5,11,17,23-tetrakis(N,N-dimethylamino)methyl-4,6,10,12,16,18,11,24-octahydroxy-2,8,14,20-tetranonylcalix[4]arene | 217651-03-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5,11,17,23-tetrakis(N,N-dimethylamino)methyl-4,6,10,12,16,18,11,24-octahydroxy-2,8,14,20-tetranonylcalix[4]arene
• 英文别名: 1,7,13,19-tetranonyl-4,10,16,22-[tetra(N-dimethylamino)methylene]calix[4]resorcynolarene；5,11,17,23-Tetrakis[(dimethylamino)methyl]-2,8,14,20-tetra(nonyl)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-4,6,10,12,16,18,22,24-octol
• CAS: 217651-03-1
• 化学式: C₇₆H₁₂₄N₄O₈
• 分子量: 1221.84
• InChiKey: XGESLHIJQZJXRG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  22.8
• 重原子数：
  88
• 可旋转键数：
  40
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  175
• 氢给体数：
  8
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  4-nitrophenyl bis(chloromethyl)phosphinate 、 5,11,17,23-tetrakis(N,N-dimethylamino)methyl-4,6,10,12,16,18,11,24-octahydroxy-2,8,14,20-tetranonylcalix[4]arene 在 1-十八烷铵,N-(2-羟基乙基)-N,N-二甲基-,溴化 作用下， 以 氯仿 为溶剂， 生成 24-[bis(chloromethyl)phosphoryloxy]-5,11,17,23-tetrakis[(dimethylamino)methyl]-2,8,14,20-tetra(nonyl)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-4,6,10,12,16,18,22-heptol
  参考文献：
  名称：

  摘要：

  Micelle formation by n-alkyl(2-hydroxyethyl)dimethylammonium bromides in chloroform was studied by dielcometric titration and kinetic method. Increase in the length of the hydrocarbon chain leads to reduced critical micelle concentration. The region of structural reorganization of micelles was determined. n-Alkyl(2-hydroxyethyl)dimethylammonium bromides catalyze phosphorylation of tetrakis(dimethylaminomethyl)calixresorcin[4]arene. The catalytic activity of micelles depends on the hydrophobic properties and concentration of the surface-active substance, as well as on structural features of its aggregates.

  DOI：

  10.1023/a:1012313219409
• 作为产物：
  描述：

  tetranonylcalix[4]recorcinolarene 、 四甲基甲烷二胺 以 乙醇 、 甲苯 为溶剂， 反应 8.0h， 以70%的产率得到5,11,17,23-tetrakis(N,N-dimethylamino)methyl-4,6,10,12,16,18,11,24-octahydroxy-2,8,14,20-tetranonylcalix[4]arene
  参考文献：
  名称：

  氨甲基化杯[4]间苯二酚与磷酸酯反应的质子分解特性和反应性

  摘要：

  用电位计、紫外分光光度法研究了氨甲基化杯[4]间苯二酚(AMC)与磷酸的对硝基苯酯在丙-2-醇(80 vol.% PriOH)水溶液中的酸碱性质和反应动力学和 31 P NMR 光谱。研究了烃基的长度和氮原子上的取代基对AMC的质子分解性质和反应活性的影响。所研究的反应分两个阶段进行。在第一阶段，形成磷酸化的 AMC，在第二阶段水解成相应的酸。

  DOI：

  10.1007/bf02496160

文献信息

• Synthesis and antioxidant activity of 3,5-di-tert-butyl-4-hydroxyphenylthiomethyltetraalkylcalix[4]resorcinarenes
  作者：G. N. Nugumanova、T. A. Barsukov、S. V. Bukharov、V. V. Syakaev、R. Ya. Deberdeev

  DOI：10.1134/s107036321509011x

  日期：2015.9

  Deamination of dimethyl- and diethylaminomethylated tetraalkylcalix[4]resorcinarenes with 3,5-di-tert-butyl-4-hydroxyphenylmercaptan afforded new 3,5-di-tert-butyl-4-hydroxyphenylthiomethyltetraalkylcalix-[4]resorcinarenes. High antioxidant activity of the synthesized alkylcalix[4]resorcinarenes was established in the model reaction of initiated oxidation of styrene.
• ——
  作者：V. V. Yanilkin、I. S. Ryzhkina、N. V. Nastapova、T. N. Pashirova、Ya. A. Babkina、A. R. Burilov、V. I. Morozov、A. I. Konovalov

  DOI：10.1023/a:1024713408780

  日期：——

  The electrochemical oxidation of a number of aminomethylated calix[4]resorcinarenes (AMC) with different substituents at the nitrogen atom and the kinetics of nucleophilic substitution reactions of these compounds with p-nitrophenyl bis(chloromethyl)phosphinate were studied. The reactivity of the ionic associates of AMC in the nucleophilic substitution and the behavior of AMC in electrooxidation are determined by the same factors, namely, the amino-roup basicity and the nature of the substituents at the nitrogen atom. These factors influence the ratio of the zwitter-ionic and anionic forms of AMC.
• Synthesis of aminomethylated calix[4]resorcinarenes
  作者：Yoh-ichi Matsushita、Takanao Matsui

  DOI：10.1016/s0040-4039(00)60145-4

  日期：1993.11

  Aminomethylation at the ortho position with respect to hydroxyl groups of calix[4]resorcinarenes, resorcinol-aldehyde cyclotetramers, was achieved by the Mannich reaction with formaldehyde and the appropriate amine in an alcoholic solution.
• Catalytic Effect of Reverse Micelles of a Cationic Surfactant on the Reaction of Calix[4]resorcinolarenes with 4-Nitrophenyl Bis(chloromethyl)phosphinate
  作者：E. P. Zhil'tsova、L. A. Kudryavtseva、A. P. Timosheva、N. I. Kharitonov、A. I. Konovalov

  DOI：10.1023/b:rugc.0000031870.38538.3d

  日期：2004.4

  The presence of the aminomethyl fragment in the calix[4]resorcinolarene molecule favors its phosphorylation in chloroform. Reverse micelles of (2- hydroxyethyl)dimethyipentadecylammonium bromide catalyze this reaction, the catalytic effect being dependent on the length of the hydrocarbon chain of a calixarene and detergent concentration.
• Protolytic properties and reactivity of aminomethylated calix[4]resorcarenes in reactions with esters of phosphorus acids
  作者：I. S. Ryzhkina、L. A. Kudryavtseva、A. R. Mustafina、Yu. E. Morozova、E. Kh. Kazakova、K. M. Enikeev、A. I. Konovalov

  DOI：10.1007/bf02496160

  日期：1999.3

  acid-base properties and the kinetics of reactions of aminomethylated calix[4]resorcarenes (AMC) withp-nitrophenyl esters of phosphorus acids in aqueous solutions of propan-2-ol (80 vol.% PriOH) were studied by potentiometry, UV spectrophotometry, and31P NMR spectroscopy. The effect of the length of the hydrocarbon radical and substituents at the nitrogen atom on the protolytic properties and reactivity

  用电位计、紫外分光光度法研究了氨甲基化杯[4]间苯二酚(AMC)与磷酸的对硝基苯酯在丙-2-醇(80 vol.% PriOH)水溶液中的酸碱性质和反应动力学和 31 P NMR 光谱。研究了烃基的长度和氮原子上的取代基对AMC的质子分解性质和反应活性的影响。所研究的反应分两个阶段进行。在第一阶段，形成磷酸化的 AMC，在第二阶段水解成相应的酸。