5,11,17,23,29,35-hexa-tert-butyl-37,40-dihydroxy-38,39,41,42-tetrakis<(2-pyridylmethyl)oxy>calix<6>arene | 139378-46-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,11,17,23,29,35-hexa-tert-butyl-37,40-dihydroxy-38,39,41,42-tetrakis<(2-pyridylmethyl)oxy>calix<6>arene
• 英文别名: 5,11,17,23,29,35-Hexa-tert-butyl-37,40-dihydroxy-38,39,41,42-tetrakis(2-pyridylmethoxy)calix<6>arene；5,11,17,23,29,35-hexatert-butyl-38,39,41,42-tetrakis(pyridin-2-ylmethoxy)heptacyclo[31.3.1.13,7.19,13.115,19.121,25.127,31]dotetraconta-1(36),3(42),4,6,9,11,13(41),15,17,19(40),21(39),22,24,27,29,31(38),33(37),34-octadecaene-37,40-diol
• CAS: 139378-46-4
• 化学式: C₉₀H₁₀₄N₄O₆
• 分子量: 1337.84
• InChiKey: YWHPXUXOIQBUSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  20.64
• 重原子数：
  100.0
• 可旋转键数：
  12.0
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  128.94
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  5,11,17,23,29,35-hexa-tert-butyl-37,40-dihydroxy-38,39,41,42-tetrakis<(2-pyridylmethyl)oxy>calix<6>arene 、 溴乙酸乙酯 在 potassium carbonate 作用下， 以 仲丁醇 为溶剂， 以58%的产率得到5,11,17,23,29,35-Hexa-tert-butyl-37,40-bis<(ethoxycarbonyl)methoxy>-38,39,41,42-tetrakis(2-pyridylmethoxy)calix<6>arene
  参考文献：
  名称：

  Syntheses and ion selectivity of conformational isomers derived from calix[4]arene

  摘要：

  Three conformational isomers (cone, partial cone, and 1,3-alternate) of 5,11,17,23-tetra-tert-butyl-25,27-bis[(ethoxycarbonyl)methoxy]-26,28-bis(2-pyridylmethoxy)calix[4]arene (3) were synthesized from 5,11,17,23-tetra-tert-butyl-25,27-dihydroxy-26,28-bis(2-pyridylmethoxy)calix[4]arene (6). The examination of the metal selectivity in two-phase solvent extraction established that the cone conformer predominantly results when the base contains template metal cations, whereas the partial cone and 1,3-alternate conformers result when the base contains nontemplate metal cations. The solvent extraction data indicated that cone-3 shows the strong metal affinity as comparable with that of cone-5,11,17,23-tetra-tert-butyl-25,26,27,28-tetrakis[(ethoxycarbonyl)methoxy]calix[4]arene (cone-2) and binds not only Na+ but Li+. On the other hand, partial-cone-2 shows a poor metal affinity. The difference was discussed on the basis of spectroscopic and X-ray crystallographic data. This paper demonstrates for the first time that the metal selectivity of ionophoric calix[n]arenes can be changed not only by the change in the ring size but also by the conformational change.

  DOI：

  10.1021/jo00031a034
• 作为产物：
  描述：

  4-叔丁基杯[6]芳烃 、 2-氯甲基吡啶盐酸盐 在 sodium hydride 作用下， 生成 5,11,17,23,29,35-hexa-tert-butyl-37,40-dihydroxy-38,39,41,42-tetrakis<(2-pyridylmethyl)oxy>calix<6>arene
  参考文献：
  名称：

  对叔丁基杯[6]芳烃对称四取代吡啶侧基：合成，X射线晶体结构，动态核磁共振谱和分子力学计算的构象分析

  摘要：

  介绍了标题化合物 1 的合成和构象分析，通过动态核磁共振光谱和 MM2 模量力学计算。质子和碳核磁共振谱的完整分配是通过在 280 K 下的 COSY、HMQC 和 HMBC 实验的组合实现的。 从 220-345 K 范围内的 VT-NMR 分析，227 (AG = 11.1 kcal/ mol) 和 315 K (AG = 14.2 kcal/mol) 在 CDCl3 中确定。1 的 14 个可能的构象异构体的 MM2 能量（根据四个吡啶基悬垂部分的相对方向分为五个家族 AE）显示构象异构体 A 是最稳定的。NMR 信号和 NOESY 数据的对称性将 1 在温度低于 315 K 的溶液中可能的构象限制为指定为 A 和 C 的构象。虽然可以根据 MM2 结果排除 C 型构象异构体，但 183 K 下 CD2C12 中 1 的 1 H-NMR 和 ROESY 光谱提供了支持构象异构体 A

  DOI：

  10.1021/ja00046a030

文献信息

• Functionalization of p-tert-butylcalix[6]arene by alkylation with 2-(chloromethyl)pyridine hydrochloride
  作者：Placido Neri、Sebastiano Pappalardo

  DOI：10.1021/jo00057a014

  日期：1993.2

  A study of the base-catalyzed alkylation of p-tert-butylcalix[6]arene (1) with 2-(chloromethyl)-pyridine in DMF has led to the isolation and identification of 10 of the 12 possible pyridinyl homologues of 1. The identity of the base applied and molar ratios between the reactants play an important role in determining the product distribution. Regioselective 1,2,4,5-tetra-O-alkylation is realized with NaH as the base, while the use of BaO/Ba(OH)2 affords in high yield 1,4-diether 5, which is isolated as a barium complex. The reactions with limiting amounts of alkylating agent and K2CO3 produce invariably complex mixtures with 1,2,3-triether 6 as the major product. The structure of the products has been established by elemental analysis, FAB (+) mass spectral measurements, and NMR techniques. [(2-Pyridylmethyl)oxy]calix[6]arene homologues show in most cases broadened H-1-NMR spectra at rt, which sharpen at higher temperatures, allowing for a distinction between the various regioisomers. FAB (+) mass spectra and some NMR features arising from the substitution patterns at the lower rim are discussed.