octakis (6-O-perfluorobutanoyl)-γ-cyclodextrin

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: octakis (6-O-perfluorobutanoyl)-γ-cyclodextrin
• 英文别名: octakis(6-O-perfluorobutanoyl)-γ-cyclodextrin；[(1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,36S,38R,40R,41R,42R,43R,44R,45R,46R,47R,48R,49R,50R,51R,52R,53R,54R,55R,56R)-10,15,20,25,30,35,40-heptakis(2,2,3,3,4,4,4-heptafluorobutanoyloxymethyl)-41,42,43,44,45,46,47,48,49,50,51,52,53,54,55,56-hexadecahydroxy-2,4,7,9,12,14,17,19,22,24,27,29,32,34,37,39-hexadecaoxanonacyclo[36.2.2.23,6.28,11.213,16.218,21.223,26.228,31.233,36]hexapentacontan-5-yl]methyl 2,2,3,3,4,4,4-heptafluorobutanoate
• 化学式: C₈₀H₇₂F₅₆O₄₈
• 分子量: 2865.33
• InChiKey: QZWOROTTYRPKAO-HSEONFRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  184
• 可旋转键数：
  40
• 环数：
  30.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  682
• 氢给体数：
  16
• 氢受体数：
  104

反应信息

• 作为产物：
  描述：

  七氟丁酸 、 γ-环糊精 反应 9.0h， 以96%的产率得到octakis (6-O-perfluorobutanoyl)-γ-cyclodextrin
  参考文献：
  名称：

  A facile one-pot synthesis of novel amphiphilic perfluoroalkyl ester functionalized γ-cyclodextrin and complex formation with anionic surfactants

  摘要：

  gamma-Cyclodextrin (gamma-CyD) was hydrophobically modified by selective functionalization at the C-6 position (primary face) with fluoroalkyl ester groups. This new amphiphilic gamma-CyD was prepared in a facile one-pot synthesis by direct esterification of gamma-CyD with perfluorobutanoic acid on the narrow rim of macrocylic molecule. The selective per-substituted product, octakis (6-O-perfluorobutanoyl)-gamma-cyclodextrin (gamma-CyD-F), was confirmed by H-1 NMR, C-13 NMR and F-19 NMR spectroscopic methods. The complexing ability of the gamma-CyD-F was investigated with different types of anionic surfactant having single or double hydrophobic tail groups. Predominant complex formation was observed in all cases with an equimolar mixture of surfactant and gamma-CyD-F in methanol irrespective of the type of the surfactant. (c) 2006 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2006.02.004

文献信息

• A facile one-pot synthesis of novel amphiphilic perfluoroalkyl ester functionalized γ-cyclodextrin and complex formation with anionic surfactants
  作者：Kwon Taek Lim、Hullathy Subban Ganapathy、Min Young Lee、Haldorai Yuvaraj、Won-Ki Lee、Hoon Heo

  DOI：10.1016/j.jfluchem.2006.02.004

  日期：2006.6

  gamma-Cyclodextrin (gamma-CyD) was hydrophobically modified by selective functionalization at the C-6 position (primary face) with fluoroalkyl ester groups. This new amphiphilic gamma-CyD was prepared in a facile one-pot synthesis by direct esterification of gamma-CyD with perfluorobutanoic acid on the narrow rim of macrocylic molecule. The selective per-substituted product, octakis (6-O-perfluorobutanoyl)-gamma-cyclodextrin (gamma-CyD-F), was confirmed by H-1 NMR, C-13 NMR and F-19 NMR spectroscopic methods. The complexing ability of the gamma-CyD-F was investigated with different types of anionic surfactant having single or double hydrophobic tail groups. Predominant complex formation was observed in all cases with an equimolar mixture of surfactant and gamma-CyD-F in methanol irrespective of the type of the surfactant. (c) 2006 Elsevier B.V. All rights reserved.