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  • Articles: DFG German National Licenses  (6)
  • Synthesis  (4)
  • Mesobiliverdin-XIIIα  (2)
  • 1
    Electronic Resource
    Electronic Resource
    On the chemistry of pyrrole pigments, XCIV: 1-(Dipyrrinon-9-yl)-3-(dipyrrinon-9-ylidene)-1-propene — a novelb-vinylogous verdin chromophore (1995)
    Springer
    Monatshefte für Chemie 126 (1995), S. 1233-1244 
    Details
    ISSN: 1434-4475
    Keywords: 1-(Dipyrrinon-9-yl)-3-(dipyrrinon-9-ylidene)-propenes ; b-Vinylogous verdin ; Synthesis ; Spectroscopy ; Protonation
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Zusammenfassung 1-(Dipyrrinon-9-yl)-3-(dipyrrinon-9-yliden)-propen, einb-vinyloges Verdin, wurde durch Kondensation von 3-(Dipyrrinon-9-yl)-propenal mit einem in Position 9 unsubstituierten Dipyrrinon dargestellt. Kondensation des Letzteren mit Dimedon oder Quadratsäure lieferte vinyloge Pigmente, welche in ihren konfigurationellen und konformationellen Freiheiten eingeschränkt sind. Die chemischen und spektroskopischen Eigenschaften dieser neuen Systeme werden diskutiert.
    Notes: Summary 1-(Dipyrrinon-9-yl)-3-(dipyrrinon-9-ylidene)-propene, ab-vinylogous verdin, was synthesized by condensation of 3-(dipyrrinon-9-yl)-propenal with a dipyrrinone unsubstituted in position 9. By condensing the latter with dimedone or squaric acid,b-vinylogous verdin pigments with restricted configurational and conformational degrees of freedom were obtained. The chemical and spectroscopic properties of these novel systems are discussed.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00824302
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    Paper (German National Licenses)
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  • 2
    Electronic Resource
    Electronic Resource
    On the chemistry of pyrrole pigments, XCV: 1,4-bis-(dipyrrinone-9-ylidene)-butene-2 — A novelb-homo-verdin chromophore (1995)
    Springer
    Monatshefte für Chemie 126 (1995), S. 1323-1329 
    Details
    ISSN: 1434-4475
    Keywords: 1,4-bis-(Dipyrrinone-9-ylidene)-1,3-butene ; Dipyrrinone ; b-homo-Verdin ; Synthesis ; Spectroscopy ; Protonation
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Zusammenfassung 1,4-bis-(Dipyrrinon-9-yliden)-buten-2, ein verdinoides, in Position 10 extendiertes System, wurde durch Kondensation eines in Position 9 unsubstituierten Dipyrrinons mit 2,5-Dihydro-2,5-dimethoxy-furan oder 2,5-Dimethoxy-tetrahydrofuran synthetisiert. Die chemischen und spektroskopischen Eigenschaften dieses neuen chromophoren Systems werden diskutiert.
    Notes: Summary 1,4-bis-(Dipyrrinone-9-ylidene)-butene-2, a verdinoid system extended at C-10, was synthesized by condensing a dipyrrinone unsubstituted in position 9 with 2,5-dihydro-2,5-dimethoxyfuran or 2,5-dimethoxy-tetrahydrofuran. The chemical and spectroscopic properties of this novel chromophoric system are discussed.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00807061
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    Paper (German National Licenses)
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  • 3
    Electronic Resource
    Electronic Resource
    A novel 16,24-dehydrobiladiene-ab system: The reaction of xanthobilirubic acid methyl ester with bromine (1995)
    Springer
    Monatshefte für Chemie 126 (1995), S. 201-209 
    Details
    ISSN: 1434-4475
    Keywords: 16,24-Dehydrobiladiene-ab ; Biladiene-ab ; Xanthobilirubic acid methyl ester ; Mesobilirubin-XIIIα ; Mesobiliverdin-XIIIα ; 14-Formyl-tripyrrinone ; 15,16-Dimethoxy-biladienes-ab
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Zusammenfassung Der Umsatz von Xanthobilirubinsäuremethylester mit Brom in Methanol ergibt in 20-prozentiger Ausbeute ein rotes Pigment, für das die bislang nicht bekannte 16,24-Dehydrobiladien-ab-Konstitution abgeleitet wurde. Darüber hinaus konnte das entsprechende Mesobiliverdin-XIIIα, Mesobilirubin-XIIIα, 14-Formyltripyrrinon, und zwei diastereomere 15,16-Dimethoxybiladiene-ab aus der Reaktionsmischung isoliert werden. Die mechanistischen Aspekte dieser Reaktion werden diskutiert.
