5,11,17,23,29,35-hexa-tert-butyl-37,40-bis<(2-pyridylmethyl)oxy>-38,39,41,42-tetrahydroxycalix<6>arene | 146300-94-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5,11,17,23,29,35-hexa-tert-butyl-37,40-bis<(2-pyridylmethyl)oxy>-38,39,41,42-tetrahydroxycalix<6>arene
• 英文别名: 5,11,17,23,29,35-Hexatert-butyl-39,42-bis(pyridin-2-ylmethoxy)heptacyclo[31.3.1.13,7.19,13.115,19.121,25.127,31]dotetraconta-1(36),3,5,7(42),9,11,13(41),15(40),16,18,21(39),22,24,27,29,31(38),33(37),34-octadecaene-37,38,40,41-tetrol
• CAS: 146300-94-9
• 化学式: C₇₈H₉₄N₂O₆
• 分子量: 1155.61
• InChiKey: CSHVJYDWBXHWHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  21
• 重原子数：
  86
• 可旋转键数：
  12
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  125
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-氯甲基吡啶盐酸盐 、 5,11,17,23,29,35-hexa-tert-butyl-37,40-bis<(2-pyridylmethyl)oxy>-38,39,41,42-tetrahydroxycalix<6>arene 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以35%的产率得到5,11,17,23,29,35-hexa-tert-butyl-37,38,39,40-tetrakis<(2-pyridylmethyl)oxy>-41,42-dihydroxycalix<6>arene
  参考文献：
  名称：

  Functionalization of p-tert-butylcalix[6]arene by alkylation with 2-(chloromethyl)pyridine hydrochloride

  摘要：

  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.

  DOI：

  10.1021/jo00057a014
• 作为产物：
  描述：

  4-叔丁基杯[6]芳烃 、 2-氯甲基吡啶盐酸盐 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以3%的产率得到5,11,17,23,29,35-hexa-tert-butyl-37,38-bis<(2-pyridylmethyl)oxy>-39,40,41,42-tetrahydroxycalix<6>arene
  参考文献：
  名称：

  Functionalization of p-tert-butylcalix[6]arene by alkylation with 2-(chloromethyl)pyridine hydrochloride

  摘要：

  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.

  DOI：

  10.1021/jo00057a014