5,11,17,23-tetrakis(1,1-dimethylethyl)-25,27-bis<(((4-methylphenyl)sulfonyl)oxy)ethoxy>-26,28-dipropoxycalix<4>arene | 145237-34-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5,11,17,23-tetrakis(1,1-dimethylethyl)-25,27-bis<(((4-methylphenyl)sulfonyl)oxy)ethoxy>-26,28-dipropoxycalix<4>arene
• 英文别名: 5,11,17,23-tetra-tert-butyl-25,27-bis(tosylethoxy)-26,28-dipropoxycalix[4]arene；5,11,17,23-tetrakis(1,1-dimethylethyl)-25,27-bis[{[(4-methylphenyl)sulfonyl]oxy}ethoxy]-26,28-dipropoxycalix[4]arene；2-[[5,11,17,23-Tetratert-butyl-27-[2-(4-methylphenyl)sulfonyloxyethoxy]-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]ethyl 4-methylbenzenesulfonate
• CAS: 145237-34-9
• 化学式: C₆₈H₈₈O₁₀S₂
• 分子量: 1129.57
• InChiKey: HLSPRXNCRZOVTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  18.7
• 重原子数：
  80
• 可旋转键数：
  22
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  140
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  sodium N,N-diethyldithiocarbamate 、 5,11,17,23-tetrakis(1,1-dimethylethyl)-25,27-bis<(((4-methylphenyl)sulfonyl)oxy)ethoxy>-26,28-dipropoxycalix<4>arene 以 丙酮 为溶剂， 以90%的产率得到25,27-bis<(diethyldithiocarbamoyl)ethoxy>-5,11,17,23-tetrakis(1,1-dimethylethyl)-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 吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 205.0h， 生成 5,11,17,23-tetrakis(1,1-dimethylethyl)-25,27-bis<(((4-methylphenyl)sulfonyl)oxy)ethoxy>-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

• Transition Metal Complexes of Lower Rim 1,3-Diphosphinite and 1,3-Diphosphino Calix[4]arenes
  作者：Beth R. Cameron、Frank C. J. M. Van Veggel、David N. Reinhoudt

  DOI：10.1021/jo00114a032

  日期：1995.5

  5,11,17,23-Tetra-tert-butyl-25,27-bis((diphenylphosphino)oxy)-26,28-dipropoxycalix[4]arene, 3, is easily prepared from chlorodiphenylphosphine and 1,3-dipropoxycalix[4]arene in exclusively the cone conformation. 5,11,17,23-Tetra-tert-butyl-25,27-bis((diphenylphosphino)ethoxy)-26,28-dipro poxycalix[4]arene, 5 (also in the cone conformation), is obtained from the reaction of KPPh(2) with the 1,3-ditosylate calix[4]arene derivative. The coordination properties of calix[4]arene ligands 3 and 5 with Rh-I, Cu-I, and Pt-II have been investigated. Isolation of both bimetallic (Rh-2(3)(COD)(2)Cl-2) and monometallic (Rh(3(P=O))(COD)CI) complexes proved that the ligand binds to the Rh-I ion in a monodentate fashion. However, in the case of the Cu-I complex, a bidentate coordination is observed. Compound 5 coordinates to both Cu-I and Pt-II in a bidentate fashion, in which the two phosphorus atoms coordinate in a cis arrangement to the Pt-II center.
• 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。