(7-exo-(diethylamino)-2-exo-methyl-3-oxabicyclo[3.2.0]heptan-6-endo-yl)methanol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: (7-exo-(diethylamino)-2-exo-methyl-3-oxabicyclo[3.2.0]heptan-6-endo-yl)methanol
• 英文别名: [(1R,2R,5R,6S,7R)-7-(diethylamino)-2-methyl-3-oxabicyclo[3.2.0]heptan-6-yl]methanol
• 化学式: C₁₂H₂₃NO₂
• 分子量: 213.32
• InChiKey: ARHHYGHZNONFHE-IYKVGLELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (7-exo-(diethylamino)-2-exo-methyl-3-oxabicyclo[3.2.0]heptan-6-endo-yl)methanol 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 5.5h， 生成
  参考文献：
  名称：

  Diastereoselective Multicomponent Cascade Reaction Leading to [3.2.0]-Heterobicyclic Compounds

  摘要：

  A general three-component triple cascade reaction through an iminium-enamine-iminium sequential activation initiated by a hetero-Michael addition to alpha,beta-unsaturated aldehydes affords [3.2.0]heterobicycles in high diastereoselectivity. The rate and diastereoselectivity of the reaction depended on the (E)-4-heterocrotonate and size of the secondary amine. The enantiomers of the major diastereoisomer of oxa- and azabicyclo[3.2.0]heptane derivatives were separated by enzymatic kinetic resolution with immobilized Candida antarctica Lipase B (CALB), with E values up to 153. The absolute configuration of the nonacylated enantiomer of oxabicyclo[3.2.0]heptane was determined by single crystal X-ray analysis.

  DOI：

  10.1021/jo3019413
• 作为产物：
  描述：

  乙基(2E)-4-羟基-2-丁烯酸酯 、 二乙胺 、 丁烯-2-醛 在 lithium aluminium tetrahydride 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 112.0h， 以166 mg的产率得到(7-exo-(diethylamino)-2-exo-methyl-3-oxabicyclo[3.2.0]heptan-6-endo-yl)methanol
  参考文献：
  名称：

  Diastereoselective Multicomponent Cascade Reaction Leading to [3.2.0]-Heterobicyclic Compounds

  摘要：

  A general three-component triple cascade reaction through an iminium-enamine-iminium sequential activation initiated by a hetero-Michael addition to alpha,beta-unsaturated aldehydes affords [3.2.0]heterobicycles in high diastereoselectivity. The rate and diastereoselectivity of the reaction depended on the (E)-4-heterocrotonate and size of the secondary amine. The enantiomers of the major diastereoisomer of oxa- and azabicyclo[3.2.0]heptane derivatives were separated by enzymatic kinetic resolution with immobilized Candida antarctica Lipase B (CALB), with E values up to 153. The absolute configuration of the nonacylated enantiomer of oxabicyclo[3.2.0]heptane was determined by single crystal X-ray analysis.

  DOI：

  10.1021/jo3019413

文献信息

• Diastereoselective Multicomponent Cascade Reaction Leading to [3.2.0]-Heterobicyclic Compounds
  作者：Kerti Ausmees、Kadri Kriis、Tõnis Pehk、Franz Werner、Ivar Järving、Margus Lopp、Tõnis Kanger

  DOI：10.1021/jo3019413

  日期：2012.12.7

  A general three-component triple cascade reaction through an iminium-enamine-iminium sequential activation initiated by a hetero-Michael addition to alpha,beta-unsaturated aldehydes affords [3.2.0]heterobicycles in high diastereoselectivity. The rate and diastereoselectivity of the reaction depended on the (E)-4-heterocrotonate and size of the secondary amine. The enantiomers of the major diastereoisomer of oxa- and azabicyclo[3.2.0]heptane derivatives were separated by enzymatic kinetic resolution with immobilized Candida antarctica Lipase B (CALB), with E values up to 153. The absolute configuration of the nonacylated enantiomer of oxabicyclo[3.2.0]heptane was determined by single crystal X-ray analysis.