(5R)-5-[(R)-hydroxy(phenyl)methyl]-3-methylideneoxolan-2-one | 350797-13-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (5R)-5-[(R)-hydroxy(phenyl)methyl]-3-methylideneoxolan-2-one
• CAS: 350797-13-6
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: SUHPYVRPWRNIIZ-GHMZBOCLSA-N

物化性质

• 沸点：
  397.0±30.0 °C(predicted)
• 密度：
  1.22±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-methoxytrifluoromethylphenylacetyl chloride 、 (5R)-5-[(R)-hydroxy(phenyl)methyl]-3-methylideneoxolan-2-one 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 生成 、
  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：

  (E)-2-diethylphosphoryl-5-phenyl-4-pentenoic acid 在 AD-mix-β 、 potassium carbonate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 48.25h， 生成 (5R)-5-[(R)-hydroxy(phenyl)methyl]-3-methylideneoxolan-2-one
  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

• Stereocontrolled synthesis of 5-(1′-hydroxyalkyl)-3-methylidenetetrahydro-2-furanones
  作者：Tomasz Janecki、Edyta Błaszczyk

  DOI：10.1016/s0040-4039(01)00316-1

  日期：2001.4

  Diastereo- and enantioselective synthesis of 5-(1′-hydroxyalkyl)-3-methylidenetetrahydro-2-furanones from 2-diethoxyphosphoryl-4-alkenoic acids or 2-diethoxyphosphoryl-4-alkenoates was readily accomplished using novel methodology involving syn- or anti-dihydroxylation procedures combined with Horner–Wadsworth–Emmons olefination techniques.

  Diastereo-和5-对映选择性合成（1'-羟基烷基）-3- methylidenetetrahydro -2-呋喃酮由2-二乙氧基磷酰基-4-链烯酸或2-二乙氧基磷酰基-4-烯酸酯使用涉及新颖的方法可以容易地完成顺式-或反-二羟基化方法与Horner-Wadsworth-Emmons烯化技术相结合。
• 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.