dibutyl (2-amino-3-cyano-4H-chromen-4-yl)phosphonate

• 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: dibutyl (2-amino-3-cyano-4H-chromen-4-yl)phosphonate
• 英文别名: 2-amino-4-dibutoxyphosphoryl-4H-chromene-3-carbonitrile
• 化学式: C₁₈H₂₅N₂O₄P
• 分子量: 364.381
• InChiKey: FDASNWGXGPIHPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  94.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  亚磷酸二丁酯 、 水杨醛 、 丙二腈 在 五甲基二乙烯三胺 作用下， 反应 0.5h， 以92%的产率得到dibutyl (2-amino-3-cyano-4H-chromen-4-yl)phosphonate
  参考文献：
  名称：

  PMDTA催化含有膦酸酯或氧化膦部分的2-氨基-4H-色烯的多组分合成及其生物活性

  摘要：

  描述了一种制备(2-氨基-3-氰基-4H-苯并-4-基)膦酸酯衍生物的新方法。五甲基二乙烯三胺（PMDTA）催化水杨醛、丙二腈和亚磷酸二烷基酯的多组分反应，以高产率提供双环衍生物。所开发的方法不需要色谱分离，因为可以通过简单的过滤从反应混合物中回收产物。我们的方法还可以与仲氧化膦缩合，并且该反应以前在文献中尚未报道过。通过单晶 XRD 分析研究了五种衍生物的晶体结构。还探讨了合成的(2-氨基-4H-铬-4-基)膦酸盐对不同细胞系的体外细胞毒性和抗菌活性。根据测定的 IC 50值，几种衍生物对小鼠成纤维细胞 (NIH/3T3) 和人早幼粒细胞白血病 (HL-60) 细胞表现出中等或有希望的活性。此外，三种(2-氨基-3-氰基-4H-铬-4-基)氧化膦对选定的革兰氏阳性菌具有活性。

  DOI：

  10.1039/d1ob01204e

文献信息

• Choline chloride based eutectic solvent for the efficient synthesis of 2-amino-4<i>H</i>-chromen-4-yl phosphonate derivatives via multicomponent reaction under mild conditions
  作者：Suresh Kumar Krishnammagari、Byung Gwon Cho、Yeon Tae Jeong

  DOI：10.1080/10426507.2017.1417296

  日期：2018.5.4

  ABSTRACT Synthesis of 2-amino-4H-chromen-4-ylphosphonate derivatives has been accomplished by the one-pot three-component reaction of salicylaldehyde, malononitrile/ethylcyanoacetate and dialkyl phosphites in the presence of reusable deep eutectic solvent (DES) under mild conditions. The advantages of this method are mild reaction conditions, simple work-up procedure, use of DES as a green solvent

  摘要 水杨醛、丙二腈/氰基乙酸乙酯和亚磷酸二烷基酯在温和条件下，在可重复使用的低共熔溶剂 (DES) 存在下，通过一锅三组分反应合成了 2-氨基-4H-色烯-4-基膦酸酯衍生物. 该方法的优点是反应条件温和，后处理程序简单，使用 DES 作为绿色溶剂，是制备重要的生物活性含磷化合物的经济方案。图形概要
• 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
• Multicomponent Synthesis of Potentially Biologically Active Heterocycles Containing a Phosphonate or a Phosphine Oxide Moiety
  作者：Nóra Popovics-Tóth、Erika Bálint

  DOI：10.17344/acsi.2022.7648

  日期：——

  Several multicomponent synthetic approaches were elaborated for plenty of novel nitrogen or oxygen heterocycles containing a phosphonate or a phosphine oxide moiety. All multicomponent reactions were optimized through a model reaction in respect of the heating mode, molar ratio of the starting materials, atmosphere, catalyst, temperature, reaction time and solvent applied, and then, the extended preparation of small libraries of structurally-related compounds was performed. Most of the reactions could be considered as “green syntheses”, as they were carried out in the absence of any catalyst and/or solvent using microwave (MW) irradiation or even at ambient temperature. The scaling-up of a MW-assisted synthesis was also elaborated in a continuous flow MW system. Altogether more than 150 heterocyclic organophosphorus compounds were synthesized, among them several derivatives showed moderate or promising activity against the HL-60 cell line and Bacillus subtilis bacteria.

  为了大量制备含有膦酸盐或氧化膦分子的新型氮杂环或氧杂环，我们精心设计了几种多组分合成方法。所有多组分反应都通过模型反应进行了优化，包括加热方式、起始原料的摩尔比、气氛、催化剂、温度、反应时间和所用溶剂等，然后扩展制备了结构相关的小化合物库。大多数反应可被视为 "绿色合成"，因为它们是在没有任何催化剂和/或溶剂的情况下，利用微波（MW）辐照甚至在环境温度下进行的。此外，还在连续流微波系统中阐述了如何扩大微波辅助合成的规模。总共合成了 150 多种杂环有机磷化合物，其中有几种衍生物对 HL-60 细胞系和枯草芽孢杆菌表现出中等或有希望的活性。
• Synthesis of 2-amino-3-cyano-4H-chromen-4-ylphosphonates and 2-amino-4H-chromenes catalyzed by tetramethylguanidine
  作者：Reddi Mohan Naidu Kalla、Seong Jin Byeon、Min Seon Heo、Il Kim

  DOI：10.1016/j.tet.2013.10.052

  日期：2013.12

  Synthesis of 2-amino-4H-chromen-4-ylphosphonates and 2-amino-4H-chromenes has been accomplished by the reaction of salicylaldehyde, malononitrile, dialkyl/diphenylphosphites catalyzed by 1,1,3,3-tetramethylguanidine (TMG) under neat conditions at room temperature. The applicability of catalytic TMG for the synthesis of 2-amino-4H-chromenes also has been described. The mild reaction conditions, simple work-up procedure, and use of TMG as an inexpensive catalyst provides an economical protocol for the preparation of important phosphorus-containing compounds. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis of 2-amino-3-cyano-4H-chromen-4-ylphosphonates and their anticancer properties
  作者：Reddi Mohan Naidu Kalla、Jin-Seok Choi、Jin-Wook Yoo、Seong Jin Byeon、Min Seon Heo、Il Kim

  DOI：10.1016/j.ejmech.2014.02.025

  日期：2014.4

  A series of 2-amino-3-cyano-4H-chromen-4-ylphosphonates have been synthesized by reacting substituted salicylaldehydes, malononitrile, and dialkylphosphites using a catalytic amount of dibutylamine as an organocatalyst employing Knoevenagel, Pinner, and phospha-Michael reactions simultaneously in ethanol. This protocol is an environmentally friendly procedure and gives high yields of the desired compounds (85-96%). In addition, no extraction or chromatography steps are needed to obtain the desired products. The compounds are tested against the viability of adenocarcinomic human alveolar basal epithelial (A549) and human epidermoid cancer (KB) cell lines using an MU assay. Among these, diethyl 2-amino-3-cyano-4H-chromen-4-ylphosphonate and diethyl 2-amino-6-bromo-3-cyano-4H-chromen-4-ylphosphonate showed promising anticancer activity against the two tested cell lines. (C) 2014 Elsevier Masson SAS. All rights reserved.