methyl (diethoxyphosphoryl)fluoroethanedithioate | 409328-59-2

• 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: methyl (diethoxyphosphoryl)fluoroethanedithioate
• 英文别名: methyl diethoxyphosphorylfluorodithioacetate；Wyhueevfbspdle-uhfffaoysa-；methyl 2-diethoxyphosphoryl-2-fluoroethanedithioate
• CAS: 409328-59-2
• 化学式: C₇H₁₄FO₃PS₂
• 分子量: 260.291
• InChiKey: WYHUEEVFBSPDLE-UHFFFAOYSA-N

物化性质

• 沸点：
  321.5±37.0 °C(predicted)
• 密度：
  1.265±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  92.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-溴乙胺氢溴酸盐 、 methyl (diethoxyphosphoryl)fluoroethanedithioate 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以87%的产率得到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 、 乙硫醇 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 16.58h， 生成 methyl (diethoxyphosphoryl)fluoroethanedithioate
  参考文献：
  名称：

  Efficient synthesis of fluorothiosparfosic acid analogues with potential antitumoral activity

  摘要：

  In this paper, we describe a short synthesis of N-(phosphonoacetyl)-L-aspartate (PALA) analogues. The mono- and difluorinated thioacetamide precursors were prepared in one step from methyl (diethoxyphosphono)di- and monofluoromethyldithioacetates 8 and 11 as starting materials. Antiproliferating properties on a L1210 strain and ATCase inhibition of these new compounds are disclosed. ThioPALA(FF) 5c showed a remarkable cytotoxic activity towards murine leukemia L1210, when used as tetraester. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.05.026

文献信息

• Redox and spin-trapping properties of phosphoryldithioacetates
  作者：Angelo Alberti、Maurizio Guerra、Philippe Hapiot、Thierry Lequeux、Dante Macciantelli、Serge Masson

  DOI：10.1039/b414998j

  日期：——

  Addition of free radicals to the three dithioesters led to the detection of the ESR spectra of the spin adducts only with the last two compounds. Based on the reduction potentials of the three dithioacetates, this may be explained by capto-dative stabilization of the adducts. On the basis of DFT calculations, the temperature dependent variations of the spectral patterns exhibited by the radicals were attributed

  通过循环伏安法测量二乙氧基磷酰基二硫代乙酸乙酯（1），二乙氧基磷酰基氟二硫代乙酸甲酯（2）和二乙氧基磷酰基二氟二硫代乙酸甲酯（3）的氧化还原性质。在三个二硫代酸酯中添加自由基导致仅对最后两种化合物检测到自旋加合物的ESR光谱。基于三种二硫代乙酸酯的还原电位，这可以通过加合物的键合-稳定性加以解释。基于DFT计算，由自由基显示的光谱图案的温度依赖性变化归因于围绕Calpha-SMe键的受限旋转。
• Synthesis of Thiazolines Linked to a Difluoromethylphosphonate Diester via Dithioester Chemistry
  作者：Emmanuel Pfund、Thierry Lequeux、Serge Masson、Michel Vazeux

  DOI：10.1021/ol025544f

  日期：2002.3.1

  A two-step, high-yielding synthesis of Delta(2)-thiazolines containing a difluoromethylphosphonate diester moiety has been devised using a building block approach. Racemic or chiral beta-amino alcohols and diols were coupled with methyl difluoro(diethoxyphosphono)dithioacetate to give predominantly the corresponding beta-hydroxythioamides, which were then cyclized to provide a series of novel substituted Delta(2)-thiazolines.
• 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.
• Efficient synthesis of fluorothiosparfosic acid analogues with potential antitumoral activity
  作者：Emmanuel Pfund、Thierry Lequeux、Serge Masson、Michel Vazeux、Alex Cordi、Alain Pierre、Valérie Serre、Guy Hervé

  DOI：10.1016/j.bmc.2005.05.026

  日期：2005.8

  In this paper, we describe a short synthesis of N-(phosphonoacetyl)-L-aspartate (PALA) analogues. The mono- and difluorinated thioacetamide precursors were prepared in one step from methyl (diethoxyphosphono)di- and monofluoromethyldithioacetates 8 and 11 as starting materials. Antiproliferating properties on a L1210 strain and ATCase inhibition of these new compounds are disclosed. ThioPALA(FF) 5c showed a remarkable cytotoxic activity towards murine leukemia L1210, when used as tetraester. (c) 2005 Elsevier Ltd. All rights reserved.

表征谱图