TAILOR-MADE HOST FOR PIPERAZINE AND RELATED AMINES

被引：6

作者：

HOSS, R ^{[1
]}

VOGTLE, F ^{[1
]}

机构：

[1] UNIV BONN,INST ORGAN CHEM & BIOCHEM,GERHARD DOMAGK STR 1,W-5300 BONN 1,GERMANY

来源：

CHEMISCHE BERICHTE-RECUEIL | 1993年 / 126卷 / 04期

关键词：

DIAMINE; HOST-GUEST CHEMISTRY; MACROCYCLE; SUPRAMOLECULAR CHEMISTRY; RECEPTOR MOLECULE; SYNTHETIC;

D O I：

10.1002/cber.19931260421

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The 38-membered bis-catechol 4b is obtained by cyclisation of the diacyl dichloride 3c with the diamine 2b in 45% yield, whereas a 68-membered octalactam 7 is formed under similar conditions from 5 and 1b. Bis-catechol 4b is a selective host compound for piperazine (8) and the structurally related diamine 9. Association constants for the 1:1 complexes have been measured by H-1-NMR titration experiments. A nucleo-base guest (pterine, 24) was extracted into a hydrochloric acid phase by complex formation with the host 4b. The results are compared with solubility and transport experiments obtained by use of analogous macrobicyclic tris-catechol hosts.

引用

页码：1003 / 1009

页数：7

共 33 条

[1] MOLECULAR RECOGNITION .16. MOLECULAR RECOGNITION OF QUINONES - 2-POINT HYDROGEN-BONDING STRATEGY FOR THE CONSTRUCTION OF FACE-TO-FACE PORPHYRIN QUINONE ARCHITECTURES [J].

AOYAMA, Y ;

ASAKAWA, M ;

MATSUI, Y ;

OGOSHI, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (16) :6233-6240

[2]

BHATTARAI KM, 1992, J CHEM SOC CHEM COMM, V10, P752

[3]

Connors K. A., 1987, BINDING CONSTANTS ME, P189

[4]

EBMEYER F, 1990, BIOORGANIC CHEM FRON, V1, P143

[5] NUCLEAR MAGNETIC RESONANCE STUDIES OF HYDROGEN BONDING [J].

EYMAN, DP ;

DRAGO, RS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (08) :1617-&

[6]

FRANKE J, 1986, TOP CURR CHEM, V132, P139

[7]

GRAMMENUDI S, 1987, THESIS U BONN, V7

[8] SYNTHESIS AND STRUCTURE ELUCIDATION OF A NEW [2]-CATENANE [J].

HUNTER, CA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (13) :5303-5311

[9]

HUNTER CA, 1991, J CHEM SOC CHEM COMM, V11, P749

[10]

Kiggen, 1984, ANGEW CHEM, V96, P712

← 1 2 3 4 →