6-O-(4-iodophenyl)-β-cyclodextrin | 925246-81-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-(4-iodophenyl)-β-cyclodextrin
• 英文别名: (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-[(4-iodophenoxy)methyl]-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
• CAS: 925246-81-7
• 化学式: C₄₈H₇₃IO₃₅
• 分子量: 1336.99
• InChiKey: OBQPVLKHPMNBPD-IHHCOHTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -12
• 重原子数：
  84
• 可旋转键数：
  9
• 环数：
  22.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  543
• 氢给体数：
  20
• 氢受体数：
  35

反应信息

• 作为反应物：
  描述：

  5,5'-di(1,2,3-dioxaborolan-2-yl)-2,2'-bithiophene 、 6-O-(4-iodophenyl)-β-cyclodextrin 在 palladium diacetate potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以10.6%的产率得到(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-[[4-[5-[5-[4-[[(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]methoxy]phenyl]thiophen-2-yl]thiophen-2-yl]phenoxy]methyl]-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
  参考文献：
  名称：

  Preparation and Properties of Rotaxanes Formed by Dimethyl-β-cyclodextrin and Oligo(thiophene)s with β-Cyclodextrin Stoppers

  摘要：

  [graphics]Novel cyclodextrin rotaxanes with oligothiophene as an axis molecule have been prepared by the Suzuki coupling reaction of 6-O-(4-iodophenyl)-beta-CD (6-I-Ph-beta-CD) with di(1,3,2-dioxaborolan-2-yl)-oligothiophene (oligothiophene diboric ethylene glycol esters) in aqueous solutions of dimethyl-beta-cyclodextrin (DM-beta-CD). These reactions gave [2]rotaxanes and [3]rotaxanes, which were isolated by reversed phase chromatography. The fluorescence intensities of rotaxanes are higher than those of dumbbell-shaped molecules (without DM-beta-CD) in aqueous solutions. The inclusion ratio and chain length of rotaxanes have been found to relate to the emission properties and emission intensities of oligothiophene. In aqueous solutions, fluorescence quantum yields of rotaxanes are higher than those of dumbbell-shaped molecules. The increase in the fluorescence efficiency of rotaxane is caused by suppression of intermolecular interactions, indicating the effect of insulated oligothiophene with DM-beta-CD. beta-CD at the both ends of rotaxanes functions not only as bulky stoppers but also as the recognition site for guest molecules, as verified by fluorescence quenching experiments.

  DOI：

  10.1021/jo061834o
• 作为产物：
  描述：

  4-碘苯酚 、 mono-6-deoxy-6-(p-toluenesulfonyl)-β-cyclodextrin 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以44.9%的产率得到6-O-(4-iodophenyl)-β-cyclodextrin
  参考文献：
  名称：

  Preparation and Properties of Rotaxanes Formed by Dimethyl-β-cyclodextrin and Oligo(thiophene)s with β-Cyclodextrin Stoppers

  摘要：

  [graphics]Novel cyclodextrin rotaxanes with oligothiophene as an axis molecule have been prepared by the Suzuki coupling reaction of 6-O-(4-iodophenyl)-beta-CD (6-I-Ph-beta-CD) with di(1,3,2-dioxaborolan-2-yl)-oligothiophene (oligothiophene diboric ethylene glycol esters) in aqueous solutions of dimethyl-beta-cyclodextrin (DM-beta-CD). These reactions gave [2]rotaxanes and [3]rotaxanes, which were isolated by reversed phase chromatography. The fluorescence intensities of rotaxanes are higher than those of dumbbell-shaped molecules (without DM-beta-CD) in aqueous solutions. The inclusion ratio and chain length of rotaxanes have been found to relate to the emission properties and emission intensities of oligothiophene. In aqueous solutions, fluorescence quantum yields of rotaxanes are higher than those of dumbbell-shaped molecules. The increase in the fluorescence efficiency of rotaxane is caused by suppression of intermolecular interactions, indicating the effect of insulated oligothiophene with DM-beta-CD. beta-CD at the both ends of rotaxanes functions not only as bulky stoppers but also as the recognition site for guest molecules, as verified by fluorescence quenching experiments.

  DOI：

  10.1021/jo061834o