5,11,17,23-tetrakis(1,1-dimethylethyl)-25,27-bis(hydroxyethoxy)-26,28-dipropoxycalix<4>arene | 145237-33-8

• 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-tetrakis(1,1-dimethylethyl)-25,27-bis(hydroxyethoxy)-26,28-dipropoxycalix<4>arene
• 英文别名: 5,11,17,23-tetra-tert-butyl-25,27-bis(hydroxyethoxy)-26,28-dipropoxycalix[4]arene；25,27-dihydroxyethoxy-26,28-dipropoxy-tert-butylcalix<4>arene；5,11,17,23-tetrakis(1,1-dimethylethyl)-25,27-bis(hydroxyethoxy)-26,28-dipropoxycalix[4]arene；25,27-Dihydroxyethoxy-26,28-dipropoxy-tert-butyl-calix[4]arene；2-[[5,11,17,23-tetratert-butyl-27-(2-hydroxyethoxy)-26,28-dipropoxy-25-pentacyclo[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-dodecaenyl]oxy]ethanol
• CAS: 145237-33-8
• 化学式: C₅₄H₇₆O₆
• 分子量: 821.194
• InChiKey: MHERBLYONRIOGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.7
• 重原子数：
  60
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5,11,17,23-tetrakis(1,1-dimethylethyl)-25,27-bis(hydroxyethoxy)-26,28-dipropoxycalix<4>arene 在 劳森试剂 、 sodium hydride 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 5,11,17,23-tetrakis(1,1-dimethylethyl)-25,27-bis<((dimethylthiocarbamoyl)methoxy)ethoxy>-26,28-dipropoxycalix<4>arene
  参考文献：
  名称：

  Transduction of selective recognition of heavy metal ions by chemically modified field effect transistors (CHEMFETs)

  摘要：

  Specifically substituted calix[4]arenes that complex selectively silver (2), copper (13), cadmium (23), and lead (29) cations were synthesized via di- and tetraalkylation of p-tert-butylcalix[4]arene. Calix[4]arenes derivatized with thioether, thioamide, and dithiocarbamoyl functionalities could be obtained in high overall yields. Integrated on a chemically modified field effect transistor (CHEMFET) the selective complexation of heavy metal ions by these calix[4]arenes is transduced directly into an electrical signal. An architecture for CHEMFETs is used in which a hydrophilic polyHEMA hydrogel is covalently attached between the gate oxide surface of a modified ISFET and the hydrophobic sensing membrane that contains the receptor molecule. CHEMFETs based on the calix[4]arene (2) with two diametrically substituted thioether functionalities responded selectively (60 mV decade-1) to a change in silver activity in the aqueous solution in the presence of potassium, calcium, cadmium, and copper ions (log K(ij) less-than-or-equal-to -4). The selectivity toward mercury (log K(ij) = -2.7) is comparable to the best neutral carrier based ISE so far. The calix[4]arene (13), with four dithiocarbamoyl groups, incorporated in a CHEMFET responsed Nernstian (30 mV decade-1) to a change in copper activity. The calix[4]arene (23), which has four dimethylthiocarbamoylmethoxyethoxy substituents, was selective in a CHEMFET (30 mV decade-1) toward cadmium in the presence of calcium and potassium ions. Two classes of ionophores can be distinguished for the selective detection of lead(II) cations by CHEMFETs, oxamide and thioamide ionophores, respectively. Tetrasubstitution of the calix[4]arene with thioamide groups (29) is a prerequisite for the selective detection of lead and leads to a highly selective CHEMFET (log K(ij) -3.4 to -5.2).

  DOI：

  10.1021/ja00052a063
• 作为产物：
  描述：

  5,11,17,23-tetrakis(1,1-dimethylethyl)-25,27-bis<(ethoxycarbonyl)methoxy>-26,28-dipropoxycalix<4>arene 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 85.0h， 以85%的产率得到5,11,17,23-tetrakis(1,1-dimethylethyl)-25,27-bis(hydroxyethoxy)-26,28-dipropoxycalix<4>arene
  参考文献：
  名称：

  钾选择性杯[4]半管。

  摘要：

  已经开发出一种新型的离子载体，该离子载体由两个通过两个乙烯链通过下缘连接的杯[4]芳烃单元与丙基醚和酚官能团组成。这些杯[4]半管分子对所有第1组金属阳离子显示出显着的钾选择性和快速络合动力学。分子建模研究使用了从晶体学数据得出的结构模型，表明钾阳离子是通过水平，侧向途径而不是通过杯[4]芳烃环复合的。半管结构的各个杯[4]芳烃之间的桥接亚烷基链的长度决定了碱金属阳离子结合的强度和选择性。

  DOI：

  10.1002/chem.200204518

文献信息

• Triazolated calix[4]arenes from 2-azidoethylated precursors: is there a difference in the way the triazoles are attached to narrow rims?
  作者：Alexander Gorbunov、Julia Kuznetsova、Kirill Puchnin、Vladimir Kovalev、Ivan Vatsouro

  DOI：10.1039/c8nj06464d

  日期：——

  and mutual arrangement of 2-azidoethyl groups at the narrow rims of calix[4]arenes as well as on the alkyne type selected. Under the optimized conditions a series of calixarenes bearing 2-(4-R-1-triazolyl)ethyl or 2-(4-ROCH2-1-triazolyl)ethyl (R = phenyl, 2-naphthyl) groups at the narrow rims was prepared, and some bis- and tetrakis(triazoles) from the series were studied for their complexation with

