5,11,17,23-Tetrabenzyl-25,26,27,28-tetrahydroxycalix<4>arene | 139934-43-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5,11,17,23-Tetrabenzyl-25,26,27,28-tetrahydroxycalix<4>arene
• 英文别名: 5,11,17,23-tetrabenzyl-25,26,27,28-tetrahydroxycalix[4]arene；tetra-benzyl-tetra-hydroxycalix[4]arene；p-benzylcalix[4]arene；4,11,18,25-tetrabenzyl-[1.1.1.1]metacyclophane-7,14,21,28-tetraol；4,11,18,25-Tetrabenzyl-[1.1.1.1]metacyclophan-7,14,21,28-tetraol；5,11,17,23-Tetrabenzylpentacyclo[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-25,26,27,28-tetrol
• CAS: 139934-43-3
• 化学式: C₅₆H₄₈O₄
• 分子量: 784.995
• InChiKey: KDLSPSUXJLDHRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.9
• 重原子数：
  60
• 可旋转键数：
  8
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,11,17,23-Tetrabenzyl-25,26,27,28-tetrahydroxycalix<4>arene 在 lithium aluminium tetrahydride 、 potassium carbonate 作用下， 以 乙醚 、 乙腈 为溶剂， 反应 24.0h， 生成 tetrakis-2-ethoxyethyloxy p-benzylcalix[4]arene
  参考文献：
  名称：

  Unsymmetrical O-bridged calixarenes derived from tBu-calix[4]arene and p-benzylcalix[4]arene

  摘要：

  通过乙烯连接对-tBu-萼[4]炔和对-tBu-萼[n]炔（n = 5，8）制备了双萼炔，并对对-tBu-萼[4]炔与对-tBu-萼[5]炔连接的化合物进行了固态结构鉴定。此外，还报道了由对-tBu-萼[4]炔与对-苄基萼[4]炔连接得到的双萼炔及其相关化学性质。

  DOI：

  10.1039/b109625g
• 作为产物：
  描述：

  p-benzylcalix[8]arene 以 二苯醚 为溶剂， 反应 5.5h， 生成 5,11,17,23-Tetrabenzyl-25,26,27,28-tetrahydroxycalix<4>arene
  参考文献：
  名称：

  Synthesis of p-benzylcalix[4]arene and its sulfonated water soluble derivative

  摘要：

  对苄基钙[4]炔通过对苄基苯酚和甲醛的直接 "一锅式 "反应生成，并选择性地转化为相应的氯磺酰和磺酸类似物，收率很高。

  DOI：

  10.1039/b106161p

文献信息

• Extension of the hydrophobic cavity of calixi[4]arene by “upper rim” functionalization
  作者：A. Arduini、A. Pochini、A. Rizzi、A.R. Sicuri、F. Ugozzoli、R. Ungaro

  DOI：10.1016/s0040-4020(01)88192-8

  日期：——

  hydrophobic cavity of calix[4]arene (1) has been extended by “Upper rim” functionalization with different alkyl groups. Using p-chloromethylcalix[4]arene (2) as the intermediate, the synthesis of ethyl (4) and p-benzylcalix[4]arenes (5 a–c) was performed. By reaction of 1 with cyclohexene p-cyclohexylcalix[4]arene (6) was obtained. The crystal structure of p-ethylcalix[4]arene (4) was solved.

  杯[4]芳烃（1）的疏水腔已通过具有不同烷基的“上边缘”官能化得到扩展。使用对氯甲基杯[4]芳烃（2）作为中间体，合成了乙基（4）和对苄基杯[4]芳烃（5 a–c）。通过1与环己烯的反应，获得对-环己基杯[4]芳烃（6）。解析了对乙基杯[4]芳烃（4）的晶体结构。
• Metal ion complexation in acetonitrile by upper-rim benzyl-substituted, di-ionized calix[4]arenes bearing two dansyl fluorophores
  作者：Űmmühan Ocak、Miraç Ocak、Xin Shen、Alexander H. Gorman、Kazimierz Surowiec、Richard A. Bartsch

