diethyl [(4-chlorophenyl)(phenylamino)methyl]phosphonate | 26321-54-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: diethyl [(4-chlorophenyl)(phenylamino)methyl]phosphonate
• 英文别名: diethyl (4-cholorophenyl)-N-(phenyl)aminomethylphosphonate；O,O'-diethyl [(anilino)(4-chlorophenyl)methyl]phosphonate；diethyl (4-chlorophenyl)-N-(phenyl)aminomethylphosphonate；diethyl ((4-chlorophenyl)(phenylamino)methyl)phosphonate；diethyl (4-chlorophenyl)(N-phenylamino)methylphosphonate；diethyl (4-chlorophenyl)(phenylamino)methylphosphonate；N-[(4-chlorophenyl)-diethoxyphosphorylmethyl]aniline
• CAS: 26321-54-0
• 化学式: C₁₇H₂₁ClNO₃P
• 分子量: 353.785
• InChiKey: KLONBEYMRHXBQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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：

  苯胺 在 盐酸 、 碘 、 铁粉 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 13.7h， 生成 diethyl [(4-chlorophenyl)(phenylamino)methyl]phosphonate
  参考文献：
  名称：

  在无溶剂条件下由芳基叠氮化物一锅法合成α-氨基膦酸酯的高效便捷方法

  摘要：

  摘要 已开发出一种新颖，简单的方法，可在室温下在无溶剂条件下进行醛，亚磷酸二乙酯和叠氮化物的多组分一锅反应以形成α-氨基膦酸酯。在碘和铁的存在下，芳基叠氮化物首次被用作合成α-氨基膦酸酯的底物。反应在5分钟至12小时内完成，并以高收率得到相应的产物。 已开发出一种新颖，简单的方法，可在室温下在无溶剂条件下进行醛，亚磷酸二乙酯和叠氮化物的多组分一锅反应以形成α-氨基膦酸酯。在碘和铁的存在下，芳基叠氮化物首次被用作合成α-氨基膦酸酯的底物。反应在5分钟至12小时内完成，并以高收率得到相应的产物。

  DOI：

  10.1055/s-0033-1339377

文献信息

• T3P®-promoted Kabachnik–Fields reaction: an efficient synthesis of α-aminophosphonates
  作者：Mátyás Milen、Péter Ábrányi-Balogh、András Dancsó、Dávid Frigyes、László Pongó、György Keglevich

  DOI：10.1016/j.tetlet.2013.07.145

  日期：2013.10

  A simple and efficient synthesis of α-aminophosphonates has been developed via the one-pot three-component reactions of aldehydes, amines, and trialkyl phosphites. The reactions occurred rapidly at room temperature in the presence of 1 equiv of propylphosphonic anhydride (T3P®) as the condensing agent, and the α-aminophosphonate products were obtained in high yields.

  通过醛，胺和亚磷酸三烷基酯的一锅式三组分反应，已经开发出一种简单而有效的α-氨基膦酸酯合成方法。该反应在室温下在1当量的丙基膦酸酐（T3P®）作为缩合剂的情况下迅速发生，并且以高收率获得了α-氨基膦酸酯产物。
• Highly efficient metal-free one-pot synthesis of <font>α</font>-aminophosphonates through reduction followed by Kabachnik–fields reaction using three-component system
  作者：Murali Krishna Kolli、Palani Elamathi、Govindasamy Chandrasekar、Vishweshwar Rao Katta、Gajendrasinh Balvantsinh Raolji

  DOI：10.1080/00397911.2017.1385083

  日期：2018.3.19

  ABSTRACT One-pot synthesis of α-aminophosphonates directly from aryl nitro compounds, aldehydes/ketones, and diethyl phosphite using sodium dithionite through reduction and followed by Kabachnik–Fields reaction under metal-free conditions is reported. The major advantages are excellent yield, high chemoselectivity, neutral reaction medium, and simple experimental procedure. This methodology consists

  摘要报道了使用连二亚硫酸钠通过还原，然后在无金属条件下进行 Kabachnik-Fields 反应，直接从芳基硝基化合物、醛/酮和亚磷酸二乙酯一锅法合成 α-氨基膦酸酯。主要优点是收率高、化学选择性高、反应介质中性、实验过程简单。该方法包括以下步骤：1) 硝基化合物形成胺，2) 胺和醛/酮形成亚胺，3) 磷酸盐加成到亚胺。图形概要
• A novel straightforward synthesis of α-aminophosphonates: one-pot three-component condensation of alcohols, amines, and diethylphosphite in the presence of CuO@Fe3O4 nanoparticles as a catalyst
  作者：Babak Kaboudin、Foad Kazemi、Narges Kadkhoda Hosseini

  DOI：10.1007/s11164-017-2890-y

  日期：2017.8

  here a novel and straightforward synthesis method for the preparation of α-aminophosphonates in relatively good yield. The method involves the one-pot three-component condensation of alcohols, amines, and diethylphosphite in the presence of CuO@Fe3O4 nanoparticles as a recyclable catalyst. CuO@Fe3O4 nanoparticles were prepared and their structures were confirmed by the FT-IR, TGA, VSM, TEM and X-ray

  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。
• Synthesis of α-aminophosphonates using carbon nanotube supported imidazolium salt-based ionic liquid as a novel and environmentally benign catalyst
  作者：Kaveh Parvanak Boroujeni、Elham Rezazadeh Shirazi、Mohammad Mahdi Doroodmand

  DOI：10.1080/10426507.2015.1072182

  日期：2016.5.3

  Abstract A supported acidic catalyst was easily prepared via anchoring imidazolium salt-based ionic liquid onto multiwalled carbon nanotube by covalent bonds. This novel immobilized acidic ionic liquid effectively catalyzed the one-pot synthesis of α-aminophosphonates from the reaction of amines and aldehydes with diethyl phosphite. The catalyst can be easily recovered and reused without appreciable

  摘要 通过将咪唑鎓盐基离子液体通过共价键锚定在多壁碳纳米管上，很容易制备负载型酸性催化剂。这种新型固定化酸性离子液体有效地催化了胺和醛与亚磷酸二乙酯反应一锅法合成 α-氨基膦酸酯。催化剂可以很容易地回收和再利用，而不会明显改变其效率。图形概要
• A simple protocol for the synthesis of<i>α</i>-substituted phosphonates
  作者：Xing Wang、Yuan Cai、Jian Chen、Francis Verpoort

  DOI：10.1080/10426507.2016.1167056

  日期：2016.9.1

  GRAPHICAL ABSTRACT ABSTRACT An efficient, easy-to-handle, and mild substitution reaction approach has been developed for the synthesis of phosphonate derivatives, which are very important in the field of industrial, agricultural, and medicinal chemistry. A large number of nucleophiles, including arylamines, alkylamines, heteroarylamines, primary amines and secondary amines, sulfides, and carbides were

  图形摘要摘要已开发出一种高效、易于操作且温和的取代反应方法来合成膦酸酯衍生物，其在工业、农业和药物化学领域非常重要。大量亲核试剂，包括芳胺、烷基胺、杂芳胺、伯胺和仲胺、硫化物和碳化物试图与 α-甲苯磺酰氧基膦酸酯 1 反应。反应在无催化剂和纯净的条件下进行，得到相应的膦酸酯 2收益良好。