dibutyl 2-amino-8-tert-butyl-3-cyano-4H-chromen-4-ylphosphonate

• 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-8-tert-butyl-3-cyano-4H-chromen-4-ylphosphonate
• 英文别名: 2-amino-8-tert-butyl-4-dibutoxyphosphoryl-4H-chromene-3-carbonitrile
• 化学式: C₂₂H₃₃N₂O₄P
• 分子量: 420.489
• InChiKey: RARMYBCXGZHCFO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 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 、 3-叔丁基-2-羟基苯甲醛 、 丙二腈 在 choline chloride-urea 作用下， 反应 2.3h， 以91%的产率得到dibutyl 2-amino-8-tert-butyl-3-cyano-4H-chromen-4-ylphosphonate
  参考文献：
  名称：

  基于氯化胆碱的低共熔溶剂，在温和条件下通过多组分反应有效合成 2-氨基-4H-色烯-4-基膦酸酯衍生物

  摘要：

  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

  DOI：

  10.1080/10426507.2017.1417296

文献信息

• 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.