4-[2-(tert-butyldimethylsilanyloxy)-ethyl]-3-fluoro-5,6-dihydropyran-2-one | 552308-04-0

• 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: 4-[2-(tert-butyldimethylsilanyloxy)-ethyl]-3-fluoro-5,6-dihydropyran-2-one
• CAS: 552308-04-0
• 化学式: C₁₃H₂₃FO₃Si
• 分子量: 274.408
• InChiKey: IHQFZZQQJQXPFS-UHFFFAOYSA-N

物化性质

• 沸点：
  328.0±42.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.57
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-[2-(tert-butyldimethylsilanyloxy)-ethyl]-3-fluoro-5,6-dihydropyran-2-one 在 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以94%的产率得到3-[2-(tert-butyldimethylsilanyloxy)-ethyl]-2-fluoropent-2-ene-1,5-diol
  参考文献：
  名称：

  Synthesis and Incorporation into PNA of Fluorinated Olefinic PNA (F-OPA) Monomers

  摘要：

  [GRAPHIC]A fluorinated OPA monomer containing the base thymine ((Z)-t-F-OPA) was synthesized in 12 steps, featuring a highly selective allylic over homoallylic Mitsunobu substitution for the introduction of the nucleobase. F-OPA modified PNA decamers were prepared by the MMTr/acyl protection strategy. The thermal stability of duplexes of PNA decamers containing (2)-t-F-OPA units with antiparallel complementary DNA was measured. We found a strong dependence of stability from the sequential position of the (2)-t-F-OPA units, ranging from DeltaT(m) of +2.4 to -8.1 degreesC/modification relative to unmodified PNA.

  DOI：

  10.1021/ol034579s
• 作为产物：
  描述：

  2-fluoro-5-[(4-methoxyphenyl)diphenylmethoxy]-3-{2-[(4-methoxyphenyl)diphenyl-methoxy]ethyl}-pent-2-enoic acid ethyl ester 在 咪唑 、 三氯化硼 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 4-[2-(tert-butyldimethylsilanyloxy)-ethyl]-3-fluoro-5,6-dihydropyran-2-one
  参考文献：
  名称：

  Synthesis and Incorporation into PNA of Fluorinated Olefinic PNA (F-OPA) Monomers

  摘要：

  [GRAPHIC]A fluorinated OPA monomer containing the base thymine ((Z)-t-F-OPA) was synthesized in 12 steps, featuring a highly selective allylic over homoallylic Mitsunobu substitution for the introduction of the nucleobase. F-OPA modified PNA decamers were prepared by the MMTr/acyl protection strategy. The thermal stability of duplexes of PNA decamers containing (2)-t-F-OPA units with antiparallel complementary DNA was measured. We found a strong dependence of stability from the sequential position of the (2)-t-F-OPA units, ranging from DeltaT(m) of +2.4 to -8.1 degreesC/modification relative to unmodified PNA.

  DOI：

  10.1021/ol034579s