N-[二乙氧基磷酰基(吡啶-2-基)甲基]苯胺 | 21081-98-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: N-[二乙氧基磷酰基(吡啶-2-基)甲基]苯胺
• 英文名称: diethyl anilino(2-pyridinyl)methylphosphonate
• 英文别名: Phosphonic acid, [(phenylamino)-2-pyridinylmethyl]-, diethyl ester；N-[diethoxyphosphoryl(pyridin-2-yl)methyl]aniline
• CAS: 21081-98-1
• 化学式: C₁₆H₂₁N₂O₃P
• 分子量: 320.328
• InChiKey: QLYYJPOTHLWBGQ-UHFFFAOYSA-N

物化性质

• 熔点：
  89-90 °C
• 沸点：
  469.7±40.0 °C(Predicted)
• 密度：
  1.202±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  60.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[二乙氧基磷酰基(吡啶-2-基)甲基]苯胺 在 甲醇 、 三甲基溴硅烷 作用下， 生成 [Anilino(pyridin-2-yl)methyl]phosphonic acid
  参考文献：
  名称：

  带有杂环部分的氨基膦酸。第 4.1 部分 2-吡啶和 4-吡啶甲基-（氨基）膦酸的合成

  摘要：

  摘要 2-吡啶基和4-吡啶基甲基（氨基）膦酸不能通过水溶液水解相应的膦酸酯获得。盐酸。在这些酯的水解过程中，CP 键发生断裂，导致磷部分的排斥和相应胺的形成。发现，吡啶基甲基（氨基）膦酸二乙酯与溴三甲基硅烷的甲硅烷基化以及随后甲硅烷基化产物与甲醇的溶剂分解导致预期的2-吡啶基和4-吡啶基甲基（氨基）膦酸以高产率产生。

  DOI：

  10.1080/10426509708043492
• 作为产物：
  描述：

  2-(phenyliminomethyl)pyridine 、 亚磷酸二乙酯 反应 0.5h， 生成 N-[二乙氧基磷酰基(吡啶-2-基)甲基]苯胺
  参考文献：
  名称：

  吡啶基甲基（氨基）膦酸酯的酸性裂解。形成相应的胺

  摘要：

  3-吡啶基甲基（氨基）膦酸酯的水解通过20％aq。水溶液进行。如所预期的，盐酸得到相应的3-吡啶基甲基（氨基）膦酸。然而，2-和4-吡啶基甲基（氨基）膦酸酯的水解导致膦酸酯的分解，具有CP键的裂解并形成相应的胺。剩余的磷部分被鉴定为磷酸。反应范围限于氨基膦酸的2-和4-吡啶基甲基衍生物及其酯，以及具有相似结构的衍生物。相反，2-和4-吡啶基甲基（氨基）膦酸酯的碱性水解产生相应的氨基膦酸酯单烷基酯，在这些情况下未观察到CP键的断裂。

  DOI：

  10.1016/0040-4020(96)00727-2

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.
• Nano Fe3O4 as magnetically recyclable catalyst for the synthesis of α-aminophosphonates in solvent-free conditions
  作者：B.V. Subba Reddy、A. Siva Krishna、A.V. Ganesh、G.G.K.S. Narayana Kumar

  DOI：10.1016/j.tetlet.2011.01.074

  日期：2011.3

  The three component, one-pot synthesis of α-aminophosphonates has been achieved using super magnetic nano iron oxide at 50 °C under solvent-free conditions in excellent yields. The major advantages of the present method are high yields, short reaction times, magnetically recyclable catalyst, and solvent-free reaction conditions.

  使用超磁性纳米氧化铁在无溶剂条件下于50°C以优异的产率实现了三组分一锅法合成α-氨基膦酸酯。本方法的主要优点是产率高，反应时间短，可磁循环的催化剂和无溶剂的反应条件。
• Platinum(II) complexes containing aminophosphonate esters: Synthesis, characterization, cytotoxicity and action mechanism
  作者：Ke-Bin Huang、Zhen-Feng Chen、Yan-Cheng Liu、Zhu-Quan Li、Jian-Hua Wei、Meng Wang、Xiao-Li Xie、Hong Liang

  DOI：10.1016/j.ejmech.2013.04.024

  日期：2013.6

  New platinum(II) complexes containing aminophosphonate ester were synthesized and fully characterized, which were found to possess better solubility in both organic solvents and water than cisplatin. These platinum(II) complexes exhibited considerable cytotoxicity against tumor cells MG-63, SK-OV-3, HepG2, BEL-7404 and low cytotoxicity to normal human liver cells HL-7702. Their antitumor activities were achieved through the induction of cell apoptosis and the cell cycle arrest at G1 phase. The electrophoretic mobility studies and CD spectral analysis revealed that the binding mode of complex 6 to DNA might be different from that of cisplatin. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Mesoporous aluminosilicate nanocage-catalyzed three-component coupling reaction: an expedient synthesis of α-aminophosphonates
  作者：Ajayan Vinu、Pranjal Kalita、Veerappan V. Balasubramanian、Hamid Oveisi、Tamil Selvan、Ajayan Mano、Murugulla A. Chari、B.V. Subba Reddy

  DOI：10.1016/j.tetlet.2009.10.003

  日期：2009.12

  Here we demonstrate for the first time the synthesis of alpha-aminophosphonates through the three-component coupling reaction of aldehydes, amines, and diethyl phosphite by using highly acidic 3D mesoporous aluminosilicate nanocage catalyst, which gave excellent yield with a high selectivity in a short reaction time due to its high acidity, 3D pores, and a huge space in the nanocages. (c) 2009 Elsevier Ltd. All rights reserved.
• General Procedure for the Synthesis of α-Amino Phosphonates from Aldehydes and Ketones Using Indium(III) Chloride as a Catalyst
  作者：Brindaban C. Ranu、Alakananda Hajra、Umasish Jana

  DOI：10.1021/ol990079g

  日期：1999.10.1

  [GRAPHICS]A simple, efficient, and general method has been developed for the synthesis of alpha-amino phosphonates through a one-pot reaction of aldehydes and ketones with amines in the presence of indium(III) chloride as a catalyst.