mono-6-[4-(2-phenoxyethyl)-1H-1,2,3-triazol-1-yl]-6-deoxy-β-cyclodextrin

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: mono-6-[4-(2-phenoxyethyl)-1H-1,2,3-triazol-1-yl]-6-deoxy-β-cyclodextrin
• 英文别名: (1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,36R,37R,38R,39R,40R,41R,42R,43R,44R,45R,46R,47R,48R,49R)-5,10,15,20,25,30-hexakis(hydroxymethyl)-35-[[4-(2-phenoxyethyl)triazol-1-yl]methyl]-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontane-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecol
• 化学式: C₅₂H₇₉N₃O₃₅
• 分子量: 1306.2
• InChiKey: SYGFWFFGXJCOMC-RECQWNEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -13.31
• 重原子数：
  90.0
• 可旋转键数：
  12.0
• 环数：
  23.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  573.76
• 氢给体数：
  20.0
• 氢受体数：
  38.0

反应信息

• 作为产物：
  描述：

  6A-叠氮基-6A-脱氧-β-环糊精 、 (but-3-yn-1-yloxy)benzene 在 copper(II) sulfate 、 维生素 C 、 三[(1-苄基-1H-1,2,3-三唑-4-基)甲基]胺 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 16.0h， 以90%的产率得到mono-6-[4-(2-phenoxyethyl)-1H-1,2,3-triazol-1-yl]-6-deoxy-β-cyclodextrin
  参考文献：
  名称：

  Improved Synthesis of C2 and C6 Monoderivatives of α- and β-Cyclodextrin via the Click Chemistry Approach

  摘要：

  An efficient multigram-scale azide-alkyne coupling of cyclodextrin derivatives mono-6-azido-6-deoxy--cyclodextrin, mono-2-O-propargyl--cyclodextrin, and mono-2-O-propargyl--cyclodextrin with terminal alkynyl aryl ethers or azides, mediated by copper(I) is reported. This process uses a stoichiometric ratio of substrates and 5 mol% of the copper catalyst to give the products with full conversion; thus, no chromatographic purification is necessary. The yields of both - and -cyclodextrin derivatives are in the range of 80 to 99%.

  DOI：

  10.1055/s-0034-1380701