3,9,15,33-Tetraiodo-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 | 877993-05-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3,9,15,33-Tetraiodo-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
• CAS: 877993-05-0
• 化学式: C₄₀H₄₂I₄O₆
• 分子量: 1126.39
• InChiKey: UMDCSHOVMMHCFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.4
• 重原子数：
  50
• 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：

  3,9,15,33-Tetraiodo-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 、 4-联苯硼酸 在 四(三苯基膦)钯 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 以75%的产率得到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：

  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 碘 、 silver trifluoroacetate 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以95%的产率得到3,9,15,33-Tetraiodo-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