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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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  • 2
    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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  • 3
    Electronic Resource
    Electronic Resource
    3,6-Dimethoxy-phenanthro[4,5—bcd]furan und (7R)-7-Methoxyneopin-methin (1974)
    Springer
    Monatshefte für Chemie 105 (1974), S. 340-345 
    Details
    ISSN: 1434-4475
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract Reaction of “9.10-Dehydro-indolinocodeine-methoperchlorate” (4) with sodium methoxide solution yields thedes-base (7R)-7-methoxyneopine-methine (5 a). Its structure was established on the basis of spectroscopic methods.Hofmann degradation of5 a affords the so far unknown 3.6-dimethoxy-phenanthro[4.5—bcd]furane (7).
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00907382
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  • 4
    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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  • 5
    Electronic Resource
    Electronic Resource
    Über eine Cyclomethinbase aus 14-Bromcodeinondimethylacetal (1971)
    Springer
    Monatshefte für Chemie 102 (1971), S. 1101-1109 
    Details
    ISSN: 1434-4475
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Zusammenfassung Aus 14-Bromcodeinon-dimethylacetal (1)** entsteht bei der Einwirkung von methanol. KOH die bromfreie Acetalbase2 a, die durch Säuren zum Keton2 b hydrolysiert wird. Die katalyt. Hydrierung beider Basen bzw. ihrer Methosalze verläuft nicht gleichartig; sie führt bei2 a zu einem Gemisch der Basen4 a und3 d, bei2 b zu5 und bei den entsprechenden Methosalzen zu Dihydrocodeinon-dihydromethin (3 a) bzw. dessen Dimethylacetal.
    Notes: Abstract 14-Bromocodeinone dimethyl acetal (1) loses HBr on treatment with methanolic KOH forming the acetal base2 a, which is hydrolysed by acids to the ketone2 b. The two bases and their N-methyl derivatives behave differently on catalytic hydrogenation:2 a yields a mixture of bases4 a and3 d, 2 b yields5, and the corresponding N-methyl derivatives yield dihydrocodeinone-dihydromethine (3 a) and its dimethyl acetal respectively.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00909937
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  • 6
    Electronic Resource
    Electronic Resource
    Methanolyse von 14-Brom-codeinondimethylacetal (1971)
    Springer
    Monatshefte für Chemie 102 (1971), S. 530-537 
    Details
    ISSN: 1434-4475
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Zusammenfassung Bei der Reaktion von 14-Brom-codeinondimethylacetal (1) mit Methanol in Gegenwart von wasserfr. Na2CO3 wurden 7-Methoxy-neopinondimethylacetal (2 b) und 14-Methoxy-codeinondimethylacetal (6 b) erhalten. Die Strukturen der neuen Verbindungen werden bewiesen.
    Notes: Abstract Reaction of 14-bromo-codeinone dimethyl acetal (1) with methanol in presence of Na2CO3 yields 7-methoxy-neopinonedimethyl acetal (2 b) and 14-methoxy-codeinone dimethyl acetal (6 b). The structures of the new compounds are proved.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00909349
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  • 7
    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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  • 8
    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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  • 9
    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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  • 10
    Electronic Resource
    Electronic Resource
    Über den Verlauf der Hofmann-Reaktion am Thebain (1968)
    Springer
    Monatshefte für Chemie 99 (1968), S. 300-315 
    Details
    ISSN: 1434-4475
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Zusammenfassung Durch “kontrollierten”Hofmann-Abbau von Thebain (1) gelangt man zum photo- und thermolabilen Thebaicyclomethinperchlorat (4 a), das in Thebaimethin-methoperchlorat (8 a) übergeführt werden kann. Die Struktur der beiden Verbindungen wird bewiesen.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00908935
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