(E)-(8-(3,7-dimethylocta-2,6-dienyl)-7-hydroxy-2,2-dimethyl-4-oxo-4H-benzo[d][1,3]dioxin-5-yl)-methyl acetate | 1351221-40-3

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (E)-(8-(3,7-dimethylocta-2,6-dienyl)-7-hydroxy-2,2-dimethyl-4-oxo-4H-benzo[d][1,3]dioxin-5-yl)-methyl acetate
• 英文别名: [8-[(2E)-3,7-dimethylocta-2,6-dienyl]-7-hydroxy-2,2-dimethyl-4-oxo-1,3-benzodioxin-5-yl]methyl acetate
• CAS: 1351221-40-3
• 化学式: C₂₃H₃₀O₆
• 分子量: 402.488
• InChiKey: NFDPBDPURWZQEP-XNTDXEJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-(8-(3,7-dimethylocta-2,6-dienyl)-7-hydroxy-2,2-dimethyl-4-oxo-4H-benzo[d][1,3]dioxin-5-yl)-methyl acetate 在 lithium aluminium tetrahydride 、 caesium carbonate 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 4.0h， 生成 hericenol A
  参考文献：
  名称：

  Total Syntheses of Angelicoin A, Hericenone J, and Hericenol A via Migratory Prenyl- and Geranylation–Aromatization Sequences

  摘要：

  A five-step synthesis of the natural product angelicoin A using a late stage highly regioselective palladium(0)-catalyzed decarboxylative prenyl migration and aromatization sequence as the key step is reported. The method was extended with geranyl migration in eight-step total syntheses of hericenone J and hericenol A from geraniol.

  DOI：

  10.1021/jo202354j
• 作为产物：
  描述：

  [(7E)-5-(2,2-dimethyl-6-oxo-1,3-dioxin-4-yl)-8,12-dimethyl-2,4-dioxotrideca-7,11-dienyl] acetate 在 silica gel 作用下， 以 四氢呋喃 为溶剂， 以660 mg的产率得到(E)-(8-(3,7-dimethylocta-2,6-dienyl)-7-hydroxy-2,2-dimethyl-4-oxo-4H-benzo[d][1,3]dioxin-5-yl)-methyl acetate
  参考文献：
  名称：

  Total Syntheses of Angelicoin A, Hericenone J, and Hericenol A via Migratory Prenyl- and Geranylation–Aromatization Sequences

  摘要：

  A five-step synthesis of the natural product angelicoin A using a late stage highly regioselective palladium(0)-catalyzed decarboxylative prenyl migration and aromatization sequence as the key step is reported. The method was extended with geranyl migration in eight-step total syntheses of hericenone J and hericenol A from geraniol.

  DOI：

  10.1021/jo202354j