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  • Electronic Resource  (29)
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  • Electronic Resource  (29)
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  • 1
    Electronic Resource
    Electronic Resource
    Gehaltsbestimmungen pharmazeutischer Präparate (1937)
    Springer
    Fresenius' Zeitschrift für analytische Chemie 110 (1937), S. 457-464 
    Details
    ISSN: 1618-2650
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01391886
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    Paper (German National Licenses)
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  • 2
    Electronic Resource
    Electronic Resource
    Verhalten von 7-Methoxy-neopinondimethylacetal-methoperchlorat gegenüber Säure (1971)
    Springer
    Monatshefte für Chemie 102 (1971), S. 770-774 
    Details
    ISSN: 1434-4475
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Zusammenfassung Saure Hydrolyse von 7-Methoxy-neopinondimethylacetal-methoperchlorat (1) liefert je nach Reaktionsbedingungen Δ8(14)-7-Oxo-metathebainon-methoperchlorat (9), 7-Methoxy-7.8-dehydro-metathebainon-methoperchlorat (13 a) oder 7-Hydroxy-morphothebain-methoperchlorat (14).
    Notes: Abstract Dependent on reaction conditions acidic hydrolysis of 7-methoxy-neopinone-dimethylacetal-methoperchlorate (1) yields Δ8(14)-7-oxo-metathebainone-methoperchlorate (9), 7-methoxy-7.8-dehydro-metathebainone-methoperchlorate (13 a) or 7-hydroxy-morphothebaine-methoperchlorate (14), resp.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01167258
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    Paper (German National Licenses)
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  • 3
    Electronic Resource
    Electronic Resource
    Darstellung und Reaktionen von 4-O-Methyl-salutaridin-methoperchlorat (1971)
    Springer
    Monatshefte für Chemie 102 (1971), S. 775-780 
    Details
    ISSN: 1434-4475
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Zusammenfassung Durch Methylierung von Δ8(14)-7-Oxo-thebainon-methaperchlorat (1) wird 4-O-Methyl-salutaridin-methoperchlorat (2) erhalten, das beimHofmannabbau das Methin3 liefert. Einwirkung von konz. HCl auf2 bei Raumtemp. führt zu 7-Hydroxy-4-O-methyl-7.8-dehydro-metathebainon-methoperchlorat (4 a), aus dem beim Erwärmen mit 10n-HClO4 7-Hydroxy-4-O-methyl-morphothebain-methoperchlorat (5) entsteht. Die Strukturen von2, 3, 4 a und5 werden bewiesen.
    Notes: Abstract Methylation of Δ8(14)-7-oxo-thebainone-methoperchlorate (1) yields 4-O-methyl-salutaridine-methoperchlorate (2), which by action of 1n-NaOH is degradated to methine3. Acidic hydrolysis of2 at room temperature yields 7-hydroxy-4-O-methyl-7.8-dehydro-metathebainone-methoperchlorate (4 a), which by heating in 10n-HClO4 solution can be rearranged to 7-hydroxy-4-O-methyl-morphothebaine-methoperchlorate (5). The structures of the new compounds2, 3, 4 a, and5 are proved.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01167259
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  • 4
    Electronic Resource
    Electronic Resource
    7-Brom-neopinon-dimethylketal-methoperchlorat (1970)
    Springer
    Monatshefte für Chemie 101 (1970), S. 362-374 
    Details
    ISSN: 1434-4475
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Abstract Contrary to thebaine base (1), which on treatment with bromoacetamide in anhydrous methanol is known to give 14-bromocodeinone dimethylketal (2 a), thebaine metho methylsulfate yields the metho salt of the isomeric 7-bromoneopinone dimethylketal (3 a). From the ketone methoperchlorate (3 b) on heating with water or in buffered solution the methoperchlorate of 7-oxo-thebainone (6) and HBr are formed. However, in strongly acidic solutions3 a as well as3 b give 7-bromo-7,8-dehydrometathebainone methoperchlorate (7 a), isomeric with3 b, a key intermediate, from which the diketone methoperchlorates8 a and8 b, the methine9, the methyl enolates10 a and10 b, and finally the 7-bromo-morphothebaine derivatives12 a–d and13 can be obtained.
