5,11,17,23-tetra(tert-butyl)-25,26,27,28-tetra-methoxyethoxycalix[4]arene | 151528-64-2

• 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(tert-butyl)-25,26,27,28-tetra-methoxyethoxycalix[4]arene
• 英文别名: 5,11,17,23-Tetratert-butyl-25,26,27,28-tetrakis(2-methoxyethoxy)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
• CAS: 151528-64-2
• 化学式: C₅₆H₈₀O₈
• 分子量: 881.246
• InChiKey: WUEJOQDQKJDNBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.7
• 重原子数：
  64
• 可旋转键数：
  20
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  73.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5,11,17,23-tetra(tert-butyl)-25,26,27,28-tetra-methoxyethoxycalix[4]arene 在 亚硝酸特丁酯 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.5h， 以15%的产率得到
  参考文献：
  名称：

  杯[4]芳烃桥单硝化与亚硝酸叔丁酯：桥接手性对叔丁基杯[4]芳烃与单硝基桥取代基的合成

  摘要：

  为探索桥式硝化反应的普适性，以亚硝酸叔丁酯为硝化试剂，对不同的对叔丁基杯[4]芳烃衍生物进行单硝化反应。系统研究了杯[4]芳烃构象、下缘取代基和反应条件对桥式单硝化的影响。对叔丁基杯[4]芳烃衍生物在1,3-交替构象、1,2-交替构象和部分锥体构象中的桥硝化可以顺利进行，而对叔丁基杯[4]芳烃衍生物的桥硝化可以顺利进行。丁基杯[4]芳烃衍生物不能严格控制在锥形构象中。硝化产物复杂度与桥氢类型呈正相关，最佳的桥单硝化底物为仅一种桥氢类型的杯[4]芳烃。下边缘的吸电子取代基显然有利于桥式单硝化。因此，已成功合成了多种具有单硝基桥取代基的桥联手性对叔丁基杯[4]芳烃。在最佳反应条件下，1,3-替代对叔丁基杯[4]芳烃biscrown-5的最高桥接单硝化收率可达27% 。

  DOI：

  10.1021/acs.joc.2c00253
• 作为产物：
  描述：

  5,11,17,23-tetra-t-butyl-25,26,27,28-tetrahydroxycalix-4-arene 在 potassium carbonate 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 173.0h， 生成 5,11,17,23-tetra(tert-butyl)-25,26,27,28-tetra-methoxyethoxycalix[4]arene
  参考文献：
  名称：

  Tetra-O-alkylated calix[4]arenes in the 1,3-alternate conformation

  摘要：

  A general method has been developed for the preparation f tetra-O-alkylated calix[4]arenes in the 1,3-alternate conformation (3a,c-e) starting from p-tert-butylcalix[4]arenes 1a,b using Cs2CO3 in DMF. The 1,3-alternate conformation was unequivocally proved by an X-ray structure determination of 3a. The scope of the reaction was investigated starting from a series of diametrically di-O-alkylated calix[4]arenes 4a-e having different substituents R2 (t-Bu, CHO, NO2, Br, CN) at the para positions of the phenolic rings. The reactions of 4a-d (R2 = t-Bu, CHO, NO2, Br) yielded the corresponding tetra-0-alkylated calix[4]arenes in the 1,3-alternate conformation 5a-d (51-73%). However, the dicyanocalix[4]arene 4e gave the partial cone conformer 6 as the major reaction product.

  DOI：

  10.1021/jo00046a021

文献信息

• Synthesis and binding properties of calix[4]arenes with [2 + 2′] mixed ligating functional groups
  作者：Lassaad Baklouti、Jamila Cherif、Rym Abidi、Françoise Arnaud-Neu、Jack Harrowfield、Jacques Vicens

  DOI：10.1039/b403598d

  日期：——

  A series of mixed [2 + 2'] p-tert-butylcalix[4]arene have been synthesised by selective 1,3-dialkylation of phenolic groups using various alkylating agents such as benzyl bromide, methyl iodide, ethyl bromoacetate, and 2-methoxyethyl tosylate. The extraction and complexation properties of the synthesized calixarenes towards alkali and alkaline earth metal cations have been investigated in acetonitrile

