diethyl ((4-tolylamino)(4-(dimethylamino)phenyl)methyl)phosphonate | 383408-85-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: diethyl ((4-tolylamino)(4-(dimethylamino)phenyl)methyl)phosphonate
• 英文别名: diethyl (4-(dimethylamino)phenyl)(p-tolylamino)methylphosphonate；p-[N-methyl(diethoxyphosphonyl)(4-dimethylaminophenyl)]toluidine；Diethyl {[4-(dimethylamino)phenyl][(4-methylphenyl)amino]methyl}phosphonate；N-[diethoxyphosphoryl-[4-(dimethylamino)phenyl]methyl]-4-methylaniline
• CAS: 383408-85-3
• 化学式: C₂₀H₂₉N₂O₃P
• 分子量: 376.436
• InChiKey: GIZKYJLPYWQOLZ-UHFFFAOYSA-N

物化性质

• 熔点：
  101-102 °C(Solv: ethanol (64-17-5))
• 沸点：
  525.0±50.0 °C(Predicted)
• 密度：
  1.149±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  50.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl ((4-tolylamino)(4-(dimethylamino)phenyl)methyl)phosphonate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 N-(4-dimethylaminobenzylidene)-p-toluidine
  参考文献：
  名称：

  两种新型蒽衍生的 BIS-氨基膦酸酯的合成和 NMR 表征。一些氨基膦酸盐衍生物的碱性水解

  摘要：

  摘要 合成两种带有蒽环的新型双氨基膦酸酯——双[N-甲基(二乙氧基膦酰基)-1-(9-蒽基)]联苯胺 (3) 和 4,4'-双[N-甲基(二乙氧基-膦酰基) -1-(9-anthryl)]diaminodiphenylmethane (4) – 报道了通过 Kabachnik-Fields 反应。这些化合物已通过元素分析、TLC、IR、NMR（1H、13C、31P）和荧光光谱表征。该反应导致两种可能形式（内消旋和外消旋）的混合物，其中主要形成一种非对映异构体。重结晶的化合物 3 和 4 仅由一种非对映异构体组成。在新化合物 4 和三种先前描述的氨基膦酸酯衍生物 5-7 的碱性水解中观察到手性中心的外消旋化和 CP 键的断裂。补充材料可用于本文。转至出版商在线版的磷、硫和硅及相关元素，查看免费的补充文件。图形概要

  DOI：

  10.1080/10426507.2011.638349
• 作为产物：
  描述：

  N-(4-dimethylaminobenzylidene)-p-toluidine 、 亚磷酸二乙酯 在 cadmium(II) iodide 作用下， 以 苯 为溶剂， 反应 3.0h， 以76%的产率得到diethyl ((4-tolylamino)(4-(dimethylamino)phenyl)methyl)phosphonate
  参考文献：
  名称：

  Synthesis, NMR characterization and in vitro antitumor evaluation of new aminophosphonic acid diesters

  摘要：

  The synthesis of three novel m-aminophosphonic acid diesters N,N-dimethyl-[N'-methy](diethoxyphosphonyl)-(2-furyl)1-1,3-diaminopropane, p-IN-methyl(diethoxyphosphonyl)-(2-furyl)]toluidine and p-[N-methyl(diethoxyphosphonyl)-(4-dimethylaminophenyl)]toluidine through an addition of diethyl phosphite to N,N-dimethyl-N'-furfurylidene-1,3-diaminopropane, N-furfurylidene-p-toluidine and N-(4-dimethylaminobenzylidene)-p-toluidine, respectively, is reported. The alpha-aminophosphonates have been characterized by elemental analysis, IR and NMR (H-1, C-13 and P-31) spectra. The compounds were tested for anti proliferative effects against 4 human leukemic cell lines, namely LAMA-84, K-562 (chronic myeloid leukemias), HL-60 (acute promyelocyte leukemia) and HL-60/Dox (multi-drug-resistant sub-line, characterized by overexpression of MRP-1 (ABC-C1)) and were found to exert concentration-dependent cytotoxic effects. A representative aminophosphonate compound was shown to induce oligonucleosomal DNA fragmentation which implies that the induction of cell death through apoptosis plays an important role for its cytotoxicity mode of action. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.03.017

文献信息

• Organic Reactions in Water: A Distinct Novel Approach for an Efficient Synthesis of α-Amino Phosphonates Starting Directly from Nitro Compounds
  作者：Biswanath Das、Gandham Satyalakshmi、Kanaparthy Suneel、Kongara Damodar

  DOI：10.1021/jo901765s

  日期：2009.11.6

  A distinct approach for high-yielding synthesis of α-amino phosphonates has been discovered through three-component reaction of nitro compounds, aldehydes, or ketones and dialkyl or trialkyl phosphites using indium in dilute aqueous HCl at room temperature. This one-pot conversion consists of the following steps: (i) reduction of nitro compounds to amines, (ii) formation of imines from amines and carbonyl

