2-propyn-1-yl 2,3-di-O-acetyl-4,6-O-butylidene-β-D-glucopyranoside | 1344116-38-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 2-propyn-1-yl 2,3-di-O-acetyl-4,6-O-butylidene-β-D-glucopyranoside
• 英文别名: 2-propyn-1-yl 2,3-di-O-acetyl-4,6-O-butylidene-β-D-glucopyranose
• CAS: 1344116-38-6
• 化学式: C₁₇H₂₄O₈
• 分子量: 356.373
• InChiKey: RTXRWWRKHIAANU-PHPOFCCKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.77
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  89.52
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2-propyn-1-yl 2,3-di-O-acetyl-4,6-O-butylidene-β-D-glucopyranoside 、 3-叠氮基-7-羟基氧杂萘邻酮 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 以82%的产率得到7-hydroxy-3-((4-(2,3-di-O-acetyl-4,6-O-butylidene-β-D-glucopyranosyl)methyl)-1,2,3-triazolyl)chromen-2-one
  参考文献：
  名称：

  FACE-selective fluorogenic cycloaddition reaction between coumarin azides and sugar terminal alkynes: an experimental and computational study

  摘要：

  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.

  DOI：

  10.1016/j.carres.2011.07.024
• 作为产物：
  描述：

  1,2,3-tri-O-acetyl-4,6-O-butylidene-β-D-glucopyranose 、 2-丙炔-1-醇 在 三氟化硼乙醚 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以72%的产率得到2-propyn-1-yl 2,3-di-O-acetyl-4,6-O-butylidene-β-D-glucopyranoside
  参考文献：
  名称：

  FACE-selective fluorogenic cycloaddition reaction between coumarin azides and sugar terminal alkynes: an experimental and computational study

  摘要：

  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.

  DOI：

  10.1016/j.carres.2011.07.024

文献信息

• Synthesis of quinoline coupled [1,2,3]-triazoles as a promising class of anti-tuberculosis agents
  作者：K. Karthik Kumar、S. Prabu Seenivasan、Vanaja Kumar、T. Mohan Das

  DOI：10.1016/j.carres.2011.06.028

  日期：2011.10

  A series of quinoline coupled 1,2,3-triazoles compounds have been synthesized by 'click chemistry' from azidomethyl quinoline with different alkynes. The efficiency and fidelity of the Cu(I)-catalyzed azide-alkyne reaction are substantiated by good yields and exclusive formation of the expected 1,4-disubstituted triazole product. All the synthesized compounds were screened for anti-tubercular activity

  通过“点击化学”从叠氮甲基喹啉与不同炔烃中合成了一系列喹啉偶联的1,2,3-三唑化合物。Cu（I）催化的叠氮化物-炔烃反应的效率和保真度通过良好的收率和预期的1,4-二取代的三唑产物的排他性得以证实。通过荧光素酶报道噬菌体（LRP）测定，筛选所有合成的化合物针对结核分枝杆菌H37Rv的抗结核活性。喹啉偶联三唑糖杂化物20是该系列中最有效的化合物，根据相对光单位在5和25 cup / mL时的减少百分比计算，减少量分别为76.41％和78.37％。