dimethyl (5-(benzyloxy)-4-oxo-4H-pyran-2-yl)methylphosphonate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: dimethyl (5-(benzyloxy)-4-oxo-4H-pyran-2-yl)methylphosphonate
• 英文别名: 2-[[Dimethoxy(oxido)phosphaniumyl]methyl]-5-phenylmethoxypyran-4-one；2-[[dimethoxy(oxido)phosphaniumyl]methyl]-5-phenylmethoxypyran-4-one
• 化学式: C₁₅H₁₇O₆P
• 分子量: 324.27
• InChiKey: ODOCSTPFLVGKIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  77
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  dimethyl (5-(benzyloxy)-4-oxo-4H-pyran-2-yl)methylphosphonate 在 盐酸 、 5%-palladium/activated carbon 、 氢气 、 sodium hydride 、 溶剂黄146 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙酸乙酯 为溶剂， 100.0 ℃ 、101.33 kPa 条件下， 反应 61.17h， 生成 5-hydroxy-2-phenethyl-4H-pyran-4-one
  参考文献：
  名称：

  Synthesis of kojic acid derivatives as secondary binding site probes of d-amino acid oxidase

  摘要：

  A series of kojic acid (5-hydroxy-2-hydroxymethyl-4H-pyran-4-one) derivatives were synthesized and tested for their ability to inhibit D-amino acid oxidase (DAAO). Various substituents were incorporated into kojic acid at its 2-hydroxymethyl group. These analogs serve as useful molecular probes to explore the secondary binding site, which can be exploited in designing more potent DAAO inhibitors. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.04.062
• 作为产物：
  描述：

  5-（苄氧基-2-（羟甲基)-4H-吡喃-4-酮 在 氯化亚砜 作用下， 生成 dimethyl (5-(benzyloxy)-4-oxo-4H-pyran-2-yl)methylphosphonate
  参考文献：
  名称：

  两种含二茂铁的铁螯合剂的设计，合成和氧化还原性能

  摘要：

  由去铁胺B和曲酸合成了两种含二茂铁的铁（III）螯合剂，并在有和没有铁离子存在的条件下，在乙腈中研究了它们的电子吸收和电化学性质。结果表明，由于竞争性氧化还原和络合过程的发生，产生了复杂的行为。这样的系统是朝化学传感器的方向迈出的第一步，该化学传感器用于溶液中铁（III）的电化学检测。

  DOI：

  10.1016/j.tetlet.2006.03.088

文献信息

• Synthesis of kojic acid derivatives as secondary binding site probes of d-amino acid oxidase
  作者：Mithun Raje、Niyada Hin、Bridget Duvall、Dana V. Ferraris、James F. Berry、Ajit G. Thomas、Jesse Alt、Camilo Rojas、Barbara S. Slusher、Takashi Tsukamoto

  DOI：10.1016/j.bmcl.2013.04.062

  日期：2013.7

  A series of kojic acid (5-hydroxy-2-hydroxymethyl-4H-pyran-4-one) derivatives were synthesized and tested for their ability to inhibit D-amino acid oxidase (DAAO). Various substituents were incorporated into kojic acid at its 2-hydroxymethyl group. These analogs serve as useful molecular probes to explore the secondary binding site, which can be exploited in designing more potent DAAO inhibitors. (c) 2013 Elsevier Ltd. All rights reserved.
• Design, synthesis and redox properties of two ferrocene-containing iron chelators
  作者：Fabrice Moggia、Hugues Brisset、Frédéric Fages、Carole Chaix、Bernard Mandrand、Marylène Dias、Eric Levillain

  DOI：10.1016/j.tetlet.2006.03.088

  日期：2006.5

  chelators were synthesized from desferrioxamine B and kojic acid and their electronic absorption and electrochemical properties were studied in acetonitrile in the absence and presence of ferric ions. The results show a complex behavior arising from the occurrence of competing redox and complexation processes. Such systems are a first step toward the generation of chemosensors for the electrochemical

  由去铁胺B和曲酸合成了两种含二茂铁的铁（III）螯合剂，并在有和没有铁离子存在的条件下，在乙腈中研究了它们的电子吸收和电化学性质。结果表明，由于竞争性氧化还原和络合过程的发生，产生了复杂的行为。这样的系统是朝化学传感器的方向迈出的第一步，该化学传感器用于溶液中铁（III）的电化学检测。