6-bromo-3-((4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)methyl)-1,2,3-triazolyl)chromen-2-one | 1344116-46-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-bromo-3-((4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)methyl)-1,2,3-triazolyl)chromen-2-one
• 英文别名: (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-((1-(6-bromo-2-oxo-2H-chromen-3-yl)-1H-1,2,3-triazol-4-yl)methoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• CAS: 1344116-46-6
• 化学式: C₂₆H₂₆BrN₃O₁₂
• 分子量: 652.409
• InChiKey: WHVSVJVKHMRJKY-HROMDODWSA-N

物化性质

• 熔点：
  130-132 °C
• 沸点：
  728.5±70.0 °C(Predicted)
• 密度：
  1?+-.0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.74
• 重原子数：
  42.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  184.58
• 氢给体数：
  0.0
• 氢受体数：
  15.0

反应信息

• 作为产物：
  描述：

  2,3,4,5-tetra-O-acetyl-D-glucopyranose 在 copper(ll) sulfate pentahydrate 、 三氟化硼乙醚 、 sodium ascorbate 作用下， 以 水 为溶剂， 反应 0.92h， 生成 6-bromo-3-((4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)methyl)-1,2,3-triazolyl)chromen-2-one
  参考文献：
  名称：

  Robust synthesis of sugar-coumarin based fluorescent 1,4-disubstituted-1,2,3-triazoles using highly efficient recyclable citrate grafted β-cyclodextrin@magnetite nano phase transfer catalyst in aqueous media

  摘要：

  Green synthesis of 1,4-disubstituted-1,2,3-triazoles via click reaction using nano magnetic Fe3O4 core decorated with cyclodextrin-citric acid (Fe3O4@CD-CIT) acting as a phase transfer nanoreactor with low copper loading under ultrasonication at 40 degrees C, in aqueous media is described. Anchoring the surface of magnetite with cyclo-dextrin (CD) prevents its agglomeration and at the same time, CD provides a hydrophobic niche for lipophilic reactants while its outer hydrophilic core makes the reaction feasible in water yielding almost quantitative yield of desired products. Magnetic separation using an external magnet, recyclability and reuse (7 times), without appreciably affecting the %yield of the products are its other attractive attributes. Gram scale synthesis was also achieved with 93% yield.

  DOI：

  10.1016/j.carres.2019.06.015

文献信息

• Sonochemical synthesis of fluorescent 1,4-disubstituted triazoles using l-phenylalanine as an accelerator ligand in aqueous media
  作者：Yachana Jain、Mitlesh Kumari、Ragini Gupta

  DOI：10.1016/j.tetlet.2019.03.045

  日期：2019.5

  A green sonochemical protocol using l-phenylalanine as a water soluble promotor ligand has been developed for the regioselective synthesis of fluorogenic 1,4-disubstituted triazoles (3a-o) via well-known click reaction at 40 °C. l-Phenylalanine is a biocompatible, economical, commercially available and non-toxic ligand which not only serves to stabilize Cu(I) oxidation state but also prevents its disproportion

  已经开发了使用1-苯丙氨酸作为水溶性促进剂配体的绿色声化学方案，用于通过众所周知的点击反应在40°C下区域选择性合成荧光1,4-二取代的三唑（3a-o）。1-苯丙氨酸是生物相容的，经济的，可商购的且无毒的配体，其不仅用于稳定Cu（I）的氧化态，而且可以防止其歧化以增强和调节反应速率。设计的催化系统具有广泛的底物相容性，可以循环使用多达5个循环，而所需产物的收率却没有明显损失。革兰氏级合成成功完成，产率为92％。
• FACE-selective fluorogenic cycloaddition reaction between coumarin azides and sugar terminal alkynes: an experimental and computational study
  作者：Ramanathan Rajaganesh、Pawar Ravinder、Venkatesan Subramanian、Thangamuthu Mohan Das

  DOI：10.1016/j.carres.2011.07.024

  日期：2011.11

  Copper catalyzed azide-alkyne cycloaddition reaction (CuAAC) of non-fluorescent coumarin azides and sugar terminal alkynes afforded intense fluorescent 1,2,3-triazoles in 75-85% of yield. The photophysical properties of coumarin-sugar triazoles influenced greatly, upon introducing different substituents at 6th and 7th positions. The experimental observations were further supported by TD-DFT computational studies. (C) 2011 Elsevier Ltd. All rights reserved.