cis-2-Hydroxy-2-methoxy-cyclohexyliden-essigsaeure-γ-lacton | 90673-76-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cis-2-Hydroxy-2-methoxy-cyclohexyliden-essigsaeure-γ-lacton
• 英文别名: 7a-methoxy-5,6,7,7a-tetrahydro-4H-benzofuran-2-one
• CAS: 90673-76-0
• 化学式: C₉H₁₂O₃
• 分子量: 168.192
• InChiKey: PYIVZSOPXBGUOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.39
• 重原子数：
  12.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  cis-2-Hydroxy-2-methoxy-cyclohexyliden-essigsaeure-γ-lacton 、 乙烯 以 丙酮 为溶剂， 反应 8.0h， 生成 (2aS,4aS,8aR)-4a-Methoxy-hexahydro-4-oxa-cyclobuta[c]inden-3-one 、 (2aS,4aR,8aR)-4a-Methoxy-hexahydro-4-oxa-cyclobuta[c]inden-3-one
  参考文献：
  名称：

  Chiral induction in photochemical reactions - 15.

  摘要：

  The mechanism of the diastereoselection in the photosensitized [2 + 2]-cycloaddition reaction of ethylene to 5-alkoxy-2(5H)-furanones is investigated. The dependence of product ratio on the reaction temperature as well as on structural features of the enone system is measured. The structure dependent activation parameter differences (Delta Delta H-#, Delta Delta S-#) obtained by this method (modified Eyring plot) are used as a tool to characterize the stereoelectronic factors, which are responsible for the diastereoselection. In detail these factors involve: pyramidalization of the beta-carbon, homoanomeric effect, and the steric requirements of the alkoxy substituent in the relaxed ((3) pi pi*)-excited furanones.

  DOI：

  10.1016/s0040-4020(01)89419-9