diethyl [(anilinocarbonyl)oxy](p-methylthiophenyl)methyl phosphonate | 1322881-48-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: diethyl [(anilinocarbonyl)oxy](p-methylthiophenyl)methyl phosphonate
• 英文别名: alpha-Oxycarbanilinophosphonate, 4d；[diethoxyphosphoryl-(4-methylsulfanylphenyl)methyl] N-phenylcarbamate
• CAS: 1322881-48-0
• 化学式: C₁₉H₂₄NO₅PS
• 分子量: 409.443
• InChiKey: KUEPTDQYGSXBGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  99.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-(甲基巯基)苯甲醛 在 magnesium oxide 作用下， 反应 3.5h， 生成 diethyl [(anilinocarbonyl)oxy](p-methylthiophenyl)methyl phosphonate
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2011.06.057

文献信息

• 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.