12-Allyloxy-3,8,13-trimethoxy-10,15-dihydro-5H-tribenzo[a,d,g]cyclononene-2,7-diol | 811867-91-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 12-Allyloxy-3,8,13-trimethoxy-10,15-dihydro-5H-tribenzo[a,d,g]cyclononene-2,7-diol
• CAS: 811867-91-1
• 化学式: C₂₇H₂₈O₆
• 分子量: 448.516
• InChiKey: CYBBLQGYJLZAOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.77
• 重原子数：
  33.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  77.38
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  12-Allyloxy-3,8,13-trimethoxy-10,15-dihydro-5H-tribenzo[a,d,g]cyclononene-2,7-diol 在 四(三苯基膦)钯 、 potassium peroxomonocarbonate 、 三正丁基氢锡 、 四丁基碘化铵 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.5h， 生成 [3-Prop-2-enoxy-4-[2-[[6,13,20-trimethoxy-12,19-bis[2-[2-methoxy-4-(oxan-2-yloxymethyl)phenoxy]ethoxy]-5-tetracyclo[15.4.0.03,8.010,15]henicosa-1(21),3,5,7,10,12,14,17,19-nonaenyl]oxy]ethoxy]phenyl]methanol
  参考文献：
  名称：

  Development of a Functionalized Xenon Biosensor

  摘要：

  NMR-based biosensors that utilize laser-polarized xenon offer potential advantages beyond current sensing technologies. These advantages include the capacity to simultaneously detect multiple analytes, the applicability to in vivo spectroscopy and imaging, and the possibility of "remote" amplified detection. Here, we present a detailed NMR characterization of the binding of a biotin-derivatized caged-xenon sensor to avidin. Binding of "functionalized" xenon to avidin leads to a change in the chemical shift of the encapsulated xenon in addition to a broadening of the resonance, both of which serve as NMR markers of ligand-target interaction. A control experiment in which the biotin-binding site of avidin was blocked with native biotin showed no such spectral changes, confirming that only specific binding, rather than nonspecific contact, between avidin and functionalized xenon leads to the effects on the xenon NMR spectrum. The exchange rate of xenon (between solution and cage) and the xenon spin-lattice relaxation rate were not changed significantly upon binding. We describe two methods for enhancing the signal from functionalized xenon by exploiting the laser-polarized xenon magnetization reservoir. We also show that the xenon chemical shifts are distinct for xenon encapsulated in different diastereomeric cage molecules. This demonstrates the potential for tuning the encapsulated xenon chemical shift, which is a key requirement for being able to multiplex the biosensor.

  DOI：

  10.1021/ja0483037
• 作为产物：
  描述：

  2,7,12-triallyloxy-3,8,13-trimethoxy-10,15-dihydro-5H-tribenzo[a,d,g]cyclononene 在 四(三苯基膦)钯 、 三正丁基氢锡 、 caesium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 12-Allyloxy-3,8,13-trimethoxy-10,15-dihydro-5H-tribenzo[a,d,g]cyclononene-2,7-diol
  参考文献：
  名称：

  Development of a Functionalized Xenon Biosensor

  摘要：

  NMR-based biosensors that utilize laser-polarized xenon offer potential advantages beyond current sensing technologies. These advantages include the capacity to simultaneously detect multiple analytes, the applicability to in vivo spectroscopy and imaging, and the possibility of "remote" amplified detection. Here, we present a detailed NMR characterization of the binding of a biotin-derivatized caged-xenon sensor to avidin. Binding of "functionalized" xenon to avidin leads to a change in the chemical shift of the encapsulated xenon in addition to a broadening of the resonance, both of which serve as NMR markers of ligand-target interaction. A control experiment in which the biotin-binding site of avidin was blocked with native biotin showed no such spectral changes, confirming that only specific binding, rather than nonspecific contact, between avidin and functionalized xenon leads to the effects on the xenon NMR spectrum. The exchange rate of xenon (between solution and cage) and the xenon spin-lattice relaxation rate were not changed significantly upon binding. We describe two methods for enhancing the signal from functionalized xenon by exploiting the laser-polarized xenon magnetization reservoir. We also show that the xenon chemical shifts are distinct for xenon encapsulated in different diastereomeric cage molecules. This demonstrates the potential for tuning the encapsulated xenon chemical shift, which is a key requirement for being able to multiplex the biosensor.

  DOI：

  10.1021/ja0483037