2,8,14,20-tetraundecylpirogallol[4]arene | 127203-21-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2,8,14,20-tetraundecylpirogallol[4]arene
• 英文别名: 2,8,14,20-tetraundecylpyrogallo[4]arene；Resorcin[4]arene；2,8,14,20-tetra(undecyl)pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaene-4,5,6,10,11,12,16,17,18,22,23,24-dodecol
• CAS: 127203-21-8
• 化学式: C₇₂H₁₁₂O₁₂
• 分子量: 1169.67
• InChiKey: CULMCZJAEKURSC-UHFFFAOYSA-N

物化性质

• 沸点：
  946.4±65.0 °C(Predicted)
• 密度：
  1.105±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  26.4
• 重原子数：
  84
• 可旋转键数：
  40
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  243
• 氢给体数：
  12
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2-溴-2-甲基丙酰溴 、 2,8,14,20-tetraundecylpirogallol[4]arene 在 吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以88.1%的产率得到[5,6,10,11,12,16,17,18,22,23,24-Undecakis[(2-bromo-2-methylpropanoyl)oxy]-2,8,14,20-tetra(undecyl)-4-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3(28),4,6,9(27),10,12,15,17,19(26),21,23-dodecaenyl] 2-bromo-2-methylpropanoate
  参考文献：
  名称：

  基于间苯二酚[4]-和邻苯三酚[4]芳烃的新型星形引发剂用于可控自由基聚合

  摘要：

  合成了基于不同间苯二酚[4]-和邻苯三酚[4]芳烃的多功能大分子引发剂，用于原子转移自由基聚合（ATRP）。通过用2-溴-异丁酰基溴将所有酚基团完全酯化，可以得到在核上具有8、12和16个叔α-溴酸酯的引发剂。获得了在次甲基碳上带有脂族链的杯芳烃衍生物，为它们的rccc（所有顺式）异构体，而带有芳族取代基的相应杯芳烃则得到了rccc和rctt（顺式，顺式，反式，反式）异构体的混合物。

  DOI：

  10.1016/j.tetlet.2004.10.158
• 作为产物：
  描述：

  十二醛 、 邻苯三酚 以48%的产率得到2,8,14,20-tetraundecylpirogallol[4]arene
  参考文献：
  名称：

  合成的离子通道衍生自在磷脂双层中起作用的金属茂芳烃胶囊。

  摘要：

  改变通道：将十二烷和邻苯三酚缩合，得到四聚体，将其结晶为双层和六聚分子胶囊。铜封的金属茂芳烃胶囊起离子转运剂的作用，在磷脂双层膜中对钾离子的选择性高于氯离子的转运（参见图片）。当在asolectin膜中检查时，该胶囊还显示出其开闭行为的电压依赖性门控。

  DOI：

  10.1002/anie.200804099

文献信息

• New lipophilic macrocyclic host molecules containing multiple ferrocenyl redox-active centres
  作者：Paul D. Beer、Andrew C. Smythe、E.Louise Tite、Arthur Ibbotson

  DOI：10.1016/0022-328x(89)88087-8

  日期：1989.10

  The syntheses and electrochemistry of two novel lipophilic macrocyclic host molecules containing eight and twelve ferrocene redox-active centres are described.

  描述了两个新的亲脂性大环主体分子，其包含八个和十二个二茂铁氧化还原活性中心的合成和电化学。
• Preparation of a Selective Receptor for Ephedrine for the Development of an Optical Spot Test for the Detection of Ephedrine in Human Urine Using Stabilized in Air Lipid Films with Incorporated Receptor
  作者：Dimitrios P. Nikolelis、Nikos Psaroudakis、Nikos Ferderigos

