5,11-Diiodo-17,23-dinitro-25,26,27,28-tetrapropoxycalix<4>arene | 156080-35-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5,11-Diiodo-17,23-dinitro-25,26,27,28-tetrapropoxycalix<4>arene
• 英文别名: 5,11-Diiodo-17,23-dinitro-25,26,27,28-tetrapropoxypentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3(28),4,6,9,11,13(27),15,17,19(26),21(25),22-dodecaene
• CAS: 156080-35-2
• 化学式: C₄₀H₄₄I₂N₂O₈
• 分子量: 934.607
• InChiKey: VGNOIGKFAUTPNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.1
• 重原子数：
  52
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  129
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5,11-Diiodo-17,23-dinitro-25,26,27,28-tetrapropoxycalix<4>arene 在 copper(I) oxide 、 盐酸 、 一水合肼 作用下， 以 various solvent(s) 为溶剂， 反应 26.5h， 生成 5,11-diamino-17,23-dinitro-25,26,27,28-tetrapropoxycalix<4>arene
  参考文献：
  名称：

  Novel Routes for the Synthesis of Upper Rim Amino and Methoxycarbonyl Functionalized Calix[4]arenes Carrying Other Types of Functional Groups

  摘要：

  描述了在其他官能团存在的情况下，通过在上缘进行碘化选择性功能化的 calix[4]arene 1。所得的（部分）碘化 calix[4]arene 2 是制备相应的羧酸酯和氨基衍生物 3 和 6 的良好起始材料。

  DOI：

  10.1055/s-1994-25435
• 作为产物：
  描述：

  cone-5,11-dinitro-25,26,27,28-tetrapropoxycalix[4]arene 在 碘 、 silver trifluoroacetate 作用下， 生成 5,11-Diiodo-17,23-dinitro-25,26,27,28-tetrapropoxycalix<4>arene
  参考文献：
  名称：

  Novel Routes for the Synthesis of Upper Rim Amino and Methoxycarbonyl Functionalized Calix[4]arenes Carrying Other Types of Functional Groups

  摘要：

  描述了在其他官能团存在的情况下，通过在上缘进行碘化选择性功能化的 calix[4]arene 1。所得的（部分）碘化 calix[4]arene 2 是制备相应的羧酸酯和氨基衍生物 3 和 6 的良好起始材料。

  DOI：

  10.1055/s-1994-25435

文献信息

• 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.