5,11,17,23-tetra-t-butyl-25,26,27,28-tetrakis(n-hexyloxy)calix[4]arene, 1,3-alternate | 212071-52-8

• 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-tetra-t-butyl-25,26,27,28-tetrakis(n-hexyloxy)calix[4]arene, 1,3-alternate
• 英文别名: tetra(5-hexenyloxy)-p-tert-butylcalix[4]arene；tetrakis(O-n-hexyloxy)calix[4]arene；HBCalix；5,11,17,23-Tetra-tert-butyl-25,26,27,28-tetrahexoxycalix[4]arene；5,11,17,23-Tetratert-butyl-25,26,27,28-tetrahexoxypentacyclo[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；5,11,17,23-tetratert-butyl-25,26,27,28-tetrahexoxypentacyclo[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
• CAS: 212071-52-8；816437-58-8；1123626-00-5
• 化学式: C₆₈H₁₀₄O₄
• 分子量: 985.571
• InChiKey: NAFREVJQRFWJLZ-UHFFFAOYSA-N

物化性质

• 熔点：
  232 °C
• 沸点：
  909.2±65.0 °C(Predicted)
• 密度：
  0.961±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  23.6
• 重原子数：
  72
• 可旋转键数：
  28
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,11,17,23-tetra-t-butyl-25,26,27,28-tetrakis(n-hexyloxy)calix[4]arene, 1,3-alternate 在 sodium nitrate 、 三氟乙酸 作用下， 反应 16.0h， 以52%的产率得到5,11,17,23-tetranitro-25,26,27,28-tetra(hexyloxy)calix[4]arene
  参考文献：
  名称：

  Preparation and physicochemical characterization of a novel paclitaxel-loaded amphiphilic aminocalixarene nanoparticle platform for anticancer chemotherapy

  摘要：

  本文描述了利用一种新型两性载体四己氧基四对氨基卡立[4]芳烃(A4C6)开发和优化纳米颗粒递送平台，用于抗癌药物紫杉醇的传递。

  通过乳液蒸发法成功制备了纳米颗粒，其中有机相含有紫杉醇：A4C6（摩尔比1:10），通过探头超声将其分散到含有0.5% w/v聚乙烯醇稳定剂的水相中，pH值为4。

  载药纳米颗粒的平均尺寸为78.7 ± 20.7 nm，表面电位为38.3 ± 7.67 mV，紫杉醇负载和包封效率分别为69.1 ± 5.3 µg药物/mg载体和50.4 ± 3.2%。透射电子显微镜照片显示离散的颗粒，没有凝聚的迹象。体外溶解实验显示，加入4%牛血清白蛋白的磷酸盐缓冲液中，分别在5、72和120小时释放的封装紫杉醇负荷量为32.7 ± 3.9%、82.6 ± 5.3%和91.0 ± 6.0%。

  这是首次报道使用氨基取代的两性卡立芳烃封装抗癌药物。所制备的纳米颗粒明显小于Abraxane纳米颗粒，但具有可比较的药物载荷，有潜力实现紫杉醇对肿瘤组织的靶向传递。

  DOI：

  10.1111/j.2042-7158.2012.01518.x
• 作为产物：
  描述：

  5,11,17,23-tetra-t-butyl-25,26,27,28-tetrahydroxycalix-4-arene 、 6-溴-1-己烯 在 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 反应 72.0h， 以32%的产率得到5,11,17,23-tetra-t-butyl-25,26,27,28-tetrakis(n-hexyloxy)calix[4]arene, 1,3-alternate
  参考文献：
  名称：

  制备热敏性杯[4]芳烃并入P（NIPAM-co-HBCalix）水凝胶作为镍（II）离子可重复使用的吸附剂

  摘要：

  甲杯共轭热响应含有15％四（5-己烯氧基）水凝胶-对-叔丁基杯[4]芳烃（HBCalix），P（NIPAM-共-HBCalix），被用来从除去镍（II）离子水。研究了制备的P（NIPAM- co- HBCalix）水凝胶的热敏性能和Ni 2+吸附能力。单体HBCalix的引入通过己烯氧基与金属离子之间的螯合大大增强了Ni 2+在水凝胶上的吸附。当HBCalix单元捕获Ni 2+并形成HBCalix / Ni 2+主体-客体络合物时，由于带电的HBCali / Ni之间的排斥，水凝胶的较低临界溶液温度转变为较高温度。2+组和水凝胶内的渗透压。通过改变接触时间，抗衡离子和Ni 2+的初始浓度进行吸附研究。吸附性能的评估表明，水凝胶与Langmuir等温线模型表现出更好的相关性。只需改变环境温度即可重复使用P（NIPAM- co- HBCalix），而吸附能力几乎没有损失。这种离子识别水凝胶有望成为一种新型的吸附和分离Ni

  DOI：

  10.1002/pola.26625

文献信息

• Sensing and Fixation of NO₂/N₂O₄ by Calix[4]Arenes
  作者：Grigory V. Zyryanov、Yanlong Kang、Dmitry M. Rudkevich

