[1-(4-nitrophenyl)-2,2-dicyanoethyl]phosphonic acid diethyl ester | 1035423-93-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [1-(4-nitrophenyl)-2,2-dicyanoethyl]phosphonic acid diethyl ester
• 英文别名: diethyl (2,2-dicyano-1-(4-nitrophenyl)ethyl)phosphonate；diethyl 2,2-dicyano-1-(4-nitrophenyl)ethylphosphonate；2-[Diethoxyphosphoryl-(4-nitrophenyl)methyl]propanedinitrile
• CAS: 1035423-93-8
• 化学式: C₁₄H₁₆N₃O₅P
• 分子量: 337.272
• InChiKey: BVTYKLLODNBCDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  129
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  对硝基苯甲醛 在 iron-doped single walled carbon nanotubes 作用下， 以 neat (no solvent) 为溶剂， 反应 8.0h， 生成 [1-(4-nitrophenyl)-2,2-dicyanoethyl]phosphonic acid diethyl ester
  参考文献：
  名称：

  铁掺杂单壁碳纳米管是无溶剂条件下合成有机磷化合物的有效且可重复使用的多相催化剂

  摘要：

  掺杂铁的单壁碳纳米管（Fe / SWCNT）是一种高效，环保且可重复使用的非均相催化剂，用于在无溶剂条件下通过胺，羰基化合物和磷化合物的多组分反应合成装饰多样化的α-氨基膦酸酯。该方法论证了非常简单的方法，具有广泛的适用性，将范围扩展到脂族和芳族胺和羰基化合物。它也使得在羰基化合物，丙二腈和磷化合物反应过程中一锅法合成β-膦酰基丙二酸酯成为可能。在每种情况下均获得了优异的结果，从而以良好的收率提供了相应的有机磷加合物。

  DOI：

  10.1016/j.tet.2013.03.073

文献信息

• A quaternary ammonium salt [H-dabco][AcO]: as a recyclable and highly efficient catalyst for the one-pot synthesis of β-phosphonomalonates
  作者：Ya-Qin Yu、Da-Zhen Xu

  DOI：10.1039/c5ra02743h

  日期：——

  A simple, green and highly efficient approach for the one-pot three-component synthesis of β-phosphonomalonates has been developed. In the presence of the quaternary ammonium salt catalysts, the β-phosphonomalonates were obtained in excellent yields within short times via tandem Knoevenagel–phospha-Michael reaction. The reaction of aldehydes/ketones, active methylene compounds, and diethyl phosphite

  已经开发出一种简单，绿色且高效的方法，用于一锅三组分合成β-膦酰基丙二酸酯。在季铵盐催化剂的存在下，通过Knoevenagel-phospha-Michael反应串联，可在短时间内以优异的产率获得β-膦酰基丙二酸酯。醛/酮，活性亚甲基化合物和亚磷酸二乙酯的反应在室温，无溶剂条件下进行。不需要柱纯化，并且可以通过简单的结晶纯化产物。催化剂可以容易地回收并重复使用几次，而不会显着降低活性。
• HClO4-SiO2 as a Novel and Recyclable Catalyst for the Phospha-Michael Addition of Phosphorous Nucleophiles to α,β-Unsaturated Malonates
  作者：Sara Sobhani、Soodabeh Rezazadeh

  DOI：10.1055/s-0029-1220069

  日期：2010.6

  An efficient synthesis of β-phosphono malonates via phospha-Michael addition of phosphorous nucleophiles to α,β-unsaturated malonates in the presence of HClO4-SiO2 as a new and ­recyclable catalyst is described.

