methyl N-[2-(diethoxyphosphoryl)-2-fluoroethanethioyl]phenylalaninate | 735333-16-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl N-[2-(diethoxyphosphoryl)-2-fluoroethanethioyl]phenylalaninate
• 英文别名: methyl (2S)-2-[(2-diethoxyphosphoryl-2-fluoroethanethioyl)amino]-3-phenylpropanoate
• CAS: 735333-16-1
• 化学式: C₁₆H₂₃FNO₅PS
• 分子量: 391.4
• InChiKey: YQVDNSHWDDPYRM-LSLKUGRBSA-N

物化性质

• 沸点：
  484.8±55.0 °C(predicted)
• 密度：
  1.243±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  乙醛酸乙酯 、 methyl N-[2-(diethoxyphosphoryl)-2-fluoroethanethioyl]phenylalaninate 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 methyl (E)-N-[4-ethoxy-2-fluoro-4-oxobut-2-enethioyl]phenylalaninate 、 methyl (Z)-N-[4-ethoxy-2-fluoro-4-oxobut-2-enethioyl]phenylalaninate
  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 、 乙硫醇 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 31.58h， 生成 methyl N-[2-(diethoxyphosphoryl)-2-fluoroethanethioyl]phenylalaninate
  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.