ethyl 2-fluoro-4-[5-(tert-butyldiphenylsilanyloxy)-pentylselanyl]-phenyloxyacetate | 831223-28-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 2-fluoro-4-[5-(tert-butyldiphenylsilanyloxy)-pentylselanyl]-phenyloxyacetate
• CAS: 831223-28-0
• 化学式: C₃₁H₃₉FO₄SeSi
• 分子量: 601.692
• InChiKey: FDHWYNSLQNUGON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.26
• 重原子数：
  38.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-fluoro-4-[5-(tert-butyldiphenylsilanyloxy)-pentylselanyl]-phenyloxyacetate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 3.0h， 以100%的产率得到2-fluoro-4-[5-(tert-butyldiphenylsilanyloxy)-pentylselanyl]-phenyloxyacetic acid
  参考文献：
  名称：

  A Fluorinated Selenide Linker for Solid-Phase Synthesis of n-Pentenyl Glycosides

  摘要：

  A fluorine-labeled selenide linker for installing terminal isolated olefins has been synthesized in high overall yield. The resin-bound linker could be glycosylated both with glycosyl trichloroacetimidates and glycosyl fluorides. The linker did not decompose after oxidation with tBuOOH but underwent beta-elimination when it was subjected to heat. This allowed the released n-pentenyl glycoside 15 to be isolated in excellent yield and purity after filtration.

  DOI：

  10.1021/ol048053z
• 作为产物：
  描述：

  4-溴-2-氟苯酚 在 叔丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 4.33h， 生成 ethyl 2-fluoro-4-[5-(tert-butyldiphenylsilanyloxy)-pentylselanyl]-phenyloxyacetate
  参考文献：
  名称：

  A Fluorinated Selenide Linker for Solid-Phase Synthesis of n-Pentenyl Glycosides

  摘要：

  A fluorine-labeled selenide linker for installing terminal isolated olefins has been synthesized in high overall yield. The resin-bound linker could be glycosylated both with glycosyl trichloroacetimidates and glycosyl fluorides. The linker did not decompose after oxidation with tBuOOH but underwent beta-elimination when it was subjected to heat. This allowed the released n-pentenyl glycoside 15 to be isolated in excellent yield and purity after filtration.

  DOI：

  10.1021/ol048053z