[Hydroxy-(4-methylsulfanyl-phenyl)-methyl]-phosphonic acid diethyl ester | 96258-70-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: [Hydroxy-(4-methylsulfanyl-phenyl)-methyl]-phosphonic acid diethyl ester
• 英文别名: diethoxyphosphoryl-(4-methylsulfanylphenyl)methanol
• CAS: 96258-70-7
• 化学式: C₁₂H₁₉O₄PS
• 分子量: 290.32
• InChiKey: DJFXRWRZNUXWJW-UHFFFAOYSA-N

物化性质

• 沸点：
  426.8±45.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.67
• 重原子数：
  18.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  [Hydroxy-(4-methylsulfanyl-phenyl)-methyl]-phosphonic acid diethyl ester 、 间苯二甲醚 在 三氟甲磺酸 作用下， 以 硝基甲烷 为溶剂， 以80%的产率得到diethyl ((2,4-dimethoxyphenyl)(4-(methylthio)phenyl)methyl)phosphonate
  参考文献：
  名称：

  通过 HOTf 催化的 α-芳基 α-羟基膦酸酯的 Friedel-crafts 芳基化方便地合成 α-二芳基甲基膦酸酯

  摘要：

  图形摘要 摘要 我们报告了 α-芳基 α-羟基膦酸酯与各种（杂）芳族化合物的方便的催化 Friedel-Crafts 芳基化。HOTf（三氟甲磺酸）被认为是最好的布朗斯台德酸催化剂，并且以高达 41-95% 的产率获得了所需的 α-二芳基甲基膦酸酯。

  DOI：

  10.1080/10426507.2017.1393424
• 作为产物：
  描述：

  [(4-Methylsulfanyl-phenyl)-trimethylsilanyloxy-methyl]-phosphonic acid diethyl ester 在 三氟乙酸 作用下， 以 甲醇 为溶剂， 生成 [Hydroxy-(4-methylsulfanyl-phenyl)-methyl]-phosphonic acid diethyl ester
  参考文献：
  名称：

  Stabilization demands of diethyl phosphonate substituted carbocations as revealed by substituent effects

  摘要：

  DOI：

  10.1021/jo00212a033

文献信息

• Hydrophosphonylation of aldehydes catalyzed by cyclopentadienyl ruthenium(II) complexes
  作者：Ivânia R. Cabrita、Pedro R. Florindo、Paulo J. Costa、M. Conceição Oliveira、Ana C. Fernandes

  DOI：10.1016/j.mcat.2018.03.001

  日期：2018.5

  This work reports the first method for the synthesis of α-hydroxyphosphonates from aldehydes catalyzed by cyclopentadienyl ruthenium(II) complexes. The best results were obtained using the system HP(O)(OEt)2/[RuClCp(PPh3)2] (5 mol%), affording the α-hydroxyphosphonates in good to excellent yields with high chemoselectivity. The catalyst [RuClCp(PPh3)2] can be used for at least 12 catalytic cycles with

  这项工作报告了由环戊二烯基钌（II）络合物催化的醛合成α-羟基膦酸酯的第一种方法。使用系统HP（O）（OEt）2 / [RuClCp（PPh 3）2 ]（5 mol％）可获得最佳结果，从而以良好的化学选择性提供了高至优异产率的α-羟基膦酸酯。催化剂[RuClCp（PPh 3）2 ]可以以优异的活性用于至少12个催化循环，并且反应在无溶剂条件下进行。进行DFT计算以合理化机理，显示与H-膦酸酯互变异构体HP（O）（OR）2相关的屏障高得离谱。这使我们建议将催化剂促进朝亚磷酸酯，P的互变异构（OH）（OR）2，经由P-原子协调，其占所观察到的反应性。
• Ultrasound-assisted one-pot synthesis of α-oxycarbanilinophosphonates via a three-component condensation of an aldehyde, diethyl phosphite and an isocyanate under solvent-free conditions
  作者：Babak Kaboudin、Maryam Fallahi

  DOI：10.1016/j.tetlet.2011.06.057

  日期：2011.8

  An efficient one-pot method has been developed for the synthesis of alpha-oxycarbanilinophosphonates via a one-pot reaction of an aldehyde with diethyl phosphite in the presence of magnesium oxide followed by reaction with an isocyanate under solvent-free conditions using ultrasonic irradiation. This method is simple, rapid and good yielding. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis of α-oxycarbanilinophosphonates and their anticholinesterase activities: the most potent derivative is bound to the peripheral site of acetylcholinesterase
  作者：Babak Kaboudin、Saeed Emadi、Mohammad Reza Faghihi、Maryam Fallahi、Vahid Sheikh-Hasani

  DOI：10.3109/14756366.2012.663362

  日期：2013.6.1

  A novel method has been developed for the synthesis of alpha-oxycarbanilino phosphonates through a reaction of alpha-hydroxyphosphonates with isocyanate under microwave irradiation. The synthesized compounds were evaluated for their acetylcholinesterase (AChE) inhibition potency through IC50 determination. Molecular modelling studies suggest that the most potent inhibitor (compound 4h, IC50 = 6.36 mu M) is bound to the peripheral site of AChE, which suggests that it decreases the catalytic activity not through binding to the active site but through blocking the entrance of the active site gorge. This puts forward the potential of compound 4h and its derivatives to be used in the design of dual inhibitors: inhibition of the catalytic activity of AChE and of amyloid beta aggregation.