diethyl (N-4-nitrophenylcarbamoyl)phosphonate | 131480-08-5

• 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: diethyl (N-4-nitrophenylcarbamoyl)phosphonate
• 英文别名: diethyl 4-nitrophenylcarbamoylphosphonate；diethyl p-nitrophenylcarbamoylphosphonate；(4-nitro-phenylcarbamoyl)-phosphonic acid diethyl ester；(4-Nitro-phenylcarbamoyl)-phosphonsaeure-diaethylester；1-diethoxyphosphoryl-N-(4-nitrophenyl)formamide
• CAS: 131480-08-5
• 化学式: C₁₁H₁₅N₂O₆P
• 分子量: 302.224
• InChiKey: XLVFFKUNDVQDJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  异氰酸对硝基苯 、 亚磷酸二乙酯 在 silica supported cerium chloride 作用下， 以 neat (no solvent) 为溶剂， 反应 0.67h， 以89%的产率得到diethyl (N-4-nitrophenylcarbamoyl)phosphonate
  参考文献：
  名称：

  CeCl₃.7H₂O-SiO₂ Catalyzed Ultrasonicated Solvent-Free Synthesis of Carbamoyl/Carbamothioyl Phosphonates and Antimicrobial Activity Evaluation

  摘要：

  an expeditious and green method has been developed for the synthesis of a series of P-C bond derivatives, diethyl substituted phenylcarbamoylphosphonates 6(a-e)/phenylcarbamothioylphosphonates 7(a-f) in high yields via simple addition reaction of isocyanates/isothiocyanates with diethyl phosphite in the presence of silica supported Lewis acid catalyst, SiO2-CeCl3.7H(2)O under solvent-free and sonication conditions. The advantages of this method are high yields, avoiding of harmful solvents, operational simplicity, shorter reaction time, and recoverability and recyclability of the catalyst. Antimicrobial activity was assayed for the title compounds, whereas the compounds 6c, 7b, and 7e against bacteria, and 6a, 7b, 7c, and 7e against fungi exhibited potential growth of inhibition.

  DOI：

  10.1080/10426507.2014.974749

文献信息

• Synthesis of organophosphorus compounds via silyl esters of phosphorous acids
  作者：Kamyar Afarinkia、Charles W. Rees、John I.G. Cadogan

  DOI：10.1016/s0040-4020(01)87899-6

  日期：1990.1

  The addition of trimethylsilyloxy phosphorus (III)derivatives generated in situ to imines at room temperature provides a mild selective and high yielding route to α-aminoalkylphosphorate and α-aminoalkylphenylphosphinate esters. Isocyanates and carbodiimides react similarly to give phosphonoureas and phosphonoguarnidines respectively aldehydes and ketones are much less reactive and cyanides are inert

  在室温下将原位产生的三甲基甲硅烷氧基磷（III）衍生物加到亚胺上，为α-氨基烷基磷酸酯和α-氨基烷基苯基次膦酸酯提供了温和的选择性和高产率的途径。异氰酸酯和碳二亚胺类似地反应，分别得到膦酰脲和膦酰胍，醛和酮的反应性低得多，氰化物是惰性的。
• The vicarious intramolecular substitution reactions. I. Synthesis of condensed indolizines based on 2-quinoxalylacetonitriles
  作者：S. V. Litvinenko、Yu. M. Volovenko、F. S. Babichev

  DOI：10.1007/bf00531507

  日期：1993.3
• CeCl₃.7H₂O-SiO₂ Catalyzed Ultrasonicated Solvent-Free Synthesis of Carbamoyl/Carbamothioyl Phosphonates and Antimicrobial Activity Evaluation
  作者：Devineni Subba Rao、Golla Madhava、Syed Rasheed、Shaik Thahir Basha、Mundla Naga Lakshmi Devamma、Chamarthi Naga Raju

  DOI：10.1080/10426507.2014.974749

  日期：2015.4.3

  an expeditious and green method has been developed for the synthesis of a series of P-C bond derivatives, diethyl substituted phenylcarbamoylphosphonates 6(a-e)/phenylcarbamothioylphosphonates 7(a-f) in high yields via simple addition reaction of isocyanates/isothiocyanates with diethyl phosphite in the presence of silica supported Lewis acid catalyst, SiO2-CeCl3.7H(2)O under solvent-free and sonication conditions. The advantages of this method are high yields, avoiding of harmful solvents, operational simplicity, shorter reaction time, and recoverability and recyclability of the catalyst. Antimicrobial activity was assayed for the title compounds, whereas the compounds 6c, 7b, and 7e against bacteria, and 6a, 7b, 7c, and 7e against fungi exhibited potential growth of inhibition.