5,11,17,23-tetra-tert-butyl-25,27-dihydroxy-26,28-dipropargylcalix[4]arene | 139214-28-1

• 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-dihydroxy-26,28-dipropargylcalix[4]arene
• 英文别名: p-tert-butylcalix[4]arene；15,35,55,75-Tetra-tert-butyl-32,72-bis(prop-2-yn-1-yloxy)-1,3,5,7(1,3)-tetrabenzenacyclooctaphane-12,52-diol；5,11,17,23-tetratert-butyl-26,28-bis(prop-2-ynoxy)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-dodecaene-25,27-diol
• CAS: 139214-28-1
• 化学式: C₅₀H₆₀O₄
• 分子量: 725.024
• InChiKey: AFFDHBIQJMXXTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.8
• 重原子数：
  54
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,11,17,23-tetra-tert-butyl-25,27-dihydroxy-26,28-dipropargylcalix[4]arene 在 硝酸 、 一水合肼 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 20.5h， 生成 11,23-diamino-5,17-di-tert-butyl-25,26,27,28-tetrahydroxycalix[4]arene
  参考文献：
  名称：

  肼辅助的一锅去炔丙基化和功能化硝基杯[4]芳烃的还原

  摘要：

  含有两个或四个O-炔丙基部分的杯 [4] 芳烃衍生物能够在水合肼的存在下进行还原去炔丙基化。炔丙基以 4,5-二氢-1H-吡唑的形式被去除，这允许为去炔丙基化提出合理的机制。炔丙基可作为二-O-炔丙基取代的杯[4]芳烃和对-叔上环末端选择性硝化的保护剂-丁基杯[4]芳烃。在将镍催化剂添加到具有水合肼的反应混合物中后，硝基在上边缘的还原与去炔丙基化一起进行，这导致含有游离羟基的杯芳胺。

  DOI：

  10.1007/s11172-023-3858-4
• 作为产物：
  描述：

  对甲苯磺酸丙炔酯 、 5,11,17,23-tetra-t-butyl-25,26,27,28-tetrahydroxycalix-4-arene 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 48.0h， 以82%的产率得到5,11,17,23-tetra-tert-butyl-25,27-dihydroxy-26,28-dipropargylcalix[4]arene
  参考文献：
  名称：

  Selective recognition of Zn2+ by salicylaldimine appended triazole-linked di-derivatives of calix[4]arene by enhanced fluorescence emission in aqueous-organic solutions: role of terminal –CH2OH moietieefs in conjunction with the imine in recognition

  摘要：

  A series of lower rim 1,3-di-derivatives possessing Schiff's base cores were synthesized using triazole unit as linker moiety by further introducing butyl (L-2), one -CH2CH (L-3) and two -CH2OH (L-4)-containing moieties, respectively, in order to bring additional support for ion binding. Based on fluorescence and absorption spectroscopies it has been shown that Zn2+ Could be selectively recognized by the Schiff's base core and not by the triazole core among the ten metal ions studied both in methanol and in aqueous Solutions of methanol and acetonitrile, wherein the -CH2OH moieties augment the fluorescence response by providing additional coordinations to the Zn2+. Thus L-4 exhibited a fluorescence enhancement of similar to 65, similar to 48 and similar to 25-fold in methanol. aqueous Solutions of methanol and acetonitrile. with minimum detection limits of 174. 3 13 and 320 ppb, respectively. Both the excitation and emission wavelengths fall in visible region. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.03.126

文献信息

• Metal ions recognition by 1,2,3-triazolium calix[4]arene esters synthesized via click chemistry
  作者：Haibing Li、Junyan Zhan、Mingliang Chen、Demei Tian、Zhilong Zou

  DOI：10.1007/s10847-009-9582-1

  日期：2010.2

  Two triazole-modified calix[4]arene diesters were synthesized via Huisgen 1,3-dipolar cycloaddition between azides esters and alkynylcalixarenes. Their structures had been deduced from 1H NMR, element analysis and ESI-MS. Two-phase extraction experiments indicated that triazole-modified calix[4]arene diethylester 3a exhibited Cs+ selectivity.

  合成了两种三唑修饰的卡利克斯[4]烷二酯，通过叠氮酯与炔基卡利克斯烷之间的惠斯根1,3-极性环加成反应。其结构通过1H NMR、元素分析和ESI-MS进行了推断。两相萃取实验表明，三唑修饰的卡利克斯[4]烷二乙酯3a表现出对铯离子的选择性。
• Synthesis of Distally Substituted Calix[4]arene Dialkyl Ethers in High Yield
  作者：Lakhbeer Singh Arora、Har Mohindra Chawla、Mohammad Shahid、Nalin Pant

  DOI：10.1080/00304948.2017.1320903

  日期：2017.5.4

  and bridged alkyl calix[4]arenes (VIII and IX) depending upon the base and the amount of alkyl halide used. The process often runs into low yield, no reaction, multiple product formation or change in the conformation of starting calixarenes. There is need for a simple high yield protocol for etherification of calix[4]arenes without undergoing change in conformational characteristics. From amongst numerous

