tetrakis-(hydroxymethyl)-tetrapropoxy-calix[4]arene | 163121-52-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: tetrakis-(hydroxymethyl)-tetrapropoxy-calix[4]arene
• 英文别名: [11,17,23-Tris(hydroxymethyl)-25,26,27,28-tetrapropoxy-5-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]methanol
• CAS: 163121-52-6
• 化学式: C₄₄H₅₆O₈
• 分子量: 712.924
• InChiKey: PJVZAXCBORZUIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  52
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  118
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tetrakis-(hydroxymethyl)-tetrapropoxy-calix[4]arene 在 sodium azide 、 叠氮磷酸二苯酯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 以55%的产率得到5,11,17,23-tetrakis-(3-azidomethyl)-25,26,27,28-tetrapropoxy-calix[4]arene
  参考文献：
  名称：

  Synthesis of sialoclusters appended to calix[4]arene platforms via multiple azide-alkyne cycloaddition. New inhibitors of hemagglutination and cytopathic effect mediated by BK and influenza A viruses

  摘要：

  通过首次利用丙炔基硫代糖苷与钙[4]炔多氮化物的多重铜催化环加成反应，制备出了四价和八价的硫代糖苷簇，并获得了良好的收率。这些环加成物的特点是在同分异构位上具有水解稳定的碳硫键，而 1,4-二取代的三唑环则是硅杂羧酸分子与平台之间的间隔。研究表明，这些非天然结构并不妨碍硅脂环的预期生物活性。事实上，在亚摩尔浓度下，它们能够抑制 BK 病毒和甲型流感病毒介导的血凝和病毒传染性。

  DOI：

  10.1039/b800598b
• 作为产物：
  描述：

  25,26,27,28-tetrapropyloxycalix[4]arene 在 盐酸 、 sodium tetrahydroborate 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 8.0h， 生成 tetrakis-(hydroxymethyl)-tetrapropoxy-calix[4]arene
  参考文献：
  名称：

  Synthesis and Properties ofO-Glycosyl Calix[4]Arenes (Calixsugars)

  摘要：

  AbstractModelO‐glycosylation reactions at either rim of calix[4]arenes are described with the aim of providing access to a new family of carbohydrate‐containing calixarene derivatives named calixsugars. One or two sugar moieties (D‐mannofuranose and D‐glucopyranose) were introduced at the lower rim of the parent calix[4]arene by glycosylation of the phenolic hydroxyl groups by means of a Mitsunobu reaction. Tetrapropoxy calix[4]arenes bearing two or four hydroxymethyl groups at the upper rim were coupled with perbenzoylated thioethyl D‐galactoside and D‐lactoside in the presence of the thiophilic promoter copper(III) triflate. In this way β‐linked bis‐ and tetrakis‐O‐galactosyl calix[4]arenes were obtained in good yield, the latter showing some solubility in water. For theO‐lactosyl derivatives only the bis‐substituted compound could be obtained because of the competing formation of an intramolecular ether linkage between 1,3‐hydroxymethyl groups. Preliminary binding studies showed some affinity of the galactose‐containing calixsugars toward charged carbohydrates and dihydrogen phosphate anion.

  DOI：

  10.1002/chem.19970031108

文献信息

• 一种含杯芳烃模块和环状磷酸酯阻燃剂及其 制备方法和应用
  申请人：中国人民武装警察部队学院

  公开号：CN107778328B

  公开（公告）日：2019-09-24

  本发明提供了一种含杯芳烃模块和环状磷酸酯阻燃剂，属于阻燃剂技术领域。本发明中，杯芳烃模块和环状磷酸酯具有较高的热稳定性，能够提高高聚物材料的阻燃性能。实施例的数据表明，本发明提供的含杯芳烃模块和环状磷酸酯阻燃剂具有较高的阻燃效率，在高聚物中使用时，使用30wt％的该阻燃剂，就能使聚丙烯的极限氧指数(LOI)由19提升到31.5。
• Glycoside-Clustering Round Calixarenes toward the Development of Multivalent Carbohydrate Ligands. Synthesis and Conformational Analysis of Calix[4]arene <i>O</i>- and <i>C</i>-Glycoconjugates
  作者：Alessandro Dondoni、Martin Kleban、Xubo Hu、Alberto Marra、Harold D. Banks

