diethyl (4-isopropylphenyl)(phenylamino)methylphosphonate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: diethyl (4-isopropylphenyl)(phenylamino)methylphosphonate
• 英文别名: N-[diethoxyphosphoryl-(4-propan-2-ylphenyl)methyl]aniline
• 化学式: C₂₀H₂₈NO₃P
• 分子量: 361.421
• InChiKey: UTMYFJDIUWNTHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-(4-isopropylbenzylidene)aniline 、 亚磷酸二乙酯 以 甲苯 为溶剂， 反应 36.0h， 以225 mg的产率得到diethyl (4-isopropylphenyl)(phenylamino)methylphosphonate
  参考文献：
  名称：

  一种新颖的直接合成α-氨基膦酸酯的方法：在CuO @ Fe 3 O 4纳米颗粒作为催化剂的情况下，醇，胺和亚磷酸二乙酯的一锅三组分缩合

  摘要：

  我们在这里报告了一种新颖而直接的合成方法，用于以相对较高的产率制备α-氨基膦酸酯。该方法涉及在CuO @ Fe 3 O 4纳米颗粒作为可循环利用催化剂的情况下，将醇，胺和亚磷酸二乙酯进行一锅三组分缩合。制备了CuO @ Fe 3 O 4纳米粒子，并通过FT-IR，TGA，VSM，TEM和X射线衍射图谱分析证实了其结构。

  DOI：

  10.1007/s11164-017-2890-y

文献信息

• Organic Reactions in Water: A Distinct Novel Approach for an Efficient Synthesis of α-Amino Phosphonates Starting Directly from Nitro Compounds
  作者：Biswanath Das、Gandham Satyalakshmi、Kanaparthy Suneel、Kongara Damodar

  DOI：10.1021/jo901765s

  日期：2009.11.6

  A distinct approach for high-yielding synthesis of α-amino phosphonates has been discovered through three-component reaction of nitro compounds, aldehydes, or ketones and dialkyl or trialkyl phosphites using indium in dilute aqueous HCl at room temperature. This one-pot conversion consists of the following steps: (i) reduction of nitro compounds to amines, (ii) formation of imines from amines and carbonyl

  通过在室温下在稀盐酸水溶液中使用铟使硝基化合物，醛或酮与亚磷酸二烷基酯或三烷基亚磷酸酯发生三组分反应，已发现了一种高产率合成α-氨基膦酸酯的独特方法。这一一锅转化包括以下步骤：（i）将硝基化合物还原为胺，（ii）由胺和羰基化合物形成亚胺，以及（iii）亚胺的氢膦酰化。
• Hydrophosphorylation of Imines Catalyzed by Tosyl Chloride for the Synthesis of α-Aminophosphonates
  作者：Babak Kaboudin、Elaheh Jafari

  DOI：10.1055/s-2008-1078509

  日期：——

  A simple, efficient, and general method has been developed for the synthesis of α-aminophosphonic esters using TsCl as an efficient catalyst. α-Aminophosphonic acids were obtained in good to high yields (65-85%) and purity under mild conditions by the reaction of diethyl phosphite with imines in the presence of TsCl.

  已开发出一种简单、高效且通用的方法，以TsCl作为高效催化剂合成α-氨基膦酸酯。在温和条件下，通过二乙基膦酸酯与亚胺在TsCl存在下反应，获得了良好至高产率（65-85%）和纯度的α-氨基膦酸。
• Microwave-assisted synthesis of 1-aminoalkyl phosphonates under solvent-free conditions
  作者：Babak Kaboudin、Rahman Nazari

  DOI：10.1016/s0040-4039(01)01627-6

  日期：2001.11

  simple, efficient and general method has been developed for the synthesis of 1-aminoalkyl phosphonates through a one-pot reaction of aldehydes with amines in the presence of acidic alumina under solvent-free conditions using microwave irradiation. It was also found that acidic alumina supported ammonium formate under solvent-free conditions is capable of the synthesis of 1-aminophosphonates from aldehydes

  已经开发了一种简单，有效且通用的方法，该方法通过在无溶剂条件下使用微波辐射在酸性氧化铝存在下，醛与胺进行一锅反应来合成1-氨基烷基膦酸酯。还发现在无溶剂条件下酸性氧化铝负载的甲酸铵能够在温和的反应条件下由醛和亚磷酸二乙酯合成1-氨基膦酸酯。
• Calcium Chloride as an Efficient Lewis Base Catalyst for the One-pot Synthesis of α-Aminophosphonic Esters
  作者：Babak Kaboudin、Hazegh Zahedi

  DOI：10.1246/cl.2008.540

  日期：2008.5.5

  A simple, efficient, and general method has been developed for the one-pot synthesis of α-aminophosphonic esters, under solvent-free conditions, with the use of CaCl 2 as a Lewis base catalyst. The esters were obtained under mild conditions and in high yield (80 to 96%) and purity. They were synthesized by the reaction of diethyl phosphite with a mixture of aldehydes and amines, in the presence of

  已经开发了一种简单、有效和通用的方法，用于在无溶剂条件下使用 CaCl 2 作为路易斯碱催化剂一锅法合成 α-氨基膦酸酯。在温和条件下以高产率（80-96%）和纯度获得酯。它们是通过亚磷酸二乙酯与醛和胺的混合物，在 CaCl 2 存在下，在无溶剂条件下反应合成的。该协议的主要优点是：产量高，方法便宜，使用无毒催化剂，最后温和无溶剂条件。
• Iron-doped single walled carbon nanotubes as an efficient and reusable heterogeneous catalyst for the synthesis of organophosphorus compounds under solvent-free conditions
  作者：Hashem Sharghi、Sakineh Ebrahimpourmoghaddam、Mohammad Mahdi Doroodmand

  DOI：10.1016/j.tet.2013.03.073

  日期：2013.6

  Iron-doped single walled carbon nanotubes (Fe/SWCNTs) is an efficient, eco-friendly, and reusable heterogeneous catalyst for the synthesis of diversely decorated α-aminophosphonates via multicomponent reaction of amines, carbonyl compounds, and phosphorus compounds under solvent-free conditions. This methodology illustrates a very simple procedure, with wide applicability, extending the scope to aliphatic

  掺杂铁的单壁碳纳米管（Fe / SWCNT）是一种高效，环保且可重复使用的非均相催化剂，用于在无溶剂条件下通过胺，羰基化合物和磷化合物的多组分反应合成装饰多样化的α-氨基膦酸酯。该方法论证了非常简单的方法，具有广泛的适用性，将范围扩展到脂族和芳族胺和羰基化合物。它也使得在羰基化合物，丙二腈和磷化合物反应过程中一锅法合成β-膦酰基丙二酸酯成为可能。在每种情况下均获得了优异的结果，从而以良好的收率提供了相应的有机磷加合物。