(2R,8aS)-3,4-dihydro-3-oxoedulan | 128660-65-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (2R,8aS)-3,4-dihydro-3-oxoedulan
• 英文别名: 2,3,6,7,8,8a-Hexahydro-7-oxo-2,5,5,8a-tetramethyl-5H-1-benzopyran, trans-；(2R,8aS)-2,5,5,8a-tetramethyl-2,3,6,8-tetrahydrochromen-7-one
• CAS: 128660-65-1
• 化学式: C₁₃H₂₀O₂
• 分子量: 208.301
• InChiKey: PYUYJSFTZPYHDW-RNCFNFMXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  15
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-[(R)-3-Hydroxy-but-(E)-ylidene]-3,5,5-trimethyl-cyclohex-2-enone 在 盐酸 作用下， 生成 (2RS,8aRS)-2,3,5,6,8a-hexahydro-2,5,5,8a-tetramethyl-7H-1-benzopyran-7-one 、 (2R,8aS)-3,4-dihydro-3-oxoedulan
  参考文献：
  名称：

  Synthesis and Enantiodifferentiation of Isomeric 2,3,5,6,8,8a-Hexahydro-2,5,5,8a-tetramethyl-7H-1-benzopyran-7-ones (3,4-Dihydro-3-oxoedulans)

  摘要：

  The benzopyran derivatives 1a-d mere prepared in a biomimetic type reaction from their presumed natural precursor 3-oxo-retro-alpha-ionol, which was available from alpha-ionone by tert-butyl chromate oxidation, reduction with NaBH4, and subsequent rearrangement of the 7,8 double bond. The so-obtained geometrical isomers of 3-oxo-retro-alpha-ionol (4a/b) were separated by preparative and analytical multilayer coil countercurrent chromatography. Racemic 3-oxo-retro-alpha-ionol (4a) was esterified with (R)-(-)-2-phenylpropionic acid, and the resulting diastereomeric esters (5a/b) were isolated in pure form by preparative HPLC. Configuration at C-9 was determined by H-1 NMR spectroscopy. The isomeric ketols 6a/b obtained from esters 5a/b by enzymatic hydrolysis were subjected to thermal treatment (simultaneous distillation extraction, pH 1), yielding two pairs of diastereomeric 3,4-dihydro-3-oxoedulans (1a/b and 1c/d). The absolute configuration at C-8a was established by NOE experiments. Using on-line coupled multidimensional gas chromatography-mass spectrometry [DB-Wax/octakis(2,6-di-O-methyl-3-O-pentyl)-gamma-cyclodextrin] with selected ion monitoring mode, enantiodifferentiation of 1a-d in a number of natural sources was carried out.

  DOI：

  10.1021/jf00055a026