dimethyl ((phenylamino)(o-tolyl)methyl)phosphonate | 1220122-24-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: dimethyl ((phenylamino)(o-tolyl)methyl)phosphonate
• CAS: 1220122-24-6
• 化学式: C₁₆H₂₀NO₃P
• 分子量: 305.313
• InChiKey: WBLMODUEMSNSPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.59
• 重原子数：
  21.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  47.56
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  N-(o-methylbenzylidene)aniline 、 亚磷酸二甲酯 在 C₂₆H₃₅AlN₂ 作用下， 以 甲苯 为溶剂， 以96 %的产率得到dimethyl ((phenylamino)(o-tolyl)methyl)phosphonate
  参考文献：
  名称：

  新型二齿N-配位烷基铝配合物：合成、表征以及氢膦酰化的有效催化

  摘要：

  成功合成并表征了五种具有不同吡啶基取代亚胺或环己基取代亚胺的新型烷基铝配合物。铝络合物[FlCHNCH(CH 3 )Py]AlMe 2 (Py=2-吡啶基)( 1 )是通过9-[2-吡啶基-CH(CH 3 )-N反应得到 CH]Fl (Fl = 芴基) ( L 1 ) 和等摩尔的 AlMe 3 。 9-(2-吡啶基-N)的反应 CH)Fl ( L 2 ) 和 9-[2-N(CH 3 ) 2 -环己基-N CH]Fl ( L 3 ) 与等摩尔 AlMe 3或 AlEt 3得到其他烷基铝络合物 [FlCHNPy]AlMe 2 (Py = 2-吡啶基) ( 2 )、[FlCHNPy]AlEt 2 (Py = 2-吡啶基) ( 3 )， [FlCHNCyN(CH 3 ) 2 ]AlMe 2 (Cy=2-环己基)( 4 )和[FlCHNCyN(CH 3 ) 2 ]AlEt 2 (Cy=2-环己基)(

  DOI：

  10.1039/d3dt04087a

文献信息

• 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。
• Silica supported polyphosphoric acid (PPA-SiO_2): an efficient and reusable heterogeneous catalyst for the one-pot synthesis of \alpha -amino phosphonates
  作者：MALEK TAHER MAGHSOODLOU、SAYYED MOSTAFA HABIBI-KHORASSANI、REZA HEYDARI、NOUROLLAH HAZERI、SEYED SAJAD SAJADIKHAH、MOHSEN ROSTAMIZADEH、LEILA KEISHAMS

  DOI：10.3906/kim-0910-28

  日期：——

  An efficient green protocol is described for the preparation of \alpha -amino phosphonates, employing a one-pot three-component condensation reaction between aldehydes, amines, and trialkyl phosphites in the presence of PPA-SiO_2 under solvent-free conditions at 80 °C. The present procedure offer advantages such as high to excellent yields, short reaction time, inexpensiveness, recovery, and reusability of catalyst.

  在 80 °C 无溶剂条件下，在 PPA-SiO_2 存在下，采用醛、胺和三烷基膦酸盐之间的单锅三组分缩合反应，描述了制备 \alpha -氨基膦酸盐的高效绿色方案。本方法具有产率高、反应时间短、无毒、可回收和催化剂可重复使用等优点。
• A green protocol for one-pot three-component synthesis of α-amino phosphonates catalyzed by succinic acid
  作者：Nourallah Hazeri、Malek Taher Maghsoodlou、Sayyed Mostafa Habibi-Khorassani、Jasem Aboonajmi、Mojtaba Lashkari、Seyed Sajad Sajadikhah

  DOI：10.1007/s11164-013-1081-8

  日期：2014.5

  Abstract A simple, efficient, and general method has been developed for the one-pot, three-component synthesis of α-amino phosphonates from a condensation reaction of trialkyl phosphite, aldehydes, and amines in the presence of a catalytic amount of succinic acid (8.5 mol %) (for the first time) under solvent-free conditions. The advantages of this protocol are excellent yields, short reaction time

  摘要 已经开发了一种简单，有效且通用的方法，用于在催化量的琥珀酸存在下，通过亚磷酸三烷基酯，醛和胺的缩合反应，进行一锅三组分合成α-氨基膦酸酯。 mol％）（首次）在无溶剂条件下。该方案的优点是产率高，反应时间短，反应条件温和，可用性更高，成本更低，更环保，无需柱色谱法和简单的后处理程序。 图形概要
• 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.