5,11,17,23,29-penta-tert-butyl-31-<(2-pyridylmethyl)oxy>-32,33,34,35-tetrahydroxycalix<5>arene | 175655-62-6

• 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-penta-tert-butyl-31-<(2-pyridylmethyl)oxy>-32,33,34,35-tetrahydroxycalix<5>arene
• 英文别名: monopicolyl-p-tert-butylcalix<5>arene；monopicolyl-p-tert-butylcalix[5]arene；5,11,17,23,29-Pentatert-butyl-35-(pyridin-2-ylmethoxy)hexacyclo[25.3.1.13,7.19,13.115,19.121,25]pentatriaconta-1(30),3,5,7(35),9,11,13(34),15,17,19(33),21(32),22,24,27(31),28-pentadecaene-31,32,33,34-tetrol
• CAS: 175655-62-6
• 化学式: C₆₁H₇₅NO₅
• 分子量: 902.27
• InChiKey: GZQMOJYLJOQVRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17
• 重原子数：
  67
• 可旋转键数：
  8
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  103
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  四乙二醇二对甲苯磺酸酯 、 5,11,17,23,29-penta-tert-butyl-31-<(2-pyridylmethyl)oxy>-32,33,34,35-tetrahydroxycalix<5>arene 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以25%的产率得到5,11,17,23,29-pentakis(1,1-dimethylethyl)-31,32-dihydroxy-33-[(2-pyridylmethyl)oxy]-34,35-crown-5-calix[5]arene
  参考文献：
  名称：

  杯[5]冠的固有手性衍生物

  摘要：

  描述了分别到达手性（1,3）-和（1,2）-杯[5]冠醚2和3的互补合成途径。O-烷基残基的区域和立体化学排列通过NMR推论得出，并由Crown-5衍生物3b的单晶X射线分析进一步证实。

  DOI：

  10.1016/0040-4039(96)00048-2
• 作为产物：
  描述：

  2-氯甲基吡啶盐酸盐 、 4-叔丁基杯[5]芳烃 在 potassium hydrogencarbonate 作用下， 以66%的产率得到5,11,17,23,29-penta-tert-butyl-31-<(2-pyridylmethyl)oxy>-32,33,34,35-tetrahydroxycalix<5>arene
  参考文献：
  名称：

  杯[5]冠的固有手性衍生物

  摘要：

  描述了分别到达手性（1,3）-和（1,2）-杯[5]冠醚2和3的互补合成途径。O-烷基残基的区域和立体化学排列通过NMR推论得出，并由Crown-5衍生物3b的单晶X射线分析进一步证实。

  DOI：

  10.1016/0040-4039(96)00048-2

文献信息

• Inherently chiral α-picolyloxy-p-tert-butylcalix[5]arene crown ethers: Synthesis, structure proof, and enantioselective HPLC resolution
  作者：Salvatore Caccamese、Anna Notti、Sebastiano Pappalardo、Melchiorre F Parisi、Grazia Principato

  DOI：10.1016/s0040-4020(99)00195-7

  日期：1999.4

  Reaction of α-picolyloxy-p-tert-butylcalix[5]arene with tri- to pentaethylene glycol ditosylates and K2CO3 regioselectively affords racemic (1,2)-bridged crown ether derivatives in the cone conformation. Their structure is firmly established by NMR spectroscopy and by comparison with appropriate (1,3)-bridged crown-6 regioisomers, synthesized by unequivocal sequences. The enantiomeric resolution of

  的反应α -picolyloxy- p -叔-butylcalix [5]芳烃与三到五乙二醇ditosylates和K 2 CO 3区域选择性地得到外消旋（1,2）-bridged冠醚在锥形构象的衍生物。它们的结构是通过NMR光谱法确定的，并与通过明确序列合成的适当的（1,3）桥连的Crown-6区域异构体进行了比较。外消旋物的对映体拆分已使用对映选择性固定相通过直接HPLC分离实现。（1,2）-桥接的Crown-5衍生物的对映异构体显示出迄今为止报道的固有手性杯芳烃的最大分离因子（α）之一。
• Functionalization of <i>p-tert</i>-Butylcalix[5]arene by Alkylation with 2-(Chloromethyl)pyridine Hydrochloride
  作者：Sebastiano Pappalardo、George Ferguson

  DOI：10.1021/jo951521l

  日期：1996.1.1

  A study of the base-catalyzed alkylation of p-tert-butylcalix[5]arene (1) with 2-(chloromethyl)pyridine hydrochloride (PicCl . HCl) in DMF has led to the isolation and identification of the 7 possible pyridinyl homologues of 1 in the cone conformation. Reactions of 1 with limiting amounts of alkylating agent (2 to 4 equiv) and base (CsF, KHCO3, BaO/Ba(OH)(2), K2CO3, NaH) produced invariably complex mixtures, which were separated into the pure components by chromatographic means. Regioselective 1,2,4- or 1,2,3-tri-O-alkylation has been achieved in moderate yield (21-22%) by an appropriate choice of molar ratios, solvent, and base. Pentaethers 8-10, endowed with 2-pyridinyl, 3-pyridinyl, and 2-quinolylmethyl pendant groups at the lower rim, respectively, have been also prepared in good yield. The cone conformation in solution for all new compounds has been established by NMR spectroscopy and confirmed for 1,2,3-tri-O-alkylated 5 by a single-crystal X-ray analysis. In the solid state the cone conformation of 5 is mainly determined by the presence of intramolecular hydrogen bonds between adjacent phenolic oxygens, and between the phenolic oxygen and the proximal pyridinyl nitrogen.