diethyl (4-methoxyphenyl)-N-(4-fluorophenyl)aminomethylphosphonate | 1036406-57-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: diethyl (4-methoxyphenyl)-N-(4-fluorophenyl)aminomethylphosphonate
• 英文别名: N-[[diethoxy(oxido)phosphaniumyl]-(4-methoxyphenyl)methyl]-4-fluoroaniline
• CAS: 1036406-57-1
• 化学式: C₁₈H₂₃FNO₄P
• 分子量: 367.357
• InChiKey: WBPYLCKEQLUIAM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 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：
  62.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-甲氧基苯甲醛 、 亚磷酸二乙酯 、 4-氟苯胺 在 [psmim][HSO₄] 作用下， 以 水 为溶剂， 反应 1.0h， 以82%的产率得到diethyl (4-methoxyphenyl)-N-(4-fluorophenyl)aminomethylphosphonate
  参考文献：
  名称：

  SO3H 功能化离子液体在水性介质中催化合成 α-氨基膦酸酯

  摘要：

  制备了 SO3H 官能化的无卤离子液体，并将其用作高效且可回收的催化剂，用于在室温下通过水介质中的一锅三组分缩合反应合成 α-氨基膦酸酯，产率高达 80-96%。后处理简单，催化剂可重复使用至少六次，催化活性不会明显降低。© 2010 Wiley Periodicals, Inc. 杂原子化学 21:546–550, 2010; 在 wileyonlinelibrary.com 上在线查看这篇文章。DOI 10.1002/hc.20644

  DOI：

  10.1002/hc.20644

文献信息

• Catalyst and solvent-free, ultrasound promoted rapid protocol for the one-pot synthesis of α-aminophosphonates at room temperature
  作者：Bashir Dar、Amrinder Singh、Akshya Sahu、Praveen Patidar、Arup Chakraborty、Meena Sharma、Baldev Singh

  DOI：10.1016/j.tetlet.2012.07.123

  日期：2012.10

  An ultrasound promoted easy, efficient, and environment friendly process has been devised for the synthesis of α-aminophosphonates within seconds through a one-pot three-component condensation of the aldehydes, amines, and triethylphosphite. The desired products were obtained in excellent yields and in high purity under solvent-free and catalyst-free conditions. Study with various aldehydes and amines

  已经设计了超声促进的简单，有效和环境友好的方法，用于通过醛，胺和亚磷酸三乙酯的一锅式三组分缩合在几秒钟内合成α-氨基膦酸酯。在无溶剂和无催化剂的条件下，可以以极高的收率和高纯度获得所需的产物。对各种醛和胺的研究表明，超声辐射在α-氨基膦酸酯的直接合成中起着关键作用。
• 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。
• A Highly Efficient Bismuth Salts-Catalyzed Route for the Synthesis of α-Aminophosphonates
  作者：Antara Banik、Sahil Batta、Debasish Bandyopadhyay、Bimal K. Banik

  DOI：10.3390/molecules15118205

  日期：——

  A convenient synthesis of different types of α-amino phosphonates via one-pot solvent-free three component reactions of aldehydes, amines and phosphites catalyzed by bismuth salts has been investigated. Bismuth triflate is found to be the most effective catalyst for this reaction.

  已经研究了通过铋盐催化的醛、胺和亚磷酸酯的一锅无溶剂三组分反应，方便地合成不同类型的 α-氨基膦酸酯。发现三氟甲磺酸铋是该反应最有效的催化剂。
• Silica supported polyphosphoric acid (PPA-SiO_2): an efficient and reusable heterogeneous catalyst for the one-pot synthesis of \alpha -amino phosphonates
  作者：MALEK TAHER MAGHSOODLOU、SAYYED MOSTAFA HABIBI-KHORASSANI、REZA HEYDARI、NOUROLLAH HAZERI、SEYED SAJAD SAJADIKHAH、MOHSEN ROSTAMIZADEH、LEILA KEISHAMS

  DOI：10.3906/kim-0910-28

  日期：——

  An efficient green protocol is described for the preparation of \alpha -amino phosphonates, employing a one-pot three-component condensation reaction between aldehydes, amines, and trialkyl phosphites in the presence of PPA-SiO_2 under solvent-free conditions at 80 °C. The present procedure offer advantages such as high to excellent yields, short reaction time, inexpensiveness, recovery, and reusability of catalyst.

  在 80 °C 无溶剂条件下，在 PPA-SiO_2 存在下，采用醛、胺和三烷基膦酸盐之间的单锅三组分缩合反应，描述了制备 \alpha -氨基膦酸盐的高效绿色方案。本方法具有产率高、反应时间短、无毒、可回收和催化剂可重复使用等优点。
• TiO2 as a new and reusable catalyst for one-pot three-component syntheses of α-aminophosphonates in solvent-free conditions
  作者：Mona Hosseini-Sarvari

  DOI：10.1016/j.tet.2008.04.016

  日期：2008.6

  the synthesis of α-aminophosphonates. A three-component reaction of an amine, an aldehyde or a ketone and a dialkyl phosphite (Kabachnik–Fields reaction) took place in one-pot, under solvent-free conditions to afford the corresponding α-aminophosphonates in high yields and short times. The TiO2 catalyzed α-aminophosphonate synthesis in the present study perhaps represents a true three-component reaction

  据报道，可商购获得的二氧化钛（TiO 2）是用于合成α-氨基膦酸酯的极其有效的催化剂。胺，醛或酮与亚磷酸二烷基酯的三组分反应（Kabachnik–Fields反应）在无溶剂条件下在一锅中进行，从而以高收率和短时间提供相应的α-氨基膦酸酯。TiO 2本研究中催化的α-氨基膦酸酯合成可能代表了真正的三组分反应，因为未观察到亚胺或α-羟基膦酸酯的中间形成，这表明羰基化合物，胺和亚磷酸酯同时参与过渡态。此外，该催化剂可以重复使用几次，而不会显着降低催化活性。