diethyl 1-hydroxy-3-(2-nitrophenyl)allyl phosphonate | 1239307-41-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: diethyl 1-hydroxy-3-(2-nitrophenyl)allyl phosphonate
• CAS: 1239307-41-5
• 化学式: C₁₃H₁₈NO₆P
• 分子量: 315.263
• InChiKey: ZDDCJNFADDJSAJ-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  diethyl 1-hydroxy-3-(2-nitrophenyl)allyl phosphonate 、 异氰酸苯酯 在 magnesium oxide 作用下， 反应 2.0h， 生成 diethyl [(anilinocarbonyl)oxy]-3-(2-nitrophenyl)allyl 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
• 作为产物：
  描述：

  亚磷酸二乙酯 、 邻硝基肉桂醛 在 magnesium oxide 作用下， 反应 2.0h， 生成 diethyl 1-hydroxy-3-(2-nitrophenyl)allyl phosphonate
  参考文献：
  名称：

  Synthesis of α-oxycarbanilinophosphonates and their anticholinesterase activities: the most potent derivative is bound to the peripheral site of acetylcholinesterase

  摘要：

  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.

  DOI：

  10.3109/14756366.2012.663362