5,11,17,23-tetra-tert-butyl-25,27-bis[(3,5-bis(2-propynyloxy)benzyl)oxy]calix[4]arene-26,28-diol | 176038-90-7

• 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-tetra-tert-butyl-25,27-bis[(3,5-bis(2-propynyloxy)benzyl)oxy]calix[4]arene-26,28-diol
• 英文别名: 26,28-Bis[[3,5-bis(prop-2-ynoxy)phenyl]methoxy]-5,11,17,23-tetratert-butylpentacyclo[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-dodecaene-25,27-diol
• CAS: 176038-90-7
• 化学式: C₇₀H₇₆O₈
• 分子量: 1045.37
• InChiKey: PJVMQMPURCHCJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.9
• 重原子数：
  78
• 可旋转键数：
  18
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  95.8
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5,11,17,23-tetra-tert-butyl-25,27-bis[(3,5-bis(2-propynyloxy)benzyl)oxy]calix[4]arene-26,28-diol 在 吡啶 、 copper diacetate 、 氧气 作用下， 以 丙酮 为溶剂， 反应 16.0h， 以55%的产率得到9,15,21,55-Tetratert-butyl-5,25,32,39,42,49-hexaoxanonacyclo[27.12.8.77,23.13,40.113,17.127,31.06,11.019,24.153,57]hexaconta-1(41),2,6(11),7,9,13,15,17(59),19(24),20,22,27,29,31(51),40(50),53(60),54,56-octadecaen-34,36,44,46-tetrayne-59,60-diol
  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：

  3,5-二羟基苯甲酸 在 lithium aluminium tetrahydride 、 potassium carbonate 、 甲基磺酰氯 、 三乙胺 、 lithium bromide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 35.0h， 生成 5,11,17,23-tetra-tert-butyl-25,27-bis[(3,5-bis(2-propynyloxy)benzyl)oxy]calix[4]arene-26,28-diol
  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