Ethyl 2-(4-formyl-5-phenyloxolan-3-yl)acetate | 1411894-65-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Ethyl 2-(4-formyl-5-phenyloxolan-3-yl)acetate
• 英文别名: ethyl 2-(4-formyl-5-phenyloxolan-3-yl)acetate
• CAS: 1411894-65-9
• 化学式: C₁₅H₁₈O₄
• 分子量: 262.306
• InChiKey: LTFOLMUMHDXEOC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  乙基(2E)-4-羟基-2-丁烯酸酯 、 二乙胺 、 肉桂醛 以 氯仿 为溶剂， 反应 24.0h， 以55.556%的产率得到
  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.