3-((4-((2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)methyl)-1H-1,2,3-triazol-1-yl)methyl)-8-methoxycoumarin | 1258309-79-3

• 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: 3-((4-((2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)methyl)-1H-1,2,3-triazol-1-yl)methyl)-8-methoxycoumarin
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[[1-[(8-methoxy-2-oxochromen-3-yl)methyl]triazol-4-yl]methoxy]oxan-2-yl]methyl acetate
• CAS: 1258309-79-3
• 化学式: C₂₈H₃₁N₃O₁₃
• 分子量: 617.566
• InChiKey: QULQCAUHPUMSMQ-HOZVGSINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  44
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  190
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  8-methoxy-3-azidomethylcoumarin 、 2-炔丙基-四-O-乙酰基-β-D-吡喃葡萄糖苷 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以53%的产率得到3-((4-((2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)methyl)-1H-1,2,3-triazol-1-yl)methyl)-8-methoxycoumarin
  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