Mirjam Kreck、Armin Mosandl

  DOI：10.1021/jf021140q

  日期：2003.4.1

  Structure elucidation of the lilac aldehyde and lilac alcohol stereoisomers was ascertained by H-1 nuclear magnetic resonance (NMR) spectroscopy, including intramolecular nuclear Overhauser effects of the separated diastereoisomers and anisotropic effects of the diastereomeric 2-phenylpropionyl ester, and H-1, H-1 COSY NMR spectroscopy of synthesized (5'R)-configured stereoisomers, synthesized from (R)-linalool. Direct stereodifferentiation of the eight stereoisomers of lilac aldehyde and lilac alcohol, respectively, has been achieved, using enantioselective capillary GC. The elution order of the isomers was deduced from the chromatographic behavior of the (5'R)-configured diastereoisomers. Additionally, the odor thresholds of lilac aldehyde and lilac alcohol stereoisomers are reported.