  DOI：10.1021/ja029166l

  日期：2003.3.1

  NO(+) is found encapsulated within the calixarene cavity, and stable charge-transfer complexes result with K(ass) > 10(6) M(-1) (CDCl(3)). The NO(+) encapsulation was also demonstrated in titration experiments with calixarenes 1, 2, and 5 and commercially available NO(+)SbF(6)(-) salt in chloroform. The complexation process is reversible, and the complexes dissociate upon addition of water and alcohol

  提出了一种对 NO(2)/N(2)O(4) 进行视觉检测和化学利用的方法，该方法采用简单的杯 [4] 芳烃。四-O-烷基化杯[4]芳烃 1 和 2，具有锥形或 1,3-交替构象，暴露于 NO(2)/N(2)O(4)，无论是在氯仿溶液中还是在氯仿溶液中固态，产生深颜色的杯芳烃-亚硝基鎓 (NO(+)) 络合物。在路易斯酸的存在下，如 SnCl(4)，稳定的杯芳烃-NO(+) 配合物 7 和 8 以定量产率分离出来，并通过紫外-可见光、FTIR、高分辨率 (1) H NMR 光谱表征和元素分析。NO(+) 被发现封装在杯芳烃腔内，稳定的电荷转移复合物导致 K(ass) > 10(6) M(-1) (CDCl(3))。NO(+) 包封也在杯芳烃 1、2、和 5 和市售的 NO(+)SbF(6)(-) 盐在氯仿中。络合过程是可逆的，加入水和醇后，络合物解离，回收母体杯芳烃。展示了功能化杯[4] 芳烃与硅胶的连接，这提供了一种固体材料
• A procedure for filling calixarene nanotubes
  作者：Valentina Sgarlata、Voltaire G. Organo、Dmitry M. Rudkevich

  DOI：10.1039/b509299j

  日期：——

  Alkyl nitrites readily transfer nitrosonium into calixarene-based synthetic nanotubes thus offering a mild, effective and precise method to fill them.

  亚硝酸烷基酯很容易将硝氮转移到基于杯芳烃的合成纳米管中，因此提供了一种温和，有效和精确的填充方法。
• Supramolecular Materials: Molecular Packing of Tetranitrotetrapropoxycalix[4]arene in Highly Stable Films with Second-Order Nonlinear Optical Properties
  作者：Paul J. A. Kenis、Oscar F. J. Noordman、Holger Schönherr、Esther G. Kerver、Bianca H. M. Snellink-Ruël、Gerrit J. van Hummel、Sybolt Harkema、Cornelis P. J. M. van der Vorst、Jeff Hare、Stephen J. Picken、Johan F. J. Engbersen、Niek F. van Hulst、G. Julius Vancso、David N. Reinhoudt

  DOI：10.1002/(sici)1521-3765(19980710)4:7<1225::aid-chem1225>3.0.co;2-6

  日期：1998.7.10

  Highly stable films of tetranitrotetrapropoxycalix[4]arene (9) with second-order nonlinear optical (NLO) properties and a noncentrosymmetric structure were obtained by a novel crystallization process at 130-140 degrees C in a de electric field. The packing of 9 in these films was elucidated by a combination of X-ray diffraction, angle-dependent second-harmonic generation, and scanning force microscopy (SFM). The experimental results agree well with solid-state molecular dynamics calculations for these films. No crystalline phase was observed for nitrocalix[4]arene derivatives with longer or branched alkyl chains; this explains the limited NLO stability of films of these calixarenes. Scanning force microscopy on the aligned films of 9 showed two distinct surface lattice structures: a rectangular lattice (a = 9.3, b = 11.7 Angstrom) and a pseudohexagonal lattice (d approximate to 11.4 Angstrom). The combination of these data with the interlayer distance of 8.9 Angstrom (X-ray diffraction) allowed the packing of molecules of 9 in these structures to be fully elucidated at the molecular level.
• Toward Synthetic Tubes for NO₂/N₂O₄:  Design, Synthesis, and Host−Guest Chemistry
  作者：Grigory V. Zyryanov、Dmitry M. Rudkevich

  DOI：10.1021/ja0392869

  日期：2004.4.1

  Design of molecular nanotubes is proposed for entrapment and conversion of NO2/N2O4 gases. Synthesis of 1,3-alternate bis-calix[4]arene tube 3 of 5 x 11 Angstrom internal dimensions is presented, and its reversible reactions with NO2/N2O4 in solution are studied. Exposure of 3 to NO2/N2O4 in chlorinated solvents results in the rapid encapsulation of nitrosonium (NO+) cations within its interior. Mono- and dinitrosonium complexes 4 and 5, respectively, were isolated and characterized by UV-vis, FTIR, and H-1 NMR spectroscopies, and also molecular modeling. The NO+ entrapment process is reversible, and addition of water quickly recovered starting tube 3. Encapsulated within the tube NO+ species act as nitrosating agents for secondary amides. These findings open wider perspectives toward NO2/NOx storing and converting materials and also offer a promise for further development of supramolecular chemistry of synthetic nanotubes.