(3-氯苯基)(苯基氨基)甲基膦酸二甲酯 | 1017241-63-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: (3-氯苯基)(苯基氨基)甲基膦酸二甲酯
• 英文名称: (3-chlorophenyl)(phenylamino)methylphosphonic acid dimethyl ester
• 英文别名: dimethyl ((3-chlorophenyl)(phenylamino)methyl)phosphonate；N-[(3-chlorophenyl)-dimethoxyphosphorylmethyl]aniline
• CAS: 1017241-63-2
• 化学式: C₁₅H₁₇ClNO₃P
• 分子量: 325.732
• InChiKey: RSSLUWIDGZWMBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  3-氯苯甲醛 、 苯胺 、 三甲氧基磷 在 solid phase supported sodium hydrogen sulfate 作用下， 反应 0.75h， 以94%的产率得到(3-氯苯基)(苯基氨基)甲基膦酸二甲酯
  参考文献：
  名称：

  使用 NaHSO4-SiO2 作为高效且可重复使用的催化剂一锅法、三组分合成 α-氨基膦酸酯

  摘要：

  摘要 已开发出一种简单、高效且环境友好的合成α-氨基膦酸酯的方法。在二氧化硅负载的硫酸氢钠 (NaHSO4-SiO2) 作为廉价且可重复使用的催化剂存在下，在 80 °C 无溶剂条件下，醛、胺和亚磷酸三烷基酯的一锅三组分反应得到相应的 α-氨基膦酸盐，收率高，反应时间短。图形概要

  DOI：

  10.1080/00397911.2010.523153

文献信息

• Graphene Oxide as Recyclable Catalyst for One-Pot Synthesis of α-Aminophosphonates
  作者：Kiran B. Dhopte、Dnyaneshwar S. Raut、Anand V. Patwardhan、Parag R. Nemade

  DOI：10.1080/00397911.2014.989447

  日期：2015.3.19

  Abstract We report the synthesis of α-aminophosphonates from aromatic aldehydes, aromatic and aliphatic amines, and trimethylphosphite (Kabachnik–Fields reaction) using a “carbocatalyst,” graphene oxide, at room temperature with excellent yield and recyclability. Enhanced catalytic activity of graphene oxide as compared to other catalysts studied is possibly due to the presence of carboxylic acid and

  摘要 我们报道了使用“碳催化剂”氧化石墨烯在室温下从芳香醛、芳香胺和脂肪胺以及亚磷酸三甲酯（Kabachnik-Fields 反应）合成 α-氨基膦酸酯，具有优异的产率和可回收性。与其他研究的催化剂相比，氧化石墨烯的催化活性增强可能是由于羧酸和羟基的存在。图形概要
• A green protocol for one-pot three-component synthesis of α-amino phosphonates catalyzed by succinic acid
  作者：Nourallah Hazeri、Malek Taher Maghsoodlou、Sayyed Mostafa Habibi-Khorassani、Jasem Aboonajmi、Mojtaba Lashkari、Seyed Sajad Sajadikhah

  DOI：10.1007/s11164-013-1081-8

  日期：2014.5

  Abstract A simple, efficient, and general method has been developed for the one-pot, three-component synthesis of α-amino phosphonates from a condensation reaction of trialkyl phosphite, aldehydes, and amines in the presence of a catalytic amount of succinic acid (8.5 mol %) (for the first time) under solvent-free conditions. The advantages of this protocol are excellent yields, short reaction time

  摘要 已经开发了一种简单，有效且通用的方法，用于在催化量的琥珀酸存在下，通过亚磷酸三烷基酯，醛和胺的缩合反应，进行一锅三组分合成α-氨基膦酸酯。 mol％）（首次）在无溶剂条件下。该方案的优点是产率高，反应时间短，反应条件温和，可用性更高，成本更低，更环保，无需柱色谱法和简单的后处理程序。 图形概要
• Al(H₂PO₄)₃as an Efficient and Reusable Catalyst for One-pot Three-component Synthesis of<i>α</i>-Amino Phosphonates under Solvent-free Conditions
  作者：Malek Taher Maghsoodlou、Sayyed Mostafa Habibi-Khorassani、Reza Heydari、Nourollah Hazeri、Seyed Sajad Sajadikhah、Mohsen Rostamizadeh

  DOI：10.1002/cjoc.201090067

  日期：2010.2

  Synthesis of α‐amino phosphonates is described under solvent‐free conditions at 100°C from reaction between aldehydes and amines in the presence of trialkyl phosphites using Al(H2PO4)3 as an efficient and reusable heterogeneous catalyst. The advantages of this procedure are short reaction time, flexibility and having high to excellent yields.

  描述了在无溶剂条件下，在亚磷酸三烷基酯存在下，使用Al（H 2 PO 4）3作为有效且可重复使用的多相催化剂，醛与胺之间的反应，在无溶剂条件下合成α-氨基膦酸酯的方法。该方法的优点是反应时间短，柔韧性好并且产率高至优异。
• Coupling of Aldehydes, Amines, and Trimethyl Phosphite Promoted by Amberlyst-15: Highly Efficient Synthesis of α-Aminophosphonates
  作者：Mahmood Tajbakhsh、Akbar Heydari、Heshmatollah Alinezhad、Mercedeh Ghanei、Samad Khaksar

  DOI：10.1055/s-2008-1032034

  日期：2008.2

  A three-component reaction promoted by Amberlyst-15 of an amine, an aldehyde, and trimethyl phosphite (Kabachnik-Fields reaction) in one pot under mild conditions affords the corresponding α-aminophosphonate in high yield after a short reaction time at ambient temperature.

  Amberlyst-15 在温和条件下在一锅中促进胺、醛和亚磷酸三甲酯的三组分反应（Kabachnik-Fields 反应），在环境温度下短反应时间后以高产率提供相应的 α-氨基膦酸酯。
• Silver‐Catalyzed One‐Pot Three‐Component Synthesis of α‐Aminonitriles and Biologically Relevant α‐Amino‐phosphonates
  作者：Vipin K. Pandey、Chandra Shekhar Tiwari、Arnab Rit

  DOI：10.1002/asia.202200703

  日期：2022.10.17

  AbstractA simple silver salt (AgSbF6)‐catalyzed aminophosphonylation and Strecker reaction have been developed and successfully applied to a wide range of substrates (>55 substrates). This solvent‐, ligand‐, and base‐free one‐pot three‐component protocol operates effectively at room temperature to provide diversified α‐aminophosphonates and α‐aminonitriles, which gave access to the respective α‐amino amides. Importantly, the present catalyst system is also capable to produce the rarely reported and biologically relevant aminophosphonates (having anti‐leishmanial activity). Further, mechanistic studies reveal that the present phosphonylation protocol follows a radical pathway.