37,38-Dipropoxy-19,22,25,28-tetraoxahexacyclo[15.12.7.17,11.131,35.05,29.013,18]octatriaconta-1(29),2,4,7(38),8,10,13,15,17,31(37),32,34-dodecaene | 877993-13-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 37,38-Dipropoxy-19,22,25,28-tetraoxahexacyclo[15.12.7.17,11.131,35.05,29.013,18]octatriaconta-1(29),2,4,7(38),8,10,13,15,17,31(37),32,34-dodecaene
• CAS: 877993-13-0
• 化学式: C₄₀H₄₆O₆
• 分子量: 622.802
• InChiKey: HWRPFJSDRXTDLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  46
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  37,38-Dipropoxy-19,22,25,28-tetraoxahexacyclo[15.12.7.17,11.131,35.05,29.013,18]octatriaconta-1(29),2,4,7(38),8,10,13,15,17,31(37),32,34-dodecaene 在 四(三苯基膦)钯 碘 、 silver trifluoroacetate 、 potassium carbonate 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 2.0h， 生成 3,9,15,33-Tetrakis(4-phenylphenyl)-37,38-dipropoxy-19,22,25,28-tetraoxahexacyclo[15.12.7.17,11.131,35.05,29.013,18]octatriaconta-1,3,5(29),7,9,11(38),13(18),14,16,31,33,35(37)-dodecaene
  参考文献：
  名称：

  Synthesis of Oligophenylene-Substituted Calix[4]crown-4s and Their Silver(I) Ion-Induced Nanocones Formation

  摘要：

  A novel series of oligophenylene OPP(n)-substituted calix[4]crown-4s bearing up to three phenylene units, 1a-d, has been efficiently synthesized by means of either microwave-assisted or silver(I) ion-assisted Pd-catalyzed Suzuki cross-coupling of tetraiodocalix[4]crown-4 and the corresponding oligo-phenylboronic acids. Complexation of OPP(n)-substituted calix[4]crown-4s with silver (I) ion was substantiated by H-1 NMR spectroscopic and high-resolution ESI- or MALDI-TOF- MS studies. The weak binding affinities of OPP(n)-substituted calix[4]crown-4s for silver (I) ion, which were estimated from H-1 NMR titrations with binding association in the range of 30-90 M-1, allows reversible disassembling in the presence of KI at ambient temperature. Remarkably, the single-crystal X-ray structures of OPP(n)-calix[4]crown-4(.)Ag(+) complexes indicate the atypical silver (I) ion-crown ether binding mode resulting in the formation of rigid nanocones with volume created up to similar to 1500 angstrom(3). Our results suggested that despite the weak binding affinity of crown ether ligands for silver (I) ion, this weak interaction is still be useful as a tool to construct supramolecular architectures.

  DOI：

  10.1021/jo051896z
• 作为产物：
  描述：

  杯[4]芳烃 在 sodium hydride 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 45.0h， 生成 37,38-Dipropoxy-19,22,25,28-tetraoxahexacyclo[15.12.7.17,11.131,35.05,29.013,18]octatriaconta-1(29),2,4,7(38),8,10,13,15,17,31(37),32,34-dodecaene
  参考文献：
  名称：

  Synthesis of Oligophenylene-Substituted Calix[4]crown-4s and Their Silver(I) Ion-Induced Nanocones Formation

  摘要：

  A novel series of oligophenylene OPP(n)-substituted calix[4]crown-4s bearing up to three phenylene units, 1a-d, has been efficiently synthesized by means of either microwave-assisted or silver(I) ion-assisted Pd-catalyzed Suzuki cross-coupling of tetraiodocalix[4]crown-4 and the corresponding oligo-phenylboronic acids. Complexation of OPP(n)-substituted calix[4]crown-4s with silver (I) ion was substantiated by H-1 NMR spectroscopic and high-resolution ESI- or MALDI-TOF- MS studies. The weak binding affinities of OPP(n)-substituted calix[4]crown-4s for silver (I) ion, which were estimated from H-1 NMR titrations with binding association in the range of 30-90 M-1, allows reversible disassembling in the presence of KI at ambient temperature. Remarkably, the single-crystal X-ray structures of OPP(n)-calix[4]crown-4(.)Ag(+) complexes indicate the atypical silver (I) ion-crown ether binding mode resulting in the formation of rigid nanocones with volume created up to similar to 1500 angstrom(3). Our results suggested that despite the weak binding affinity of crown ether ligands for silver (I) ion, this weak interaction is still be useful as a tool to construct supramolecular architectures.

  DOI：

  10.1021/jo051896z

文献信息

• Synthesis and evaluation of novel 1,3-bridged calix[4]arene-crown ethers for selective interaction with Na+/K+ cations
  作者：Har Mohindra Chawla、Geeta Hundal、S. Kumar、Parminder Singh

  DOI：10.1007/s10847-011-9979-5

  日期：2012.4

  synthesized 1,3-bridged calix[4]arene-crown ethers for alkali metal cations have been investigated by atomic emission spectrometric analysis. It has been observed that recognition of sodium and potassium varies with the size of the polyether chain as well as the substituents on the free phenolics of the calix[4]arene-crown ether. The potassium/sodium selectivity seems to be governed primarily by the size

  当在碱性条件下与甲苯磺酰化聚醚反应时，杯[4]芳烃在下缘具有给电子基团（OH和OR），得到相应的1,3-二取代杯[4]芳烃-冠醚2a-2h，产率良好. 已通过原子发射光谱分析研究了合成的 1,3-桥接杯 [4] 芳烃冠醚对碱金属阳离子的结合特性。已经观察到钠和钾的识别随着聚醚链的大小以及杯[4]芳烃-冠醚的游离酚类上的取代基而变化。钾/钠选择性似乎主要受冠环大小、相对疏水性和阳离子-π 相互作用能力的控制，从而给出效率顺序为 2a、2d > 2 h > 2c、2e > 2b、2f > 2 g。
• Synthesis of Oligophenylene-Substituted Calix[4]crown-4s and Their Silver(I) Ion-Induced Nanocones Formation
  作者：Man Shing Wong、Ping Fang Xia、Pik Kwan Lo、Xiao Hua Sun、Wai Yeung Wong、Shaomin Shuang

  DOI：10.1021/jo051896z

  日期：2006.2.1

  A novel series of oligophenylene OPP(n)-substituted calix[4]crown-4s bearing up to three phenylene units, 1a-d, has been efficiently synthesized by means of either microwave-assisted or silver(I) ion-assisted Pd-catalyzed Suzuki cross-coupling of tetraiodocalix[4]crown-4 and the corresponding oligo-phenylboronic acids. Complexation of OPP(n)-substituted calix[4]crown-4s with silver (I) ion was substantiated by H-1 NMR spectroscopic and high-resolution ESI- or MALDI-TOF- MS studies. The weak binding affinities of OPP(n)-substituted calix[4]crown-4s for silver (I) ion, which were estimated from H-1 NMR titrations with binding association in the range of 30-90 M-1, allows reversible disassembling in the presence of KI at ambient temperature. Remarkably, the single-crystal X-ray structures of OPP(n)-calix[4]crown-4(.)Ag(+) complexes indicate the atypical silver (I) ion-crown ether binding mode resulting in the formation of rigid nanocones with volume created up to similar to 1500 angstrom(3). Our results suggested that despite the weak binding affinity of crown ether ligands for silver (I) ion, this weak interaction is still be useful as a tool to construct supramolecular architectures.