Novel synthesis and characterization of 1,3-bis(2-dihydrothiazolyl)thiaalkoxy-p-tert-butylcalix[4]arenes

被引：2

作者：

Zhao, Bing ^{[1
]}

Feng, Ya-Qing ^{[1
]}

Zhang, Sha-Sha ^{[1
]}

机构：

[1] Tianjin Univ, Sch Chem Engn & Technol, Tianjin 300072, Peoples R China

来源：

SYNTHETIC COMMUNICATIONS | 2007年 / 37卷 / 19-21期

基金：

中国国家自然科学基金;

关键词：

calix[4]arenes; characterization; conformation; dihydrothiazolyl; synthesis; X-ray structure;

D O I：

10.1080/00397910701555212

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel series of 1,3-bis(2-dihydrothiazolyl)thiaalkoxy-p-tert-butylcalix[4]-arenes generated by the reaction between 4,5-dihydrothiazole-2-thiol and the different dibromide calix[4]aryl groups have been synthesized and structurally characterized by IR, H-1 NMR, C-13 NMR, and MS. From their analytical data, it was found that compounds 8, 9, and 10 had cone conformations, whereas compound 11 existed as a mixture conformation. To verify the structure of the synthetic compounds, a single-crystal X-ray structure of compound 8 was obtained.

引用

页码：3479 / 3484

页数：6

共 13 条

[1] Studies on calix(aza)crowns, .1. Synthesis, alkylation reactions and comprehensive NMR investigation of capped calix[4]arenes [J].

Bitter, I ;

Grun, A ;

Toth, G ;

Balazs, B ;

Toke, L .

TETRAHEDRON, 1997, 53 (28) :9799-9812

[2] TRANSDUCTION OF SELECTIVE RECOGNITION OF HEAVY-METAL IONS BY CHEMICALLY MODIFIED FIELD-EFFECT TRANSISTORS (CHEMFETS) [J].

COBBEN, PLHM ;

EGBERINK, RJM ;

BOMER, JG ;

BERGVELD, P ;

VERBOOM, W ;

REINHOUDT, DN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (26) :10573-10582

[3]

Gutsche C. D., 1989, ROYAL SOC CHEM, V1

[4] Calix[4]arene-constrained cyclopeptides, a novel type of macrocyclic host molecule [J].

Hu, XB ;

Chan, ASC ;

Han, XX ;

He, JQ ;

Cheng, JP .

TETRAHEDRON LETTERS, 1999, 40 (39) :7115-7118

[5] C-13 NMR CHEMICAL-SHIFTS - A SINGLE RULE TO DETERMINE THE CONFORMATION OF CALIX[4]ARENES [J].

JAIME, C ;

DEMENDOZA, J ;

PRADOS, P ;

NIETO, PM ;

SANCHEZ, C .

JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (10) :3372-3376

[6] Aminolysis of p-tert-butyl-tetrakis-[(ethoxycarbonyl)methoxy]thiacalix[4]arene [J].

Jin, Y ;

Zhang, CL ;

Gong, SL ;

Chen, YY .

SYNTHETIC COMMUNICATIONS, 2005, 35 (24) :3179-3186

[7] Self-assembling calix[4]arene [2]catenanes. Preorganization, conformation, selectivity, and efficiency [J].

Li, ZT ;

Ji, GZ ;

Zhao, CX ;

Yuan, SD ;

Ding, H ;

Huang, C ;

Du, AL ;

Wei, M .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (10) :3572-3584

[8]

Liu DQ, 2006, CHINESE CHEM LETT, V17, P747

[9] Dinuclear and trinuclear Zn(II) calix[4]arene complexes as models for hydrolytic metallo-enzymes. Synthesis and catalytic activity in phosphate diester transesterification [J].

Molenveld, P ;

Stikvoort, WMG ;

Kooijman, H ;

Spek, AL ;

Engbersen, JFJ ;

Reinhoudt, DN .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (11) :3896-3906

[10] Highly efficient phosphate diester transesterification by a calix[4]arene-based dinuclear zinc(II) catalyst [J].

Molenveld, P ;

Kapsabelis, S ;

Engbersen, JFJ ;

Reinhoudt, DN .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (12) :2948-2949

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