5-Methyl-3-vinyl-cyclohex-2-enol | 177336-32-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-Methyl-3-vinyl-cyclohex-2-enol
• 英文别名: 3-ethenyl-5-methylcyclohex-2-en-1-ol
• CAS: 177336-32-2
• 化学式: C₉H₁₄O
• 分子量: 138.21
• InChiKey: FGUVUBBHBJGNHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-Methyl-3-vinyl-cyclohex-2-enol 在 咪唑 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 (1R,3S,12bS)-1-[(tert-butyldimethylsilyl)oxy]-3-methyl-1,2,3,4,6,12b-hexahydrobenz[a]anthracen-7,12-dione
  参考文献：
  名称：

  Enantioselective Diels−Alder Cycloadditions with (SS)-2-(p-Tolylsulfinyl)-1,4-naphthoquinone:  Efficient Kinetic Resolution of Chiral Racemic Vinylcyclohexenes

  摘要：

  Chiral racemic vinylcyclohexenes 1a-m, bearing allylic and nonallylic oxygenated substituents on the cyclohexene ring, were submitted to Diels-Alder reactions with enantiomerically pure (SS)(2-p-tolylsulfinyl)-1,4-naphthoquinone. The tandem cycloaddition/pyrolytic sulfoxide elimination led to the formation of enantiomerically enriched angularly tetracyclic quinones (+)-8a and (+)-12, arising from the kinetic resolution of the racemic diene. Dienes la-c, bearing an alkoxy substituent at the allylic position C-3, and 1d-g, with C-3 alkoxy and C-5 methyl groups, gave exclusively quinones (+)-8a-g, resulting from the anti approach to the dienophile. A similar anti selectivity occurred in cycloadditions of dienes 1ij, viith the alkoxy group situated at the allylic position C-6. Nonallylic 4-substituted vinylcyclohexenes 1k-m evolved to ca. 75:25 mixtures of (+)-anti-8k-m and (+)-syn-12k-m derivatives. In all cases, (SS)-(2-p-tolylsulfinyl)-1,4-naphthoquinone reacted from the less hindered face of the more reactive s-cis conformation, giving rise to products in moderate to excellent enantiomeric excesses. Steric effects and torsional interactions in the corresponding approaches account for the observed pi-facial diastereoselectivities at both partners.

  DOI：

  10.1021/jo9811874
• 作为产物：
  描述：

  (1SR,5SR)-3-vinyl-5-methylcyclohex-2-en-1-ol 在 sodium hydroxide 、 ethyl azodicarboxylate 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 24.0h， 生成 5-Methyl-3-vinyl-cyclohex-2-enol
  参考文献：
  名称：

  Enantioselective Diels−Alder Cycloadditions with (SS)-2-(p-Tolylsulfinyl)-1,4-naphthoquinone:  Efficient Kinetic Resolution of Chiral Racemic Vinylcyclohexenes

  摘要：

  Chiral racemic vinylcyclohexenes 1a-m, bearing allylic and nonallylic oxygenated substituents on the cyclohexene ring, were submitted to Diels-Alder reactions with enantiomerically pure (SS)(2-p-tolylsulfinyl)-1,4-naphthoquinone. The tandem cycloaddition/pyrolytic sulfoxide elimination led to the formation of enantiomerically enriched angularly tetracyclic quinones (+)-8a and (+)-12, arising from the kinetic resolution of the racemic diene. Dienes la-c, bearing an alkoxy substituent at the allylic position C-3, and 1d-g, with C-3 alkoxy and C-5 methyl groups, gave exclusively quinones (+)-8a-g, resulting from the anti approach to the dienophile. A similar anti selectivity occurred in cycloadditions of dienes 1ij, viith the alkoxy group situated at the allylic position C-6. Nonallylic 4-substituted vinylcyclohexenes 1k-m evolved to ca. 75:25 mixtures of (+)-anti-8k-m and (+)-syn-12k-m derivatives. In all cases, (SS)-(2-p-tolylsulfinyl)-1,4-naphthoquinone reacted from the less hindered face of the more reactive s-cis conformation, giving rise to products in moderate to excellent enantiomeric excesses. Steric effects and torsional interactions in the corresponding approaches account for the observed pi-facial diastereoselectivities at both partners.

  DOI：

  10.1021/jo9811874