diethyl (2-furyl)-N-(4-methoxyphenyl)aminomethylphosphonate

• 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 (2-furyl)-N-(4-methoxyphenyl)aminomethylphosphonate
• 英文别名: diethyl furan-2-yl(4-methoxyphenylamino)methylphosphonate；Diethyl [(furan-2-YL)[(4-methoxyphenyl)amino]methyl]phosphonate；N-[diethoxyphosphoryl(furan-2-yl)methyl]-4-methoxyaniline
• 化学式: C₁₆H₂₂NO₅P
• 分子量: 339.328
• InChiKey: NOIMXYKDCVNWGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  69.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  甲氧苯胺 在 三氟乙酸 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 96.0h， 生成 diethyl (2-furyl)-N-(4-methoxyphenyl)aminomethylphosphonate
  参考文献：
  名称：

  Dimethyl (2-Furyl)-N-(2-Methoxyphenyl)Aminomethylphosphonate Induces Apoptosis in Esophageal Squamous Cancer Cells. Structure Versus Activity of its Selected Analogs

  摘要：

  Cytotoxicities of several new aminophosphonic compounds bearing 2-furyl moiety 2b-d and 3a-c on KYSE 30, 150, and 270 esophageal cancer cell lines are reported here. The qualitative study on correlations between the structure and cytotoxic activity of furan-deriving aminophosphonates has been performed.Dimethyl (2-furyl)-N-(2-methoxyphenyl)aminomethylphosphonate (2a), which has been previously shown to have the interesting values of cytotoxicity on these esophageal cancer cell lines was tested and found to induce apoptosis. The analyses of correlations between apoptosis, necrosis, and viability were also performed.

  DOI：

  10.1080/10426507.2014.965821

文献信息

• Montmorillonite K10 Catalyzed Nucleophilic Addition Reaction to Aldimines in Water
  作者：Takahiko Akiyama、Keiichiro Matsuda、Kohei Fuchibe

  DOI：10.1055/s-2005-872162

  日期：——

  Montmorillonite K10 catalyzed Mannich-type reaction and hydrophosphonylation proceeded smoothly in water at room temperature to give β-amino esters and α-amino phosphonates, respectively, in good to high yields.

  蒙脱石K10催化下的曼尼希型反应和水相膦酰化反应在室温下的水中顺利进行，分别以良好至高产率得到β-氨基酯和α-氨基膦酸盐。
• 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.
• ZnO Nanoparticles as an Efficient Catalyst for the One-Pot Synthesis of α-Amino Phosphonates
  作者：Mohammad Kassaee、Farnaz Movahedi、Hassan Masrouri

  DOI：10.1055/s-0028-1088135

  日期：——

  Zinc oxide nanoparticles (ZnO NPs, ca. 22 nm) were used as an effective catalyst in the solvent-free, three-component couplings of aldehydes, aromatic amines and dialkyl phosphites at room temperature to produce various α-amino phosphonates. Compared to known methods, satisfactory results were obtained with high yields through a simple experimental procedure. The catalyst was recycled and reused five times with minor decrease in its catalytic activity.

  氧化锌纳米颗粒（ZnO NPs，约22纳米）被用作有效催化剂，在无溶剂的条件下，室温下对醛、芳香胺和双烷基磷酸酯进行三组分耦合反应，以生成各种α-氨基膦酸酯。与已知方法相比，通过简单的实验程序获得了满意的结果，产率高。该催化剂经过回收和重复使用五次后，其催化活性仅略有下降。
• A facile and highly efficient route to α-amino phosphonates via three-component reactions catalyzed by Mg(ClO₄)₂or molecular iodine
  作者：Jie Wu、Wei Sun、Hong-Guang Xia、Xiaoyu Sun

  DOI：10.1039/b602536f

  日期：——

  Three-component reactions of aldehydes, amines, and diethyl phosphite catalyzed by Mg(ClO4)2 or molecular iodine afforded the corresponding α-amino phosphonates in excellent yields under mild reaction conditions.

  在 Mg(ClO4)2 或分子碘的催化下，醛、胺和亚磷酸二乙酯发生三组分反应，在温和的反应条件下以极好的收率得到了相应的δ-氨基膦酸盐。