Methyl 1-methyltricyclo[3.2.1.02,7]oct-3-ene-4-carboxylate | 37464-29-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: Methyl 1-methyltricyclo[3.2.1.02,7]oct-3-ene-4-carboxylate
• CAS: 37464-29-2
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: SOOXCUCLMNZFGK-UHFFFAOYSA-N

物化性质

• 沸点：
  230.0±9.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Methyl 1-methyltricyclo[3.2.1.02,7]oct-3-ene-4-carboxylate 在 palladium on activated charcoal 作用下， 以 二苯醚 为溶剂， 反应 4.0h， 以32%的产率得到4-异丙基苯甲酸甲酯
  参考文献：
  名称：

  Thermal Conversion of Methyl 8-Vinyl-3-oxo-2-oxabicyclo[2.2.2]oct-5-en-6-carboxylates to Tetrahydrocoumarins and Methyl Benzoates

  摘要：

  Methyl 8-methyl- and 8-methoxy-8-vinyl-3-oxo-2-oxabicyclo[2.2.2]oct-5-en-6-carboxylates (3 and 5), prepared by the Diels-Alder reaction of methyl 2-oxo-2H-pyran-5-carboxylate with 2-methyl- and 2-methoxy-1,3-butadienes, were converted into methyl 9-methyl- and 9-methoxy-3-oxo-2-oxabicyclo[4.4.0]deca-4,8-diene-6-carboxylates (tetrahydrocoumarins) by a Cope rearrangement at about 140-degrees-C, respectively. On the other hand, 3 and 5 were transformed into methyl 4-isopropyl- and 4-acetylbenzoates via the reaction of methyl tricyclo[3.2.1.0(2,7)]oct-3-en-4-carboxylates at about 257-degrees-C in the presence of Pd-C, respectively.

  DOI：

  10.3987/com-91-5941
• 作为产物：
  描述：

  methyl 8-isopropenyl-3-oxo-2-oxabicyclo<2.2.2>oct-5-ene-6-carboxylate 以 间二甲苯 为溶剂， 反应 4.0h， 生成 Methyl 1-methyltricyclo[3.2.1.02,7]oct-3-ene-4-carboxylate
  参考文献：
  名称：

  Thermal Conversion of Methyl 8-Vinyl-3-oxo-2-oxabicyclo[2.2.2]oct-5-en-6-carboxylates to Tetrahydrocoumarins and Methyl Benzoates

  摘要：

  Methyl 8-methyl- and 8-methoxy-8-vinyl-3-oxo-2-oxabicyclo[2.2.2]oct-5-en-6-carboxylates (3 and 5), prepared by the Diels-Alder reaction of methyl 2-oxo-2H-pyran-5-carboxylate with 2-methyl- and 2-methoxy-1,3-butadienes, were converted into methyl 9-methyl- and 9-methoxy-3-oxo-2-oxabicyclo[4.4.0]deca-4,8-diene-6-carboxylates (tetrahydrocoumarins) by a Cope rearrangement at about 140-degrees-C, respectively. On the other hand, 3 and 5 were transformed into methyl 4-isopropyl- and 4-acetylbenzoates via the reaction of methyl tricyclo[3.2.1.0(2,7)]oct-3-en-4-carboxylates at about 257-degrees-C in the presence of Pd-C, respectively.

  DOI：

  10.3987/com-91-5941