  准备了一系列在其窄边的一个，两个（远端或近端）和四个位置用2-叠氮基乙基修饰的圆锥杯[4]芳烃。研究了这些化合物作为铜（I）与芳基乙炔和芳基炔丙基醚的叠氮化物-炔烃环加成反应（CuAAC）的叠氮化物组分。研究表明，要使叠氮化物完全转化为三唑，需要采用相对温和或更强的条件，这取决于杯[4]芳烃窄边上2-叠氮基乙基的数量和相互排列。以及所选的炔烃类型。在优化条件下，一系列带有2-（4-R-1-三唑基）乙基或2-（4-ROCH 2）的杯芳烃制备了在狭窄边缘的-1-三唑基）乙基（R =苯基，2-萘基），并研究了该系列中的一些双和四（三唑）与过渡金属阳离子的络合作用。对带有（1-R-4-三唑基）甲基（R = 2-萘甲基）取代基的相关杯芳烃进行了同样的络合研究。两种类型的三氮唑烷杯芳烃都能有效地结合阳离子，但是发现络合偏好和阳离子结合模式极大地取决于三唑单元附着在杯芳烃核心上的一侧。
• Novel nucleotide–calixarene conjugates via phosphoester linkage
  作者：Grazia M.L. Consoli、Giuseppe Granata、Eva Galante、Francesca Cunsolo、Corrada Geraci

  DOI：10.1016/j.tetlet.2006.03.043

  日期：2006.5

  Calix[4]arenes bearing thymine, adenine, cytosine, guanine 2'-deoxynucleotide residues have been synthesized following the phosphoramidite chemistry. Hybrid Compounds 2a-d and 3a-d represent the first example of nucleotides linked to the calixarene lower rim by a phosphoester bond. Preliminary studies about their assembling in apolar solvent and host properties toward biologically interesting guests are also reported. (c) 2006 Elsevier Ltd. All rights reserved.
• 25,27-Dihydroxyethoxy-26,28-dipropoxy-<i>tert</i>-butylcalix[4]arene
  作者：M. Nissinen、P. Parzuchowski、V. Böhmer、G. Rokicki、K. Rissanen

  DOI：10.1107/s0108270198010221

  日期：1999.1.15

  In the solid state, the title compound, C54H76O6, adopts a pinched cone conformation, which is somewhat distorted.
• Transduction of selective recognition of heavy metal ions by chemically modified field effect transistors (CHEMFETs)
  作者：Peter L. H. M. Cobben、Richard J. M. Egberink、Johan G. Bomer、Piet Bergveld、Willem Verboom、David N. Reinhoudt

  DOI：10.1021/ja00052a063

  日期：1992.12

  Specifically substituted calix[4]arenes that complex selectively silver (2), copper (13), cadmium (23), and lead (29) cations were synthesized via di- and tetraalkylation of p-tert-butylcalix[4]arene. Calix[4]arenes derivatized with thioether, thioamide, and dithiocarbamoyl functionalities could be obtained in high overall yields. Integrated on a chemically modified field effect transistor (CHEMFET) the selective complexation of heavy metal ions by these calix[4]arenes is transduced directly into an electrical signal. An architecture for CHEMFETs is used in which a hydrophilic polyHEMA hydrogel is covalently attached between the gate oxide surface of a modified ISFET and the hydrophobic sensing membrane that contains the receptor molecule. CHEMFETs based on the calix[4]arene (2) with two diametrically substituted thioether functionalities responded selectively (60 mV decade-1) to a change in silver activity in the aqueous solution in the presence of potassium, calcium, cadmium, and copper ions (log K(ij) less-than-or-equal-to -4). The selectivity toward mercury (log K(ij) = -2.7) is comparable to the best neutral carrier based ISE so far. The calix[4]arene (13), with four dithiocarbamoyl groups, incorporated in a CHEMFET responsed Nernstian (30 mV decade-1) to a change in copper activity. The calix[4]arene (23), which has four dimethylthiocarbamoylmethoxyethoxy substituents, was selective in a CHEMFET (30 mV decade-1) toward cadmium in the presence of calcium and potassium ions. Two classes of ionophores can be distinguished for the selective detection of lead(II) cations by CHEMFETs, oxamide and thioamide ionophores, respectively. Tetrasubstitution of the calix[4]arene with thioamide groups (29) is a prerequisite for the selective detection of lead and leads to a highly selective CHEMFET (log K(ij) -3.4 to -5.2).
• Potassium Selective Calix[4]semitubes
  作者：Philip R. A. Webber、Andrew Cowley、Michael G. B. Drew、Paul D. Beer

  DOI：10.1002/chem.200204518

  日期：2003.6.6

  ionophore consisting of two calix[4]arene units linked through the lower rim by two ethylene chains, in combination with propyl ether and phenolic functional groups, has been developed. These calix[4]semitube molecules exhibit remarkable selectivity and fast complexation kinetics for potassium over all Group 1 metal cations. Molecular modelling studies, using structural models derived from crystallographic

  已经开发出一种新型的离子载体，该离子载体由两个通过两个乙烯链通过下缘连接的杯[4]芳烃单元与丙基醚和酚官能团组成。这些杯[4]半管分子对所有第1组金属阳离子显示出显着的钾选择性和快速络合动力学。分子建模研究使用了从晶体学数据得出的结构模型，表明钾阳离子是通过水平，侧向途径而不是通过杯[4]芳烃环复合的。半管结构的各个杯[4]芳烃之间的桥接亚烷基链的长度决定了碱金属阳离子结合的强度和选择性。