  通过在室温下在稀盐酸水溶液中使用铟使硝基化合物，醛或酮与亚磷酸二烷基酯或三烷基亚磷酸酯发生三组分反应，已发现了一种高产率合成α-氨基膦酸酯的独特方法。这一一锅转化包括以下步骤：（i）将硝基化合物还原为胺，（ii）由胺和羰基化合物形成亚胺，以及（iii）亚胺的氢膦酰化。
• An Eco-friendly Three Component Manifold for the Synthesis of<i>α</i>-Aminophosphonates under Catalyst and Solvent-free Conditions, X-ray Characterization and Their Evaluation as Anticancer Agents
  作者：Mahdi Mirzaei、Hossein Eshghi、Mohammad Rahimizadeh、Mehdi Bakavoli、Maryam M. Matin、Minoo Hosseinymehr、Hadi Amiri Rudbari、Giuseppe Bruno

  DOI：10.1002/jccs.201500250

  日期：2015.12

  A series of α‐aminophosphonates were synthesized through one‐pot condensation of aryl aldehydes, aryl amines and diethyl phosphite in the absence of any catalyst and organic solvents. All the synthesized α‐aminophosphonates were characterized by spectral and elemental analysis and in the case of compound 4j by X‐ray crystallography. Some of these new α‐aminophosphonate derivatives were found to have

  在不存在任何催化剂和有机溶剂的情况下，通过芳基醛，芳基胺和亚磷酸二乙酯的一锅缩合反应，合成了一系列α-氨基膦酸酯。所有合成的α-氨基膦酸酯均通过光谱和元素分析进行​​表征，对于化合物4j，则通过X射线晶体学进行表征。通过MTT方法，发现其中一些新的α-氨基膦酸酯衍生物在体外对癌细胞系DU145具有细胞毒活性。
• Synthesis and NMR Characterization of Two Novel Anthracene-Derived BIS-Aminophosphonates. Basic Hydrolysis of Some Aminophosphonate Derivatives
  作者：I. Kraicheva、E. Vodenicharova、E. Tashev、T. Tosheva、I. Tsacheva、K. Troev

  DOI：10.1080/10426507.2011.638349

  日期：2012.5

  of only one diastereomer. A racemization at the chiral centers and a cleavage of the C-P bond are observed in the alkaline hydrolysis of the new compound 4 and three previously described aminophosphonate derivatives 5–7. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental

  摘要 合成两种带有蒽环的新型双氨基膦酸酯——双[N-甲基(二乙氧基膦酰基)-1-(9-蒽基)]联苯胺 (3) 和 4,4'-双[N-甲基(二乙氧基-膦酰基) -1-(9-anthryl)]diaminodiphenylmethane (4) – 报道了通过 Kabachnik-Fields 反应。这些化合物已通过元素分析、TLC、IR、NMR（1H、13C、31P）和荧光光谱表征。该反应导致两种可能形式（内消旋和外消旋）的混合物，其中主要形成一种非对映异构体。重结晶的化合物 3 和 4 仅由一种非对映异构体组成。在新化合物 4 和三种先前描述的氨基膦酸酯衍生物 5-7 的碱性水解中观察到手性中心的外消旋化和 CP 键的断裂。补充材料可用于本文。转至出版商在线版的磷、硫和硅及相关元素，查看免费的补充文件。图形概要
• Synthesis, NMR characterization and in vitro antitumor evaluation of new aminophosphonic acid diesters
  作者：I. Kraicheva、A. Bogomilova、I. Tsacheva、G. Momekov、K. Troev

  DOI：10.1016/j.ejmech.2009.03.017

  日期：2009.8

  The synthesis of three novel m-aminophosphonic acid diesters N,N-dimethyl-[N'-methy](diethoxyphosphonyl)-(2-furyl)1-1,3-diaminopropane, p-IN-methyl(diethoxyphosphonyl)-(2-furyl)]toluidine and p-[N-methyl(diethoxyphosphonyl)-(4-dimethylaminophenyl)]toluidine through an addition of diethyl phosphite to N,N-dimethyl-N'-furfurylidene-1,3-diaminopropane, N-furfurylidene-p-toluidine and N-(4-dimethylaminobenzylidene)-p-toluidine, respectively, is reported. The alpha-aminophosphonates have been characterized by elemental analysis, IR and NMR (H-1, C-13 and P-31) spectra. The compounds were tested for anti proliferative effects against 4 human leukemic cell lines, namely LAMA-84, K-562 (chronic myeloid leukemias), HL-60 (acute promyelocyte leukemia) and HL-60/Dox (multi-drug-resistant sub-line, characterized by overexpression of MRP-1 (ABC-C1)) and were found to exert concentration-dependent cytotoxic effects. A representative aminophosphonate compound was shown to induce oligonucleosomal DNA fragmentation which implies that the induction of cell death through apoptosis plays an important role for its cytotoxicity mode of action. (C) 2009 Elsevier Masson SAS. All rights reserved.