(R)-7-hydroxy-5-(2-hydroxypropyl)-2,2-dimethyl-8-(3-methylbut-2-enyl)-4H-benzo[d][1,3]dioxin-4-one | 1334485-25-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: (R)-7-hydroxy-5-(2-hydroxypropyl)-2,2-dimethyl-8-(3-methylbut-2-enyl)-4H-benzo[d][1,3]dioxin-4-one
• CAS: 1334485-25-4
• 化学式: C₁₈H₂₄O₅
• 分子量: 320.386
• InChiKey: GXOLKWNLUNOZQI-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  75.99
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (R)-7-hydroxy-5-(2-hydroxypropyl)-2,2-dimethyl-8-(3-methylbut-2-enyl)-4H-benzo[d][1,3]dioxin-4-one 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 以90%的产率得到angelicoin 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：

  (R)-7-hydroxy-2,2-dimethyl-8-(3-methylbut-2-enyl)-5-(2-(tri-isopropylsilyloxy)propyl)-4H-benzo[d][1,3]dioxin-4-one 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以97%的产率得到(R)-7-hydroxy-5-(2-hydroxypropyl)-2,2-dimethyl-8-(3-methylbut-2-enyl)-4H-benzo[d][1,3]dioxin-4-one
  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

文献信息

• Biomimetic Total Synthesis of Angelicoin A and B via a Palladium-Catalyzed Decarboxylative Prenylation-Aromatization Sequence
  作者：Katie Anderson、Frederick Calo、Toni Pfaffeneder、Andrew J. P. White、Anthony G. M. Barrett

  DOI：10.1021/ol202320m

  日期：2011.11.4

  Five-step total syntheses of angelicoin A and B from 2,2,6-trimethyl-4-dioxinone are reported using late stage biomimetic aromatization reactions via diketo-dioxinones as intermediates. In addition, with angelicoin A, this aromatization was coupled with a palladium-catalyzed decarboxylative prenylation in a one-pot sequence as the key step.