SYNTHESIS OF NEW 5-ATOM-LINKED CAPPED PORPHYRINS

被引:15
作者
MA, WP [1 ]
SLEBODNICK, C [1 ]
IBERS, JA [1 ]
机构
[1] NORTHWESTERN UNIV,DEPT CHEM,EVANSTON,IL 60208
关键词
D O I
10.1021/jo00075a031
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis and characterization of three new five-atom-linked ''capped'' porphyrins, 6, 12, and 18, are reported. The general synthetic procedure involves synthesis of a tetraaldehyde ''cap'' by reacting the five-atom ''arm'' with 1,2,4,5-tetrahydroxybenzene in DMSO solvent in the presence of KOH. The tetraaldehyde and pyrrole are reacted to form the capped porphyrin. These compounds are useful as models for the active sites of heme proteins.
引用
收藏
页码:6349 / 6353
页数:5
相关论文
共 23 条
[1]   CONDENSATION OF TETRAALDEHYDES WITH PYRROLE - DIRECT SYNTHESIS OF CAPPED PORPHYRINS [J].
ALMOG, J ;
BALDWIN, JE ;
DYER, RL ;
PETERS, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (01) :226-227
[2]   SYNTHESIS OF CAPPED PORPHYRINS [J].
ALMOG, J ;
BALDWIN, JE ;
CROSSLEY, MJ ;
DEBERNARDIS, JF ;
DYER, RL ;
HUFF, JR ;
PETERS, MK .
TETRAHEDRON, 1981, 37 (21) :3589-3601
[3]   The actionon of alcoholic monomethylamine on derivatives of benzoquinone and toluquinone Part I The methoxy- and hydroxymethoxy-derivatives [J].
Anslow, WK ;
Raistrick, H .
JOURNAL OF THE CHEMICAL SOCIETY, 1939, :1446-1457
[4]  
BALDWIN JE, 1984, TOP CURR CHEM, V121, P181
[5]   FE-57 NUCLEAR-MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF HINDERED IRON PORPHYRINS - RUFFLING AS A POSSIBLE MECHANISM FOR D-ORBITAL ENERGY-LEVEL INVERSION [J].
BALTZER, L ;
LANDERGREN, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (07) :2804-2805
[6]   SYNTHESIS AND CHARACTERIZATION OF THE POCKET PORPHYRINS [J].
COLLMAN, JP ;
BRAUMAN, JI ;
COLLINS, TJ ;
IVERSON, BL ;
LANG, G ;
PETTMAN, RB ;
SESSLER, JL ;
WALTERS, MA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (10) :3038-3052
[7]  
DAVID S, 1986, FRONTIERS BIOINORGAN, P163
[8]   PENDANT-CAPPED PORPHYRINS .1. THE SYNTHESIS OF A BIPHENYL PENDANT-CAPPED IRON(III) PORPHYRIN MODEL OF CATALASE [J].
GARCIA, B ;
LEE, CH ;
BLASKO, A ;
BRUICE, TC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (21) :8118-8126
[9]   HYDROGEN-BOND STABILIZATION OF DIOXYGEN, CONFORMATION EXCITATION, AND AUTOXIDATION MECHANISM IN HEMOPROTEIN MODELS AS REVEALED BY O-17 NMR-SPECTROSCOPY [J].
GEROTHANASSIS, IP ;
MOMENTEAU, M ;
LOOCK, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (18) :7006-7012
[10]   REACTION OF CARBON-MONOXIDE WITH ALKYLIRON PORPHYRINS GENERATED FROM ALKYL-HALIDES AND ELECTROCHEMICALLY PRODUCED IRON(I) AND IRON(0) PORPHYRINS [J].
GUEUTIN, C ;
LEXA, D ;
MOMENTEAU, M ;
SAVEANT, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (05) :1874-1880