  通过使用各种烷基化剂，例如苄基溴，碘甲烷，溴乙酸乙酯和2-烷基苯酚基团进行选择性1,3-二烷基化，合成了一系列混合的[2 + 2']对叔丁基杯[4]芳烃甲氧基乙基甲苯磺酸酯。已通过紫外分光光度法和1H NMR光谱研究了乙腈中合成的杯芳烃对碱金属和碱土金属阳离子的提取和络合特性。结果显示取决于配体和阳离子的ML和/或ML2物质的形成。由量热法测量已经获得了由四甘醇，二甘醇-二苄基和二甘醇-二酯衍生物络合的碱金属阳离子的焓和熵。
• A highly efficient and selective turn-on fluorescent sensor for Cu2+ ion based on calix[4]arene bearing four iminoquinoline subunits on the upper rim
  作者：Guang-Ke Li、Zhen-Xiang Xu、Chuan-Feng Chen、Zhi-Tang Huang

  DOI：10.1039/b800258d

  日期：——

  A new fluorescent chemosensor based on calix[4]arene bearing four iminoquinoline subunits on the upper rim was conveniently synthesized, which showed a remarkable enhanced fluorescent intensity in the presence of Cu(2+) ion and a high selectivity toward Cu(2+) ion over a wide range of tested metal ions in acetonitrile.

  方便地合成了一种基于杯形[4]亚芳基的新型荧光化学传感器，该传感器在上缘带有四个亚氨基喹啉亚基，在存在Cu（2+）离子时，荧光强度显着增强，并且对Cu（2+）的选择性高。乙腈中的各种测试金属离子中的离子。
• Tetra-O-alkylated calix[4]arenes in the 1,3-alternate conformation
  作者：Willem Verboom、Sumana Datta、Zouhair Asfari、Sybolt Harkema、David N. Reinhoudt

  DOI：10.1021/jo00046a021

  日期：1992.9

  A general method has been developed for the preparation f tetra-O-alkylated calix[4]arenes in the 1,3-alternate conformation (3a,c-e) starting from p-tert-butylcalix[4]arenes 1a,b using Cs2CO3 in DMF. The 1,3-alternate conformation was unequivocally proved by an X-ray structure determination of 3a. The scope of the reaction was investigated starting from a series of diametrically di-O-alkylated calix[4]arenes 4a-e having different substituents R2 (t-Bu, CHO, NO2, Br, CN) at the para positions of the phenolic rings. The reactions of 4a-d (R2 = t-Bu, CHO, NO2, Br) yielded the corresponding tetra-0-alkylated calix[4]arenes in the 1,3-alternate conformation 5a-d (51-73%). However, the dicyanocalix[4]arene 4e gave the partial cone conformer 6 as the major reaction product.
• Calix[4]arene Bridge Mononitration with <i>tert</i>-Butyl Nitrite: Synthesis of Bridging Chiral <i>p</i>-<i>tert</i>-Butylcalix[4]arene with a Mononitro Bridge Substituent
  作者：Ying-Hong Ma、Yu Yu、Shuai Fan、Xiao-Pu Jia、Sheng-An Tang、Shu-Qing Wang、Wei-Li Dong、Shao-Yong Li

  DOI：10.1021/acs.joc.2c00253

  日期：2022.6.17

  different p-tert-butylcalix[4]arene derivatives was executed with tert-butyl nitrite as a nitration reagent. The effects of calix[4]arene conformations, substituents on the lower rim, and reaction conditions on bridge mononitration are systematically studied. The bridge nitration of p-tert-butylcalix[4]arene derivatives in 1,3-alternate, 1,2-alternate, and partial cone conformations can be smoothly executed

  为探索桥式硝化反应的普适性，以亚硝酸叔丁酯为硝化试剂，对不同的对叔丁基杯[4]芳烃衍生物进行单硝化反应。系统研究了杯[4]芳烃构象、下缘取代基和反应条件对桥式单硝化的影响。对叔丁基杯[4]芳烃衍生物在1,3-交替构象、1,2-交替构象和部分锥体构象中的桥硝化可以顺利进行，而对叔丁基杯[4]芳烃衍生物的桥硝化可以顺利进行。丁基杯[4]芳烃衍生物不能严格控制在锥形构象中。硝化产物复杂度与桥氢类型呈正相关，最佳的桥单硝化底物为仅一种桥氢类型的杯[4]芳烃。下边缘的吸电子取代基显然有利于桥式单硝化。因此，已成功合成了多种具有单硝基桥取代基的桥联手性对叔丁基杯[4]芳烃。在最佳反应条件下，1,3-替代对叔丁基杯[4]芳烃biscrown-5的最高桥接单硝化收率可达27% 。