8,9-dimethoxy-7-phenyl-3-oxatricyclo<8.2.0.0^1,5>dodeca-5,9,11-trien-4-one | 144744-73-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 8,9-dimethoxy-7-phenyl-3-oxatricyclo<8.2.0.0^1,5>dodeca-5,9,11-trien-4-one
• 英文别名: (1R,7R,8R)-8,9-dimethoxy-7-phenyl-3-oxatricyclo[6.2.2.01,5]dodeca-5,9,11-trien-4-one
• CAS: 144744-73-0
• 化学式: C₁₉H₁₈O₄
• 分子量: 310.35
• InChiKey: KRQGKCIGQXFHQB-MDASCCDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8,9-dimethoxy-7-phenyl-3-oxatricyclo<8.2.0.0^1,5>dodeca-5,9,11-trien-4-one 以 苯 为溶剂， 反应 24.0h， 以78%的产率得到3,4-dimethoxy-7-phenyl-11-oxatricyclo<7.3.0.01,6>dodeca-2,4,8-trien-10-one
  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
• 作为产物：
  描述：

  7-(2-phenylethenyl)-3,4-dimethoxy-9-oxatricyclo<5.3.0.0^1,6>deca-2,4-dien-8-one 以 氘代氯仿 为溶剂， 反应 72.0h， 生成 8,9-dimethoxy-7-phenyl-3-oxatricyclo<8.2.0.0^1,5>dodeca-5,9,11-trien-4-one
  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