  描述了一种高效合成β-膦酸丙二酸酯的方法，通过在HClO4-SiO2这一新型且可回收催化剂的存在下，利用磷亲核试剂对α,β-不饱和丙二酸酯进行膦-迈克尔加成反应。
• Aqueous microwave-assisted DMAP catalyzed synthesis of β-phosphonomalonates and 2-amino-4H-chromen-4-ylphosphonates via a domino Knoevenagel-phospha-Michael reaction
  作者：Parteek Kour、Anil Kumar、Vijai K. Rai

  DOI：10.1016/j.crci.2016.05.013

  日期：2017.2

  Résumé An aqueous microwave (mw)-assisted DMAP catalyzed one-pot highly efficient route to synthesize β-phosphonomalonates and 2-amino-4H-chromen-4-yl phosphonates has been demonstrated via the domino Knoevenagel-phospha-Michael reaction of aryl aldehyde/salicylaldehyde, malononitrile/ethyl cyanoacetate and alkyl phosphite ester. Optimization of reaction conditions were performed by using conventional and microwave synthetic approaches. This conversion proceeded smoothly to deliver the desired product in good to excellent yields (75–95%) in a short reaction time (10–12 min). The present methodology is very simple, environmentally benign, high yielding and has very well demonstrated the synergistic effect of water and microwaves. Supplementary Materials: Supplementary material for this article is supplied as a separate file: mmc1.docx

  摘要 我们展示了一种水相微波（mw）辅助的DMAP催化一锅法高效合成β-磷酰基丙二酸酯和2-氨基-4H-色烯-4-基磷酸酯的方法，该方法通过芳醛/水杨醛、马来腈/乙基氰乙酸酯和烷基磷酸酯的多米诺Knoevenagel-磷酰-迈克尔反应实现。通过常规和微波合成方法对反应条件进行了优化。该转化过程顺利进行，在短时间内（10-12分钟）以良至优异的收率（75-95%）获得所需产物。该方法简单、环保、产率高，并很好地展示了水和微波的协同效应。 补充材料： 本文的补充材料作为单独文件提供：mmc1.docx
• Phospha-Michael addition of diethyl phosphite to α,β-unsaturated malonates catalyzed by nano γ-Fe2O3-pyridine based catalyst as a new magnetically recyclable heterogeneous organic base
  作者：Sara Sobhani、Mahboobeh Bazrafshan、Amin Arabshahi Delluei、Zahra Pakdin Parizi

  DOI：10.1016/j.apcata.2013.01.009

  日期：2013.3

  Nano γ-Fe2O3-pyridine based catalyst as a new magnetically recyclable heterogeneous organic base was synthesized. The synthesized odorless pyridine based catalyst was used as a new catalyst for the efficient synthesis of β-phosphonomalonates by the reaction of diethyl phosphite with α,β-unsaturated malonates. The catalyst was easily isolated from the reaction mixture by a magnetic bar and reused at

  纳米了γ-Fe 2 ö 3基于吡啶催化剂作为新的磁可回收异构有机碱的合成。合成的无味吡啶基催化剂被用作通过亚磷酸二乙酯与α，β-不饱和丙二酸酯反应有效合成β-膦酰基丙二酸酯的新催化剂。容易通过磁力棒将催化剂从反应混合物中分离出来，并重复使用至少10次，而活性没有明显降低。
• LiBr-catalyzed one-pot three-component domino strategy toward the construction of <i>β</i>-phosphonomalonates scaffolds in aqueous conditions
  作者：Vikas Kumar、Parteek Kour、Anil Kumar

  DOI：10.1080/10426507.2019.1702988

  日期：2020.8.2

  Abstract LiBr-mediated domino Knoevenagel-phospha-Michael strategy has been established for the synthesis of β-phosphonomalonates under aqueous conditions. It is noteworthy that the developed protocol is effective with a wide range of aldehydes to deliver a diverse range of β-phosphonomalonates in good to excellent yields. The mild reaction conditions, easier procedure, use of aqueous media, inexpensive

  摘要 LiBr 介导的多米诺 Knoevenagel-phospha-Michael 策略已被建立用于在水性条件下合成 β-膦酰丙二酸酯。值得注意的是，所开发的协议对多种醛类均有效，可提供多种 β-膦酰丙二酸酯，收率良好至极好。温和的反应条件、更简单的程序、使用水性介质、廉价和耐水的溴化锂是该协议的重要优势。图形概要