methyl 8-methyl-8-vinyl-3-oxo-2-oxabicyclo<2.2.2>oct-5-ene-6-carboxylate | 118481-25-7

• 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 8-methyl-8-vinyl-3-oxo-2-oxabicyclo<2.2.2>oct-5-ene-6-carboxylate
• 英文别名: methyl 8-methyl-8-vinyl-3-oxo-2-oxabicyclo<2.2.2>oct-5-en-6-carboxylate；methyl 8-methyl-8-vinyl-3-oxo-2-oxabicyclo[2.2.2]oct-5-en-6-carboxylate；methyl (1R,4R,8S)-8-ethenyl-8-methyl-3-oxo-2-oxabicyclo[2.2.2]oct-5-ene-6-carboxylate
• CAS: 118481-25-7；142758-77-8
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: XTNLUGWYUADKBU-YGOYTEALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.22
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 8-methyl-8-vinyl-3-oxo-2-oxabicyclo<2.2.2>oct-5-ene-6-carboxylate 以 间二甲苯 为溶剂， 反应 4.0h， 以21%的产率得到9-methyl-6-methoxycarbonyl-2-oxabicyclo<4.4.0>deca-4,8-dien-3-one
  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：

  香豆灵酸甲酯 、 天然橡胶 、 苯 生成 methyl 8-methyl-8-vinyl-3-oxo-2-oxabicyclo<2.2.2>oct-5-ene-6-carboxylate
  参考文献：
  名称：

  MATSUI, TAKANAO;KITAJIMA, SHINJI;NAKAYAMA, MITSURU, BULL. CHEM. SOC. JAP., 61,(1988) N 1, 316-318

  摘要：

  DOI：

文献信息

• Structures of New [4+2]-Cycloadducts from Diels–Alder Reactions of Methyl 2-Oxo-2<i>H</i>-pyran-5-carboxylate with 2-Methyl- and 2-Methoxy-1,3-butadienes
  作者：Takanao Matsui、Shinji Kitajima、Mitsuru Nakayama

  DOI：10.1246/bcsj.61.316

  日期：1988.1

  A Diels–Alder reaction of methyl 2-oxo-2H-pyran-5-carboxylate (1) with isoprene gave two stereoisomers, methyl 8-methyl-8-vinyl- and 8-isopropenyl-3-oxo-2-oxabicyclo[2.2.2]oct-5-ene-6-carboxylates. On the other hand, only a stereoisomer from a reaction of 1 with 2-methoxy-1,3-butadiene, methyl 8-methoxy-8-vinyl-3-oxo-2-oxabicyclo[2.2.2]oct-5-ene-6-carboxylate was obtained. The stereostructures of these

  2-oxo-2H-pyran-5-carboxylate 甲酯 (1) 与异戊二烯的 Diels-Alder 反应生成了两种立体异构体，即 8-methyl-8-vinyl- 和 8-isopropenyl-3-oxo-2-oxabicyclo[2.2 .2]oct-5-ene-6-羧酸盐。另一方面，只有 1 与 2-甲氧基-1,3-丁二烯、甲基 8-甲氧基-8-乙烯基-3-氧-2-氧杂双环[2.2.2] 辛-5-烯反应的立体异构体得到-6-羧酸盐。这些加合物的立体结构由 NMR 光谱数据和单晶 X 射线分析确定。