diethyl (p-tolyl(p-tolylamino)methyl)phosphonate | 857471-34-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: diethyl (p-tolyl(p-tolylamino)methyl)phosphonate
• 英文别名: N-[[diethoxy(oxido)phosphaniumyl]-(4-methylphenyl)methyl]-4-methylaniline
• CAS: 857471-34-2
• 化学式: C₁₉H₂₆NO₃P
• 分子量: 347.394
• InChiKey: LTCPJUWGPMJIBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  53.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl (p-tolyl(p-tolylamino)methyl)phosphonate 、 1,1-亚甲基-2-萘酚 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 以58%的产率得到4-methyl-N-[(4-methylphenyl)-(14-oxo-13,15-dioxa-14lambda5-phosphapentacyclo[14.8.0.03,12.04,9.019,24]tetracosa-1(16),3(12),4,6,8,10,17,19,21,23-decaen-14-yl)methyl]aniline
  参考文献：
  名称：

  Syntheses of substituted 8-(aminobenzyl)dinaphthodioxaphosphocine 8-oxides

  摘要：

  DOI：

  10.1007/s10593-007-0203-x
• 作为产物：
  描述：

  N-(4-methylbenzyl)-4-methylaniline 、 亚磷酸二乙酯 在 氧气 、 tris(p-bromophenylammoniumyl) hexachloroantimonate 作用下， 以 乙腈 为溶剂， 反应 10.0h， 以86%的产率得到diethyl (p-tolyl(p-tolylamino)methyl)phosphonate
  参考文献：
  名称：

  N-苄基苯胺的自由基阳离子盐引发的好氧CH磷酸化：α-氨基膦酸酯的合成

  摘要：

  N-苄基苯胺的自由基阳离子盐引发的磷酸化通过对sp 3 C-H键的需氧氧化实现，从而以高收率提供了一系列α-氨基膦酸酯。对反应范围的研究表明，该温和的催化剂体系在良好的官能团耐受性和高反应效率方面是优异的。机理研究表明，sp 3 C-H键的断裂参与了速率确定步骤。

  DOI：

  10.1002/asia.201800584

文献信息

• 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。
• Catalyst free one-pot synthesis of α-aminophosphonates in aqueous ethyl lactate
  作者：Ge Gao、Meng-Nan Chen、Li-Ping Mo、Zhan-Hui Zhang

  DOI：10.1080/10426507.2018.1542395

  日期：2019.5.27

  Abstract An highly efficient and environmentally friendly process for the synthesis of α-aminophosphonates has been devised, through a one-pot three-component condensation of various aldehydes, amines and triethyl phosphate in water-ethyl lactate under ultrasonic irradiation conditions at room temperature. The expected products were obtained in high yield without the need for any additional catalyst

  摘要 通过在室温下超声辐照条件下，各种醛、胺和磷酸三乙酯在水-乳酸乙酯中的一锅三组分缩合反应，设计了一种高效、环保的α-氨基膦酸酯合成工艺。无需任何额外的催化剂即可以高收率获得预期产物。图形概要
• One-pot synthesis of α-aminophosphonates catalyzed by antimony trichloride adsorbed on alumina
  作者：Ambica、Satish Kumar、Subhash C. Taneja、Maninder S. Hundal、Kamal K. Kapoor

  DOI：10.1016/j.tetlet.2008.02.047

  日期：2008.3

  SbCl3 adsorbed on Al2O3 is found to be an efficient and recyclable catalyst in promoting three-component coupling reactions of aldehydes (aromatic and aliphatic), amines (aryl amines, aliphatic amines and esters of S-cc-amino acids) and dialkylphosphites to afford the corresponding alpha-aminophosphonates in high yields. The ethyl ester of S-phenylalanine was observed to yield the corresponding ot-aminophosphonate with S,S-diastereoisomer formed in dominance over the S,R-diastereoisomer. (C) 2008 Elsevier Ltd. All rights reserved.
• Gold complex-catalyzed C P bond formation by Kabachnik–Fields reactions
  作者：Yan Zhang、Chengjian Zhu

  DOI：10.1016/j.catcom.2012.08.001

  日期：2012.11

  C - P bond formation was realized through the three-component reaction of an amine, an aldehyde and a dialkylphosphite catalyzed by gold complex. The corresponding alpha-aminophosphonates were afforded in one-pot reaction with high yields under mild conditions. (C) 2012 Elsevier B.V. All rights reserved.
• Radical Cation Salt-initiated Aerobic C−H Phosphorylation of <i>N</i> -Benzylanilines: Synthesis of α-Aminophosphonates
  作者：Xiaodong Jia、Xiaofei Liu、Yu Yuan、Pengfei Li、Wentao Hou、Kaixuan He

  DOI：10.1002/asia.201800584

  日期：2018.8.6

  A radical cation salt‐initiated phosphorylation of N‐benzylanilines was realized through an aerobic oxidation of the sp3 C−H bond, providing a series of α‐aminophosphonates in high yields. An investigation of the reaction scope revealed that this mild catalyst system is superior in good functional group tolerance and high reaction efficiency. The mechanistic study implied that the cleavage of the sp3

  N-苄基苯胺的自由基阳离子盐引发的磷酸化通过对sp 3 C-H键的需氧氧化实现，从而以高收率提供了一系列α-氨基膦酸酯。对反应范围的研究表明，该温和的催化剂体系在良好的官能团耐受性和高反应效率方面是优异的。机理研究表明，sp 3 C-H键的断裂参与了速率确定步骤。