diethyl (4,5-dihydro-1,3-thiazol-2-yl)fluoromethylphosphonate | 735333-17-2

• 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 (4,5-dihydro-1,3-thiazol-2-yl)fluoromethylphosphonate
• 英文别名: Nnebrqpcehpwed-uhfffaoysa-；2-[diethoxyphosphoryl(fluoro)methyl]-4,5-dihydro-1,3-thiazole
• CAS: 735333-17-2
• 化学式: C₈H₁₅FNO₃PS
• 分子量: 255.25
• InChiKey: NNEBRQPCEHPWED-UHFFFAOYSA-N

物化性质

• 沸点：
  320.0±37.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  73.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,2:3,4-di-O-isopropylidene-α-D-galacto-hexodialdo-1,5-pyranose 、 diethyl (4,5-dihydro-1,3-thiazol-2-yl)fluoromethylphosphonate 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以79%的产率得到2-[(E)-1-Fluoro-2-((3aR,5S,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-vinyl]-4,5-dihydro-thiazole
  参考文献：
  名称：

  Syntheses of α-Fluoro-α,β-unsaturated Thioamides and Thiazolines from a Fluorophosphonodithioacetate

  摘要：

  A high-yielding synthesis of methyl fluoro(diethoxyphosphono)dithioacetate starting from its difluorinated analogue is reported. Fluorophosphonothioacetamides and -methylthiazolines, prepared from this new dithioester, have been successfully transformed into highly functionalized fluoroalkenes. Good stereoselectivity in favor of the E isomer was observed from the fluorophosphonomethylthiazolines. The potential of these new fluorinated olefinating reagents for the synthesis of modified peptides and glycosides is also disclosed.

  DOI：

  10.1021/jo049560x
• 作为产物：
  描述：

  diethyl 1-fluoro-2-(tert-butyldisulfanyl)-2-(methylsulfanyl)vinylphosphonate 在 正丁基锂 、 三乙胺 、 乙硫醇 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 diethyl (4,5-dihydro-1,3-thiazol-2-yl)fluoromethylphosphonate
  参考文献：
  名称：

  Syntheses of α-Fluoro-α,β-unsaturated Thioamides and Thiazolines from a Fluorophosphonodithioacetate

  摘要：

  A high-yielding synthesis of methyl fluoro(diethoxyphosphono)dithioacetate starting from its difluorinated analogue is reported. Fluorophosphonothioacetamides and -methylthiazolines, prepared from this new dithioester, have been successfully transformed into highly functionalized fluoroalkenes. Good stereoselectivity in favor of the E isomer was observed from the fluorophosphonomethylthiazolines. The potential of these new fluorinated olefinating reagents for the synthesis of modified peptides and glycosides is also disclosed.

  DOI：

  10.1021/jo049560x

文献信息

• Syntheses of α-Fluoro-α,β-unsaturated Thioamides and Thiazolines from a Fluorophosphonodithioacetate
  作者：Emmanuel Pfund、Serge Masson、Michel Vazeux、Thierry Lequeux

  DOI：10.1021/jo049560x

  日期：2004.7.1

  A high-yielding synthesis of methyl fluoro(diethoxyphosphono)dithioacetate starting from its difluorinated analogue is reported. Fluorophosphonothioacetamides and -methylthiazolines, prepared from this new dithioester, have been successfully transformed into highly functionalized fluoroalkenes. Good stereoselectivity in favor of the E isomer was observed from the fluorophosphonomethylthiazolines. The potential of these new fluorinated olefinating reagents for the synthesis of modified peptides and glycosides is also disclosed.

表征谱图