  DOI：10.3998/ark.5550190.0011.707

  日期：——

  properties of two dansyl (1dimethylaminonaphthalene-5-sulfonyl) groups linked to the lower rims of a series of three, structurally related, di-ionized calix[4]arenes is investigated by means of emission spectrophotometry. Di(tetramethylammonium) salts of the di-ionized ligands, L, L1 and L2, which differ in having no, two and four benzyl groups, respectively, on the upper rim of the calix[4]arene scaffold

  Li、Na、K、Rb、Cs、Mg、Ca、Sr、Ba、Ag、Cd、Co、Fe、Hg、Mn、Pb、Zn 和 Fe 对两种丹磺酰（1-二甲基氨基萘-5-）光谱性质的影响通过发射分光光度法研究了与一系列三个结构相关的双电离杯[4]芳烃的下边缘相连的磺酰基）基团。双离子化配体 L、L1 和 L2 的二（四甲基铵）盐分别在杯 [4] 芳烃支架的上缘上没有、两个和四个苄基，用于荧光光谱分析MeCN 中的滴定实验。在与碱土金属阳离子络合时，发射光谱发生明显的红移。碱金属阳离子导致苄基取代的双电离杯[4]芳烃 L1 和 L2 的荧光增强，并伴有红移，但 Li 和 Cs 除外。过渡金属阳离子和 Pb 与配体强烈相互作用。特别是，Fe、Hg 和 Pb 导致所有三种配体的丹磺酰荧光猝灭率超过 99%。
• Evaluation of calix[4]arene-based chiral diphosphite ligands in Rh-catalyzed asymmetric hydrogenation of simple dehydroamino acid derivatives
  作者：Shasha Liu、Christian A. Sandoval

  DOI：10.1016/j.molcata.2010.03.034

  日期：2010.6.15

  The calix[4]arene framework was readily modified to generate a number of chiral BINOL-based diphosphite ligands (3) capable of forming in situ Rh-complexes which catalyzed the asymmetric hydrogenation of model substrates methyl-(Z)-2-(acetamido)acrylate (1a) and methyl-(Z)-2-(acetamido)cinnamate (1b). The (S,S)-catalyst generated the (R)-product. Upper rim (R-1) and 1,3-O-alkylation (R-2) substitution on the calixarene strongly influenced catalyst activity and chiral induction. Optimum results were obtained when RI was -C(CH3)(3) and R-2 was -CH2CH2CH3 (3b). Under optimized conditions, 3b hydrogenated la and 1b in 98 and 96% ee, respectively. Overall, better catalyst performance was observed for "locked" cone-conformers of 3, with higher activity evident for the less sterically hindered 1a (TOF up to 1300h(-1) at P(H-2) = 5 atm). (C) 2010 Elsevier B.V. All rights reserved.
• Synthesis of p-benzylcalix[4]arene and its sulfonated water soluble derivative
  作者：Mohamed Makha、Colin L. Raston

  DOI：10.1039/b106161p

  日期：2001.11.22

  p-Benzylcalix[4]arene is formed in good yield by a direct “one pot” reaction involving p-benzylphenol and formaldehyde, selectively converted to the corresponding chlorosulfonyl and sulfonate analogues.

  对苄基钙[4]炔通过对苄基苯酚和甲醛的直接 "一锅式 "反应生成，并选择性地转化为相应的氯磺酰和磺酸类似物，收率很高。
• Unsymmetrical O-bridged calixarenes derived from tBu-calix[4]arene and p-benzylcalix[4]arene
  作者：Mohamed Makha、Peter J. Nichols、Michaele J. Hardie、Colin L. Raston

  DOI：10.1039/b109625g

  日期：2002.1.23

  Bis-calixarenes derived from linking p-tBu-calix[4]arene with p-tBu-calix[n]arenes (n = 5, 8) via ethylene linkages have been prepared and structural authentication in the solid state for the compound with p-tBu-calix[4]arene linked to p-tBu-calix[5]arene has been carried out. The bis-calixarene derived from linking p-tBu-calix[4]arene with p-benzylcalix[4]arene and its related chemistry are also reported.

  通过乙烯连接对-tBu-萼[4]炔和对-tBu-萼[n]炔（n = 5，8）制备了双萼炔，并对对-tBu-萼[4]炔与对-tBu-萼[5]炔连接的化合物进行了固态结构鉴定。此外，还报道了由对-tBu-萼[4]炔与对-苄基萼[4]炔连接得到的双萼炔及其相关化学性质。