3-acetyl-4-hydroxy-2,6-dimethoxyphenyl acetate | 21919-63-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-acetyl-4-hydroxy-2,6-dimethoxyphenyl acetate
• 英文别名: 3-Acetoxy-6-hydroxy-2,4-dimethoxyacetophenone；(3-acetyl-4-hydroxy-2,6-dimethoxyphenyl) acetate
• CAS: 21919-63-1
• 化学式: C₁₂H₁₄O₆
• 分子量: 254.24
• InChiKey: KLEFCRYIDASDQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  3-acetyl-4-hydroxy-2,6-dimethoxyphenyl acetate 在 盐酸 作用下， 生成 1-(3,6-二羟基-2,4-二甲氧基苯基)-乙酮
  参考文献：
  名称：

  Boron Trifluoride-Catalyzed Acetylation of Methoxyhydroxybenzenes¹

  摘要：

  DOI：

  10.1021/jo01050a033
• 作为产物：
  描述：

  4-(acetyloxy)-3,5-dimethoxyphenyl acetate 在 三氯化铝 作用下， 生成 3-acetyl-4-hydroxy-2,6-dimethoxyphenyl acetate
  参考文献：
  名称：

  3-Acetoxy-6-hydroxy-2,4-dimethoxyacetophenone

  摘要：

  The title compound, C12H14O6, has been isolated from a Fries reaction on 3,6-dihydroxy-2,4-dimethoxyacetophenone. Its molecular structure contains an intramolecular hydrogen-bonded unit involving the -COCH3 and -OH substituents. The best plane through the acetoxy group makes a dihedral angle of 88.74(5)degrees with the plane of the aromatic ring.

  DOI：

  10.1107/s0108270197012894

文献信息

• A Practical and Economical High-Yielding, Six-Step Sequence Synthesis of a Flavone: Application to the Multigram-Scale Synthesis of Ladanein
  作者：Xavier Martin-Benlloch、Mourad Elhabiri、Don Antoine Lanfranchi、Elisabeth Davioud-Charvet

  DOI：10.1021/op4003642

  日期：2014.5.16

  Herein we report a short and economic synthesis of the antiviral flavonoid lead ladanein (1). Ladanein is obtained from 2,6-dimethoxyquinone (11) in six steps with 51% overall yield. After a high-yielding reductive acetylation and Fries rearrangement, the flavone skeleton is built by means of a Baker-Venkataraman rearrangement. Throughout the synthetic pathway no chromatographic columns were used, and the reaction products were isolated and purified by optimized work-up and crystallization processes. This new process has been tested on a multigram-scale with an improved overall yield from 16 to 51% through six steps, and three chromatographic purifications used in the earlier synthesis were eliminated.
• 4′,5,6,7-Oxygenated Flavones and Flavanones
  作者：Mason G. Stout、Hans Reich、Max N. Huffman

  DOI：10.1002/jps.2600530218

  日期：1964.2
• Boron Trifluoride-Catalyzed Acetylation of Methoxyhydroxybenzenes¹
  作者：W. J. HORTON、MASON G. STOUT

  DOI：10.1021/jo01050a033

  日期：1962.3
• 3-Acetoxy-6-hydroxy-2,4-dimethoxyacetophenone
  作者：S. Mukherjee、V. S. Parmar、W. Errington

  DOI：10.1107/s0108270197012894

  日期：1998.1.15

  The title compound, C12H14O6, has been isolated from a Fries reaction on 3,6-dihydroxy-2,4-dimethoxyacetophenone. Its molecular structure contains an intramolecular hydrogen-bonded unit involving the -COCH3 and -OH substituents. The best plane through the acetoxy group makes a dihedral angle of 88.74(5)degrees with the plane of the aromatic ring.