diethyl ((3-methoxyphenyl)(phenylamino)methyl)phosphonate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: diethyl ((3-methoxyphenyl)(phenylamino)methyl)phosphonate
• 英文别名: N-[diethoxyphosphoryl-(3-methoxyphenyl)methyl]aniline
• 化学式: C₁₈H₂₄NO₄P
• 分子量: 349.367
• InChiKey: MKKVLMJQWPARTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 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：
  56.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  磷酸三乙酯 、 苯胺 、 3-甲氧基苯甲醛 以 水 为溶剂， 反应 0.68h， 以92%的产率得到diethyl ((3-methoxyphenyl)(phenylamino)methyl)phosphonate
  参考文献：
  名称：

  α-氨基膦酸酯在乳酸乙酯水溶液中的无催化剂一锅法合成

  摘要：

  摘要 通过在室温下超声辐照条件下，各种醛、胺和磷酸三乙酯在水-乳酸乙酯中的一锅三组分缩合反应，设计了一种高效、环保的α-氨基膦酸酯合成工艺。无需任何额外的催化剂即可以高收率获得预期产物。图形概要

  DOI：

  10.1080/10426507.2018.1542395

文献信息

• Amberlite-IR 120 catalyzed three-component synthesis of α-amino phosphonates in one-pot
  作者：Asish K. Bhattacharya、Kalpeshkumar C. Rana

  DOI：10.1016/j.tetlet.2008.02.102

  日期：2008.4

  A simple, efficient, and environmentally benign method for a three-component reaction of an amine, an aldehyde or a ketone, and diethyl phosphite catalyzed by Amberlite-IR 120 resin has been developed to afford α-amino phosphonates in high yields and short reaction times under solvent-free reaction conditions. The major advantages of the present method are good yields, inexpensive, ecofriendly and

  已开发出一种简单，有效且环境友好的方法，用于由Amberlite-IR 120树脂催化的胺，醛或酮与亚磷酸二乙酯的三组分反应，从而以高收率和短反应时间提供α-氨基膦酸酯无溶剂反应条件下的反应时间。本方法的主要优点是产率高，价格便宜，生态友好且可重复使用的催化剂，温和且无溶剂的反应条件以及对基质中存在的各种功能的耐受性。
• Supported sulfonic acid on magnetic nanoparticles used as a reusable catalyst for rapid synthesis of <b>α</b>-aminophosphonates
  作者：Mozhgan Afshari、Maryam Gorjizadeh、Mohammad Naseh

  DOI：10.1080/15533174.2016.1186096

  日期：2017.4.3

  Sulfonic acid was anchored on the surface of silica-coated cobalt ferrite core to obtain a new magnetically separable catalyst. The resultant composite was characterized by various techniques, including FT-IR, X-ray diffraction, FESEM, energy-dispersive X-ray, TEM, TGA, and vibrating sample magnetometer. The immobilized sulfonic acid was shown to be an efficient heterogeneous catalyst for the synthesis

  磺酸被锚固在二氧化硅涂层的钴铁氧体磁芯的表面上，从而获得了一种新型的可磁分离的催化剂。所得复合材料通过多种技术进行表征，包括FT-IR，X射线衍射，FESEM，能量色散X射线，TEM，TGA和振动样品磁力计。固定化的磺酸是在室温下无溶剂条件下合成α-氨基膦酸酯的有效多相催化剂。通过简单的磁倾析可以很容易地回收催化剂，并且可以循环使用7次，而不会明显降低催化活性。
• An Efficient One-Pot Synthesis of α-Amino Phosphonates Catalyzed by Bismuth Nitrate Pentahydrate
  作者：Asish Bhattacharya、Tanpreet Kaur

  DOI：10.1055/s-2007-970762

  日期：2007.3

  A simple, efficient, and environmentally benign method has been developed for the synthesis of α-amino phosphonates through a one-pot reaction of aldehydes with amines and diethyl phosphite in the presence of bismuth nitrate pentahydrate as a catalyst. Some of the major advantages of this protocol are: good yields, the involvement of a less-expensive and non-toxic catalyst, mild and solvent-free reaction conditions and also tolerance towards other functional groups present in the substrates. Eighteen examples are described, highlighting the substrate scope of the reaction.

