dimethyl (p-tolylamino)(2-chlorophenyl)methylphosphonate | 1439894-90-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: dimethyl (p-tolylamino)(2-chlorophenyl)methylphosphonate
• 英文别名: N-[(2-chlorophenyl)-[dimethoxy(oxido)phosphaniumyl]methyl]-4-methylaniline
• CAS: 1439894-90-2
• 化学式: C₁₆H₁₉ClNO₃P
• 分子量: 339.759
• InChiKey: AMJVYRNQMHPPGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  53.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氯苯甲醛 、 乙烷,三氯氟- 、 亚磷酸二甲酯 在 1-(n-butyl)-3-methylimidazolium tetrachloroaluminate 作用下， 以 乙醇 为溶剂， 反应 0.08h， 以91%的产率得到dimethyl (p-tolylamino)(2-chlorophenyl)methylphosphonate
  参考文献：
  名称：

  Ultrasonic and Lewis acid ionic liquid catalytic system for Kabachnik-Fields reaction

  摘要：

  摘要：在Kabachnik-Fields反应中，将超声波（US）和[bmim]AlCl4离子液体组合使用作为传统酸催化剂的替代品，反应胺和芳香醛与亚磷酸酯形成氨基膦酸盐。反应时间显著缩短，反应进行非常顺利。

  DOI：

  10.2478/s11696-013-0516-4

文献信息

• A new procedure for synthesis of $$\upalpha $$ α -aminophosphonates by aqueous formic acid as an effective and environment-friendly organocatalyst
  作者：Esmaeil Mohammadiyan、Hossein Ghafuri、Ali Kakanejadifard

  DOI：10.1007/s12039-017-1394-z

  日期：2017.12

  AbstractAqueous formic acid (37%) as a green organocatalyst was used to synthesis of \(\upalpha \)-aminophosphonates in one-pot, three-component Kabachnik–Fields reaction. The structures of compounds were determined by FT-IR, \(}^1}\hbox H}\)-NMR and \(}^13}\hbox C}\)-NMR spectroscopy. After optimization of the experimental conditions, the reaction was carried out at \(65\,^\circ }}\hbox C}\)

  摘要甲酸水溶液（37％）为绿色有机催化剂，用于在一锅三组分Kabachnik-Fields反应中合成\（upalpha \） -氨基膦酸酯。通过FT-IR，\（} ^ 1} \ hbox H} \）- NMR和\（} ^ 13} \ hbox C} \）- NMR光谱确定化合物的结构。在优化实验条件之后，反应在无溶剂的条件下在\（65 \，^ \ circ}} \ hbox C} \）下进行。使用无毒有效的有机催化剂，易于处理的过程和低成本的清洁程序是这项研究的主要优点。 图形概要 报道了在无溶剂条件下一锅三组分Kabachnik-Fields反应中\（\ upalpha \）-氨基膦酸酯的合成和表征。使用无毒有效的有机催化剂，易于处理的过程和低成本的清洁程序是这项研究的主要优点。
• An ultra-sound assisted synthesis of α-aminophosphonates from benzyl halides <i>via</i> sequential Kornblum and Kabachnik-fields reaction
  作者：Rabia Amin、Tabassum Ara

  DOI：10.1080/10426507.2022.2157830

  日期：——

  Abstract An ultrasound-assisted simple, easy and straightforward method for the synthesis of α-aminophosphonates has been developed via Kornblum/Kabachnik-fields reaction. The method involves in situ generation of an aldehyde intermediate from benzyl halides via oxidative dehalogenation followed by coupling with aryl amine and trialkyl phosphite in a one-pot three component manner under ultrasonic

  摘要 通过Kornblum/Kabachnik-fields 反应开发了一种超声波辅助合成 α-氨基膦酸盐的简单、容易和直接的方法。该方法涉及通过氧化脱卤从苄基卤化物中原位生成醛中间体，然后在超声辐射下以一锅三组分方式与芳基胺和亚磷酸三烷基酯偶联。所开发的方法与各种功能兼容，并且在温和条件下以良好到极好的收率获得所需的产品。
• Simultaneously application of SBA-15 sulfonic acid nanoreactor and ultrasonic irradiation as a very useful novel combined catalytic system: An ultra-fast, selective, reusable and waste-free green approach
  作者：Sadegh Rostamnia、Hongchuan Xin、Xiao Liu、Kamran Lamei

  DOI：10.1016/j.molcata.2013.03.017

  日期：2013.8

  Sonicated catalytically amount of the SBA-15/SO3H nanoreactor with organic substrate was found to be an efficient, ultra-fast and waste-free green approach for the synthesis of the indazolophthalazinetriones, polyhydroquinolines and alpha-aminophosphonates as models of organic reactions. The advantages of present combined method are the use of a low scale catalyst, simple procedure with an easy filterable work-up method, waste-free, green and direct synthetic entry to excellent yield of products in a high reusability and a short reaction time. SBA-15 nanoreactor anchored covalently bonded PrSO3H organic groups, to produce organic-inorganic mesochannels, in reaction condition (combined ultrasound/nanoreactor system) as catalyst provide a synergistic means of an efficient approach of the reactants to acidic sites, and suitable mesochannels to drive out the products and water for next recycles. (C) 2013 Elsevier B.V. All rights reserved.
• Simultaneous application of ultrasonic irradiation and immobilized ionic liquid onto the SBA-15 nanoreactor (US/[MPIm]Cl@SBA-15): A robust, recyclable, and useful combined catalytic system for selective and waste-free Kabachnik Fields reaction
  作者：Sadegh Rostamnia、Hongchuan Xin

  DOI：10.1016/j.molliq.2014.01.031

  日期：2014.7

  Simultaneous application of the ultrasonic irradiation (US) and immobilized ionic liquid (IL@SBA-15) is used as an alternative to conventional catalysts in the Kabachnik-Fields reaction of an amine, aldehyde with phosphite leading to the formation of (alpha-aminoalkyl)phosphonate. The reaction time is reduced drastically and the reaction is progressed in an environmentally friendly way. The yields are around 93-96%. (C) 2014 Elsevier B.V. All rights reserved.
• Ultrasonic and Lewis acid ionic liquid catalytic system for Kabachnik-Fields reaction
  作者：Sadegh Rostamnia、Mojtaba Amini

  DOI：10.2478/s11696-013-0516-4

  日期：2014.1.1

  A combination of ultrasonic (US) and [bmim]AlCl4 ionic liquid is used as an alternative to conventional acid catalysts in the Kabachnik-Fields reaction of an amine and aryl aldehyde with phosphite leading to the formation of aminophosphonates. The reaction time was significantly reduced and the reaction progressed very smoothly.

  摘要：在Kabachnik-Fields反应中，将超声波（US）和[bmim]AlCl4离子液体组合使用作为传统酸催化剂的替代品，反应胺和芳香醛与亚磷酸酯形成氨基膦酸盐。反应时间显著缩短，反应进行非常顺利。