diethyl (2,2-dicyano-1-(2-methoxyphenyl)ethyl)phosphonate | 1537917-48-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: diethyl (2,2-dicyano-1-(2-methoxyphenyl)ethyl)phosphonate
• 英文别名: 2-[[Diethoxy(oxido)phosphaniumyl]-(2-methoxyphenyl)methyl]propanedinitrile；2-[[diethoxy(oxido)phosphaniumyl]-(2-methoxyphenyl)methyl]propanedinitrile
• CAS: 1537917-48-8
• 化学式: C₁₅H₁₉N₂O₄P
• 分子量: 322.301
• InChiKey: XPYCKXHXXFTPLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.67
• 重原子数：
  22.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  92.34
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  2-甲氧基苄亚基丙二腈 、 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 3.0h， 以82%的产率得到diethyl (2,2-dicyano-1-(2-methoxyphenyl)ethyl)phosphonate
  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

• Tris(hydroxymethyl)aminomethane as an efficient organobase catalyst for the synthesis of β-phosphonomalonates
  作者：Reddi Mohan Naidu Kalla、Il Kim

  DOI：10.1016/j.tetlet.2016.12.035

  日期：2017.2

  Tris(hydroxymethyl)aminomethane (THAM) is a highly efficient and recyclable organobase catalyst for the nucleophilic phosphonylation of benzylidene malononitrile under solvent-free conditions. This new catalytic methodology is applicable without a solvent, eco-friendly, economically viable, avoids conventional isolation procedures, and has a facile work-up procedure and wide scope. THAM is an inexpensive

  三（羟甲基）氨基甲烷（THAM）是高效和可回收的有机碱催化剂，可在无溶剂条件下进行亚苄基丙二腈的亲核膦酰化反应。这种新的催化方法学适用于无溶剂，生态友好，经济可行，避免常规分离程序，后处理程序简便，适用范围广的情况。THAM是一种廉价的，可商购的，无毒且可生物降解的新型有机催化剂。此外，它最多可以重复使用五个循环而不会降低催化活性，并且不需要色谱分离即可获得所需的产物。
• Efficient, Solvent-Free, Multicomponent Method for Organic-Base-Catalyzed Synthesis of β-Phosphonomalonates
  作者：Reddi Mohan Naidu Kalla、Huiju Park、Hye Ri Lee、Hongsuk Suh、Il Kim

  DOI：10.1021/acscombsci.5b00109

  日期：2015.11.9

  An efficient, one-pot, di-n-butylamine-catalyzed, three-component synthesis of beta-phosphonomalonates has been developed. A wide range of substrates, including aromatic and fused aromatic aldehydes, were condensed with enolizable C-H activated compounds and dialkylphosphites to give the desired products in excellent yields. This method provides an eco-friendly alternative approach to rapid construction of a diversity-oriented library of beta-phosphonomalonates.
• 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.