  在五水硝酸铋作为催化剂的存在下，通过醛与胺和亚磷酸二乙酯的一锅反应合成δ-氨基膦酸盐，开发出了一种简单、高效且对环境无害的方法。该方法的一些主要优点包括：产率高、使用的催化剂成本较低且无毒、反应条件温和且无溶剂、对底物中存在的其他官能团具有耐受性。本文介绍了 18 个实例，突出了该反应的底物范围。
• Silica-coated MgAl2O4 nanoparticles supported phosphotungstic acid as an effective catalyst for synthesis of α-aminophosphonates
  作者：Reza Hajavazzade、Ali Reza Mahjoub、M. Kargarrazi

  DOI：10.1007/s11164-019-03737-z

  日期：2019.4

  In this research, a recoverable catalyst (MgAl2O4@SiO2–PTA) was prepared by a simple utilization method. The prepared catalyst was characterized by XRD, FT-IR, SEM, EDX, ICP-AES, and BET techniques. The average crystallite size of MgAl2O4 was calculated to be 40 nm by the Debye–Scherrer formula. The nanocomposite was examined as a heterogeneous catalyst for synthesis of α-aminophosphonates under solvent-free conditions at room temperature. In this process, magnesium aluminate spinel (MgAl2O4), used as the base and supporting catalyst for H3PW12O40 (PTA), provides the recycling and reusing of the catalyst and also increases the efficiency of the reaction, which is due to the increase in the surface/volume ratio. In order to obtain optimal conditions, the synthesis of α-aminophosphonates reactions was investigated with different solvents and catalysts. The results showed that α-aminophosphonate prepared from the benzaldehyde and aniline reaction has higher efficiency and a shorter time than other reactions. The catalyst was recovered by simple filtration, and it can be recycled for at least five successive times without loss of catalytic activity.

  本研究采用简单的利用方法制备了一种可回收催化剂（MgAl2O4@SiO2-PTA）。对制备的催化剂进行了 XRD、FT-IR、SEM、EDX、ICP-AES 和 BET 表征。根据 Debye-Scherrer 公式计算出 MgAl2O4 的平均晶粒尺寸为 40 nm 。该纳米复合材料作为一种异相催化剂，在室温无溶剂条件下用于合成α-氨基膦酸盐。在这一过程中，铝酸镁尖晶石（MgAl2O4）作为 H3PW12O40（PTA）的基质和支撑催化剂，可实现催化剂的循环和重复使用，同时由于表面/体积比的增加，也提高了反应的效率。为了获得最佳条件，研究人员使用不同的溶剂和催化剂研究了 α-氨基膦酸盐反应的合成。结果表明，与其他反应相比，苯甲醛和苯胺反应制备的 α-氨基膦酸盐具有更高的效率和更短的时间。催化剂可通过简单过滤回收，且可连续循环使用至少五次而不会丧失催化活性。
• CAN Catalyzed One‐Pot Synthesis of α‐Amino Phosphonates from Carbonyl Compounds
  作者：K. Ravinder、A. Vijender Reddy、P. Krishnaiah、G. Venkataramana、V. L. Niranjan Reddy、Y. Venkateswarlu

  DOI：10.1081/scc-120030755

  日期：2004.12.31

  Abstract α‐Amino phosphonates are synthesized by three component condensation of aldehydes, amines, and diethyl phosphite using ceric ammonium nitrate at room temperature to afford the corresponding α‐amino phosphonates in high yields. #IICT Communication No. 020214. ‡Dedicated to Professor Goverdhan Mehta on his 60th Birthday.

  摘要 α-氨基膦酸酯是通过醛、胺和亚磷酸二乙酯在室温下使用硝酸铈铵三组分缩合反应合成的，以高产率得到相应的α-氨基膦酸酯。#IICT 通讯第 020214 号。‡献给 Goverdhan Mehta 教授 60 岁生日。