mono-6-deoxy-6-(3-(2-aminoethyl)amino-N-butylbenzamide)-β-cyclodextrin | 1309597-00-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: mono-6-deoxy-6-(3-(2-aminoethyl)amino-N-butylbenzamide)-β-cyclodextrin
• 英文别名: N-butyl-3-[2-[[(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]methylamino]ethylamino]benzamide
• CAS: 1309597-00-9
• 化学式: C₅₅H₈₉N₃O₃₅
• 分子量: 1352.31
• InChiKey: LNSSHYIMKDHZLL-BBHNDYCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -12.6
• 重原子数：
  93
• 可旋转键数：
  16
• 环数：
  22.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  587
• 氢给体数：
  23
• 氢受体数：
  37

反应信息

• 作为产物：
  描述：

  3-(2-aminoethyl)amino-N-butylbenzamide 、 mono-6-deoxy-6-(p-toluenesulfonyl)-β-cyclodextrin 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以17%的产率得到mono-6-deoxy-6-(3-(2-aminoethyl)amino-N-butylbenzamide)-β-cyclodextrin
  参考文献：
  名称：

  Fluorescent β-Cyclodextrins Modified by Isomeric Aminobenzamides: Synthesis, Conformational Analysis, and Fluorescent Behaviors

  摘要：

  Three isomeric fluorescent beta-cydodextrins bearing 2-, 3-, and 4-(2-aminoethyl)amino-N-butylbenzamide, respectively (1-3) have been synthesized. The conformations of these fluorescent CDs have been investigated by 2D NMR and induced circular dichromism. It is confirmed that the ortho isomer 1 takes a butyl-included conformation, while the other two isomers 2 and 3 display a phenyl-included conformation, respectively. The three fluorescent CDs 1-3 exhibited totally different self- and guest-inclusion fluorescence behavior. In the presence of adamantane carboxylate sodium (ADA) or deoxycholate sodium (DCA), the fluorescence intensity of 1 showed an enhancement over 1-fold, while 2 exhibited dramatic fluorescence quenching. Interestingly, the fluorescent responses of 3 toward two guests respectively were highly distinguishable. The fluorescence intensity of 3 only showed a slight increase upon the addition of ADA, but the addition of DCA led to a large decrease in fluorescence intensity. The investigations have been further carried out by 2D NMR, induced circular dichromism, fluorescence spectroscopy and molecular modeling to explore the relationships between the conformations and the fluorescence characteristics of CDs 1-3 in the absence and presence of guest molecules. On the basis of the above investigations, the origins for the different fluorescence behaviors have been proposed.

  DOI：

  10.1021/jo2007829

文献信息

• Fluorescent β-Cyclodextrins Modified by Isomeric Aminobenzamides: Synthesis, Conformational Analysis, and Fluorescent Behaviors
  作者：Lei Wang、Cheng Zhong、Peng Xue、Enqin Fu

  DOI：10.1021/jo2007829

  日期：2011.6.17

  Three isomeric fluorescent beta-cydodextrins bearing 2-, 3-, and 4-(2-aminoethyl)amino-N-butylbenzamide, respectively (1-3) have been synthesized. The conformations of these fluorescent CDs have been investigated by 2D NMR and induced circular dichromism. It is confirmed that the ortho isomer 1 takes a butyl-included conformation, while the other two isomers 2 and 3 display a phenyl-included conformation, respectively. The three fluorescent CDs 1-3 exhibited totally different self- and guest-inclusion fluorescence behavior. In the presence of adamantane carboxylate sodium (ADA) or deoxycholate sodium (DCA), the fluorescence intensity of 1 showed an enhancement over 1-fold, while 2 exhibited dramatic fluorescence quenching. Interestingly, the fluorescent responses of 3 toward two guests respectively were highly distinguishable. The fluorescence intensity of 3 only showed a slight increase upon the addition of ADA, but the addition of DCA led to a large decrease in fluorescence intensity. The investigations have been further carried out by 2D NMR, induced circular dichromism, fluorescence spectroscopy and molecular modeling to explore the relationships between the conformations and the fluorescence characteristics of CDs 1-3 in the absence and presence of guest molecules. On the basis of the above investigations, the origins for the different fluorescence behaviors have been proposed.