diethyl ((2-methylphenyl)(phenylamino)methyl)phosphonate

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: diethyl ((2-methylphenyl)(phenylamino)methyl)phosphonate
• 英文别名: O,O'-diethyl [(anilino)(2-methylphenyl)methyl]phosphonate；diethyl ((phenylamino)(o-tolyl) methyl)phosphonate；N-[diethoxyphosphoryl-(2-methylphenyl)methyl]aniline
• 化学式: C₁₈H₂₄NO₃P
• 分子量: 333.367
• InChiKey: FQOGVWJCPQJFDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  2-甲基苯甲醛 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 生成 diethyl ((2-methylphenyl)(phenylamino)methyl)phosphonate
  参考文献：
  名称：

  合成α-取代膦酸盐的简单方案

  摘要：

  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。

  DOI：

  10.1080/10426507.2016.1167056

文献信息

• 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。
• Magnetic Fe₃O₄Nanoparticle-Supported Phosphotungstic Acid as a Recyclable Catalyst for the Kabachnik-Fields Reaction of Isatins, Imines, and Aldehydes under Solvent-Free Conditions
  作者：Mohd Nazish、S. Saravanan、Noor-ul H. Khan、Prathibha Kumari、Rukhsana I. Kureshy、Sayed H. R. Abdi、Hari C. Bajaj

  DOI：10.1002/cplu.201402191

  日期：2014.9.22

  reaction of isatins, imines, and aldehydes using dimethyl and diethyl phosphite as a nucleophile to give the corresponding α‐hydroxy and α‐amino phosphonates in excellent yields for a wide range of substrates. The reaction conditions were simple, green, and efficient. The catalyst was recycled up to five times with retention of its activity. Based on the NMR spectroscopy studies, a probable catalytic cycle

  磁性纳米颗粒负载的磷钨酸已被用于以亚磷酸二甲酯和亚磷酸二乙酯为亲核试剂，有效地催化靛红，亚胺和醛的加氢膦酰化反应，从而在宽范围内以优异的收率得到相应的α-羟基和α-氨基膦酸酯。的基板。反应条件简单，绿色，高效。在保持活性的情况下，将催化剂再循环至五次。基于NMR光谱学研究，提出了可能的催化循环。
• A green one-pot three-component synthesis of α-aminophosphonates under solvent-free conditions and ultrasonic irradiation using Fe₃O₄@SiO₂-imid-PMAⁿ as magnetic catalyst
  作者：Mohsen Esmaeilpour、Saeed Zahmatkesh、Jaber Javidi、Elahe Rezaei

  DOI：10.1080/10426507.2016.1269232

  日期：2017.5.4

  GRAPHICAL ABSTRACT ABSTRACT An efficient and environment friendly process for the synthesis of α-aminophosphonates has been devised. Through a one-pot three-component condensation of various aldehydes, amines, and triethyl phosphite in the presence of Fe3O4@SiO2-imid-PMAn nanoparticles as magnetic catalysts under solvent-free conditions and ultrasonic irradiation, α-aminophosphonates were obtained

  图形摘要 摘要 已设计出一种高效且环境友好的合成 α-氨基膦酸酯的方法。在Fe3O4@SiO2-imid-PMAn纳米粒子作为磁性催化剂存在下，在无溶剂条件和超声波照射下，通过各种醛、胺和亚磷酸三乙酯的一锅三组分缩合反应，以优异的收率获得了α-氨基膦酸酯. 将室温下无溶剂条件下的反应与超声辅助反应进行了比较。这种新方法具有显着的优点，例如反应时间短、收率高、易于纯化以及无需任何繁琐的后处理或纯化。上述催化剂可以很容易地通过外部磁场回收，并且可以重复使用六个连续的反应循环而不会显着损失活性。此外，还研究了反应循环后催化剂的 SEM 和 DLS。
• ZrOCl₂·8H₂O: An Efficient Catalyst for One-Pot Synthesis of α-Amino Phosphonates Under Solvent-Free Conditions
  作者：Mayur J. Bhanushali、Nitin S. Nandurkar、Sachin R. Jagtap、Bhalchandra M. Bhanage

  DOI：10.1080/00397910802431206

  日期：2009.2.9

  environmentally friendly catalyst, at ambient temperature. The catalyst exhibited remarkable activity and tolerated a wide variety of functional groups, providing the desired amino phosphonates in excellent yields under solvent-free conditions. Alternatively, the reaction rate can be significantly enhanced by carrying out the reaction in a monomode microwave reactor as a promoter.

  摘要 建立了环境友好型催化剂ZrOCl2·8H2O在常温下催化胺、醛和亚磷酸二乙酯三组分反应的高效方案。该催化剂表现出显着的活性并能耐受多种官能团，在无溶剂条件下以优异的产率提供所需的氨基膦酸酯。或者，可以通过在单模微波反应器中作为促进剂进行反应来显着提高反应速率。
• Lanthanide triflate-catalyzed three component synthesis of α-amino phosphonates in ionic liquids. A catalyst reactivity and reusability study
  作者：Sang-gi Lee、Jung Hwan Park、Jae Kyun Lee、Jahyo Kang

  DOI：10.1039/b104967b

  日期：——

  The catalyst reactivity and reusability for the lanthanide triflate-catalyzed three component synthesis of α-amino phosphonates have been examined in room temperature ionic liquids, [bmim][X], in which the catalytic activities were very dependent on the counter anion, X, as well as on the phosphorus nucleophile, and moreover, the catalyst immobilized in an ionic liquid was reused several times without any loss of activity.

  在室温离子液体[bmim][X]中，对镧系三氟甲磺酸盐催化下的β-氨基膦酸盐的三组分合成的催化剂反应性和可重复性进行了研究，其中催化活性非常依赖于对离子X以及磷亲核体，此外，固定在离子液体中的催化剂可重复使用多次，且活性不会降低。