6-deoxy-6-(pyrene-1-carboxamido)-β-cyclodextrin

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-deoxy-6-(pyrene-1-carboxamido)-β-cyclodextrin
• 英文别名: N-[[(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-10,15,20,25,30,35-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-5-yl]methyl]pyrene-1-carboxamide
• 化学式: C₅₉H₇₉NO₃₅
• 分子量: 1362.26
• InChiKey: GLBURZMGRXTCIE-BCHCNFOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -10.3
• 重原子数：
  95
• 可旋转键数：
  9
• 环数：
  25.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  563
• 氢给体数：
  21
• 氢受体数：
  35

反应信息

• 作为产物：
  描述：

  1-芘甲酸 、 单-6-O-氨基-Β-环糊精 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 50.0h， 以40%的产率得到6-deoxy-6-(pyrene-1-carboxamido)-β-cyclodextrin
  参考文献：
  名称：

  Homodimerization and Heteroassociation of 6-O-(2-Sulfonato-6-naphthyl)-γ-cyclodextrin and 6-Deoxy-(pyrene-1-carboxamido)-β-cyclodextrin

  摘要：

  6-O-(2-Sulfonato-6-naphthyl)-gamma-cyclodextrin (1) and 6-deoxy-(pyrene-1-carboxamido)-beta-cyclodextrin (2) were prepared. Homodimerizations of 1 and 2 and heteroassociation between 1 and 2 were investigated by H-1 NMR, circular dichroism, and fluorescence spectroscopic methods. The compounds I and 2 form head-to-head dimers with dimerization constants of 140 +/- 50 and 270 +/- 70 M-1, respectively. We also determined the association constants of 1 with beta-CD as 270 +/- 20 M-1 and 2 with gamma-CD as 100 +/- 30 M-1 from fluorescence and circular dichroism titration data, respectively. The heteroassociation between 1 and 2 was manifested in increased circular dichroism ellipticities of 2, downfield shift of the H-2 proton of the pyrene group of 2, and upfield shift of the H-5 proton of the naphthyl group of 1 upon mixing 1 and 2. The analysis of circular dichroism titration data of 2 with 1 gave the association constant as 9300 1600 M-1. The NMR and circular dichroism spectra suggested that the naphthyl group of 1 is deeply included into the beta-CD cavity of 2, while the pyrene group of 2 is partially inserted in the gamma-CD cavity of 1 in the complex. The energy-minimized structure from molecular modeling of the complex supports this. We believe that the facile heteroassociation of two cyclodextrin derivatives having different sizes of cavity and pendant group could be utilized as a useful strategy for assembling functionalized CDs for various applications.

  DOI：

  10.1021/jo034623h

文献信息

• Homodimerization and Heteroassociation of 6-<i>O</i>-(2-Sulfonato-6-naphthyl)-γ-cyclodextrin and 6-Deoxy-(pyrene-1-carboxamido)-β-cyclodextrin
  作者：Joon Woo Park、Hee Eun Song、Soo Yeon Lee

  DOI：10.1021/jo034623h

  日期：2003.9.1

  6-O-(2-Sulfonato-6-naphthyl)-gamma-cyclodextrin (1) and 6-deoxy-(pyrene-1-carboxamido)-beta-cyclodextrin (2) were prepared. Homodimerizations of 1 and 2 and heteroassociation between 1 and 2 were investigated by H-1 NMR, circular dichroism, and fluorescence spectroscopic methods. The compounds I and 2 form head-to-head dimers with dimerization constants of 140 +/- 50 and 270 +/- 70 M-1, respectively. We also determined the association constants of 1 with beta-CD as 270 +/- 20 M-1 and 2 with gamma-CD as 100 +/- 30 M-1 from fluorescence and circular dichroism titration data, respectively. The heteroassociation between 1 and 2 was manifested in increased circular dichroism ellipticities of 2, downfield shift of the H-2 proton of the pyrene group of 2, and upfield shift of the H-5 proton of the naphthyl group of 1 upon mixing 1 and 2. The analysis of circular dichroism titration data of 2 with 1 gave the association constant as 9300 1600 M-1. The NMR and circular dichroism spectra suggested that the naphthyl group of 1 is deeply included into the beta-CD cavity of 2, while the pyrene group of 2 is partially inserted in the gamma-CD cavity of 1 in the complex. The energy-minimized structure from molecular modeling of the complex supports this. We believe that the facile heteroassociation of two cyclodextrin derivatives having different sizes of cavity and pendant group could be utilized as a useful strategy for assembling functionalized CDs for various applications.