6-bromo-3-((4-(bromomethyl)-1H-1,2,3-triazol-1-yl)methyl)coumarin | 1258307-14-0

• 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: 6-bromo-3-((4-(bromomethyl)-1H-1,2,3-triazol-1-yl)methyl)coumarin
• 英文别名: 6-Bromo-3-[[4-(bromomethyl)triazol-1-yl]methyl]chromen-2-one；6-bromo-3-[[4-(bromomethyl)triazol-1-yl]methyl]chromen-2-one
• CAS: 1258307-14-0
• 化学式: C₁₃H₉Br₂N₃O₂
• 分子量: 399.041
• InChiKey: CKGITCGWSJWCCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  57
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  6-bromo-3-azidomethylcoumarin 、 3-溴丙炔 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 以71%的产率得到6-bromo-3-((4-(bromomethyl)-1H-1,2,3-triazol-1-yl)methyl)coumarin
  参考文献：
  名称：

  Expedient synthesis of coumarin-coupled triazoles via ‘click chemistry’ leading to the formation of coumarin–triazole–sugar hybrids

  摘要：

  Coumarin-based triazoles were synthesized from 3-azidomethylcoumarin and a terminal acetylenic compound. Uncatalysed thermal conditions result in a mixture of both 1,4- and 1,5-regioisomers or the thermodynamically more stable 1,4-regioisomer, whereas the Cu(I)-catalysed reaction affords only the favourable 1,4-regioisomer. B3LYP/6-31G(d) level of theory has been used to calculate geometry and frequency features of the reactants, transition states (TSs) and products. Computational studies further reveal that 1,4-regioisomeric products are more favourable and also thermodynamically more stable compared to the 1,5-regioisomers. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.07.037

文献信息

• Expedient synthesis of coumarin-coupled triazoles via ‘click chemistry’ leading to the formation of coumarin–triazole–sugar hybrids
  作者：K. Karthik Kumar、R. Mahesh Kumar、V. Subramanian、T. Mohan Das

  DOI：10.1016/j.carres.2010.07.037

  日期：2010.11

  Coumarin-based triazoles were synthesized from 3-azidomethylcoumarin and a terminal acetylenic compound. Uncatalysed thermal conditions result in a mixture of both 1,4- and 1,5-regioisomers or the thermodynamically more stable 1,4-regioisomer, whereas the Cu(I)-catalysed reaction affords only the favourable 1,4-regioisomer. B3LYP/6-31G(d) level of theory has been used to calculate geometry and frequency features of the reactants, transition states (TSs) and products. Computational studies further reveal that 1,4-regioisomeric products are more favourable and also thermodynamically more stable compared to the 1,5-regioisomers. (C) 2010 Elsevier Ltd. All rights reserved.