5-methyl-1-oxaspiro[2.5]octane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: 5-methyl-1-oxaspiro[2.5]octane
• 英文别名: (3R,5S)-5-methyl-1-oxaspiro[2.5]octane
• 化学式: C₈H₁₄O
• 分子量: 126.199
• InChiKey: WMHAWNWXMPALBK-JGVFFNPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-methyl-1-oxaspiro[2.5]octane 在 高氯酸 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 生成 (+/-)-1-hydroxymethyl-cis-3-methylcyclohexanol 、 (+/-)-1-hydroxymethyl-trans-3-methylcyclohexanol
  参考文献：
  名称：

  Kinetic resolution by epoxide hydrolase catalyzed hydrolysis of racemic methyl substituted methylenecyclohexene oxides

  摘要：

  A complete kinetic resolution of 2,2-dimethylmethylenecyclobexene oxide and a partial resolution of the cis and trans-2-methylmethylenecyclohexene oxides, but not of their 3-methyl substituted isomers, have been achieved by partial hydrolysis to the corresponding diols using the microsomal epoxide hydrolase. No substrate enantioselectivity was in found for the hydrolysis of all these substrates by the cytosolic epoxide hydrolase.

  DOI：

  10.1016/0957-4166(95)00250-s
• 作为产物：
  描述：

  1-methyl-3-methylene-cyclohexane 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 5-methyl-1-oxaspiro[2.5]octane 、 5-methyl-1-oxaspiro[2.5]octane
  参考文献：
  名称：

  Facial Stereoselectivity of Two-Step Additions Initiated by Electrophilic Halogens to Methylenecyclohexanes. A Comparison with Epoxidation

  摘要：

  DOI：

  10.1021/jo00124a047

文献信息

• Stereoselectivity and Substrate Specificity in the Kinetic Resolution of Methyl-Substituted 1-Oxaspiro[2.5]octanes by <i>Rhodotorula </i><i>g</i><i>lutinis</i> Epoxide Hydrolase
  作者：Carel A. G. M. Weijers、Petra Meeuwse、Robert L. J. M. Herpers、Maurice C. R. Franssen、Ernst J. R. Sudhölter

  DOI：10.1021/jo050533w

  日期：2005.8.1

  [GRAPHICS]The kinetic resolution of a range of methyl-substituted 1-oxaspiro[2.5]octanes by yeast epoxide hydrolase (YEH) from Rhodotorula glutinis has been investigated. The structural determinants of substrate specificity and stereoselectivity of YEH toward these substrates appeared to be the configuration of the epoxide ring and the substitution pattern of the cyclohexane ring. For all compounds tested, O-axial epoxides were hydrolyzed faster than the corresponding O-equatorial compounds. In concern of the ring substituents,.YEH preferred methyl groups on the Re side of the ring. Placement of substituents close to the spiroepoxide carbon decreased the reaction rate but increased enantioselectivity. YEH-catalyzed kinetic resolutions of 4-methyl 1-oxaspiro [2.5] octane epimers were most enantioselective,(E > 100).
• Facial Stereoselectivity of Two-Step Additions Initiated by Electrophilic Halogens to Methylenecyclohexanes. A Comparison with Epoxidation
  作者：Giuseppe Bellucci、Cinzia Chiappe、Giacomo Lo Moro、Giovanni Ingrosso

  DOI：10.1021/jo00124a047

  日期：1995.9
• Kinetic resolution by epoxide hydrolase catalyzed hydrolysis of racemic methyl substituted methylenecyclohexene oxides
  作者：Giuseppe Bellucci、Cinzia Chiappe、Giovanni Ingrosso、Carlo Rosini

  DOI：10.1016/0957-4166(95)00250-s

  日期：1995.8

  A complete kinetic resolution of 2,2-dimethylmethylenecyclobexene oxide and a partial resolution of the cis and trans-2-methylmethylenecyclohexene oxides, but not of their 3-methyl substituted isomers, have been achieved by partial hydrolysis to the corresponding diols using the microsomal epoxide hydrolase. No substrate enantioselectivity was in found for the hydrolysis of all these substrates by the cytosolic epoxide hydrolase.