  杯[4]芳烃是大环环芳烃，在离子识别、传感、药物输送、纳米技术、自组装和催化等方面有着广泛的应用。它们具有四个酚-OH 基团，它们在环状阵列中参与强分子内氢键，以产生显着的疏水和亲水区域，称为杯 [4] 芳烃的上缘和下缘。可以修改这些站点以用于目标应用程序。下缘杯[4]芳烃羟基的选择性醚化是实现分子受体进行化学和生物识别的重要方法。由于杯芳烃羟基的 pKa 值范围很窄，当使用不同的碱作为催化剂时，它们的醚化作用通常会导致产物的混合物（图 1）。使用二卤代烷烃进行烷基化也可能导致双杯[4]芳烃（VI和VII）和桥接烷基杯[4]芳烃（VIII和IX），这取决于所使用的烷基卤化物的碱和量。该过程通常会遇到产率低、无反应、形成多种产物或起始杯芳烃构象发生变化的情况。需要一种简单的高产率方案用于杯 [4] 芳烃的醚化，而不会改变构象特征。在众多已知的获得醚的方法中，只有少数可用于杯[4]芳烃化学。许
• A novel hybrid macrocyclic receptor based on bile acid and calix[4]arene frameworks for metal ion recognition
  作者：Manish K. Jaiswal、Pradeep K. Muwal、Shubha Pandey、Pramod S. Pandey

  DOI：10.1016/j.tetlet.2017.04.067

  日期：2017.5

  A novel hybrid macrocyclic receptor based on bile acid and calix[4]arene has been synthesized using the α-face of the bile acid and cone-conformation of calix[4]arene. Metal recognition properties of receptor were investigated. The receptor showed the strongest affinity for Hg2+ in acetonitrile. The stoichiometry of the Receptor:Hg2+ was 1:1.

  利用胆汁酸的α面和杯状[4]芳烃的锥构，合成了一种新的基于胆汁酸和杯状[4]芳烃的杂化大环受体。研究了受体的金属识别特性。该受体对乙腈中的Hg 2+具有最强的亲和力。受体：Hg 2+的化学计量为1：1。
• Highly Selective Fluorimetric Turn‐Off Detection of Copper(II) by Two Different Mechanisms in Calix[4]arene‐Based Chemosensors and Chemodosimeters
  作者：Justine O'Sullivan、John Colleran、Brendan Twamley、Frances Heaney

  DOI：10.1002/cplu.201900448

  日期：2019.10

  Isoxazolo-pyrene tethered calix[4]arenes selectively detect copper(II) ions without interference from related perchlorate ions. The fluorescence emission of the probes, synthesised by nitrile oxide alkyne cycloaddition, and characterised by spectroscopic and crystallographic data, is rapidly reduced by Cu(II) ions. Detection limits are in the micromolar or sub-micromolar range (0.3-3.6 μM) based on

  异恶唑-py系留的杯芳烃[4]芳烃选择性地检测铜（II）离子，而不受相关高氯酸根离子的干扰。Cu（II）离子可快速减少由一氧化氮炔烃环加成合成的探针的荧光发射，并通过光谱和晶体学数据进行表征。基于1：1的传感器：分析物相互作用，检测限在微摩尔或亚微摩尔范围内（0.3-3.6μM）。伏安行为和1 H NMR数据为依赖于杯芳烃取代模式的传感机制提供了新见解。当杯芳烃的下边缘被完全取代时，通过传统的螯合机制进行铜（II）检测。相反，对于下部边缘上的杯芳烃1,3-二取代，检测是通过化学计量氧化还原反应进行的。
• Selectivity of original C-hexopyranosyl calix[4]arene conjugates towards lectins of different origin
  作者：Martina Kašáková、Lenka Malinovská、Tomáš Klejch、Martina Hlaváčková、Hana Dvořáková、Eva Fujdiarová、Zdeňka Rottnerová、Olga Maťátková、Pavel Lhoták、Michaela Wimmerová、Jitka Moravcová

  DOI：10.1016/j.carres.2018.08.012

  日期：2018.11

  As a part of ongoing activities towards the design of ligands against pathogenic lectins, a synthesis of original α-C-galacto/α-C-manno/α-C-fucopyranosyl glycomimetics based on a calix[4]arene scaffold and their binding evaluation is described. The interactions of the glycomimetics with seven lectins of various origins were carried out using agglutination inhibition assays. The 1,3-alternate tetra-C-fucosylated

  作为设计针对致病性凝集素的配体的一项正在进行的活动，基于杯[4]芳烃骨架的原始α-C-半乳糖/α-C-甘露聚糖/α-C-呋喃果糖基糖模拟物的合成及其结合评价描述。使用凝集抑制测定法进行了模拟糖与七种不同来源的凝集素的相互作用。在杯[4]芳烃支架的上边缘具有叔丁基的1,3-交替四碳岩藻糖基化配体及其衍生物对AAL凝集素家族（RSL，AFL，AAL，AOL）和BC2L-C。由于AFL和RSL源自重要的人类（烟曲霉）和植物（青枯雷尔氏菌）病原体，因此通过表面等离振子共振评估了两种主要结构的抑制能力。有了AFL，与参考I-岩藻糖相比，这两种结构都显示出大约三个数量级的亲和力增加。NMR说明了tertBu基团作为“糖苷配基”事件的作用。此外，这两种化合物均显示出显着提高的抑制BC2L-C（来自人类病原体伯克霍尔德森cenocepacia）细胞凝集的能力，并且能够交联整个cenocepacia细胞。尽