5,11,17,23-tetrakis(1,1,3,3-tetramethylbutyl)calix<4>arene-25,26,27,28-tetrol | 42607-92-1

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: 5,11,17,23-tetrakis(1,1,3,3-tetramethylbutyl)calix<4>arene-25,26,27,28-tetrol
• 英文别名: 5,11,17,23-tetrakis(1,1,3,3-tetramethylbutyl)calix[4]arene-25,26,27,28-tetol；5,11,17,23-tetra-tert-octylcalix<4>arene-25,226,27,28-tetrol；5,11,17,23-tetra(p-t-octyl)-25,26,27,28-tetrahydroxy-calix(4)arene；p-(1,1,3,3-tetramethylbutyl)calix<4>arene；p-tert-octylcalix[4]arene；4,11,18,25-tetrakis-(1,1,3,3-tetramethyl-butyl)-[1.1.1.1]metacyclophane-7,14,21,28-tetraol；5,11,17,23-Tetrakis(1,1,3,3-tetramethylbutyl)calix[4]arene-25,26,27,28-tetrol；5,11,17,23-tetrakis(2,4,4-trimethylpentan-2-yl)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-25,26,27,28-tetrol
• CAS: 42607-92-1
• 化学式: C₆₀H₈₈O₄
• 分子量: 873.356
• InChiKey: KCUQVAUQRGDGKP-UHFFFAOYSA-N

物化性质

• 沸点：
  807.7±65.0 °C(Predicted)
• 密度：
  1.019±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  19.9
• 重原子数：
  64
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,11,17,23-tetrakis(1,1,3,3-tetramethylbutyl)calix<4>arene-25,26,27,28-tetrol 在 barium hydroxide octahydrate 、 水 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 72.25h， 生成 25,26,27‑trioctoxyoxy‑28‑carboxymethoxy‑5,11,17,23‑tetrakis(1,1,3,3‑tetramethylbutyl)calix[4]arene
  参考文献：
  名称：

  具有三烷基单乙酸基团的锂选择性杯[4]芳烃：三个烷基支链和对位叔辛基对锂萃取选择性的影响

  摘要：

  制备了对叔辛基杯[4]芳烃和杯[4]芳烃的三烷基单乙酸衍生物，研究苯氧基氧原子上的烷基支链和对位对选择性萃取Li +的影响。钠+。苯氧基氧原子上的烷基支链对Li +选择性影响显着，而对位的烷基支链影响较小。前者有助于排除Na +萃取，同时实现Li +萃取。烷基支链的优化选择提高了杯[4]芳烃的Li +选择性。然而，具有三个2-乙基丁基支链的空间位阻对叔辛基杯[4]芳烃表现出相反的选择性。

  DOI：

  10.1007/s10847-024-01233-5
• 作为产物：
  描述：

  聚合甲醛 、 对特辛基苯酚 在 sodium hydroxide 作用下， 生成 5,11,17,23-tetrakis(1,1,3,3-tetramethylbutyl)calix<4>arene-25,26,27,28-tetrol
  参考文献：
  名称：

  Optimization of phase-transfer catalysts designed from calix[4]arene

  摘要：

  To optimize the calix[4]arene structure for a phase-transfer catalyst, we modified the upper rim with lipophilic tert-octyl groups and the lower rim with O(CH2CH2O)mMe (m=1, 2, and 3). Through two-phase solvent extraction, H-1 NMR studies on the metal-binding site, and phase-transfer catalysis we have reached conclusions that (i) lipophilic groups introduced into the upper rim effectively enhance the catalytic activity whereas (ii) to compose an effective ionophoric cavity on the lower rim, OCH2CH2OMe (i.e., m=1) suffices and m=2 and m=3 rather decrease the catalytic activity and cause emulsification. The optimized calix[4]arene-based phase-transfer catalyst showed the catalytic activity comparable with dicyclohexyl-18-crown-6.

