25,27-bis(2-ethoxyethoxy)-p-tert-butylcalix[4]arene | 143328-88-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 25,27-bis(2-ethoxyethoxy)-p-tert-butylcalix[4]arene
• 英文别名: 5,11,17,23-tetrakis(1,1-dimethylethyl)-26,28-bis(ethoxyethoxy)-25,27-dihydroxycalix<4>arene；5,11,17,23-Tetrakis(1,1-dimethylethyl)-25,27-bis(2-ethoxyethoxy)calix<4>arene；5,11,17,23-Tetratert-butyl-26,28-bis(2-ethoxyethoxy)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-25,27-diol
• CAS: 143328-88-5；143490-89-5
• 化学式: C₅₂H₇₂O₆
• 分子量: 793.14
• InChiKey: CBOHBPLGPLZODR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14
• 重原子数：
  58
• 可旋转键数：
  14
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  25,27-bis(2-ethoxyethoxy)-p-tert-butylcalix[4]arene 在 三氯化铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 3.0h， 以70%的产率得到11,23-Bis(1,1-dimethylethyl)-25,27-bis(2-ethoxyethoxy)calix<4>arene
  参考文献：
  名称：

  Direct Regioselective Formylation of Tetraalkoxycalix[4]arenes Fixed in the Cone Conformation and Synthesis of New Cavitands

  摘要：

  Regioselectivity of the formylation of tetraalkoxycalix[4]arene fixed in the cone conformation has been studied. Direct, diametrical (1,3) diformylation of calix[4]arenes having four chelating chains at the lower rim has been achieved. Simple tetraalkoxycalix[4]arenes produce a mixture of diametrical (1,3) and proximal (1,2) diformylated products. The (1,3) functionalized compounds have been used for the synthesis of double calix[4]arenes 12a,d linked via the upper rim. The residual mobility of these cone conformers is indicated by the X-ray crystal structure of compound 12d, which shows a flattened cone conformation, and by the reactive behavior of 1,3-bis(hydroxymethyl) derivatives 9a,d which give very distorted 1,3-bridged compounds 11a,d, through an intramolecular cyclization process.

  DOI：

  10.1021/jo00110a054
• 作为产物：
  描述：

  5,11,17,23-tetra-t-butyl-25,26,27,28-tetrahydroxycalix-4-arene 以90%的产率得到
  参考文献：
  名称：

  Arduini Arturo, Fanni Stefano, Manfredi Giuseppe, Pochini Andrea, Ungaro +, J, Org. Chem, 60 (1995) N 5, S 1448-1453

  摘要：

  DOI：

文献信息

• Light-Responsive Metal Encapsulation in Calix[4]arene
  作者：Gang Deng、Toru Sakaki、Kazuaki Nakashima、Seiji Shinkai

  DOI：10.1246/cl.1992.1287

  日期：1992.7

  An ionophoric calix[4]arene (1), in which the metal-binding ability is photochemically controlled, was designed by introducing two anthracenes near the metal-binding site. Compound 1 itself showed the poor ion affinity and the poor ion selectivity whereas photochemically-produced isomer showed the much improved ion affinity and the sharp Na+ selectivity.

  一种离子载体型钙克斯[4]芳烃（1）被设计成其金属结合能力可通过光化学控制，方法是在金属结合位置附近引入两个蒽分子。化合物1本身表现出较差的离子亲和力和选择性，而光化学产生的异构体则表现出显著改善的离子亲和力和明显的Na+选择性。
• Writing Patterns of Molecules on Molecular Printboards
  作者：Tommaso Auletta、Barbara Dordi、Alart Mulder、Andrea Sartori、Steffen Onclin、Christiaan M. Bruinink、Mária Péter、Christian A. Nijhuis、Hans Beijleveld、Holger Schönherr、G. Julius Vancso、Alessandro Casnati、Rocco Ungaro、Bart Jan Ravoo、Jurriaan Huskens、David N. Reinhoudt

  DOI：10.1002/anie.200352767

  日期：2004.1.5
• 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.
• Divalent Binding of a Bis(adamantyl)-Functionalized Calix[4]arene to β-cyclodextrin-based Hosts:  An Experimental and Theoretical Study on Multivalent Binding in Solution and at Self-Assembled Monolayers
  作者：Alart Mulder、Tommaso Auletta、Andrea Sartori、Susanna Del Ciotto、Alessandro Casnati、Rocco Ungaro、Jurriaan Huskens、David N. Reinhoudt

  DOI：10.1021/ja0317168

  日期：2004.6.1

  The divalent binding of a bis(adamantyl)-functionalized calix[4]arene (1) to an EDTA-tethered beta-cyclodextrin (CD) dimer (2) in solution (1.2 x 10(7) M-1) was 3 orders of magnitude weaker than the binding constant (similar to10(10) M-1) for the interaction of 1 at CD self-assembled monolayers (SAMS) on gold. This difference in binding is rationalized using a theoretical model, which interprets the divalent binding as two consecutive monovalent binding events, i.e., an intermolecular interaction followed by an intramolecular binding event, the latter of which is associated with an effective concentration term accounting for the close proximity of the two interacting species. The methodology presented in the model is applicable to divalent binding both in solution and at SAMS and indicates that the difference in observed binding constants mainly stems from a difference in effective concentration.