cryptophane-223 | 864920-31-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: cryptophane-223
• 英文别名: 7,15,22,29,36,43-Hexamethoxy-9,13,31,34,44,47-hexaoxadecacyclo[21.20.4.38,38.317,30.114,18.135,39.03,41.020,25.05,50.027,53]pentapentaconta-1(43),2,5,7,14,16,18(55),20,22,24,27,29,35,37,39(48),41,50,52-octadecaene；7,15,22,29,36,43-hexamethoxy-9,13,31,34,44,47-hexaoxadecacyclo[21.20.4.38,38.317,30.114,18.135,39.03,41.020,25.05,50.027,53]pentapentaconta-1(43),2,5,7,14,16,18(55),20,22,24,27,29,35,37,39(48),41,50,52-octadecaene
• CAS: 864920-31-0
• 化学式: C₅₅H₅₆O₁₂
• 分子量: 909.042
• InChiKey: UKHHICLPDQRGDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.9
• 重原子数：
  67
• 可旋转键数：
  6
• 环数：
  20.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  cryptophane-223 在 二苯基膦酸锂 、 盐酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 72.0h， 以71%的产率得到9,13,31,34,44,47-Hexaoxadecacyclo[21.20.4.38,38.317,30.114,18.135,39.03,41.020,25.05,50.027,53]pentapentaconta-1(43),2,5,7,14,16,18(55),20,22,24,27,29,35,37,39(48),41,50,52-octadecaene-7,15,22,29,36,43-hexol
  参考文献：
  名称：

  Water Soluble Cryptophanes Showing Unprecedented Affinity for Xenon:  Candidates as NMR-Based Biosensors

  摘要：

  Cryptophanes bearing OCH2COOH groups in place of the methoxy groups represent a new class of xenon-carrier molecules soluble in water at biological pH. By using H-1 and Xe-129 NMR (thermally-and laser-polarized dissolved gas), the structural and dynamical behaviors of these host molecules as well as their interaction with xenon are studied. They are shown to exist in aqueous solution under different conformations in very slow exchange. A saddle form present for one of these conformations could explain the H-1 NMR spectra. Whereas the cryptophanes in such a conformation are unable to complex xenon, unprecedented high binding constants are found for cryptophanes in the other canonical crown-crown conformation. These host molecules could therefore be valuable candidates for biosensing using Xe-129 MRI.

  DOI：

  10.1021/ja060266r
• 作为产物：
  描述：

  2-[4-(3-iodopropoxy)-3-methoxybenzyloxy]tetrahydropyran 在 caesium carbonate 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 cryptophane-223
  参考文献：
  名称：

  Improved Synthesis of Functional CTVs and Cryptophanes Using Sc(OTf)₃ as Catalyst

  摘要：

  Functional cyclotriveratrylene (CTV) and cryptophane derivatives are synthesized in the presence of scandium triflate [Sc(OTf)(3)]. This route allows the preparation of new derivatives that could not be prepared or easily obtained by using the previously reported experimental procedures. With a catalytic amount of scandium triflate (1% mol), CTVs were obtained with yields similar to or higher than those reported previously in reactions run under strong acidic conditions. Cryptophanes were also synthesized in fairly good yields by performing the ring-closure step in the presence of a stoichiometric amount of Sc(OTf)(3). Interestingly, this novel approach strongly reduces the formation of side products and gives rise to novel functionalized molecules for the construction of supramolecular host-guest systems.

  DOI：

  10.1021/jo050495g

文献信息

• Cryptophane-Xenon Complexes in Organic Solvents Observed through NMR Spectroscopy
  作者：Gaspard Huber、Lætitia Beguin、Hervé Desvaux、Thierry Brotin、Heather A. Fogarty、Jean-Pierre Dutasta、Patrick Berthault

  DOI：10.1021/jp807425t

  日期：2008.11.13

  The interaction of xenon with cryptophane derivatives is analyzed by NMR by using either thermal or hyperpolarized. noble gas. Twelve hosts differing by their stereochemistry, cavity size, and the nature and the number of the substituents on the aromatic rings have been included in the study, in the aim of extracting some clues for the optimization of Xe-129-NMR based biosensors derived from these cage molecules. Four important properties have been examined: xenon-host binding constant, in-out exchange rate of the noble gas, chemical shift, and relaxation of caged xenon. This work aims at understanding the main characteristics of the host-guest interaction in order to choose the best candidate for the biosensing approach. Moreover, rationalizing xenon chemical shift as a function of structural parameters would also help for setting up multiplexing applications. Xenon exhibits the highest affinity for the smallest cryptophane, namely cryptophane-111, and a long relaxation time inside it, convenient for conservation of its hyperpolarization. However, very slow in-out xenon exchange could represent a limitation for its future applicability for the biosensing approach, because the replenishment of the cage in laser-polarized xenon, enabling a further gain in sensitivity, cannot be fully exploited.
• Improved Synthesis of Functional CTVs and Cryptophanes Using Sc(OTf)₃ as Catalyst
  作者：Thierry Brotin、Vincent Roy、Jean-Pierre Dutasta

  DOI：10.1021/jo050495g

  日期：2005.8.1

  Functional cyclotriveratrylene (CTV) and cryptophane derivatives are synthesized in the presence of scandium triflate [Sc(OTf)(3)]. This route allows the preparation of new derivatives that could not be prepared or easily obtained by using the previously reported experimental procedures. With a catalytic amount of scandium triflate (1% mol), CTVs were obtained with yields similar to or higher than those reported previously in reactions run under strong acidic conditions. Cryptophanes were also synthesized in fairly good yields by performing the ring-closure step in the presence of a stoichiometric amount of Sc(OTf)(3). Interestingly, this novel approach strongly reduces the formation of side products and gives rise to novel functionalized molecules for the construction of supramolecular host-guest systems.
• Water Soluble Cryptophanes Showing Unprecedented Affinity for Xenon:  Candidates as NMR-Based Biosensors
  作者：Gaspard Huber、Thierry Brotin、Lionel Dubois、Hervé Desvaux、Jean-Pierre Dutasta、Patrick Berthault

  DOI：10.1021/ja060266r

  日期：2006.5.1

  Cryptophanes bearing OCH2COOH groups in place of the methoxy groups represent a new class of xenon-carrier molecules soluble in water at biological pH. By using H-1 and Xe-129 NMR (thermally-and laser-polarized dissolved gas), the structural and dynamical behaviors of these host molecules as well as their interaction with xenon are studied. They are shown to exist in aqueous solution under different conformations in very slow exchange. A saddle form present for one of these conformations could explain the H-1 NMR spectra. Whereas the cryptophanes in such a conformation are unable to complex xenon, unprecedented high binding constants are found for cryptophanes in the other canonical crown-crown conformation. These host molecules could therefore be valuable candidates for biosensing using Xe-129 MRI.