diethyl 8-methoxytricyclo<6.3.2.0^2,7>trideca-2,3,5,10,12-pentaene-9,11-dicarboxylate | 144766-15-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: diethyl 8-methoxytricyclo<6.3.2.0^2,7>trideca-2,3,5,10,12-pentaene-9,11-dicarboxylate
• 英文别名: diethyl 8-methoxytricyclo[6.3.2.0^2,7]trideca-2,3,5,10,12-pentaene-9,11-dicarboxylate；diethyl (1S,8R,11S)-1-methoxytricyclo[6.3.2.02,7]trideca-2,4,6,9,12-pentaene-9,11-dicarboxylate
• CAS: 144766-15-4
• 化学式: C₂₀H₂₂O₅
• 分子量: 342.392
• InChiKey: HMSKNWFXGRMSFC-YXKFXFPPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.86
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  diethyl 4-diazo-2-pentenedioate 、 1-甲氧基萘 在 dirhodium tetraacetate 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以39%的产率得到diethyl 8-methoxytricyclo<6.3.2.0^2,7>trideca-2,3,5,10,12-pentaene-9,11-dicarboxylate
  参考文献：
  名称：

  Divergent reaction pathways between rhodium(II)-stabilized vinylcarbenoids and benzenes

  摘要：

  Rhodium(II) carboxylate stabilized vinylcarbenoids reacted intermolecularly with benzenoid compounds by two distinct modes. With benzene, alkylbenzenes, and 1-methoxynaphthalene, 3 + 4 annulations were observed, presumably arising through initial cyclopropanation followed by a Cope rearrangement. In contrast, alkylation products were formed with methoxy-substituted benzenes. In an intramolecular reaction a delicate balance existed between norcaradiene formation, 3 + 4 annulation, and 3 + 2 annulation.

  DOI：

  10.1021/jo00051a041