[1-(3-nitrophenyl)-2,2-dicyanoethyl]phosphonic acid diethyl ester | 1402820-72-7

• 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-(3-nitrophenyl)-2,2-dicyanoethyl]phosphonic acid diethyl ester
• 英文别名: diethyl 2,2-dicyano-1-(3-nitrophenyl)ethylphosphonate；2-[[Diethoxy(oxido)phosphaniumyl]-(3-nitrophenyl)methyl]propanedinitrile；2-[[diethoxy(oxido)phosphaniumyl]-(3-nitrophenyl)methyl]propanedinitrile
• CAS: 1402820-72-7
• 化学式: C₁₄H₁₆N₃O₅P
• 分子量: 337.272
• InChiKey: WILQDVCJNSVHAP-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：
  135
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3-(2,2-二氰基乙烯基)-N-羟基苯胺氧化物 、 亚磷酸二乙酯 在 ionic tagged propyl amine immobilized on magnetic nanoparticles 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以89%的产率得到[1-(3-nitrophenyl)-2,2-dicyanoethyl]phosphonic acid diethyl ester
  参考文献：
  名称：

  Novel Ionic Tagged Amine Anchored on Magnetic Nanoparticles: An Efficient and Magnetically Recyclable Catalyst for Phospha-Michael Addition

  摘要：

  Ionic tagged propyl amine immobilized on magnetic nanoparticles (MNPs) was synthesized and fully characterized. The novel catalyst (MNPs@PA-IL) was applied in phospha-Michael addition and gave the desired beta-phosphonomalonates in good yields. The MNPs supported catalyst with ionic tag could be readily recovered from the reaction mixture using an external magnet. Compared with ionic-free counterpart (MNPs@PA), MNPs@PA-IL present better catalytic activity. The proposed mechanism regarding the MNPs@PA-IL catalyzed phospha-Michael reaction was also discussed.

  DOI：

  10.1007/s10562-014-1342-1

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。
• A practical and highly efficient protocol for multicomponent synthesis of β-phosphonomalononitriles and 2-amino-4H-chromen-4-yl phosphonates using diethylamine as a novel organocatalyst
  作者：M.A. Kulkarni、V.R. Pandurangi、U.V. Desai、P.P. Wadgaonkar

  DOI：10.1016/j.crci.2012.07.001

  日期：2012.9

  has been demonstrated for the first time to be a highly efficient organocatalyst in the solvent-free synthesis of β-phosphonomalononitriles by a three component condensation of aldehyde, malononitrile and dialkyl phosphite at ambient temperature. The applicability of the same catalyst in the synthesis of diethyl (2-amino-3-cyano-chromene-4-yl) phosphonic acid esters has also been described.

  摘要 二乙胺在室温下通过醛、丙二腈和亚磷酸二烷基酯的三组分缩合反应，首次被证明是一种高效的有机催化剂，可用于无溶剂合成 β-膦酰基丙二腈。还描述了相同催化剂在二乙基（2-氨基-3-氰基-色烯-4-基）膦酸酯的合成中的适用性。
• Heterogeneous reusable catalyst, ultrasound energy, and no solvent: a quick and green recipe for one-pot synthesis of β-phosphonomalononitriles at room temperature
  作者：Bashir Ahmad Dar、Nalini Pandey、Snehil Singh、R.K. Bamezai、Meena Sharma、Ram A. Vishwakarma、Baldev Singh

  DOI：10.1016/j.tetlet.2013.11.095

  日期：2014.1

  Clay-supported heteropolyacid catalyst has been prepared and investigated as a novel heterogeneous, reusable and efficient catalyst for the one-pot synthesis of beta-phosphonomalononitriles under ultrasound irradiation at room temperature. Compared with traditional methods, the present method is solvent-free, works under milder and cleaner conditions, furnishes products with higher purity and yields, needs shorter reaction time, easier work-up procedure, and generates less waste. No column purification is required and the products can be purified by simple crystallization. The catalyst can be easily recovered and reused several times without significant loss of its catalytic activity. The catalyst was characterized by scanning electron microscopy, X-ray powder diffraction, and thermal gravimetric, surface area, and elemental analyses. (C) 2013 Elsevier Ltd. All rights reserved.