2-hydroxy-2,6,10,10-tetramethyl-1-oxaspiro[4.5]dec-6-en-8-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-hydroxy-2,6,10,10-tetramethyl-1-oxaspiro[4.5]dec-6-en-8-one
• 英文别名: 2-Hydroxy-2,6,6,10-tetramethyl-1-oxaspiro[4.5]dec-9-en-8-one；2-hydroxy-2,6,6,10-tetramethyl-1-oxaspiro[4.5]dec-9-en-8-one
• 化学式: C₁₃H₂₀O₃
• 分子量: 224.3
• InChiKey: YAZKQQFIRYUXBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  dehydrovomifoliol 在 palladium/alumina 氢气 作用下， 以 四氢呋喃 为溶剂， 生成 2-hydroxy-2,6,10,10-tetramethyl-1-oxaspiro[4.5]dec-6-en-8-one
  参考文献：
  名称：

  2-Hydroxy-2,6,10,10-tetramethyl-1-oxaspiro[4.5]dec-6-en-8-one:  Precursor of 8,9-Dehydrotheaspirone in White-Fleshed Nectarines

  摘要：

  2-Hydroxy-2,6,10,10-tetramethyl-1-oxaspiro[4.5]dec-6-en-8-one (2) was identified as precursor of 2,6,10,10-tetramethyl-1-oxaspiro[4.5]deca-2,6-dien-8-one (8,9-dehydrotheaspirone, 1) in an Et2O extract from white-fleshed nectarine (Prunus persica Batsch var. nucipersica Schneid) juice. The identification was verified by comparison of chromatographic and spectral data (MS, H-1 and C-13 NMR) of the new natural product with those of an authentic reference compound synthesized from dehydrovomifoliol (3). NMR spectral data revealed that the precursor compound 2 is present in 5:1 mixture of diastereomeric hemiacetals 2a/b. The absolute stereochemistry of the diastereoisomers (major isomer, 2S,5S; minor isomer, 2R,5S) was elucidated by NOE experiments and dehydration to optically pure (S-configured) spiroether 1. In addition to hemiacetals 2a/b, (6S)-dehydrovomifoliol (3) as well as the beta-D-glucoside of (3S,5R,6S)-3-hydroxy-5,6-epoxy-beta-ionone (5) was also identified in nectarine juice.

  DOI：

  10.1021/jf960598n

文献信息

• 2-Hydroxy-2,6,10,10-tetramethyl-1-oxaspiro[4.5]dec-6-en-8-one:  Precursor of 8,9-Dehydrotheaspirone in White-Fleshed Nectarines
  作者：Holger Knapp、Cornelia Weigand、Jürgen Gloser、Peter Winterhalter

  DOI：10.1021/jf960598n

  日期：1997.4.1

  2-Hydroxy-2,6,10,10-tetramethyl-1-oxaspiro[4.5]dec-6-en-8-one (2) was identified as precursor of 2,6,10,10-tetramethyl-1-oxaspiro[4.5]deca-2,6-dien-8-one (8,9-dehydrotheaspirone, 1) in an Et2O extract from white-fleshed nectarine (Prunus persica Batsch var. nucipersica Schneid) juice. The identification was verified by comparison of chromatographic and spectral data (MS, H-1 and C-13 NMR) of the new natural product with those of an authentic reference compound synthesized from dehydrovomifoliol (3). NMR spectral data revealed that the precursor compound 2 is present in 5:1 mixture of diastereomeric hemiacetals 2a/b. The absolute stereochemistry of the diastereoisomers (major isomer, 2S,5S; minor isomer, 2R,5S) was elucidated by NOE experiments and dehydration to optically pure (S-configured) spiroether 1. In addition to hemiacetals 2a/b, (6S)-dehydrovomifoliol (3) as well as the beta-D-glucoside of (3S,5R,6S)-3-hydroxy-5,6-epoxy-beta-ionone (5) was also identified in nectarine juice.