diethyl (4-nitrophenylamino)(4-chlorophenyl)methylphosphonate | 71511-66-5

• 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-nitrophenylamino)(4-chlorophenyl)methylphosphonate
• 英文别名: Diethyl 4-chloro-a-(4-nitroanilino)benzylphosphonate；N-[(4-chlorophenyl)-diethoxyphosphorylmethyl]-4-nitroaniline
• CAS: 71511-66-5
• 化学式: C₁₇H₂₀ClN₂O₅P
• 分子量: 398.783
• InChiKey: MXVAWSJYPGJSHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  93.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-(4-氯苯基)-N-(4-硝基苯基)甲亚胺 、 亚磷酸二乙酯 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以85%的产率得到diethyl (4-nitrophenylamino)(4-chlorophenyl)methylphosphonate
  参考文献：
  名称：

  Exceptional effect of nitro substituent on the phosphonation of imines: the first report on phosphonation of imines to α-iminophosphonates and α-(N-phosphorylamino)phosphonates

  摘要：

  一种新颖的化学选择性方法，用H-膦酸二乙酯对亚胺进行简单的磷化，并研究取代基对磷酸化反应的电子效应和取向效应。

  DOI：

  10.1039/c5ra14393d

文献信息

• Titanocene Dichloride as an Efficient Catalyst for One-Pot Synthesis of α-Aminophosphonates
  作者：Hong-Ying Niu、Hui-Juan Li、Jian-Ping Li、Yu Huang、Run-Ze Mao、De-Yang Li、Gui-Rong Qu、Hai-Ming Guo

  DOI：10.2174/157017811799304359

  日期：2011.11.1

  Commercially available titanocene dichloride was firstly used as an extremely efficient catalyst for a three component one-pot reaction of an amine, an aldehyde (ketone), and a dialkyl phosphite to form α-aminophosphonates under solvent-free conditions at ambient temperature in good to high yields, providing a green, rapid and convenient method for the synthesis of α-aminophosphonates.

  商业上可获得的二氯钛烯首先被用作三组分一锅反应的高效催化剂，该反应涉及一种胺、一种醛（酮）和一种双烷基磷酸酯，在无溶剂的条件下于常温下进行，产率良好至高，为合成α-氨基磷酸酯提供了一种绿色、快速和方便的方法。
• Exceptional effect of nitro substituent on the phosphonation of imines: the first report on phosphonation of imines to α-iminophosphonates and α-(N-phosphorylamino)phosphonates
  作者：Somayeh Motevalli、Nasser Iranpoor、Elham Etemadi-Davan、Khashayar Rajabi Moghadam

  DOI：10.1039/c5ra14393d

  日期：——

  A novel chemoselective method for the simple phosphonation of imines withH-phosphonate diethyl ester and study of the electronic and orientation effects of the substituents on phosphorylation reaction.

  一种新颖的化学选择性方法，用H-膦酸二乙酯对亚胺进行简单的磷化，并研究取代基对磷酸化反应的电子效应和取向效应。
• TfOH/C-catalyzed one-pot three-component synthesis of α-amino phosphonates under solvent-free conditions
  作者：Abbas Ali Jafari、Sakineh Amini、Fatemeh Tamaddon

  DOI：10.1007/s13738-012-0200-6

  日期：2013.8

  The TfOH/C was readily prepared via simple absorption of triflic acid onto activated charcoal. This solid acid was used as an efficient catalyst for the synthesis of α-aminophosphonates through the Kabachnik–Fields reaction of carbonyl compound, amine and diethyl phosphite under solvent-free conditions.

  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。
• Cd(ClO4)2∙xH2O as a novel catalyst for the synthesis of α-aminophosphonates under solvent-free conditions
  作者：Someshwar D. Dindulkar、Mudumala Veeranarayana Reddy、Yeon Tae Jeong

  DOI：10.1016/j.catcom.2011.10.025

  日期：2012.1

  we report cadmium perchlorate hydrate to be an novel, expeditious catalyst for the three-component one-pot reaction of an amine, an aldehyde and a H-phosphonate diesters in open air without any solvent, leads to α-aminophosphonates in excellent yields. To the best of our knowledge this finding is the first example of a cadmium perchlorate hydrate catalyzed Kabachnik-Fields reaction.

  在本文中，我们报告了高氯酸镉水合物是一种新颖，快速的催化剂，用于在没有任何溶剂的情况下在空气中将胺，醛和H膦酸酯二酯进行三组分一锅反应，从而导致α-氨基膦酸酯的生成。优异的产量。据我们所知，这一发现是水合高氯酸镉催化的Kabachnik-Fields反应的第一个例子。
• Xanthan Sulfuric Acid as an Efficient Biodegradable and Recyclable Catalyst for the One-Pot Synthesis of α-Amino Phosphonates
  作者：Guo-Ying Sun、Jun-Tao Hou、Jing-Jie Dou、Jun Lu、Yong-Jie Hou、Tuo Xue、Zhan-Hui Zhang

  DOI：10.1002/jccs.201000194

  日期：2010.12

  convenient and efficient procedure for the synthesis of α‐amino phosphonates by a one‐pot, three‐component condensation of aldehydes, amine, and diethyl phosphite in the presence of xanthan sulfuric acid as a bio‐supported catalyst under solvent‐free conditions has been developed. A wide range of α‐amino phosphonates have been obtained in high to excellent yields. Furthermore, the catalyst can be recovered

  在无溶剂条件下，以黄原酸作为生物负载催化剂，通过醛，胺和亚磷酸二乙酯的一锅，三组分缩合反应合成α-氨基膦酸酯的便捷高效方法具有已开发。以高到极好的产率获得了各种各样的α-氨基膦酸酯。此外，可以简单地回收催化剂，并在随后的反应中重复使用几次。