diethyl 1-fluoro-2-(tert-butyldisulfanyl)-2-(methylsulfanyl)vinylphosphonate

• 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 1-fluoro-2-(tert-butyldisulfanyl)-2-(methylsulfanyl)vinylphosphonate
• 英文别名: 2-[[(Z)-2-diethoxyphosphoryl-2-fluoro-1-methylsulfanylethenyl]disulfanyl]-2-methylpropane
• 化学式: C₁₁H₂₂FO₃PS₃
• 分子量: 348.464
• InChiKey: WNDHVYRLRJTVPK-KTKRTIGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  二氟甲基膦酸二乙酯 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.08h， 生成 diethyl 1-fluoro-2-(tert-butyldisulfanyl)-2-(methylsulfanyl)vinylphosphonate
  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.