  DOI：10.1021/ac0484023

  日期：2005.5.1

  The present technique describes the preparation of a selective receptor for ephedrine and a simple sensitive spot optical test for the rapid one-shot detection of ephedrine in human urine using lipid films with an incorporated receptor that are synthesized by a chemical reaction with a methacrylate polymer on a glass fiber filter. The selective receptor was synthesized using a resorcin[4]arene receptor and by transforming all the −OH groups into methoxy groups. The lipid films without this receptor provided fluorescence under a UV lamp. The use of the receptor in these films quenched this fluorescence, and the color became similar to that of the filters without the lipid films. A drop of aqueous solution of ephedrine provided a “switching on” of the fluorescence, which allows the rapid detection of this stimulant in human urine at the levels of 10-8 M concentrations. The effect of potent interferences (i.e., proteins, lipids, ascorbic aid, glucose, leucine, glycine, tartrate, citrate, bicarbonate, and caffeine) was examined. The results showed no interferences from these compounds in concentration levels usually found in human urine samples. Dopamine was also investigated as a potent interfering agent, and the results have shown that the transformation of the hydroxy to methoxy groups has altered the selectivity of the receptor. This species does not cause interference at concentration levels lower than 10-6 M. A drop of urine containing ephedrine provided also a “switching on” of the fluorescence, which allows the rapid detection of this stimulant in human urine at the levels of 10-8 M concentrations. The reproducibility of the method was checked in ∼100 samples, and all of them were found to provide similar results. Note that the colors of the filters remain stable for periods of more than 2 months.

  本技术描述了制备一种选择性麻黄碱受体的方法，以及一种快速一次性检测人尿中麻黄碱的简单灵敏点光学测试方法，该方法使用脂质膜，该膜含有通过与甲基丙烯酸酯聚合物在玻璃纤维滤膜上发生化学反应而合成的受体。选择性受体是通过使用间苯二酚[4]芳烃受体并将所有-OH基团转化为甲氧基基团而合成的。不含该受体的脂质膜在紫外灯下会发出荧光。在这些膜中使用该受体可以熄灭这种荧光，颜色变得与不含脂质膜的滤膜的颜色相似。一滴麻黄碱水溶液可以“开启”荧光，从而可以快速检测人尿中浓度为10-8 M的这种兴奋剂。对强效干扰物（即蛋白质、脂质、抗坏血酸、葡萄糖、亮氨酸、甘氨酸、酒石酸盐、柠檬酸盐、碳酸氢盐和咖啡因）的影响进行了检查。结果表明，这些化合物在通常存在于人尿样本中的浓度水平下不会产生干扰。多巴胺也被研究为一种强效干扰剂，结果表明，羟基向甲氧基基团的转化改变了受体的选择性。在低于10-6 M的浓度水平下，该物质不会产生干扰。一滴含有麻黄碱的尿液也可以“开启”荧光，从而可以快速检测人尿中浓度为1
• Novel starshaped initiators for the controlled radical polymerization based on resorcin[4]- and pyrogallol[4]arenes
  作者：Tilo Krause、Margit Gruner、Dirk Kuckling、Wolf D. Habicher

  DOI：10.1016/j.tetlet.2004.10.158

  日期：2004.12

  Multifunctional macrocyclic initiators for the atom transfer radical polymerization (ATRP) based on different resorcin[4]- and pyrogallol[4]arenes have been synthesized. The initiators with 8, 12 and 16 tertiary α-bromoesters on the core were received by complete esterification of all phenolic groups with 2-bromo-isobutyryl bromide. The calixarene derivatives with aliphatic chains on the bridging methine

  合成了基于不同间苯二酚[4]-和邻苯三酚[4]芳烃的多功能大分子引发剂，用于原子转移自由基聚合（ATRP）。通过用2-溴-异丁酰基溴将所有酚基团完全酯化，可以得到在核上具有8、12和16个叔α-溴酸酯的引发剂。获得了在次甲基碳上带有脂族链的杯芳烃衍生物，为它们的rccc（所有顺式）异构体，而带有芳族取代基的相应杯芳烃则得到了rccc和rctt（顺式，顺式，反式，反式）异构体的混合物。
• A Synthetic Ion Channel Derived from a Metallogallarene Capsule That Functions in Phospholipid Bilayers
  作者：Oleg V. Kulikov、Ruiqiong Li、George W. Gokel

  DOI：10.1002/anie.200804099

  日期：2009.1.2

  Changing the channel: Dodecanal and pyrogallol were condensed to give a tetramer, which was crystallized as the bilayer and the hexameric molecular capsule. A copper‐seamed metallogallarene capsule functioned as an ion transporter and showed selectivity for potassium over chloride ion transport in a phospholipid bilayer (see picture). The capsule also showed voltage‐dependent gating of its open–close

  改变通道：将十二烷和邻苯三酚缩合，得到四聚体，将其结晶为双层和六聚分子胶囊。铜封的金属茂芳烃胶囊起离子转运剂的作用，在磷脂双层膜中对钾离子的选择性高于氯离子的转运（参见图片）。当在asolectin膜中检查时，该胶囊还显示出其开闭行为的电压依赖性门控。