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  • 1980-1984  (7)
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  • 1
    Electronic Resource
    Electronic Resource
    Synthese von Baicalin und einiger anderer Baicalein-glycoside (1980)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 113 (1980), S. 1945-1949 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthesis of Baicalin and Some Other Baicalein GlycosidesThe 6- and 7-O-β-D-glucopyranosides 14 and 7 and the 6- and 7-O-β-D-glucopyranosiduronic acids 18 and 9 of baicalein (1) have been synthesized. 9 was identical with baicalin but 14 and tetuin, further 18 and a “baicalein-6-glucuronide” from Oroxylum indicum were different.
    Notes: Die 6- und 7-O-β-D-Glucopyranoside 14 und 7 bzw. die 6- und 7-O-β-D-Glucopyranosiduron-säuren 18 und 9 des Baicaleins (1) wurden hergestellt. 9 ist mit Baicalin identisch, jedoch stimmte weder 14 mit Tetuin, noch 18 mit „Baicalein-6-glucuronid“ aus Oroxylum indicum überein.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19801130529
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  • 2
    Electronic Resource
    Electronic Resource
    Synthese von rac-4′-O-Methylglabridin, einem antimikrobiellen prenylierten Isoflavan aus Glycyrrhiza glabra L. (1983)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1983 (1983), S. 2034-2037 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Synthesis of rac-4′-O-Methylglabridin, an Antimicrobial Prenylated Isoflavan from Glycyrrhiza glabra L.A synthesis of racemic -4′-O-methylglabridin (1) is described. The key steps are the transformation of the isoflavan-4-one 4 into a dithioacetal 5 followed by desulfuration with Raney nickel.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198319831119
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  • 3
    Electronic Resource
    Electronic Resource
    Synthese der Pterocarpane aus Swartzia laevicarpa (1984)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1984 (1984), S. 127-132 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthesis of Pterocarpan Constituents of Swartzia laevicarpaThe synthesis of 2,8-dihydroxy-3,4-dimethoxy- (1), 2,8-dihydroxy-3,9,10-trimethoxy- (2), 8-hydroxy-3,4,9,10-tetramethoxy- (3), and 2,8-dihydroxy-3,4,9,10-tetramethoxypterocarpan (4)  -  each of them as racemate  -  confirmed the constitution of four new pterocarpans isolated from Swartzia laevicarpa.
    Notes: Durch die eindeutige Synthese von jeweils racemischem 2,8-Dihydroxy-3,9-dimethoxy- (1), 2,8-Dihydroxy-3,9,10-trimethoxy-(2), 8-Hydroxy-3,4,9,10-tetramethoxy-(3) und 2,8-Dihydroxy-3,4,9,10-tetramethoxypterocarpan (4) wurde die Konstitution von vier neuen, aus Swartzia laevicarpa isolierten Pterocarpanen bestätigt.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198419840113
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  • 4
    Electronic Resource
    Electronic Resource
    Versuche zur Synthese des Polystachins (1984)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1984 (1984), S. 1068-1077 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: An Attempted Synthesis of Polystachin[1′RS(3RS)]-1-(2,3-Dihydro-4-hydroxy-6-methoxy-1-benzofuran-3-yl)-2-methyl-1,2-propandiol (21), a partial structure of the title substance 1 was synthetized in 11 steps from phloroglucinol. The key steps were the oxidative rearrangement of the benzylidenacetone derivative 5 by Tl(NO3)3 in methanol to yield the 2-aryl-1,1-dimethoxythane 8 followed by ring closure involving the hydroxy group of 9 liberated by debenzylation. Conversion of 21 into compounds of structure 1 was just as unsuccessful as the synthesis of rac-polystachin (rac-1) from tachrosin (23 via the flavone derivative 29.
    Notes: [1′RS(3RS)]-1-(2,3-Dihydro-4-hydroxy-6-methoxy-1-benzofuran-3-yl)-2-methyl-1,2-propandiol (21), eine Teilstruktur der Titelsubstanz 1, wurde aus Phloroglucin in 11 Schritten synthetisiert. Als Schlüsselreaktion diente die oxidative Umlagerung des Benzalacetonderivates 5 mit Tl(NO3)3 in Methanol zu dem 2-Aryl-1,1-dimethoxyethan 8 gefolgt vom Ringschluß an der durch Entbenzylierung freigesetzten Hydroxygruppe von 9. Die Überführung von 21 in Verbindungen der Struktur 1 blieb ebenso erfolglos wie die Synthese von rac-Polystachin (rac-1) aus Tachrosin (23) über das Flavonderivat 29.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198419840603
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  • 5
    Electronic Resource
    Electronic Resource
    Oxidative Umlagerung von α-Benzylidenketonen mit Thallium(III)-nitrat in Methanol (1980)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1980 (1980), S. 1283-1295 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Oxidative Rearrangement of α-Benzylideneketones with Thallium(III) Nitrate in MethanolSterically unhindered arylidene- and diarylideneacetones 1 or 2 having electron releasing aryl groups yielded with thallium(III) nitrate in methanol β-ketoacetals 3, 4 and 5, respectively. Electronegatively substituted 1f and sterically hindered 1g and 1h gave the 4-arylcrotonic esters 7 and by-products, while 1,3-dibenzylidenacetone (2a) yielded besides the expected products also the branched acetal esters 13a and 13b. Formation of the anomalous products 7 and 13 can be rationalized assuming a common cyclopropanone type intermediate.
