methyl 1,2,3,5,8,8a-hexahydro-1-oxo-6,7,8a-trimethyl-4-azulenecarboxylate | 131216-63-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 1,2,3,5,8,8a-hexahydro-1-oxo-6,7,8a-trimethyl-4-azulenecarboxylate
• 英文别名: Methyl 6,7,8a-trimethyl-1-oxo-2,3,5,8-tetrahydroazulene-4-carboxylate
• CAS: 131216-63-2
• 化学式: C₁₅H₂₀O₃
• 分子量: 248.322
• InChiKey: HWRQTJHGPDORLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  methyl α-diazo-2-methyl-3-oxo-1-cyclopentene-1-acetate 、 2,3-二甲基-1,3-丁二烯 在 dirhodium tetraacetate 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以41%的产率得到methyl 1,2,3,5,8,8a-hexahydro-1-oxo-6,7,8a-trimethyl-4-azulenecarboxylate
  参考文献：
  名称：

  Stereoselective convergent synthesis of hydroazulenes via an intermolecular cyclopropanation/Cope rearrangement

  摘要：

  Rhodium(II) acetate catalyzed decomposition of vinyldiazomethane 1 to a vinylcarbenoid intermediate in the presence of oxygenated dienes led to the direct formation of hydroazulenes 7, 13, and 15-19. The 3 + 4 annulation proceeds by a tandem cyclopropanation/Cope rearrangement sequence. The cyclopropanation is highly stereoselective, favoring the formation of cis-divinylcyclopropanes. Due to the boat transition state required for the Cope rearrangement of cis-divinylcyclopropanes, the hydroazulenes are formed with predictable stereocontrol.

  DOI：

  10.1021/jo00002a044

文献信息

• Stereoselective convergent synthesis of hydroazulenes via an intermolecular cyclopropanation/Cope rearrangement
  作者：William R. Cantrell、Huw M. L. Davies

  DOI：10.1021/jo00002a044

  日期：1991.1

  Rhodium(II) acetate catalyzed decomposition of vinyldiazomethane 1 to a vinylcarbenoid intermediate in the presence of oxygenated dienes led to the direct formation of hydroazulenes 7, 13, and 15-19. The 3 + 4 annulation proceeds by a tandem cyclopropanation/Cope rearrangement sequence. The cyclopropanation is highly stereoselective, favoring the formation of cis-divinylcyclopropanes. Due to the boat transition state required for the Cope rearrangement of cis-divinylcyclopropanes, the hydroazulenes are formed with predictable stereocontrol.