25,27-bis(1-octyloxy)calix<4>warene-crown-6 | 162301-47-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 25,27-bis(1-octyloxy)calix<4>warene-crown-6
• 英文别名: 43,44-dioctoxy-3,6,9,12,15,18-hexaoxahexacyclo[18.15.7.126,30.137,41.02,32.019,24]tetratetraconta-1(35),2(32),19(24),20,22,26,28,30(44),33,37(43),38,40-dodecaene
• CAS: 162301-47-5
• 化学式: C₅₄H₇₄O₈
• 分子量: 851.177
• InChiKey: FNRLFHMTAOXYRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.6
• 重原子数：
  62
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  25,27-bis(1-octyloxy)calix<4>warene-crown-6 在 硝酸 、 乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以81%的产率得到22,28,34,39-Tetranitro-43,44-dioctoxy-3,6,9,12,15,18-hexaoxahexacyclo[18.15.7.126,30.137,41.02,32.019,24]tetratetraconta-1,19,21,23,26(44),27,29,32,34,37,39,41(43)-dodecaene
  参考文献：
  名称：

  Study of the nitration of di-n-octylcrown-6 calix[4]arene using LC–MS, NMR, and molecular modelling

  摘要：

  使用不同条件进行有选择性的硝化反应，利用LC-MS和NMR (¹H和¹³C)光谱技术研究了二正辛基冠-6杯[4]芳烃的硝化反应，鉴定了大部分预期的硝基衍生物同分异构体化合物。利用分子模拟探讨了这些同分异构体在酸性和辐射条件下的形成。关键词：杯冠化合物，杯芳烃的硝化反应，同分异构体硝基杯芳烃的NMR，LC-ESI-MS。

  DOI：

  10.1139/v05-126
• 作为产物：
  描述：

  1-碘辛烷 在 potassium carbonate 、 caesium carbonate 作用下， 以 乙腈 为溶剂， 生成 25,27-bis(1-octyloxy)calix<4>warene-crown-6
  参考文献：
  名称：

  Dideoxygenated calix[4]arene crown-6 ethers enhanced selectivity for caesium over potassium and rubidium

  摘要：

  源自双脱氧杯[4]芳烃的杯[4]芳烃冠6醚对铯的萃取选择性高于对钾的萃取选择性；未络合的杯[4]芳烃单苯并冠6醚的晶体结构在固态时以1,3-alt构象存在。

  DOI：

  10.1039/a905682c

文献信息

• Synthesis, Complexation, and Membrane Transport Studies of 1,3-Alternate Calix[4]arene-crown-6 Conformers: A New Class of Cesium Selective Ionophores
  作者：Alessandro Casnati、Andrea Pochini、Rocco Ungaro、Franco Ugozzoli、Francoise Arnaud、Stefano Fanni、Marie-Jose Schwing、Richard J. M. Egberink、Feike de Jong、David N. Reinhoudt

  DOI：10.1021/ja00115a012

  日期：1995.3

  1,3-Dialkoxycalix[3]arene-crown-6 ionophores (4a-d) are obtained in the fixed 1,3-alternate conformation in 63-85% yield by the reaction of the corresponding 1,3-dialkoxycalix[4]arenes 3a-d with pentaethylene glycol ditosylate in CH3CN in the presence of Cs2CO3. The corresponding cone conformer of the diisopropyl derivative (6) was synthesized via selective demethylation of the 1,3-dimethoxycalix-crown (2a) and subsequent dialkylation. Extraction experiments with alkali picrates reveal a strong preference of ligands 4 for Cs+. Thermodynamic parameters obtained for the complexation of 4a show that the high stability constant in MeOH (log beta = 6.4 +/- 0.4) is reflected mainly in the large -Delta H-c value of 50.2 +/- 0.2 kJ . mol(-1). The entropy of complexation (T Delta S-c = -15 kJ . mol(-1)), less negative than for other crown ethers, is explained in terms of preorganization of 4a. The X-ray structure of the cesium picrate . 4a complex shows clearly that the cation is positioned between the two aromatic rings with short Cs-C distances of 3.49 and 3.69 Angstrom, respectively. H-1 MMR spectroscopy confirms this type of structure in solution. Ligands 4 incorporated in supported liquid membranes transport Cs+ cations with a high preference over Na+. By the application of an anion gradient, traces of Cs+ can be removed (greater than or equal to 99.8%) from acidic solutions (pH = 0) that contain 4 M of NaNO3.