diethyl (4-methoxyphenyl)(4-nitrophenyl amino)methylphosphonate | 683231-60-9

• 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 (4-methoxyphenyl)(4-nitrophenyl amino)methylphosphonate
• 英文别名: N-[diethoxyphosphoryl-(4-methoxyphenyl)methyl]-4-nitroaniline
• CAS: 683231-60-9
• 化学式: C₁₈H₂₃N₂O₆P
• 分子量: 394.364
• InChiKey: WXEUMAALRMBCJB-UHFFFAOYSA-N

物化性质

• 熔点：
  115 °C(Solv: ethyl acetate (141-78-6); ligroine (8032-32-4))
• 沸点：
  562.1±50.0 °C(Predicted)
• 密度：
  1.275±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-甲氧基苯甲醛 、 4-硝基苯胺 、 diethyl phosphite 反应 2.5h， 以93%的产率得到diethyl (4-methoxyphenyl)(4-nitrophenyl amino)methylphosphonate
  参考文献：
  名称：

  TfOH / C催化无溶剂条件下的一锅三组分合成α-氨基膦酸酯

  摘要：

  通过简单地将三氟甲磺酸吸收到活性炭上，可以容易地制备TfOH / C。该固体酸在无溶剂条件下通过羰基化合物，胺和亚磷酸二乙酯的Kabachnik-Fields反应被用作合成α-氨基膦酸酯的有效催化剂。

  DOI：

  10.1007/s13738-012-0200-6

文献信息

• Micellar Solution of Sodium Dodecyl Sulfate (SDS) Catalyzes Kabacknik-Fields Reaction in Aqueous Media
  作者：Sara Sobhani、Asieh Vafaee

  DOI：10.1055/s-0029-1216789

  日期：2009.6

  for the one-pot synthesis of diethyl α-aminophosphonates from aldehydes, amines and diethyl phosphite (Kabacknik-Fields reaction) in SDS micellar solution in aqueous media is described. The synthesis of α-aminophosphonates in the present study represents a three-component reaction in which no intermediate formation of either an imine or α-hydroxyphosphonate was observed. aldehydes - amines - α-aminophosphonates

  描述了一种新的，方便且高产的方法，该方法可以在水介质中的SDS胶束溶液中从醛，胺和亚磷酸二乙酯一锅法合成α-氨基膦酸二乙酯（Kabacknik-Fields反应）。在本研究中，α-氨基膦酸酯的合成代表三组分反应，其中未观察到亚胺或α-羟基膦酸酯的中间形成。 醛-胺-α-氨基膦酸酯-胶束-十二烷基硫酸钠-水性介质
• Clean Procedure for the Synthesis of Α-Aminophosphonates Catalyzed by Choline-Based Ionic Liquid
  作者：Huan Peng、Siyu Sun、Yulin Hu、Rong Xing、Dong Fang

  DOI：10.1002/hc.21251

  日期：2015.5

  choline-based ionic liquid [Ch-OSO3H] was prepared and used as a novel catalyst for the synthesis of α-aminophosphonates via a one-pot three-component reaction with aldehydes, amines, and triethyl phosphite/diethyl phosphite at room temperature under solvent-free conditions or in aqueous media. The reaction was completed in short times and products could be simply separated from the reaction mixture in

  制备了一种硫酸化胆碱基离子液体[Ch-OSO3H]，并将其用作一种新型催化剂，在室温下通过与醛、胺和亚磷酸三乙酯/亚磷酸二乙酯的一锅三组分反应合成α-氨基膦酸酯在无溶剂条件下或在水性介质中。反应在短时间内完成，产物可以简单地从反应混合物中分离出来，收率很好。催化剂可以循环使用多次，催化活性不会明显降低。
• Silica Sulfuric Acid as a Recyclable Catalyst for a One-Pot Synthesis of α-Aminophosphonates in Solvent-Free Conditions
  作者：Jing-Jun Yang、Jin-Ning Dang、Yu-Wei Chang

  DOI：10.2174/157017809789124830

  日期：2009.9.1

  A simple and efficient method has been developed for the synthesis of α-aminophosphonates by a one-pot three-component condensation of aldehydes, amines and diethyl phosphite in the presence of a catalytic amount of silica sulfuric acid under solvent-free reaction conditions. The major advantages of the present method are good yields, inexpensive, ecofriendly and reusable catalyst, short reaction times

  已开发出一种简单有效的方法，在无溶剂反应条件下，在催化量的二氧化硅硫酸存在下，通过一锅三组分缩合醛，胺和亚磷酸二乙酯合成α-氨基膦酸酯。本方法的主要优点是产率高，价格便宜，环境友好且可重复使用的催化剂，反应时间短，反应条件温和且无溶剂。
• NbCl5: an efficient catalyst for one-pot synthesis of α-aminophosphonates under solvent-free conditions
  作者：Jun-Tao Hou、Jian-Wu Gao、Zhan-Hui Zhang

  DOI：10.1002/aoc.1687

  日期：2011.1

  NbCl5 has been found to be a very effective catalyst for the synthesis of a variety of α‐aminophosphonates through the Kabachnik–Fields reaction of carbonyl compound, amine and diethyl phosphite under solvent‐free conditions. Copyright © 2010 John Wiley & Sons, Ltd.

  通过无溶剂条件下的羰基化合物，胺和亚磷酸二乙酯的Kabachnik-Fields反应，发现NbCl 5是用于合成多种α-氨基膦酸酯的非常有效的催化剂。版权所有©2010 John Wiley＆Sons，Ltd.
• Silica gel and polystyrene supported aluminum chloride as heterogeneous catalysts for the preparation of α-aminophosphonates
  作者：Kaveh Parvanak Boroujeni、Amir Nasrolahi Shirazi

  DOI：10.1002/hc.20629

  日期：——

  Silica gel supported aluminum chloride (SiO2-AlCl3) and cross-linked polystyrene-supported aluminum chloride (PS-AlCl3) are environment- friendly heterogeneous catalysts for the condensation of amines and aldehydes with diethyl phosphite to afford α-aminophosphonates. These solid acid catalysts are stable (as bench top catalysts) and can be easily recovered and reused without appreciable change in

  硅胶负载的氯化铝 (SiO2-AlCl3) 和交联聚苯乙烯负载的氯化铝 (PS- ) 是环境友好的多相催化剂，用于胺和醛与亚磷酸二乙酯缩合生成 α-氨基膦酸酯。这些固体酸催化剂是稳定的（作为台式催化剂）并且可以很容易地回收和重复使用，而不会显着改变其效率。© 2010 Wiley Periodicals, Inc. 杂原子化学 21:418–422, 2010; 在 wileyonlinelibrary.com 上在线查看这篇文章。DOI 10.1002/hc.20629