dimethyl ((2-bromophenyl)(phenylamino)methyl)phosphonate | 1433901-24-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: dimethyl ((2-bromophenyl)(phenylamino)methyl)phosphonate
• 英文别名: N-[(2-bromophenyl)-dimethoxyphosphorylmethyl]aniline
• CAS: 1433901-24-6
• 化学式: C₁₅H₁₇BrNO₃P
• 分子量: 370.183
• InChiKey: AFRBZVSLFAUYTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  磷酸三甲酯 、 苯胺 、 邻溴苯甲醛 在 phosphotungstic acid supported on imidazole functionalized silica coated cobalt ferrite nanoparticle 作用下， 以 neat (no solvent) 为溶剂， 反应 0.33h， 以94%的产率得到dimethyl ((2-bromophenyl)(phenylamino)methyl)phosphonate
  参考文献：
  名称：

  Magnetic nanoparticle supported polyoxometalate: An efficient and reusable catalyst for solvent-free synthesis of α-aminophosphonates

  摘要：

  A new magnetically separable catalyst consisting of phosphotungstic acid (PTA) supported on imidazole functionalized silica coated cobalt ferrite nanoparticles was prepared. The synthesized catalyst was characterized by X-ray powder diffraction (XRD), transmission electron microscopy (TEM), vibrating sample magnetometry (VSM), thermogravimetric analysis (TGA), Fourier transform infrared (FT-IR), and inductively coupled plasma atomic emission spectroscopy (ICP-AES). The immobilized phosphotungstic acid was shown to be an efficient heterogeneous catalyst for the synthesis of alpha-aminophosphonates under solvent-free conditions at room temperature. The catalyst is readily recovered by simple magnetic decantation and can be recycled several times with no significant loss of catalytic activity. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2013.02.018

文献信息

• α-Aminophosphonates as novel anti-leishmanial chemotypes: synthesis, biological evaluation, and CoMFA studies
  作者：Srikant Bhagat、Parth Shah、Sanjeev K. Garg、Shweta Mishra、Preet Kamal Kaur、Sushma Singh、Asit K. Chakraborti

  DOI：10.1039/c3md00388d

  日期：——

  α-Aminophosphonates have been identified as novel anti-leishmanial chemotypes against theL. donovanipromastigote with low μM range activity.

  α-氨基膦酸酯已被确定为针对L. donovani原虫具有低微米范围活性的新型抗利什曼病化合物。
• Silver‐Catalyzed One‐Pot Three‐Component Synthesis of α‐Aminonitriles and Biologically Relevant α‐Amino‐phosphonates
  作者：Vipin K. Pandey、Chandra Shekhar Tiwari、Arnab Rit

  DOI：10.1002/asia.202200703

  日期：2022.10.17

  AbstractA simple silver salt (AgSbF6)‐catalyzed aminophosphonylation and Strecker reaction have been developed and successfully applied to a wide range of substrates (>55 substrates). This solvent‐, ligand‐, and base‐free one‐pot three‐component protocol operates effectively at room temperature to provide diversified α‐aminophosphonates and α‐aminonitriles, which gave access to the respective α‐amino amides. Importantly, the present catalyst system is also capable to produce the rarely reported and biologically relevant aminophosphonates (having anti‐leishmanial activity). Further, mechanistic studies reveal that the present phosphonylation protocol follows a radical pathway.