  DOI：

  10.1016/s0040-4020(01)80420-8

文献信息

• Relationship between chemical structure and extraction efficiency toward palladium with ketonic derivatives of p-tert-octylcalix[4]arene in nitric acid media
  作者：Jee Young Kim、Shintaro Morisada、Hidetaka Kawakita、Keisuke Ohto、Yang Kim

  DOI：10.1007/s10847-014-0467-6

  日期：2015.6

  A p-tert-octylcalix[4]arene derivative with four phenyl ketonic side arms has been synthesized as a solvent extraction reagent for precious metal ions in order to compare the extraction behavior with that of the corresponding methyl ketonic derivative of p-tert-octylcalix[4]arene in nitric acid media. The extraction efficiency of the phenyl ketonic derivative for palladium was superior to that of the methyl ketonic one over the whole nitric acid concentration range. Silver and platinum were also moderately extracted by the phenyl ketonic derivative in low nitric acid concentration. The results demonstrated that the extraction behavior of the ligands towards precious metals is related to several structural factors, such as the flexibility of the side arms, the electric charge on the carbonyl oxygen atoms and the lipophilic properties. This work also determined the extraction mechanism of palladium with the phenyl ketonic derivative of p-tert-octylcalix[4]arene based on slope analysis and the peak shift for the FT-IR spectra of the ligand before and after the metal loading. Stripping from the organic phase after forward extraction was performed to separate palladium and silver.

  合成了一种具有四个苯基酮侧臂的p-叔辛基杯[4]芳烃衍生物，作为贵金属离子的溶剂萃取剂，以便在硝酸介质中比较其萃取行为与相应的甲基酮p-叔辛基杯[4]芳烃衍生物的萃取行为。苯基酮衍生物对钯的萃取效率在整个硝酸浓度范围内均优于甲基酮衍生物。在低硝酸浓度下，苯基酮衍生物也能适度萃取银和铂。结果表明，配体对贵金属的萃取行为与多个结构因素有关，如侧臂的柔韧性、羰基氧原子上的电荷以及脂溶性。本文还基于斜率分析和配体金属负载前后的傅里叶变换红外光谱峰位移，确定了p-叔辛基杯[4]芳烃苯基酮衍生物对钯的萃取机理。正向萃取后，从有机相中剥离，以分离钯和银。
• The effect of phenoxy oxygen atoms on extremely high extraction ability and less separation efficiency of trivalent rare earth elements with tetraphosphonic acid derivative of calix[4]arene
  作者：Keisuke Ohto、Akihito Takedomi、Anup Basnet Chetry、Shintaro Morisada、Hidetaka Kawakita、Tatsuya Oshima

  DOI：10.1007/s10847-012-0255-0

  日期：2013.12

  tetraphosphonic acid at the upper rim, and tetraacetic acid at the lower rim. A dependence on the pH was observed for the new extractant in the highly acidic region, and the extraction took place via a simple ion-exchange mechanism. Using slope analysis, the stoichiometries of tetrameric and monomeric extractants to rare earth metal ions were determined to be 2:1 and 3:1, respectively. Using the proposed extraction

  合成了下缘带有四个亚甲基膦酸的锥形构象 pt-辛基杯 [4] 芳烃及其单体类似物作为一种新的萃取试剂，用于研究 9 种三价稀土元素的萃取行为：Y、La、Pr 、Nd、Sm、Eu、Gd、Ho 和 Er。新的杯[4]芳烃不仅比单体衍生物和商业萃取试剂2-乙基己基氢2-乙基己基膦酸酯具有更高的萃取能力，而且比我们之前工作中使用的锥形构象杯[4]芳烃萃取剂具有更高的萃取能力。间隔较长的四亚丙基膦酸、上缘的四膦酸和下缘的四乙酸。在高酸性区域观察到新萃取剂对 pH 值的依赖性，提取是通过简单的离子交换机制进行的。使用斜率分析，四聚体和单体萃取剂对稀土金属离子的化学计量分别确定为 2:1 和 3:1。使用提出的萃取方程，估计萃取平衡常数和分离因子。极高的萃取能力和中等的分离效率归因于膦酸和苯氧基氧原子的螯合作用。发现苯氧基氧原子对杯[4]芳烃衍生物的萃取能力和分离效率的影响是显着的。使用提出的萃取方程，
• Preparation of antituberculous polyoxyethylene ethers of homogeneous structure
  作者：J.W. Cornforth、E.D. Morgan、K.T. Potts、R.J.W. Rees

