6-O-monodansyl-β-cyclodextrin

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-monodansyl-β-cyclodextrin
• 英文别名: 6-O-dansyl-β-cyclodextrin；D-β-CD；[(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)-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecahydroxy-5,15,20,25,30,35-hexakis(hydroxymethyl)-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]nonatetracontan-10-yl]methyl 5-(dimethylamino)naphthalene-1-sulfonate
• 化学式: C₅₄H₈₁NO₃₇S
• 分子量: 1368.29
• InChiKey: XECYHEXIDOAWLR-AOXBXKJUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -12
• 重原子数：
  93
• 可旋转键数：
  11
• 环数：
  23.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  589
• 氢给体数：
  20
• 氢受体数：
  38

反应信息

• 作为反应物：
  描述：

  、 6-O-monodansyl-β-cyclodextrin 以 乙醇 、 水 为溶剂， 生成
  参考文献：
  名称：

  Modulation of dansyl moiety fluorescence in systems containing cyclodextrins

  摘要：

  The present study reports on the changes in dansyl moiety fluorescence due to the interactions with the β-cyclodextrin cavity observed by steady-state fluorescence spectroscopy. First, the interaction of a guest molecule, dansyl-TEMPO (DT), which has in its structure a dansyl group as a fluorescent moiety and a paramagnetic fragment (TEMPO), with β-cyclodextrin was studied. Analysis of the EPR spectral parameters provided additional information on the host–guest interaction, suggesting that the cyclodextrin cavity accommodates dansyl rather than a TEMPO moiety. Second, the affinity between 1-adamantol or adamantane end-capped polyethylene glycols – A2Pnn – (as guests) and dansyl-β-cyclodextrin (D-β-CD, as a host) was investigated. In the presence of adamantol, the intensity of fluorescence of D-β-CD decreases and a hypsochromic effect was noticed. The same behaviour was observed in the presence of A2Pnn. Using Benesi–Hildebrand and Stern–Volmer equations and also the sensitivity factor made possible to obtain quantitative data on the interaction between the dansyl moiety and the cyclodextrin cavity. The formation of inclusion complexes in the solid state between D-β-CD and A2Pnn was evidenced analysing the DSC curves of the pure solids, physical mixture and prepared solid complexes. In addition, the use of D-β-CD for fluorescent labeling of a covalently based network hydrogel and diffusion of dansyl derivatives into a gel are shown as possible further application of this study.

  DOI：

  10.1039/c2nj40174f
• 作为产物：
  描述：

  丹酰氯 、 β-环糊精 在 吡啶 作用下， 以65%的产率得到6-O-monodansyl-β-cyclodextrin
  参考文献：
  名称：

  Dansyl-β-cyclodextrins as Fluorescent Sensors Responsive to Organic Compounds

  摘要：

  合成并鉴定了 6-O-、2-O-和 3-O-丹酰-β-环糊精（1、2 和 3）。化合物 1 和 2 在分子间形成复合物时会降低其荧光强度。这一特性使 1 和 2 能够充当荧光传感器，将有机化合物的结合转化为荧光变化。

  DOI：

  10.1246/bcsj.67.1598

文献信息

• Dansyl-<i>β</i>-cyclodextrins as Fluorescent Sensors Responsive to Organic Compounds
  作者：Yong Wang、Tsukasa Ikeda、Hiroshi Ikeda、Akihiko Ueno、Fujio Toda

  DOI：10.1246/bcsj.67.1598

  日期：1994.6

  6-O-, 2-O-, and 3-O-Dansyl-β-cyclodextrins (1, 2, and 3) were synthesized and characterized. Compounds 1 and 2 decrease their fluorescence intensities upon intermolecular complex formation. This property enables 1 and 2 to act as fluorescent sensors, converting binding of organic compounds into fluorescence variations.

  合成并鉴定了 6-O-、2-O-和 3-O-丹酰-β-环糊精（1、2 和 3）。化合物 1 和 2 在分子间形成复合物时会降低其荧光强度。这一特性使 1 和 2 能够充当荧光传感器，将有机化合物的结合转化为荧光变化。
• Modulation of dansyl moiety fluorescence in systems containing cyclodextrins
  作者：Marilena Vasilescu、Elena Pincu、Viorica Meltzer、Gabriela Ionita

  DOI：10.1039/c2nj40174f

  日期：——

  The present study reports on the changes in dansyl moiety fluorescence due to the interactions with the β-cyclodextrin cavity observed by steady-state fluorescence spectroscopy. First, the interaction of a guest molecule, dansyl-TEMPO (DT), which has in its structure a dansyl group as a fluorescent moiety and a paramagnetic fragment (TEMPO), with β-cyclodextrin was studied. Analysis of the EPR spectral parameters provided additional information on the host–guest interaction, suggesting that the cyclodextrin cavity accommodates dansyl rather than a TEMPO moiety. Second, the affinity between 1-adamantol or adamantane end-capped polyethylene glycols – A2Pnn – (as guests) and dansyl-β-cyclodextrin (D-β-CD, as a host) was investigated. In the presence of adamantol, the intensity of fluorescence of D-β-CD decreases and a hypsochromic effect was noticed. The same behaviour was observed in the presence of A2Pnn. Using Benesi–Hildebrand and Stern–Volmer equations and also the sensitivity factor made possible to obtain quantitative data on the interaction between the dansyl moiety and the cyclodextrin cavity. The formation of inclusion complexes in the solid state between D-β-CD and A2Pnn was evidenced analysing the DSC curves of the pure solids, physical mixture and prepared solid complexes. In addition, the use of D-β-CD for fluorescent labeling of a covalently based network hydrogel and diffusion of dansyl derivatives into a gel are shown as possible further application of this study.