5,11,23,29-tetra-p-tert-butylcalix[6]arene | 176038-72-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5,11,23,29-tetra-p-tert-butylcalix[6]arene
• 英文别名: 5,11,23,29-tetra-tert-butylcalix[6]arene-37,38,39,40,41,42-hexol；5,11,23,29-tetratert-butylheptacyclo[31.3.1.13,7.19,13.115,19.121,25.127,31]dotetraconta-1(37),3(42),4,6,9,11,13(41),15(40),16,18,21(39),22,24,27,29,31(38),33,35-octadecaene-37,38,39,40,41,42-hexol
• CAS: 176038-72-5
• 化学式: C₅₈H₆₈O₆
• 分子量: 861.174
• InChiKey: UGYSMDYRCPQSHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.97
• 重原子数：
  64.0
• 可旋转键数：
  0.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  121.38
• 氢给体数：
  6.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  5,11,23,29-tetra-p-tert-butylcalix[6]arene 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 丁酮 为溶剂， 反应 24.0h， 以70%的产率得到5,11,23,29-tetra-tert-butyl-17,35-dibromocalix[6]arene-37,38,39,40,41,42-hexol
  参考文献：
  名称：

  Selective Upper Rim Functionalization and Lower Rim Bridge Building with Calix[4]arenes and Calix[6]arenes¹

  摘要：

  Selective upper rim functionalization of calix[6]arenes has been achieved by selective lower rim benzoylation at the 1,2,4,5 positions followed by AlCl3-induced removal of the tert-butyl groups of the unesterified aryl residues and introduction of various functionalities into the vacated para positions, including bromo (5), dialkylamino, (7-11) cyanomethyl (12), and (propargyloxy)methyl (13) groups. Lower rim bridge building has been achieved via oxidative coupling reactions between the aryne moieties of calix[4]arenes and calix[6]arenes in which O-benzyl groups carry one (from 23 and 24) or two (from 25) propargyloxy residues. In the calix[4]arene series both a single-spanned (32) and a double-spanned (33) double-cavity calixarene were obtained. In the calix[6]arene series only a single-spanned double cavity calixarene (36) could be characterized.

  DOI：

  10.1021/jo952054a
• 作为产物：
  描述：

  11,17,29,35-Tetra-tert-butyl-39,42-dihydroxy-37,38,40,41-tetrakis<(4-nitrobenzoyl)oxy>calix<6>arene 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以93%的产率得到5,11,23,29-tetra-p-tert-butylcalix[6]arene
  参考文献：
  名称：

  Selective Upper Rim Functionalization and Lower Rim Bridge Building with Calix[4]arenes and Calix[6]arenes¹

  摘要：

  Selective upper rim functionalization of calix[6]arenes has been achieved by selective lower rim benzoylation at the 1,2,4,5 positions followed by AlCl3-induced removal of the tert-butyl groups of the unesterified aryl residues and introduction of various functionalities into the vacated para positions, including bromo (5), dialkylamino, (7-11) cyanomethyl (12), and (propargyloxy)methyl (13) groups. Lower rim bridge building has been achieved via oxidative coupling reactions between the aryne moieties of calix[4]arenes and calix[6]arenes in which O-benzyl groups carry one (from 23 and 24) or two (from 25) propargyloxy residues. In the calix[4]arene series both a single-spanned (32) and a double-spanned (33) double-cavity calixarene were obtained. In the calix[6]arene series only a single-spanned double cavity calixarene (36) could be characterized.

  DOI：

  10.1021/jo952054a

文献信息

• ——
  作者：E. A. Shokova、E. V. Khomich、N. N. Akhmetov、I. M. Vatsuro、Yu. N. Luzikov、V. V. Kovalev

  DOI：10.1023/a:1025541731033

  日期：——

  Procedures have been developed for the preparation of completely and partially adamantylated calix[n]arenes (n = 5, 6) by reaction of 3-R-substituted 1-hydroxyadamantanes (R = H, 4-MeC(6)H(4), 4-MeSO(2)C(6)H(4),4-HO-3-HOCOC(6)H(3), HOCOCH(2)) with p-H-calix[n]arenes (n = 5, 6) and 5,11,23,29-tetra-tert-butylcalix[6]arene in trifluoroacetic acid. Lower- and upper-rim modification of the prepared compounds has been studied. According to the (1)H NMR data, adamantylcalix[6]arenes possessing carboxymethyl groups in the adamantane moieties are characterized by reduced conformational mobility.