SYNTHESES WITH ALIPHATIC DIALDEHYDES .44. CHIRAL PENTAMETHINE CYANINE DYES AND HETEROCYCLES FROM DERIVATIVES OF (S)-(+)-2-SEC-BUTYLMALONALDEHYDE

被引:16
作者
REICHARDT, C
BUDNIK, U
机构
[1] Fachbereich Chemie, Universität Marburg, Marburg, D-3550, Hans-Meerwein-Straße
关键词
Cyanine dyes; chiral; Heterocycles; Malonaldehyde; 2‐sec‐butyl‐; Pentamethine dyes;
D O I
10.1002/cber.19901231013
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Syntheses with Aliphatic Dialdehydes. XLIV. — Chiral Pentamethine Cyanine Dyes and Heterocycles from Derivatives of (S)‐(+)‐2‐sec‐Butylmalonaldehyde Syntheses and UV/Vis‐spectroscopic properties of the chain‐substituted, homochiral pentamethine cyanine dyes 16 and 17 are described. 16 and 17 as well as the homochiral five‐, six‐, and seven‐membered heterocycles 11–15 are prepared from derivatives (5 and 6) of homochiral (S)‐(+)‐2‐sec‐Butylmalonaldehyde (8), the first known chiral malonaldehyde, which in turn is synthesized in a seven‐step procedure from homochiral (S)‐(‐)‐2‐methyl‐1‐butanol (1). Copyright © 1990 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim
引用
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页码:2023 / 2030
页数:8
相关论文
共 38 条
[1]   SYNTHESES WITH SUBSTITUTED MALONALDEHYDES .23. "GAMMA-CYCLOALKYLPENTAMETHINECYANINE DYES [J].
ALLMANN, R ;
DEBAERDEMAEKER, T ;
FERWANAH, AR ;
PRESSLER, W ;
REICHARDT, C .
CHEMISCHE BERICHTE-RECUEIL, 1976, 109 (09) :3005-3016
[2]  
BUDNIK U, 1989, THESIS U MARBURG
[3]  
CROMBIE L, 1950, J CHEM SOC, V3, P2685
[4]  
DAHNE S, 1970, Z CHEM, V10, P133
[5]  
DAHNE S, 1970, Z CHEM, V10, P168
[6]   COLOR AND CONSTITUTION - 100 YEARS OF RESEARCH [J].
DAHNE, S .
SCIENCE, 1978, 199 (4334) :1163-1167
[7]   DER POLYMETHINZUSTAND .3. MITTEILUNG UBER ALLGEMEINE ZUSAMMENHANGE ZWISCHEN FARBE UND STRUKTUR ORGANISCHER VERBINDUNGEN [J].
DAHNE, S ;
LEUPOLD, D .
BERICHTE DER BUNSEN-GESELLSCHAFT FUR PHYSIKALISCHE CHEMIE, 1966, 70 (06) :618-&
[8]  
Dahne S., 1980, WISS Z TU DRESDEN, V29, P101
[9]   ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].
DALE, JA ;
DULL, DL ;
MOSHER, HS .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&
[10]   NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].
DALE, JA ;
MOSHER, HS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519