C-undecylcavitandtetrol | 169219-14-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: C-undecylcavitandtetrol
• 英文别名: 25,29,33,37-Tetra(undecyl)-2,4,8,10,14,16,20,22-octaoxanonacyclo[21.15.1.124,38.05,36.07,34.011,32.013,30.017,28.019,26]tetraconta-1(39),5,7(34),11,13(30),17(28),18,23,26,31,35,38(40)-dodecaene-6,12,18,39-tetrol
• CAS: 169219-14-1
• 化学式: C₇₆H₁₁₂O₁₂
• 分子量: 1217.72
• InChiKey: BQBALKMHQFRAHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  28.5
• 重原子数：
  88
• 可旋转键数：
  40
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  155
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  4-氯甲基吡啶盐酸盐 、 C-undecylcavitandtetrol 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以75%的产率得到4-[[12,18,39-Tris(pyridin-4-ylmethoxy)-25,29,33,37-tetra(undecyl)-2,4,8,10,14,16,20,22-octaoxanonacyclo[21.15.1.124,38.05,36.07,34.011,32.013,30.017,28.019,26]tetraconta-1(39),5,7(34),11,13(30),17(28),18,23,26,31,35,38(40)-dodecaen-6-yl]oxymethyl]pyridine
  参考文献：
  名称：

  具有用于[60]富勒烯封装的纳米级空腔的二聚体胶囊。

  摘要：

  通过将卤代乙酸添加到间苯二酚[4]芳烃衍生物1和[60]富勒烯的甲苯溶液中，实现了酸辅助和客体诱导的上层结构的形成。当将适当的酸（例如卤乙酸）和适当的客体分子（例如[60]富勒烯）共添加到具有四个吡啶单元的cavitand 1的甲苯溶液中时，观察到了包裹纳米级客体分子的二聚体超结构的形成。 ，而在没有[60]富勒烯的情况下，检测到几种物质之间存在复杂的平衡，并且在不存在卤代乙酸的情况下，未检测到离散的超结构的形成。光谱数据表明形成的[60]富勒烯包封的配合物具有2的结构。这些络合物通过吡啶鎓-阴离子-吡啶鎓相互作用以及pi-pi和van der Waals相互作用而自组装。从2D交换NMR光谱估计2的解复速率为3.1 s（-1）。通过改变所用酸的量，改变体系的温度，改变酸/碱的比例，甚至改变溶剂的极性，都可以控制[60]富勒烯的包封过程。此外，荧光光谱显示窄带光谱变化和分离的和各向同性的[

  DOI：

  10.1002/chem.200701767
• 作为产物：
  描述：

  6,12,18,39-Tetrabromo-25,29,33,37-tetra(undecyl)-2,4,8,10,14,16,20,22-octaoxanonacyclo[21.15.1.124,38.05,36.07,34.011,32.013,30.017,28.019,26]tetraconta-1(39),5,7(34),11,13(30),17(28),18,23,26,31,35,38(40)-dodecaene 在 正丁基锂 、 硼酸三甲酯 、 双氧水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.83h， 以53%的产率得到C-undecylcavitandtetrol
  参考文献：
  名称：

  Pore formation in phospholipid bilayers by amphiphilic cavitands

  摘要：

  制备了五种新的腔体分子，这些腔体分子具有四个悬挂的正十一烷链和由两个碳间隔相连的“头部”。头部的结构分别为∼OCH2CONH-Ala-OCH3（1）；∼OCH2CONH-Phe-OCH3（2）；∼OCH2CONH-Ala-OH（3）；∼OCH2CONH-Phe-OH（4）；和∼OCH2CONHCH2CH2-胸苷基（5）。通过平面双层电导实验研究了每个腔体分子的孔形成。发现所有五种化合物均能在asolectin双层膜中形成孔。化合物1-3的行为一般相似，并显示出开闭动态。化合物4和5形成孔的速度更快，更具动态性，并且更快导致膜破裂。离子传输活性的差异可以从结构和聚集腔体分子组装的角度进行解释。

  DOI：

  10.1039/c0ob01236j

文献信息

• Partial Etherification Reactions of Cavitand Phenol Bowls
  作者：E. S. Barrett、J. L. Irwin、K. Picker、M. S. Sherburn

  DOI：10.1071/ch02031

  日期：——

  Reactions between the C4v-symmetrical cavitand tetraphenol (2), various bases, and less than 4 molar equivalents of alkyl halides result in the generation of statistical mixtures of the five possible ether products along with unreacted starting material. Useful quantities of monoalkoxytriphenol (8), A,B-dialkoxydiphenol (9) and trialkoxymonophenol (11) are obtained by controlling the reaction stoichiometry and the desired products can, in general, be isolated by straightforward chromatographic means.

