diethyl[anilino(phenyl)methyl]phosphonate

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: diethyl[anilino(phenyl)methyl]phosphonate
• 英文别名: diethyl (phenyl(phenylamino)methyl)phosphonate；diethyl (phenyl)-N-(phenyl)aminomethylphosphonate；diethyl ((phenylamino)(phenyl)methyl)phosphonate；(phenyl(phenylamino)methyl)phosphonic acid diethyl ester；N-[diethoxyphosphoryl(phenyl)methyl]aniline
• 化学式: C₁₇H₂₂NO₃P
• 分子量: 319.34
• InChiKey: IKTPAIHRGPPIDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl[anilino(phenyl)methyl]phosphonate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 10.0h， 以60%的产率得到sodium monoethyl (α-anilino-N-benzyl)phosphonate
  参考文献：
  名称：

  Failla, Salvatore; Finocchiaro, Paolo, Phosphorus, Sulfur and Silicon and the Related Elements, 1993, vol. 85, # 1-4, p. 65 - 72

  摘要：

  DOI：
• 作为产物：
  描述：

  N-苯基亚胺苄基氯 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 diethyl[anilino(phenyl)methyl]phosphonate
  参考文献：
  名称：

  Gross,H. et al., Phosphorus and the Related Group V Elements, 1974, vol. 4, p. 241 - 246

  摘要：

  DOI：

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。
• 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。
• 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。
• 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
• Phenylphosphonic Acid as Efficient and Recyclable Catalyst in the Synthesis of α-Aminophosphonates under Solvent-Free Conditions
  作者：Mario Ordóñez、Mercedes Bedolla-Medrano、Eugenio Hernández-Fernández

  DOI：10.1055/s-0033-1341069

  日期：——

  Phenylphosphonic acid is an efficient, friendly and reusable heterogeneous catalyst for the synthesis of α-aminophosphonates through a ‘one-pot’ three-component reaction of amines, carbonyl compounds and dialkyl phosphites under solvent-free conditions. This methodology illustrates a very simple procedure, with wide applicability, extending the scope to aliphatic and aromatic amines, aliphatic and

  苯基膦酸是一种高效、友好且可重复使用的多相催化剂，用于在无溶剂条件下通过胺、羰基化合物和亚磷酸二烷基酯的“一锅法”三组分反应合成 α-氨基膦酸酯。该方法说明了一个非常简单的程序，具有广泛的适用性，将范围扩展到脂肪族和芳香族胺、脂肪族和芳香族醛以及脂肪族酮。它还能够大规模合成 α-氨基膦酸盐，清洁转化，易于后处理和纯化。在每种情况下都获得了优异的结果，以中等至良好的产率获得了所需化合物。

表征谱图