    Notes: Summary On treating xanthobilirubic acid methyl ester with bromine in methanol, a red bile pigment, which was assigned the hitherto unknown 16,24-dehydrobiladiene-ab constitution, is obtained in 20% yield. In addition, the corresponding mesobiliverdin-XIIIα, mesobilirubin-XIIIα, 14-formyl-tripyrrinone, and two diastereomeric 15,16-dimethoxybiladienes-ab could be isolated from the reaction mixture. The mechanistic aspects of this reaction are discussed.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00812248
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    Paper (German National Licenses)
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  • 4
    Electronic Resource
    Electronic Resource
    1,2-bis-Dipyrrinon-9-yl-ethene — a novelb-homo-verdian chromophore: the reaction of 9-methyl-10H-dipyrrin-1-ones with bromine (1995)
    Springer
    Monatshefte für Chemie 126 (1995), S. 983-991 
    Details
    ISSN: 1434-4475
    Keywords: 1,2-bis-Dipyrrinon-9-yl-ethene ; b-homo-Verdin ; Mesobiliverdin-XIIIα
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Zusammenfassung Die Reaktion von 9-Methyl-10H-dipyrrin-1-onen mit Brom in Dichlormethan ergab in mäßigen Ausbeuten rotgefärbte Gallenfarbstoffderivate. Sie konnten strukturell als 1,2-bis-Dipyrrinon-ethene zugeordnet werden, die ein Beispiel für die bisher unbekanntenb-Homoverdine darstellen. Darüber hinaus konnten aus der Reaktionsmischung die entsprechenden Mesobiliverdine-XIIIα isoliert werden. Die mechanistischen Aspekte dieser Reaktion werden diskutiert.
    Notes: Summary Upon treatment of 9-methyl-10H-dipyrrin-1-ones with bromine in dichloromethane, red bile pigment derivatives were obtained in moderate yields. They were structurally assigned as 1,2-bis-dipyrrinon-9-yl-ethenes, which are examples of the hitherto unknownb-homo-verdins. In addition, the correspondingmeso-biliverdins-XIIIα could be isolated from the reaction mixture. The mechanistic aspects of the reaction are discussed.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00811018
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    Paper (German National Licenses)
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  • 5
    Electronic Resource
    Electronic Resource
    On the chemistry of pyrrole pigments, XCVI: An efficient synthesis of corrphycenes (1996)
    Springer
    Monatshefte für Chemie 127 (1996), S. 69-75 
    Details
    ISSN: 1434-4475
    Keywords: 1,2-bis-(1-Iodo-dipyrrin)-ethane ; Porphyrin ; Corrphycene ; Synthesis ; Ullmann coupling
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Zusammenfassung Durch Kupfer katalysierte intramolekulare Kupplung der leicht zugänglichen 1,2-bis-(1-Iod-dipyrrin-9-yl)-ethane und anschließende Demetallierung der gebildeten Kupferkomplexe ergibt Corrphycene in Gesamtausbeuten von fast 40%.
    Notes: Summary By means of copper catalyzed intramolecular coupling of the easily accessible 1,2-bis-(1-iodo-dipyrrin-9-yl)-ethanes and subsequent demetallation of the intermediate copper complexes corrphycenes could be prepared in nearly 40% overall yields.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00807410
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    Paper (German National Licenses)
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  • 6
    Electronic Resource
    Electronic Resource
    On the chemistry of pyrrole pigments, XCVII: Synthesis, stereochemistry, and solvatochromic effects of a 1-(dipyrrinon-9-yl)-3-(dipyrrinon-9-ylidene)-1-propene (1996)
    Springer
    Monatshefte für Chemie 127 (1996), S. 77-83 
    Details
    ISSN: 1434-4475
    Keywords: 1-(Dipyrrinon-9-yl)-3-(dipyrrinon-9-ylidene)-propene ; b-Vinylogous verdin ; Synthesis ; Spectroscopy ; Protonation
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Zusammenfassung Durch Kondensation eines Dipyrrinon-9-yl-acroleins mit einem in Position 9 unsubstituierten Dipyrrinon wurde ein unsymmetrischesb-vinyloges verdinoides Pigment dargestellt. Die Konfiguration dieses Moleküls wurde mit Hilfe von 2D-1H-NMR-Experimenten in Lösungen von und Dimethylsulfoxid als (4Z,10E,12Z,17Z) abgeleitet; seine Konformation konnte zu 5syn,9syn,11anti,16syn festgelegt werden. Die ausgeprägte Solvatochromie dieses Moleküls mit cyclisch helikaler Geometrie konnte auf solvensinduzierte konformative Veränderungen zurückgeführt werden.
    Notes: Summary By condensing a dipyrrinon-9-yl-acrolein with a dipyrrinone unsubstituted in position 9, an unsymmetricb-vinylogous verdinoid pigment was prepared. The configuration of this molecule was elucidated by means of 2D1H NMR experiments to be (4Z,10E,12Z,17Z) in solutions of chloroform and dimethylsulfoxide, and its conformation was derived to be 5syn,9syn,11anti,16syn. The pronounced solvatochromic effect of this molecule with a cyclic helical geometry could be explained by solvent induced conformational changes.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00807411
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    Paper (German National Licenses)
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