    Notes: Zusammenfassung Thebain-metho-methylsulfat liefert mit Bromacetamid in absol. Methanol das Methosalz des 7-Brom-neopinon-dimethylketals (3 a) im Gegensatz zur Thebain-Base (1), die das isomere 14-Bromcodeinon-dimethylketal (2 a) ergibt. Aus dem Ketonmethoperchlorat3 b entstehen beim Erwärmen in Wasser oder gepufferter Lösung das Methoperchlorat des 7-Oxo-thebainons (6) und HBr. In stark saurer Lösung hingegen gelangt man von3 a oder3 b zu dem mit3 b isomeren 7-Brom-7,8-dehydrometathebainon-methoperchlorat (7 a). Von diesem ausgehend, wurden die Diketon-methoperchlorate8 a und8 b sowie das Methin9 gewonnen, weiters auch die entsprechenden Methylenolate10 a und10 b. Über7 a führte auch der Weg zu den 7-Brom-morphothebain-derivaten12 a–d und13.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00910221
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    Paper (German National Licenses)
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  • 5
    Electronic Resource
    Electronic Resource
    Die Methanolyseprodukte von 14-Brom-codeinon-dimethylacetal: (14S)-14-Methoxy-codeinon (1972)
    Springer
    Monatshefte für Chemie 103 (1972), S. 1066-1077 
    Details
    ISSN: 1434-4475
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Zusammenfassung Beim Erhitzen von 14-Brom-codeinon-dimethylacetal (1) in absol. Methanol mit einer äquivalenten Menge Na2CO3 entstehen die drei isomeren Methoxycodeinon-acetale3, 4 und5 sowie die beiden Indolino-codeinonderivate6 und7. Die Strukturen und Konfigurationen der Verbindungen3–6 werden auf Grund der NMR- und IR-Spektren sowie durch Umwandlung in bekannte Verbindungen bewiesen.
    Notes: Abstract 14-Bromocodeinone dimethyl acetal (1) reacts in methanol containing sodium carbonate (0.5 moles) to give the three isomeric methoxycodeinone acetals3, 4, and5 besides the indolino-codeinones6 and7. The structures and configurations of3–6 were established on the basis of NMR- and IR-spectroscopy and by conversion to known compounds.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00905182
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  • 6
    Electronic Resource
    Electronic Resource
    Struktur- und Konfigurationsbeweis für das Diketon aus 14-Bromcodeinon (1970)
    Springer
    Monatshefte für Chemie 101 (1970), S. 1215-1222 
    Details
    ISSN: 1434-4475
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Abstract The diketo compounds formed in the hydrolysis of 14-bromocodeinone (1) and 7-bromoneopinone methoperchlorate, resp., have been shown to possess structure and configuration of Δ8(14)-7-oxothebainone (5) and its methoperchlorate, resp. The quinoxaline derivative7, obtained by condensation of5 with o-phenylenediamine, yields two dihydro compounds (8 and10) diastereomeric at C-6a.8 has been found to be the enantiomer of the condensation product obtained from sinomeninone (6) and o-phenylenediamine.
    Notes: Zusammenfassung Es wird nachgewiesen, daß den aus 14-Brom-codeinon (1)* bzw. 7-Brom-neopinon-methoperchlorat durch einfache Hydrolyse entstehenden Diketoverbindungen die Struktur und Konfiguration von Δ8(14)-7-Oxo-thebainon (5) bzw. des entsprechenden Methoperchlorats zukommt. Das durch Kondensation von5 mit o-Phenylendiamin entstehende Chinoxalinderivat7 gibt zwei am C-6a diastereomere Dihydroverbindungen (8 und10), wobei8 das Enantiomere des Kondensationsproduktes von Sinomeninon (6) und o-Phenylendiamin darstellt.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00908568
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  • 7
    Electronic Resource
    Electronic Resource
    10-Methoxy-des-Basen der Codeinonreihe (1970)
    Springer
    Monatshefte für Chemie 101 (1970), S. 1253-1262 
    Details
    ISSN: 1434-4475
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Abstract Action of sodium methoxide solution upon 7-bromoneopinonedimethylacetal-methoperchlorat* (1) yields twodes-bases, (10S)-methoxycodeinonedimethylaeetal-Δ9(14)-methine (3 d) and 10-methoxyneopinonedimethylacetal-methine (4 d). The structures of the new compounds3 d and4 d are proved and the mechanism of reaction is elucidated.