  C4v 对称空位四苯酚 (2)、各种碱和少于 4 摩尔当量的烷基卤化物之间的反应会产生五种可能的醚产物的统计混合物以及未反应的起始物质。通过控制反应的化学计量，可以得到适量的单烷氧基三苯酚 (8)、A,B-二烷氧基二苯酚 (9) 和三烷氧基一苯酚 (11)。
• Synthetic receptors with preorganized cavities that complex prednisolone-21-acetate
  作者：Peter Timmerman、Erik A. Brinks、Willem Verboom、David N. Reinhoudt

  DOI：10.1039/c39950000417

  日期：——

  Receptors 3a–c composed of two upper rim 1,2-difunctionalized calix[4]arene fragments, oriented either endo or exo, and one bridging cavitand unit, complex prednisolone-21-acetate with association constants of 4.3–8.3 × 102 dm3 mol–1 in CDCl3.

  受体3a-c由两个上缘1,2-二官能化杯[4]芳烃片段组成，分别以内或外为取向，以及一个桥连空位单元，即复杂的泼尼松龙-21-乙酸酯，在CDCl3中的关联常数为4.3-8.3×102 dm3 mol-1。
• Calix[4]arene-Based (Hemi)carcerands and Carceplexes: Synthesis, Functionalization, and Molecular Modeling Study
  作者：André M. A. van Wageningen、Peter Timmerman、John P. M. van Duynhoven、Willem Verboom、Frank C. J. M. van Veggel、David N. Reinhoudt

  DOI：10.1002/chem.19970030421

  日期：1997.4

  AbstractThe synthesis of 11 calix[4]arene‐based carceplexes obtained by solvent or doped inclusion is reported. Carceplexes with amides, for example, DMF, NMP, and 1,5‐dimethyl‐2‐pyrrolidinone, and sulfoxides, for example, DMSO and thiolane‐1‐oxide, were obtained by solvent inclusion. In these cases the yield of the carceplex decreases with increasing guest size. Potential guests that do not form carceplexes by solvent inclusion, such as 2‐butanone and 3‐sulfolene, could be incarcerated by doped inclusion with 1,5‐dimethyl‐2‐pyrrolidinone as a solvent “doped” with 5–15 vol% of potential guest. The amide bridges of the carceplexes were converted into thioamide bridges in essentially quantitative yield by means of Lawesson's reagent in refluxing xylene. The dynamic properties of the incarcerated guests were examined by 2D NMR spectroscopy. Whereas for most guests a preference for one orientation inside the calix[4]arene‐based (thia)carcerands was observed, for DMA, NMP, and ethyl methyl sulfoxide inside calix[4]arene‐based (thia)carcerandstwo different orientationswere present. The energy barriers for interconversion between the various orientations of DMA, NMP, and ethyl methyl sulfoxide inside calix[4]arene‐based (thia)‐carcerands were determined with 2D EXSY NMR. The energy barriers are higher for the thiacarcerands than for the corresponding carcerands with amide bridges. This may be due to the stronger hydrogen‐bond‐donating character of the thioamide group. Furthermore, molecular modeling simulations indicate that in case of the thiacarcerand the cavity is smaller as a result of a smaller diametrical distance between the NHatoms. Our results demonstrate that molecular modeling can be used to estimate the energy barriers for interconversion; the calculated activation energies showed good quantitative agreement with the experimental values.
• Combination of Calix[4]arenes and Resorcin[4]arenes for the Complexation of Steroids
  作者：Irene Higler、Peter Timmerman、Willem Verboom、David N. Reinhoudt

  DOI：10.1021/jo960256g

  日期：1996.1.1

  Receptor molecules with large cavities synthesized by the combination of building blocks that already possess a cavity, viz. calix[4]arenes and resorcin[4]arenes, are described. These receptor molecules are synthesized by reaction of one or two upper rim 1,2-difunctionalized calix[4]arene fragments oriented either endo or exo toward a cavitand unit. The endo:exo ratio depends on the substituents at the 3- and 4-positions of the calix[4]arenes. These novel receptor molecules complex steroids with association constants of (0.9-9.5) x 10(2) M(-1) in CDCl3.
• Timmerman, Peter; Verboom, Willem; Veggel, Frank C. J. M. van, Angewandte Chemie, 1994, vol. 106, # 12, p. 1313 - 1315
  作者：Timmerman, Peter、Verboom, Willem、Veggel, Frank C. J. M. van、Hoorn, Willem P. van、Reinhoudt, David N.

  DOI：——

  日期：——