  DOI：10.1016/s0040-4020(01)83411-6

  日期：1973.1

  Polyoxyethylene ethers of homogeneous structure have been prepared from a macrocyclic, tetrahydric phenol (“HOC”), and from cholesterol by reaction with monofunctional derivatives of polyethylene glycols. Many practical difficulties had to be overcome in the preparation of these compounds. The effect on experimental tuberculosis of some of these products was compared with that of corresponding polyoxyethylene

  均质结构的聚氧乙烯醚已经由大环四元酚（“ HOC”）和胆固醇通过与聚乙二醇的单官能衍生物反应而制得。在制备这些化合物中必须克服许多实际困难。将其中一些产品对实验性肺结核的影响与通过无规聚合生产的相应聚氧乙烯醚的影响进行了比较。在探索化学治疗活性的结构要求时，还制备了其他几种表面活性化合物。
• Solvent Extraction of Silver(I) and Palladium(II) Ions with Ketone Derivative of Calix[4]arene from Highly Acidic Nitrate Media
  作者：Keisuke Ohto、Emi Murakami、Koji Shiratsuchi、Katsutoshi Inoue、Mineto Iwasaki

  DOI：10.1246/cl.1996.173

  日期：1996.2

  extraction of silver (I) and palladium (II) ions with 25,26,27,28-tetrakis(acetomethoxy)-5,11,17,23-tetrakis(1,1,3,3-tetramethylbutyl)calix[4]arene (1) in chloroform from nitric acid solution was investigated. The compound 1 was capable of highly selectively extracting silver over palladium from about 1 mol dm−3 nitric acid solution and was effective in removing trace amounts of silver from a large

  25,26,27,28-四(乙酰甲氧基)-5,11,17,23-四(1,1,3,3-四甲基丁基)杯对银(I)和钯(II)离子进行溶剂萃取[ 4]芳烃 (1) 在氯仿中的硝酸溶液中进行了研究。化合物 1 能够从约 1 mol dm-3 硝酸溶液中高度选择性地从钯中提取银，并能有效地从大量过量的钯中去除痕量银。银离子在 1 上的配位点也由 1H-NMR 光谱中的化学位移确定。
• Synthesis of a para-tert-octylcalix[4]arene fitted with phosphinoyl pendant arms and its complexation properties towards f-elements
  作者：Flor de María Ramírez、Tania Tosheva、Emil Tashev、Eduardo García-Villafaña、Stoycho Shenkov、Sabi Varbanov

  DOI：10.1016/j.poly.2013.04.003

  日期：2013.6

  aim of isolating Eu(III) and UO22+ complexes with 1 M:2 L stoichiometry. However, the characterisation of the complexes indicated 1 M:1 L stoichiometry. The luminescence properties, such as emission and excitation spectra, lifetimes and quantum yields, of the UO22+ (2) and Eu(III) (3) isolated complexes were analysed. The molecular modelling of the europium complex molecule based on the experimental

  合成并充分表征了一种新的功能化杯芳烃，对-叔辛基杯[4]芳烃，其装有膦酰基悬垂臂（B 4 boctL 4）1。相对于所报道的使用二甲苯的方法，通过杯芳烃的四钠衍生物与二甲基-氯甲基-膦氧化物之间的威廉姆森反应使用二甲苯的方法将反应时间从96减少到15 h，并将反应收率从46％增加到89％。甲苯，用于合成具有对叔丁基取代基的次膦酰化杯芳烃。La（III），Lu（III），Th（IV）和UO 2的分光光度滴定B 4 boctL 4在0.01 M（CH 3 CH 2）4 NCl存在下，在CH 3 CN中进行Tb（III）和UO 2 2+的2+发光滴定。结果表明，形成了两个主要物种，金属和配体的比例为1：1和1：2。前者有一个日志β 11倍的8.4和4.5的值的La（III）和UO 2根2+离子，分别，后者有一个日志β 12个的分别13.8和7.4，值。基于此结果，使用1 M：2 L的摩尔比以分离Eu（III）和UO