N-(5-bromo-2-oxo-2H-chromen-6-yl)acetamide | 1447950-19-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: N-(5-bromo-2-oxo-2H-chromen-6-yl)acetamide
• CAS: 1447950-19-7
• 化学式: C₁₁H₈BrNO₃
• 分子量: 282.093
• InChiKey: XGRHGOVRTXTTKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.51
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  59.31
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-(5-bromo-2-oxo-2H-chromen-6-yl)acetamide 在 sodium sulfide 、 iron(III) chloride 、 盐酸 作用下， 以 N,N-二甲基甲酰胺 、 水 为溶剂， 反应 12.0h， 以81%的产率得到2-methyl-7H-chromeno[6,5-d]thiazol-7-one
  参考文献：
  名称：

  An efficient synthesis of coumarin- and quinolone-annulated thiazole derivatives via ligand-free iron (III)-catalyzed coupling followed by acid-promoted condensation

  摘要：

  An efficient strategy for the synthesis of coumarin- and quinolone-annulated thiazole derivatives using sodium sulfide as a sulfur source has been achieved via ligand-free iron (III)-catalyzed coupling followed by acid-promoted condensation. This synthetic protocol is one-pot, less expensive, and affords the products in good yields. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.06.017

文献信息

• Synthesis of novel pyrano[3,2-f]quinoline, phenanthroline derivatives and studies of their interactions with proteins: An application in mammalian cell imaging
  作者：K.C. Majumdar、Sudipta Ponra、Tapas Ghosh、Ratan Sadhukhan、Utpal Ghosh

  DOI：10.1016/j.ejmech.2013.10.067

  日期：2014.1

  A series of tri-cyclic pyrano[3,2-f]quinoline and phenanthroline derivatives have been synthesized by a HCl-mediated 6-'endo-trig' Michael type ring closure reaction of 6-amino-5-(3-hydroxy-3-methylbut-1-ynyl)-2H-chromen-2-one in excellent yields. The process is very simple, facile and inexpensive and can provide a diverse range of substituted quinoline derivatives from simple and easily available starting materials. Moreover, the synthesized derivatives exhibit staining property to the cultured HeLa cells after fixing and can be used as fluorophores which can bind with protein molecule. (C) 2013 Published by Elsevier Masson SAS.