diethyl 5-(1'-hydroxyethyl)-2-oxotetrahydrofuran-3-ylphosphonate | 406213-80-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: diethyl 5-(1'-hydroxyethyl)-2-oxotetrahydrofuran-3-ylphosphonate
• 英文别名: 3-[Diethoxy(oxido)phosphaniumyl]-5-(1-hydroxyethyl)oxolan-2-one；3-[diethoxy(oxido)phosphaniumyl]-5-(1-hydroxyethyl)oxolan-2-one
• CAS: 406213-80-7
• 化学式: C₁₀H₁₉O₆P
• 分子量: 266.231
• InChiKey: WFCHBGPHAKJEHY-UHFFFAOYSA-N

物化性质

• 沸点：
  432.6±38.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  88
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 diethyl 5-(1'-hydroxyethyl)-2-oxotetrahydrofuran-3-ylphosphonate 在 potassium carbonate 作用下， 以 水 为溶剂， 反应 0.25h， 生成 (5R*,1'R*)-5-(1'-hydroxyethyl)-3-methylidenetetrahydro-2-furanone 、 (5R*,1'S*)-5-(1'-hydroxyethyl)-3-methylidenetetrahydro-2-furanone
  参考文献：
  名称：

  New Stereocontrolled Synthesis and Biological Evaluation of 5-(1‘-Hydroxyalkyl)-3-methylidenetetrahydro-2-furanones as Potential Cytotoxic Agents

  摘要：

  A series of 3-methylidenetetrahydro-2-furanones 7 bearing various hydroxyalkyl substituents in position 5 were synthesized using novel diastereo- and enantioselective methodology. In vitro cytotoxicity data demonstrated that all prepared compounds were active against L-1210 and HL-60 tissue culture cells with 7e being the most potent (IC50 = 6.9 muM). Also an increase in activity with an increase in lipophilicity of the substituents in the order H < alkyl < phenyl was observed.

  DOI：

  10.1021/jm011019v
• 作为产物：
  描述：

  ethyl 4,5-epoxy-2-diethylphosphorylhexanoate 在 高氯酸 作用下， 生成 diethyl 5-(1'-hydroxyethyl)-2-oxotetrahydrofuran-3-ylphosphonate
  参考文献：
  名称：

  New Stereocontrolled Synthesis and Biological Evaluation of 5-(1‘-Hydroxyalkyl)-3-methylidenetetrahydro-2-furanones as Potential Cytotoxic Agents

  摘要：

  A series of 3-methylidenetetrahydro-2-furanones 7 bearing various hydroxyalkyl substituents in position 5 were synthesized using novel diastereo- and enantioselective methodology. In vitro cytotoxicity data demonstrated that all prepared compounds were active against L-1210 and HL-60 tissue culture cells with 7e being the most potent (IC50 = 6.9 muM). Also an increase in activity with an increase in lipophilicity of the substituents in the order H < alkyl < phenyl was observed.

  DOI：

  10.1021/jm011019v

文献信息

• New Stereocontrolled Synthesis and Biological Evaluation of 5-(1‘-Hydroxyalkyl)-3-methylidenetetrahydro-2-furanones as Potential Cytotoxic Agents
  作者：Tomasz Janecki、Edyta Błaszczyk、Kazimierz Studzian、Marek Różalski、Urszula Krajewska、Anna Janecka

  DOI：10.1021/jm011019v

  日期：2002.2.1

  A series of 3-methylidenetetrahydro-2-furanones 7 bearing various hydroxyalkyl substituents in position 5 were synthesized using novel diastereo- and enantioselective methodology. In vitro cytotoxicity data demonstrated that all prepared compounds were active against L-1210 and HL-60 tissue culture cells with 7e being the most potent (IC50 = 6.9 muM). Also an increase in activity with an increase in lipophilicity of the substituents in the order H < alkyl < phenyl was observed.