diethyl phenyl-N-{4-[N-(phenyl)amino-(diethoxyphosphoryl)methyl]phenyl}aminomethylphosphonate | 13336-73-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: diethyl phenyl-N-{4-[N-(phenyl)amino-(diethoxyphosphoryl)methyl]phenyl}aminomethylphosphonate
• 英文别名: tetraethyl {benzene-1,4-diylbis[imino(phenylmethanediyl)]}bis(phosphonate)；tetraethyl (1,4-phenylenebis(azanediyl))bis(phenylmethylene)diphosphonate；N,N'-Bis-<α-(O,O-diethyl-phosphono)-benzyl>-p-phenylendiamin；N,N'-Bis-<α-(di-O-ethyl-phosphono)-benzyl>-p-phenylendiamin；N,N'-Bis-[α-(di-O-ethyl-phosphono)-benzyl]-p-phenylendiamin；1-N,4-N-bis[diethoxyphosphoryl(phenyl)methyl]benzene-1,4-diamine
• CAS: 13336-73-7
• 化学式: C₂₈H₃₈N₂O₆P₂
• 分子量: 560.567
• InChiKey: GJBBUFPHMJKMBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  38
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  95.1
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  二乙基亚磷酸氢酯 、 N,N'-dibenzylidene-benzene-1,4-diamine 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 生成 diethyl phenyl-N-{4-[N-(phenyl)amino-(diethoxyphosphoryl)methyl]phenyl}aminomethylphosphonate
  参考文献：
  名称：

  Pudovik,A.N.; Pudovik,M.A., Journal of general chemistry of the USSR, 1963, vol. 33, p. 3280 - 3284

  摘要：

  DOI：

文献信息

• 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.
• Design and one-pot synthesis of α-aminophosphonates and bis(α-aminophosphonates) by iron(III) chloride and cytotoxic activity
  作者：Zahra Rezaei、Habib Firouzabadi、Nasser Iranpoor、Abbas Ghaderi、Mohammad Reza Jafari、Abbas Ali Jafari、Hamid Reza Zare

  DOI：10.1016/j.ejmech.2009.07.009

  日期：2009.11

  amine and phosphite compounds to form corresponding α-aminophosphonates in a one-pot, three-component reaction. Selected α-aminophosphonates were entered into a biological assay test and were studied by docking methods, using Autodock 3.0. The results showed that the reactions were carried out mildly and eco-friendly to form α-aminophosphonates in high yields. Some were found to have cytotoxic activity

  在这项研究中，我们使用FeCl 3在THF中的溶液来促进醛，胺和亚磷酸酯化合物的曼尼希式反应，从而在一锅三组分反应中形成相应的α-氨基膦酸酯。选定的α-氨基膦酸酯进入生物学分析测试，并使用Autodock 3.0通过对接方法进行研究。 结果表明，反应温和且生态友好地进行，以高收率形成α-氨基膦酸酯。发现一些对RAJI，JURKAT和MCF-7细胞系具有细胞毒活性。吲哚衍生的双（α-氨基膦酸酯）具有与阿霉素相当的最大细胞毒性作用。尽管最具细胞毒性的化合物的FDE（最终对接能）具有最大的负值，但FDE与细胞毒性之间没有相关性。
• 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。
• Highly efficient one-pot multi-component synthesis of α-aminophosphonates and bis-α-aminophosphonates catalyzed by heterogeneous reusable silica supported dodecatungstophosphoric acid (DTP/SiO2) at ambient temperature and their antitubercular evaluation against Mycobactrium Tuberculosis
  作者：Shafeek A. R. Mulla、Mohsinkhan Y. Pathan、Santosh S. Chavan、Suwara P. Gample、Dhiman Sarkar

  DOI：10.1039/c3ra45853a

  日期：——

  A highly efficient one-pot multi-component reaction (MCR) protocol over DTP/SiO2 has been developed for the synthesis of α-aminophosphonate derivatives (4a–x) in excellent yields. The α-aminophosphonate derivatives were for the first time evaluated for their antitubercular activity against the M. tuberculosis H37Ra (MTB) strain. An evaluation of the data on the cytotoxicity and antimicrobial activity shows that 4n and 4v are promising antitubercular agents.

  开发了一种高效的一锅多组分反应（MCR）方法，利用DTP/SiO2合成α-氨基膦酸酯衍生物（4a–x），产率极佳。这些α-氨基膦酸酯衍生物首次被评估了对结核分枝杆菌H37Ra（MTB）株的抗结核活性。对细胞毒性和抗微生物活性的数据评估显示，4n和4v是有前景的抗结核剂。
• An eco-friendly procedure for the efficient synthesis of dialkyl α-aminophosphonates in aqueous media
  作者：Sara Sobhani、Elham Safaei、Mozaffar Asadi、Fariba Jalili

  DOI：10.1016/j.jorganchem.2008.07.037

  日期：2008.10

  A new, convenient and high yielding procedure for the preparation of diethyl α-aminophosphonates in water by one-pot reaction of aldehydes, amines, tri/dialkyl phosphites in the presence of a low catalytic amount of [Cu(3,4-tmtppa)](MeSO4)4 (0.16 mol%) as a highly stable and re-usable catalyst is described.

  在低催化量的[Cu（3,4-tmtppa）存在下，通过一锅反应醛，胺，亚磷酸三/二烷基酯，在水中制备α-氨基膦酸二乙酯的新型，便捷且高收率的方法描述了作为高度稳定且可重复使用的催化剂的]（MeSO 4）4（0.16 mol％）。