dimethyl [(2-chlorophenyl)(phenylamino)methyl]phosphonate

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: dimethyl [(2-chlorophenyl)(phenylamino)methyl]phosphonate
• 英文别名: N-[(2-chlorophenyl)-dimethoxyphosphorylmethyl]aniline
• 化学式: C₁₅H₁₇ClNO₃P
• 分子量: 325.732
• InChiKey: KJEDINPGFCQBMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 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：

  2-chlorobenzalaniline 、 亚磷酸二甲酯 在 甲酸 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以75%的产率得到dimethyl [(2-chlorophenyl)(phenylamino)methyl]phosphonate
  参考文献：
  名称：

  甲酸催化一锅合成α-氨基膦酸酯：一种高效，廉价且环保的有机催化剂

  摘要：

  摘要甲酸水溶液通过Kabachnik-Fields反应（使用芳香胺，亚磷酸酯和羰基化合物）用于合成α-氨基膦酸酯。使用甲酸作为一种高效且低成本的有机催化剂可提供环保，高产率，短反应时间和温和的反应条件。通过IR，NMR和质量技术分析分离的产物。 图形概要

  DOI：

  10.1007/s11696-018-0434-6

文献信息

• <i>P</i>-Dodecylbenzenesulfonic Acid: A Highly Efficient Catalyst for One-Pot Synthesis of α-Aminophosphonates in Aqueous Media
  作者：Barahman Movassagh、Saba Alapour

  DOI：10.1002/hc.21079

  日期：2013.5

  A highly efficient one-pot three-component reaction of aldehydes or ketones, amines, and trimethyl or triethyl phosphite catalyzed by p-dodecylbenzensulfonic acid is developed for the synthesis of α-aminophosphonates at room temperature in water. © 2013 Wiley Periodicals, Inc. Heteroatom Chem 24:174–178, 2013; View this article online at wileyonlinelibrary.com. DOI 10.1002/hc.21079

  开发了一种由对十二烷基苯磺酸催化的醛或酮、胺和亚磷酸三甲酯或三乙酯的高效一锅三组分反应，用于在室温下在水中合成 α-氨基膦酸酯。© 2013 Wiley Periodicals, Inc. 杂原子化学 24:174–178, 2013; 在 wileyonlinelibrary.com 上在线查看这篇文章。DOI 10.1002/hc.21079
• 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 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
• Organocatalytic synthesis of α-hydroxy and α-aminophosphonates
  作者：Seyed Mohammad Vahdat、Robabeh Baharfar、Mahmood Tajbakhsh、Akbar Heydari、Seyed Meysam Baghbanian、Samad Khaksar

  DOI：10.1016/j.tetlet.2008.08.094

  日期：2008.11

  A new and highly flexible procedure is described for the synthesis of α-amino- and α-hydroxy phosphonates. In the presence of a catalytic amount of oxalic acid (10 mol %), trimethyl phosphite reacts with aldehydes or imines (generated in situ from an aldehyde and an amine) to yield the corresponding coupled products in good yield.

  描述了用于合成α-氨基-和α-羟基膦酸酯的新的且高度灵活的方法。在催化量的草酸（10mol％）的存在下，亚磷酸三甲酯与醛或亚胺（由醛和胺原位产生）反应，以高收率得到相应的偶联产物。
• An efficient synthesis of α-Amino phosphonates using silica sulfuric acid as a heterogeneous catalyst
  作者：Malek Taher Maghsoodlou、Sayyed Mostafa Habibi Khorassani、Nourollah Hazeri、Mohsen Rostamizadeh、Seyed Sajad Sajadikhah、Zahra Shahkarami、Nariman Maleki

  DOI：10.1002/hc.20543

  日期：——

  α-Amino phosphonates were obtained in a one-pot, simple, and efficient method from the reaction between aldehyde, aniline, trialkyl phosphite, and silica sulfuric acid as a catalyst in acetonitrile at room temperature. © 2009 Wiley Periodicals, Inc. Heteroatom Chem 20:316–318, 2009; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20543

  以醛、苯胺、亚磷酸三烷基酯和硫酸二氧化硅为催化剂，在室温下在乙腈中反应，以一锅法、简单、高效的方式制备了α-氨基膦酸酯。© 2009 Wiley Periodicals, Inc. 杂原子化学 20:316–318, 2009; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20543