diisopropyl 2-amino-8-tert-butyl-3-cyano-4H-chromen-4-ylphosphonate | 1586760-57-7

• 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: diisopropyl 2-amino-8-tert-butyl-3-cyano-4H-chromen-4-ylphosphonate
• 英文别名: 2-amino-8-tert-butyl-4-di(propan-2-yloxy)phosphoryl-4H-chromene-3-carbonitrile
• CAS: 1586760-57-7
• 化学式: C₂₀H₂₉N₂O₄P
• 分子量: 392.435
• InChiKey: UMUHWLODBQPVTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 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：

  亚磷酸二异丙酯 、 4-叔丁基-2-羟基苯甲醛 、 丙二腈 在 二正丁胺 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以86%的产率得到diisopropyl 2-amino-8-tert-butyl-3-cyano-4H-chromen-4-ylphosphonate
  参考文献：
  名称：

  Synthesis of 2-amino-3-cyano-4H-chromen-4-ylphosphonates and their anticancer properties

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2014.02.025

文献信息

• 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.