    Notes: Zusammenfassung Aus 7-Bromneopinondimethylacetal-methoperchlorat* (1) werden bei der Einwirkung von Natriummethylatlösung die bisher nicht beschriebenenDes-Basen, (10S)-methoxycodeinonedimethylaeetal-Δ9(14)-methine (3 d) und 10-Methoxy-neopinondimethylacetal-methin (4 d) gebildet. Die Strukturen von3 d und4 d werden bewiesen, der Reaktions-mechanismus geklärt.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00911391
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  • 8
    Electronic Resource
    Electronic Resource
    „9,10-Dehydro-indolinocodein” (1974)
    Springer
    Monatshefte für Chemie 105 (1974), S. 213-219 
    Details
    ISSN: 1434-4475
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract Reduction of “9.10-dehydro-indolinocodeinone” (2 b) with sodium borohydride yields two isomeric carbinols5 a and5 b. Their structures were established on the basis of NMR-spectroscopy and by conversion to known compounds.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00911309
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  • 9
    Electronic Resource
    Electronic Resource
    Eine neuc Umlagerung an einem Metathebainon-Derivat mit Cyclohexa-2,5-dienon-Struktur (1969)
    Springer
    Monatshefte für Chemie 100 (1969), S. 163-174 
    Details
    ISSN: 1434-4475
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Abstract 4-O-Methyl-7.8-dehydrometathebainonemethine (1) in alkaline solution rearranges to the naphthalene derivative3, which eliminates formiate to give7. The occurrence of3 was confirmed by isolation of13a after reduction with NaBH4. The hydroxy compounds8a and13a, obtained by reduction, eliminate methanol and cyclize to the 2.3-dihydronaphtho[1.8-bc]pyrans9 and14.
    Notes: Zusammenfassung 4-O-Methyl-7,8-dehydro-metathebainon-methin (1) geht in alkalischer Lösung in das Naphthalin-Derivat3 über, das unter Abspaltung von Formiat7 liefert. Das Auftreten von3 kann durch Isolierung von13a nach Reduktion mit NaBH4 nachgewiesen werden. Die aus3 und7 durch Reduktion erhaltenen Alkohole8a und13a werden in saurer Lösung unter Methanol-Abspaltung zu den 2,3-Dihydro-naphtho[1,8-bc]pyranen9 und14 cyclisiert.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00938253
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  • 10
    Electronic Resource
    Electronic Resource
    Reduktive Öffnung der Ätherbrücke am Methylmorphenol und 6-Methoxymethylmorphenol (1965)
    Springer
    Monatshefte für Chemie 96 (1965), S. 1512-1519 
    Details
    ISSN: 1434-4475
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Abstract The ether-linkage of 6-methoxymethylmorphenol (I) is cleaved on reduction with LiAlH4 if the reaction is carried out during irradiation with ultraviolet light; other methods of reduction lead to saturation of the 9,10-double bond. Using methylmorphenol (III) as a model substance the cleavage occurs between the oxygen atom of the ether-bridge and C-4 yielding 3-methoxy-5-hydroxy-phenanthrene (IV). Its structure has been proved by synthesis. This procedure may be employed for the hydrogenolytical cleavage of diphenylethers.
    Notes: Zusammenfassung Die Ätherbrücke des 6-Methoxymethylmorphenols (I) kann durch LiAlH4 reduktiv geöffnet werden, wenn die Reaktion unter UV-Bestrahlung durchgeführt wird, während bei anderen Reduktionsmethoden gleichzeitig Hydrierung der 9,10-Doppelbindung erfolgt. Bei dem als Modellsubstanz verwendeten Methylmorphenol (III) wird die Brücke zwischen dem Äthersauerstoff und C-4 geöffnet, so daß 3-Methoxy-5-hydroxyphenanthren (IV) entsteht, dessen Struktur durch Synthese bewiesen wurde. Die Methode eignet sich auch zur hydrogenolytischen Spaltung von Diphenyläthern.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00902084
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