mono [6-O-(8-quinolyl)]-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-O-(8-quinolyl)]-β-cyclodextrin
• 英文别名: (6-O-8-quinolyl)-β-cyclodextrin；mono-6-deoxy-6-(8-oxymethylquinolino)-β-CD；β-CD-HQ；(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)-5,10,15,20,30,35-hexakis(hydroxymethyl)-25-(quinolin-8-yloxymethyl)-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: C₅₁H₇₅NO₃₅
• 分子量: 1262.14
• InChiKey: HNGYNYFZVGGWTF-YTZZGHLOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -12.4
• 重原子数：
  87
• 可旋转键数：
  9
• 环数：
  23.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  556
• 氢给体数：
  20
• 氢受体数：
  36

反应信息

• 作为反应物：
  描述：

  冰片 、 mono [6-O-(8-quinolyl)]-β-cyclodextrin 以 aq. phosphate buffer 为溶剂， 生成
  参考文献：
  名称：

  带有芳香族取代基的β-环糊精与球形客体的分子结合热力学

  摘要：

  导致更强的结合能力。在热力学上，包合络合是由焓驱动的，化学计量比为 1:1。另一个有助于增强结合能力的因素是熵损失较小的焓增益。

  DOI：

  10.1016/j.tca.2013.11.021
• 作为产物：
  描述：

  8-羟基喹啉 、 β-环糊精 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 mono [6-O-(8-quinolyl)]-β-cyclodextrin
  参考文献：
  名称：

  用于检测 Pb2+ 离子和维生素 C 的开关超分子荧光开关

  摘要：

  β-环糊精-羟基喹啉功能化的氧化石墨烯（GO-CD-HQ）被轻松制造用于监测和定量分析水介质中的阳离子。与其他测试离子如 Cu 2+、Hg 2+、Ca 2+、Na +、K +、Zn 2+、Fe 2+、Fe 3+、Ag +相比，该光学探针对 Pb 2+离子的选择性增强显着。 , Mg 2+ , 和 Cd 2+发射波长为 468 nm。该探针在pH值5和最佳时间1分钟时表现出最佳性能。吸收光谱清楚地证实了GO-CD-HQ的静态型荧光增强机制。在最佳条件下，Pb 2+离子的检测限和线性浓度范围分别为3.72 × 10 –5  M 和(5–60) × 10 –5  M。此外，所开发的分析显示出以 Pb 2+离子和维生素 C 作为引用离子的掩蔽剂的逻辑门行为。

  DOI：

  10.1007/s10895-021-02797-y

文献信息

• Molecularly imprinted fluorescent chemosensor synthesized using quinoline-modified-β-cyclodextrin as monomer for spermidine recognition
  作者：Yang Cheng、Ping Jiang、Xiangchao Dong

  DOI：10.1039/c5ra07761c

  日期：——

  Preparation of imprinted fluorescent chemosensor using quinoline-modified-β-cyclodextrin as monomer for spermidine recognition.

  使用喹啉修饰的β-环糊精作为单体制备印迹荧光化学传感器，用于亚精胺的识别。
• Quinolinotriazole-β-cyclodextrin and its adamantanecarboxylic acid complex as efficient water-soluble fluorescent Cd2+ sensors
  作者：Ying-Ming Zhang、Yong Chen、Zhi-Qiang Li、Nan Li、Yu Liu

  DOI：10.1016/j.bmc.2010.01.024

  日期：2010.2

  A novel beta-cyclodextrin derivative 1 bearing 8-hydroxyquinolino and triazole groups was synthesized in satisfactory yield by 'click chemistry'. With a good water solubility up to 0.03 mol/L, 1 exhibited an effective switch-on fluorescence response to Cd2+ over other common metal ions under physiological conditions. Studies on the recognition mechanism indicated that the cooperative coordination of Cd2+ with both the 8-hydroxyquinolino moiety excluded from the beta-CD cavity and the triazole moiety was a crucial and basic factor to achieve the fluorescent sensing process. Significantly, spectrophotometric studies also demonstrated that, after inclusion complexation with 1-adamantanecarboxylic acid sodium salt (AdCA), the resultant 1/AdCA system gave a more effective fluorescent sensing to Cd2+ through a cyclodextrin/substrate/Cd2+ triple binding mode. (C) 2010 Elsevier Ltd. All rights reserved.
• Molecular Recognition Study on Supramolecular System. 14.¹ Synthesis of Modified Cyclodextrins and Their Inclusion Complexation Thermodynamics with <scp>l</scp>-Tryptophan and Some Naphthalene Derivatives
  作者：Yu Liu、Bao-Hang Han、Bin Li、Yi-Min Zhang、Peng Zhao、Yun-Ti Chen、Takehiko Wada、Yoshihisa Inoue

  DOI：10.1021/jo971466b

  日期：1998.3.1

  A series of beta-cyclodextrin derivatives, carrying pyridinio (4-6), phosphonyl (7, 8), seleno (9-11), m-and p-picolinyl (12, 13), o-chloroanilino (16), 8-quinolyl. (17), furfuryl (18), and 9-fluorenyl (19) moieties in the side chain, were newly synthesized, and their complexation behavior was assessed and discussed thermodynamically, using L-tryptophan and a few naphthalene derivatives as representative guests. Calorimetric titrations have been performed at 25.0 degrees C in buffered aqueous solution (pH 7.20) to give the complex stability constants and thermodynamic parameters for the 1:1 inclusion complexation of these guests with the native and modified alpha-, beta-, and/or gamma-cyclodextrins (1-20). All of the chemical modifications to the primary side of cyclodextrins examined led to significant changes in complex stability and thermodynamic parameters, which are elucidated in terms of the conformational, electrostatic, hydrogen-bonding, and hydration effects. Thermodynamically, the inclusion complexation is mainly enthalpy-driven with a negative or minor positive entropic contribution, which in some cases determines the complex stability. The induced circular dichroism spectral analyses of these cyclodextrin derivatives indicated that the aromatic moiety in modified beta-cyclodextrins (4-6, 9-19) only shallowly penetrates into the hydrophobic cavity of beta-cyclodextrin, while the phenyl phosphate and fluorenyl moieties in 7 and 20 are embedded into the hydrophobic cavity of beta-cyclodextrin because of the longer linking chain. Using all the thermodynamic data for a wide variety of cyclodextrin derivatives obtained in this and previous studies, the entropy changes (T Delta S) were plotted against the enthalpy changes (Delta H) to give an excellent linear relationship. The slope (alpha) of 1.02 and an intercept (T Delta S-o) of 4.3 of the regression line indicate substantial conformational changes and extensive desolvation caused upon complexation,respectively.