    Notes: Sterisch unbehinderte Aryliden- und Diarylidenacetone 1 bzw. 2 mit elektronenspendenden Aryl-gruppen liefern mit Thallium(III)-nitrat in Methanol die β-Ketoacetale 3, 4 bzw. 5. Das elektronegativ substituierte 1f sowie die sterisch gehinderten Acetonderivate 1g und 1h ergeben die 4-Arylcrotonsäureester 7 und Nebenprodukte, während aus 1,3-Dibenzylidenaceton (2a) neben den erwarteten Produkten auch die verzweigten Acetalester 13a und 13b entstehen. Für die Bildung der anomalen Produkte 7 und 13 wird als gemeinsames Zwischenprodukt ein Cyclopropanonderivat vorgeschlagen.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198019800812
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  • 6
    Electronic Resource
    Electronic Resource
    Oxidation von 1,3-Diphenyl-1,3-propandionen mit Thallium-(III)-nitrat in Methanol (1980)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1980 (1980), S. 1271-1282 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Oxidation of 1,3-Diphenyl-1,3-propanediones with Thallium(III) Nitrate in MethanolOn oxidation with thallium(III) nitrate in methanol, 1,3-diphenyl-1,3-propanediones 1 rearrange to give 3-oxo-2,3-diphenylpropanoic esters 2 and products derived therefrom. However, 1-(2-hydroxyphenyl)-3-phenyl-1,3-propanediones 1h-k undergo oxidative cyclization to 2-aroyl-3(2H)-benzofuranones 5. The alkali and acid catalysed cleavage of 5 is discussed.
    Notes: Bei der Oxidation mit Thallium(III)-nitrat in Methanol werden die 1,3-Diphenyl-1,3-propandione 1 zu den 3-Oxo-2,3-diphenylpropansäureestern 2 und deren Folgeprodukte umgelagert. Die 1-(2-Hydroxyphenyl)-3-phenyl-1,3-propandione 1h-k werden dagegen oxidativ zu den 2-Aroyl-3(2H)-benzofuranonen 5 cyclisiert.  -  Der durch Alkalilauge und Säure katalysierte Abbau von 5 wird diskutiert.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198019800811
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  • 7
    Electronic Resource
    Electronic Resource
    Eine einfache Methode zur Herstellung von 2-Arylbenzofuranen und die Synthese von Moracin A und B (1984)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1984 (1984), S. 734-741 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: A Practical Method for the Preparation of 2-Arylbenzofurans and the Synthesis of Moracin A and BOxidative rearrangement of 2-benzyloxychalcones 2 with Ti(No3)3 in methanol to 1,2-diaryl-3,3-dimethoxy-1-propanones 3, alkaline degradation to aryl 2-benzyloxybenzyl ketones 4, debenzylation, and ring closure gave 2-arylbenzofurans 1. In this way moracin A and B (1a, b), further 2-(2,4-dihydroxyphenyl_-5,6-dimethoxybenzofuran (1c) were synthesized. The latter was not identical with a substance isolated from Myroxylon balsamum for which structure 1c was claimed.
    Notes: Die oxidative Umalgerung von 2-Benzyloxychalkonen J. Amer. Chem. Soc.2 mit Ti(NO3)3 in Methanol, alkalischer Abbau der entstandenen 1,2-Diaryl-3,3-dimethoxy-1-propanone 3 zu Aryl(2-benzyloxybenzyl)-ketonen 4, Entbenzylierung und Ringschluß führte zu 2-Arylbenzofuranen 1. Mit dieser Methode wurden u. a. Moracin A und b (1a, b) sowie 2-(2,4-Dihydroxyphenyl)-5,6-dimethoxybenzofuran (1c) synthetisiert. Letzteres war mit einer aus Myroxylon balsamum isolierten und als 1c beschriebenen Substanz nicht identisch.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198419840410
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