diethyl (2-amino-3-cyano-7-methoxy-4H-chromen-4-yl)phosphonate | 1351992-40-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: diethyl (2-amino-3-cyano-7-methoxy-4H-chromen-4-yl)phosphonate
• 英文别名: 2-amino-4-[diethoxy(oxido)phosphaniumyl]-7-methoxy-4H-chromene-3-carbonitrile
• CAS: 1351992-40-9
• 化学式: C₁₅H₁₉N₂O₅P
• 分子量: 338.3
• InChiKey: JFVPGUDKXITNIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  110
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-羟基-4-甲氧基苯甲醛 、 亚磷酸二乙酯 、 丙二腈 在 咪唑 作用下， 以 乙醇 为溶剂， 反应 7.0h， 以80%的产率得到diethyl (2-amino-3-cyano-7-methoxy-4H-chromen-4-yl)phosphonate
  参考文献：
  名称：

  咪唑作为合成2-氨基-3-氰基-4H-铬-4-基膦酸酯的有效催化剂

  摘要：

  通过廉价，环保的咪唑作为有机催化剂，通过水杨醛，丙二腈和亚磷酸三烷基酯或亚磷酸二乙酯的三组分反应，制备2-氨基-3-氰基-4H-铬-4-基膦酸酯衍生物的有效方法已得到广泛应用。报告。除了优异的产率和容易的后处理之外，该反应在几乎中性的介质中进行。

  DOI：

  10.1007/s11164-016-2710-9

文献信息

• A silver nanoparticles-catalyzed efficient three-component synthesis of polysubstituted 4<i>H</i>-chromenylphosphonates and their antioxidant activity
  作者：Sara Mahdjoub、Raouf Boulcina、Muhammet Yildirim、Sihem Lakehal、Houssem Boulebd、Abdelmadjid Debache

  DOI：10.1080/00397911.2018.1484487

  日期：2018.9.17

  one-pot three-component synthesis of structurally diverse dialkyl 2-amino-3-cyano-4H-chromen-4-ylphosphonates from the condensation of salicylaldehydes, malononitrile, and trialkyl phosphite using silver nanoparticles as catalyst in ethanol at reflux has been developed. Selected new compounds were evaluated for their antioxidant activity by free radical screening using 2,2-diphenyl-1-picrylhydrazyl (DPPH)

  摘要 使用银纳米粒子作为催化剂，从水杨醛、丙二腈和亚磷酸三烷基酯的缩合反应一锅三组分合成结构多样的二烷基 2-氨基-3-氰基-4H-色烯-4-基膦酸酯的简单有效方案。已开发出回流乙醇。使用 2,2-二苯基-1-苦基肼 (DPPH) 方法通过自由基筛选来评估选定的新化合物的抗氧化活性。在使用的化合物中，5a、5b 和 5 h 与低浓度 (100 µg/mL) 孵育 24 小时后的实验标准相比，显示出有希望的 DPPH 自由基清除活性。图形概要
• Efficient one-pot synthesis of β-phosphono malonates and 2-amino-4H-chromen-4-ylphosphonate derivatives by ethylenediamine diacetate-catalyzed three-component reactions
  作者：Srinivasa Rao Kolla、Yong Rok Lee

  DOI：10.1016/j.tet.2011.10.060

  日期：2012.1

  One-pot three-component reactions of arylaldehyde or salicylaldehyde with malononitrile (or ethyl-cyanoacetate) and triethyl phosphite are carried out in the presence of ethylenediamine diacetate (EDDA) as a catalyst for the synthesis of biologically interesting beta-phosphono malonates and 2-amino-4H-chromen-4-ylphosphonate derivatives. The value of this method lies in its mild reaction catalyst and conditions, good yields, and ease of handling. (C) 2011 Elsevier Ltd. All rights reserved.
• Sulfochitosan encapsulated nano-Fe3O4 as an efficient and reusable magnetic catalyst for green synthesis of 2-amino-4H-chromen-4-yl phosphonates
  作者：Reza Mohammadi、Mohammad Zaman Kassaee

  DOI：10.1016/j.molcata.2013.09.027

  日期：2013.12

  Highly dispersed chitosan-coated nano Fe3O4 core-shell structures (Fe3O4@CS NPs) are prepared simply through in situ co-precipitation of Fe3+ and Fe2+ ions via NH4OH in an aqueous solution of chitosan. Treatment of Fe3O4@CS NPs with chlorosulfonic acid leads to the formation of Fe3O4@CS-SO3H NPs which exerts excellent catalytic activity toward one-pot, three-component synthesis of 2-amino-4H-chromen-4-yl phosphonate derivatives. The core-shell structure and the composition of produced magnetic nanocatalyst are analyzed using FT-IR, XRD, TGA, VSM, ICP, SEM, TEM and BET. The results reveal that the unique heterogeneous Fe3O4@CS-SO3H NPs appears as an excellent acid catalyst which produces high yields, impressive turnover number (TON) and turnover frequency (TOF) values with good recyclability without significant loss of the activity. Moreover, the proposed green synthetic method takes advantage of nontoxic reagents in an aqueous media through a simple procedure. (C) 2013 Elsevier B.V. All rights reserved.
• Imidazole as an efficient catalyst for the synthesis of 2-amino-3-cyano-4H-chromen-4yl-phosphonates
  作者：Fatemeh Darvish、Ana Abdollahzade、Danial Saravani

  DOI：10.1007/s11164-016-2710-9

  日期：2017.3

  An efficient procedure for the preparation of 2-amino-3-cyano-4H-chromen-4-yl phosphonate derivatives via a three-component reaction of salicylaldehyde, malononitrile and trialkyl phosphites or diethyl phosphite using inexpensive and environmentally friendly imidazole as organocatalyst has been reported. Beside excellent yields and easy workup, the reaction is done in an almost neutral medium.

  通过廉价，环保的咪唑作为有机催化剂，通过水杨醛，丙二腈和亚磷酸三烷基酯或亚磷酸二乙酯的三组分反应，制备2-氨基-3-氰基-4H-铬-4-基膦酸酯衍生物的有效方法已得到广泛应用。报告。除了优异的产率和容易的后处理之外，该反应在几乎中性的介质中进行。