3-benzyloxy-2-methyl-5-phenyl-4H-pyran-4-one | 152804-80-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 3-benzyloxy-2-methyl-5-phenyl-4H-pyran-4-one
• 英文别名: 2-Methyl-5-phenyl-3-phenylmethoxypyran-4-one
• CAS: 152804-80-3
• 化学式: C₁₉H₁₆O₃
• 分子量: 292.334
• InChiKey: OGUOYHHBAPYWCE-UHFFFAOYSA-N

物化性质

• 沸点：
  515.7±50.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-benzyloxy-2-methyl-5-phenyl-4H-pyran-4-one 在 selenium(IV) oxide 作用下， 以 various solvent(s) 为溶剂， 反应 12.0h， 生成 3-Benzyloxy-4-oxo-5-phenyl-4H-pyran-2-carbaldehyde
  参考文献：
  名称：

  The monoethyl ester of meconic acid is an active site inhibitor of HCV NS5B RNA-dependent RNA polymerase

  摘要：

  Screening of the in-house sample collection for compounds with HCV NS5B RNA dependent RNA polymerase inhibition led to the identification of a new lead. Afterwards, we discovered that the screening lead, rather than containing the expected structure 1, was comprised of roughly a 1:1 mixture of meconic acid 2 and its monoethyl ester 3, with all inhibitory potency residing with 3. We propose that this compound shares critical common features for activity with alpha,gamma-diketoacids inhibitors previously discovered by our group. SAR around this molecule will be presented to provide an improved basis for structure-based ligand design. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.087
• 作为产物：
  描述：

  5-溴-3-羟基-2-甲基吡喃-4-酮 在 四(三苯基膦)钯 、 双氧水 、 sodium hydride 、 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 3-benzyloxy-2-methyl-5-phenyl-4H-pyran-4-one
  参考文献：
  名称：

  Synthesis of 5-Aryl-3-hydroxy-4H-pyran-4-ones

  摘要：

  The palladium-catalyzed coupling reaction of 3-benzyl-oxy-5-bromo-2-methyl-4H-pyran-4-one (2b) with phenylboronic acid afforded efficiently 3-benzyloxy-2-methyl-5-phenyl-4H-pyran-4-one (3b-1), and the benzyloxy group of the resultant product was cleaved by hydrolysis with conc. hydrochloric acid in acetic acid to give 5-phenyl-3-hydroxy-2-methyl-4H-pyran-4-one (4b-1) in high yield. This method was applicable as a general method for synthesizing 5-aryl-3-hydroxy-4H-pyran-4-ones (4) from the 5-bromo-4H-pyran-4-ones(1).

  DOI：

  10.3987/com-93-6364

文献信息

• The monoethyl ester of meconic acid is an active site inhibitor of HCV NS5B RNA-dependent RNA polymerase
  作者：Paola Pace、Emanuela Nizi、Barbara Pacini、Silvia Pesci、Victor Matassa、Raffaele De Francesco、Sergio Altamura、Vincenzo Summa

  DOI：10.1016/j.bmcl.2004.03.087

  日期：2004.6

  Screening of the in-house sample collection for compounds with HCV NS5B RNA dependent RNA polymerase inhibition led to the identification of a new lead. Afterwards, we discovered that the screening lead, rather than containing the expected structure 1, was comprised of roughly a 1:1 mixture of meconic acid 2 and its monoethyl ester 3, with all inhibitory potency residing with 3. We propose that this compound shares critical common features for activity with alpha,gamma-diketoacids inhibitors previously discovered by our group. SAR around this molecule will be presented to provide an improved basis for structure-based ligand design. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis of 5-Aryl-3-hydroxy-4H-pyran-4-ones
  作者：Hisashi Takao、Yoshinori Endo、Tokunaru Horie

  DOI：10.3987/com-93-6364

  日期：——

  The palladium-catalyzed coupling reaction of 3-benzyl-oxy-5-bromo-2-methyl-4H-pyran-4-one (2b) with phenylboronic acid afforded efficiently 3-benzyloxy-2-methyl-5-phenyl-4H-pyran-4-one (3b-1), and the benzyloxy group of the resultant product was cleaved by hydrolysis with conc. hydrochloric acid in acetic acid to give 5-phenyl-3-hydroxy-2-methyl-4H-pyran-4-one (4b-1) in high yield. This method was applicable as a general method for synthesizing 5-aryl-3-hydroxy-4H-pyran-4-ones (4) from the 5-bromo-4H-pyran-4-ones(1).