5,11,17,23-Tetra-tert-butyl-25,26,27,28-tetrakis<<(1-oxopyrid-2-yl)methyl>oxy>calix<4>arene | 178153-20-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,11,17,23-Tetra-tert-butyl-25,26,27,28-tetrakis<<(1-oxopyrid-2-yl)methyl>oxy>calix<4>arene
• 英文别名: 1-oxido-2-[[5,11,17,23-tetratert-butyl-26,27,28-tris[(1-oxidopyridin-1-ium-2-yl)methoxy]-25-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaenyl]oxymethyl]pyridin-1-ium
• CAS: 178153-20-3；170373-35-0；170373-36-1；170553-92-1；170553-93-2
• 化学式: C₆₈H₇₆N₄O₈
• 分子量: 1077.37
• InChiKey: KOMBCJSWUNSBDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.4
• 重原子数：
  80.0
• 可旋转键数：
  12.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  144.68
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  sodium thiocyanide 、 5,11,17,23-Tetra-tert-butyl-25,26,27,28-tetrakis<<(1-oxopyrid-2-yl)methyl>oxy>calix<4>arene 以 氯仿 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Synthesis and Complexation Studies of Regioisomers and Conformational Isomers of p-tert-Butylcalix[4]arene Bearing Pyridine or Pyridine N-Oxide Pendant Groups at the Lower Rim

  摘要：

  Selected title compounds have been prepared in order to provide calix[4]arene ligands having different shapes of the calix[4]arene skeleton (cone, partial cone, 1,2-alternate, or 1,3-alternate) and spacial arrangements (syn-proximal, syn-distal, or anti-distal) of pendant pyridine or pyridine N-oxide binding groups. The structure of 1,2-alternate tetrakis[(2-pyridylmethyl)oxy]calix[4]arene 9, obtained in low yield by direct alkylation of the parent p-tert-butylcalix[4]arene 1 with PicCl . HCl and Cs2CO3, has been elucidated by single crystal X-ray analysis. N-Oxide derivatives have been obtained in good yield by m-CPBA oxidation of the appropriate pyridinocalix[4]arene precursors in dry Et(2)O or THF. The H-1 and C-13 NMR spectral changes upon N-oxide formation are discussed. Extraction studies with alkali metal picrates from an aqueous solution into CH2Cl2 have shown that the ionophoric efficiency is low. The highest phase-transfer values are observed for cone tetrapyridinocalix[4]arene 7 (selectivity follows the order Na+ > K+ > Rb+ > Cs+ > Li+), whereas the corresponding N-oxide 7a has no activity. However, NMR complexation studies with Na+ and K+, while confirming a low complexation rate, indicate that in aprotic solvents tetra-N-oxide derivative 7a is a good complexer having a faster kinetic than its pyridino precursor 7.

  DOI：

  10.1021/jo00119a040
• 作为产物：
  描述：

  5,11,17,23-Tetra-tert-butyl-25,26,27,28-tetrakis<(2-pyridylmethyl)oxy>calix<4>arene 在 间氯过氧苯甲酸 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 5,11,17,23-Tetra-tert-butyl-25,26,27,28-tetrakis<<(1-oxopyrid-2-yl)methyl>oxy>calix<4>arene
  参考文献：
  名称：

  Synthesis and Complexation Studies of Regioisomers and Conformational Isomers of p-tert-Butylcalix[4]arene Bearing Pyridine or Pyridine N-Oxide Pendant Groups at the Lower Rim

  摘要：

  Selected title compounds have been prepared in order to provide calix[4]arene ligands having different shapes of the calix[4]arene skeleton (cone, partial cone, 1,2-alternate, or 1,3-alternate) and spacial arrangements (syn-proximal, syn-distal, or anti-distal) of pendant pyridine or pyridine N-oxide binding groups. The structure of 1,2-alternate tetrakis[(2-pyridylmethyl)oxy]calix[4]arene 9, obtained in low yield by direct alkylation of the parent p-tert-butylcalix[4]arene 1 with PicCl . HCl and Cs2CO3, has been elucidated by single crystal X-ray analysis. N-Oxide derivatives have been obtained in good yield by m-CPBA oxidation of the appropriate pyridinocalix[4]arene precursors in dry Et(2)O or THF. The H-1 and C-13 NMR spectral changes upon N-oxide formation are discussed. Extraction studies with alkali metal picrates from an aqueous solution into CH2Cl2 have shown that the ionophoric efficiency is low. The highest phase-transfer values are observed for cone tetrapyridinocalix[4]arene 7 (selectivity follows the order Na+ > K+ > Rb+ > Cs+ > Li+), whereas the corresponding N-oxide 7a has no activity. However, NMR complexation studies with Na+ and K+, while confirming a low complexation rate, indicate that in aprotic solvents tetra-N-oxide derivative 7a is a good complexer having a faster kinetic than its pyridino precursor 7.

  DOI：

  10.1021/jo00119a040