3,8,13-Trimethoxy-7,12-bis-{2-[2-methoxy-4-(tetrahydro-pyran-2-yloxymethyl)-phenoxy]-ethoxy}-10,15-dihydro-5H-tribenzo[a,d,g]cyclononen-2-ol | 811867-93-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3,8,13-Trimethoxy-7,12-bis-{2-[2-methoxy-4-(tetrahydro-pyran-2-yloxymethyl)-phenoxy]-ethoxy}-10,15-dihydro-5H-tribenzo[a,d,g]cyclononen-2-ol
• CAS: 811867-93-3
• 化学式: C₅₄H₆₄O₁₄
• 分子量: 937.094
• InChiKey: DVOZUBXBDJGXLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.52
• 重原子数：
  68.0
• 可旋转键数：
  21.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  140.22
• 氢给体数：
  1.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  3,8,13-Trimethoxy-7,12-bis-{2-[2-methoxy-4-(tetrahydro-pyran-2-yloxymethyl)-phenoxy]-ethoxy}-10,15-dihydro-5H-tribenzo[a,d,g]cyclononen-2-ol 在 甲酸 、 potassium peroxomonocarbonate 、 四丁基碘化铵 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.5h， 生成 7,14,21,28,35-pentamethoxy-42-prop-2-enoxy-9,12,30,33,43,46-hexaoxadecacyclo[20.20.4.38,37.316,29.113,17.134,38.03,40.019,24.05,49.026,52]tetrapentaconta-1(42),2,5,7,13,15,17(54),19,21,23,26,28,34,36,38(47),40,49,51-octadecaene
  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 、 四丁基碘化铵 、 potassium carbonate 、 caesium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 3,8,13-Trimethoxy-7,12-bis-{2-[2-methoxy-4-(tetrahydro-pyran-2-yloxymethyl)-phenoxy]-ethoxy}-10,15-dihydro-5H-tribenzo[a,d,g]cyclononen-2-ol
  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

文献信息

• Synthesis of Cryptophanes with Two Different Reaction Sites: Chemical Platforms for Xenon Biosensing
  作者：Laure-Lise Chapellet、James R. Cochrane、Emilie Mari、Céline Boutin、Patrick Berthault、Thierry Brotin

  DOI：10.1021/acs.joc.5b00653

  日期：2015.6.19

  We report the synthesis of new water-soluble cryptophane host molecules that can be used for the preparation of Xe-129 NMR-based biosensors. We show that the cryptophane-223 skeleton can be modified to introduce a unique secondary alcohol to the propylenedioxy linker. This chemical functionality can then be exploited to introduce a functional group that is different from the six chemical groups attached to the aromatic rings. In this approach, the generation of a statistical mixture when trying to selectively functionalize a symmetrical host molecule is eliminated, which enables the efficient large-scale production of new cryptophanes that can be used as chemical platforms ready to use for the preparation of xenon biosensors. To illustrate this approach, two molecular platforms have been prepared, and the ability of these new derivatives to bind xenon has been investigated.