  DOI：10.1021/jo020178z

  日期：2002.7.1

  and C-glycosyl calixarenes (calixsugars) have been prepared by tethering carbohydrate moieties to a tetrapropoxycalix[4]arene scaffold through alkyl chains. Two methodologies have been employed. One consisted of the stereoselective multiple glycosylation of upper rim calix[4]arene polyols leading to calix-O-glycosides; the other involved a multiple Wittig olefination of upper rim calix[4]arene-derived

  通过将碳水化合物部分通过烷基链束缚到四丙氧基杯[4]芳烃骨架上，制备了双-和四-O-和C-糖基杯芳烃（杯糖）。已经采用了两种方法。一种是由上边缘杯[4]芳烃多元醇的立体选择性多重糖基化反应而形成杯-O-糖苷。另一种涉及通过使用糖磷烷将上边缘杯[4]芳烃衍生的多醛进行多次维蒂希烯烃化反应，并还原烯烃双键，得到杯-C-糖苷。双糖基化产物的NMR光谱和NOE实验表明，带有糖保护残基的化合物优先以扁平圆锥排列形式（远构象）存在于溶液中，而脱保护的衍生物则采用紧密构象。
• Phosphorylated Calixarenes in Design of Receptors for Metal Cations and Organic Molecules
  作者：V. Kalchenko、L. Atamas、O. Klimchuk、V. Rudzevich、Yu. Rudzevich、V. Boyko、A. Drapailo、S. Miroshnichenko

  DOI：10.1080/10426500212293

  日期：2002.6.1

  series of calix[4,6]arenes functionalized with phosphinoxyde, diphosphindioxyde, and carbamoylphosphinoxide groups, which possess high binding ability to metal cations or protodonative organic molecules and are linked to the wide rim of macrocyclic skeleton by different spacers, has been synthesized.

  合成了一系列由氧化膦、二膦二氧化和氨基甲酰基氧化膦基团官能化的杯[4,6]芳烃，它们对金属阳离子或质子有机分子具有高结合能力，并通过不同的间隔基与大环骨架的宽边相连。
• Marra, Alberto; Scherrmann, Marie-Christine; Dondoni, Alessandro, Angewandte Chemie, 1994, vol. 106, # 23/24, p. 2533 - 2535
  作者：Marra, Alberto、Scherrmann, Marie-Christine、Dondoni, Alessandro、Casnati, Alessandro、Minari, Patrizia、Ungaro, Rocco

  DOI：——

  日期：——
• Synthesis and Properties ofO-Glycosyl Calix[4]Arenes (Calixsugars)
  作者：Alessandro Dondoni、Alberto Marra、Marie-Christine Scherrmann、Alessandro Casnati、Francesco Sansone、Rocco Ungaro

  DOI：10.1002/chem.19970031108

  日期：1997.11

  AbstractModelO‐glycosylation reactions at either rim of calix[4]arenes are described with the aim of providing access to a new family of carbohydrate‐containing calixarene derivatives named calixsugars. One or two sugar moieties (D‐mannofuranose and D‐glucopyranose) were introduced at the lower rim of the parent calix[4]arene by glycosylation of the phenolic hydroxyl groups by means of a Mitsunobu reaction. Tetrapropoxy calix[4]arenes bearing two or four hydroxymethyl groups at the upper rim were coupled with perbenzoylated thioethyl D‐galactoside and D‐lactoside in the presence of the thiophilic promoter copper(III) triflate. In this way β‐linked bis‐ and tetrakis‐O‐galactosyl calix[4]arenes were obtained in good yield, the latter showing some solubility in water. For theO‐lactosyl derivatives only the bis‐substituted compound could be obtained because of the competing formation of an intramolecular ether linkage between 1,3‐hydroxymethyl groups. Preliminary binding studies showed some affinity of the galactose‐containing calixsugars toward charged carbohydrates and dihydrogen phosphate anion.