(+/-)-cryptophane-E | 102683-14-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (+/-)-cryptophane-E
• 英文别名: (rac)-cryptophane E；cryptophane E；cryptophane-E；Cryptophan-E；7,15,22,29,37,44-hexamethoxy-9,13,31,35,45,49-hexaoxadecacyclo[21.21.5.38,39.317,30.114,18.136,40.03,42.020,25.05,52.027,55]heptapentaconta-1(44),2,5,7,14,16,18(57),20,22,24,27,29,36,38,40(50),42,52,54-octadecaene
• CAS: 102683-14-7；102735-01-3；110352-20-0；155322-30-8
• 化学式: C₅₇H₆₀O₁₂
• 分子量: 937.096
• InChiKey: FFDNAZBGSMCNRE-UHFFFAOYSA-N

物化性质

• 熔点：
  >260°C
• 沸点：
  731.58°C (rough estimate)
• 密度：
  1.0827 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  11.6
• 重原子数：
  69
• 可旋转键数：
  6
• 环数：
  20.0
• sp3杂化的碳原子比例：
  0.37
• 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-E 在 二苯基膦酸锂 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以82%的产率得到
  参考文献：
  名称：

  Remarkable effect of the receptor size in the binding of acetylcholine and related ammonium ions to water-soluble cryptophanes

  摘要：

  DOI：

  10.1021/ja00077a096
• 作为产物：
  描述：

  4-羟基-3-甲氧基苄醇 在 sodium hydroxide 、 甲酸 、 potassium carbonate 、 sodium iodide 作用下， 以 六甲基磷酰三胺 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 28.0h， 生成 (+/-)-cryptophane-E
  参考文献：
  名称：

  Synthesis and exciton optical activity of D3-cryptophanes

  摘要：

  DOI：

  10.1021/ja00255a035

文献信息

• Facile, Near-Quantitative, Aqueous Routes to Nearly Any [Cp*Ru(η⁶-arene)]Cl Compound
  作者：Robert M. Fairchild、K. Travis Holman

  DOI：10.1021/om0701773

  日期：2007.6.1

  Facile syntheses of water-soluble [Cp*Ru(arene)]Cl compounds exploiting the extraordinary properties of [Cp*Ru(μ3-Cl)]4 in aqueous media are described. These methods produce no byproducts, involve little to no workup, and are applicable to almost any simple arene.

  的水溶性的[Cp *的Ru（芳烃）]氯化合物利用的的[Cp *茹（μ的非凡特性容易合成3 -Cl）] 4在含水介质中进行了描述。这些方法不产生副产物，几乎不需要或不需要任何后处理，并且几乎适用于任何简单的芳烃。
• A new cryptophane forming unusually stable inclusion complexes with neutral guests in a lipophilic solvent
  作者：Josette. Canceill、Liliane. Lacombe、Andre. Collet

  DOI：10.1021/ja00274a067

  日期：1986.7

  trimethylenedioxy entre les 6 noyaux benzeniques pris 2 a 2 a partir de trimethoxy-3,8,13 5H,10H,15H-tribenzo [a,d,g] cyclononenetriol-2,7,12 et d'alcool iodo-3' propoxy-4 methoxy-3 benzylique. Etude des complexes formes avec divers halomethanes

  Synthese d'un cyclophane constitue de 2party tribenzo [a,d,g] cyclononenes reliees par 3 ponts triethylenedioxy entre les 6 noyaux benzeniques pris 2 a 2 a partir de trimethoxy-3,8,13 5H,10H,15H-tribenzo [ a,d,g] cyclononenetriol-2,7,12 et d'alcool iodo-3' propoxy-4 methoxy-3 benzylique。Etude des complexes formes avec divers 卤甲烷
• Access to the <i>Syn</i> diastereomers of cryptophane cages using HFIP
  作者：Oriane Della-Negra、Yoann Cirillo、Thierry Brotin、Jean-Pierre Dutasta、Pierre-Loic Saaidi、Bastien Chatelet、Alexandre Martinez

  DOI：10.1039/d1cc06607b

  日期：——

  The use of the HFIP/bisulfate salt combination provides convenient and fast access to syn-cryptophanes.

  使用HFIP / bisulfate盐组合物提供了方便快捷的方法来获得syn-cryptophanes。
• 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.
• 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.