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  • 1
    Electronic Resource
    Electronic Resource
    1,2,3-Tricarbonylverbindungen, XII. Konstitutionsermittlung der Reaktionsprodukte von Ninhydrin mit 2-Aminophenol bzw. 2-Aminothiophenol (1977)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 110 (1977), S. 3954-3958 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 1,2,3-Tricarbonyl Compounds, XII. Elucidation of the Constitution of the Reaction Products of Ninhydrin with 2-Aminophenol and 2-AminothiophenolNinhydrin (1) reacts with 2-aminophenol (2) and 2-aminothiophenol (6) to give products the constitutions of which were elucidated by means of the 1H- and 13C NMR spectra to be 10a-hydroxy-indeno[2,1-b]benz[1,4]oxazine-11(10aH)-one (3) and 10a-hydroxy-indeno[2,1-b]benz-[1,4]thiazine-11(10aH)-one (7), respectively. Structures mentioned in the literature are on the one hand corrected and on the other hand doubtless established.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19771101229
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  • 2
    Electronic Resource
    Electronic Resource
    Mikrobiologische Umwandlungen nichtsteroider Strukturen. IX Mikrobiologische Hydroxylierung von Δ8-Tetrahydrocannabinol (1976)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 109 (1976), S. 3606-3614 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Microbiological Transformations of Nonsteroidal Structures, IX Microbiological Hydroxylation of Δ8TetrahydrocannabinolΔ8Tetrahydrocannabinol (5) is hydroxylated at the ring system and the side chain by fermentations with Pellicularia flilamentosa or Streptomyces lavendulae. P. filamentosa yields the compounds 7β,3′- (1) und 7β,4′-dihydroxy-Δ8-tetrahydrocannabinol (3) as well as 8β,9α-dihydroxy-(2a) und 8β,9α,4′-trihydroxy-6a,10a-trans-hexahydrocannabinol (4a), whereas S. lavendulae leads to 7α-hydroxy- (6), 7α,2′- (7), 7α,3′- (8), 7α4′-Dihydroxy-Δ8-tetrahydrocannabinol (9) und 4′-hydroxy-7-oxo-Δ8-tetrahydrocannabinol (10).
    Notes: Δ8Tetrahydrocannabinol (5) wird durch Fermentationen mit Pellicularia filamentosa oder Streptomyces lavendulae gleichzeitig am Ringsystem und in der Seitenkette hydroxyliert. P. filamentosa ergibt die Produkte 7β,3′- (1) und 7β,4′-Dihydroxy-Δ8-tetrahydrocannabinol (3) sowie 8β,9α-Dihydroxy-(2a) und 8β,9α,4′-Trihydroxy-6A,10a-trans-hexahydrocannabinol (4a), während S. lavendulae zu 7α-Hydroxy-(6), 7α,2′- (7), 7α,3′- (8), 7α4′-Dihydroxy-Δ8-tetrahydrocannabinol (9) und 4′-Hydroxy-7-oxo-Δ8-tetrahydrocannabinol (10) führt.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19761091114
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  • 3
    Electronic Resource
    Electronic Resource
    Mikrobiologische Umwandlung von Steroiden, XV: Mikrobiologische Hydroxylierung von 3α-Acetoxy-5β-pregnan-20-carbonsäure und deren Methylester mit Calonectria decora und Syncephalastrum racemosum (1978)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 111 (1978), S. 2143-2151 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Microbial Transformations of Steroids, XV: Microbial Hydroxylation of 3α-Acetoxy-5β-pregnane-20-carboxylic Acid and of its Methyl Ester by Calonectria decora and Syncephalastrum racemosum3α-Acetoxy-5β-pregnane-20-carboxylic Acid (1) is hydroxylated by fermentation with Calonectria decora in 12β- (3), 7β,11β- (4), and 1β,12β-position (5) with hydrolysis of the 3-acetoxy group. The methyl ester 2 is attacked in 7α,12β- (6), 7β, 11α- (7), and 12β,15α-position (8), Syncephalastrum racemosum forms from 1 the hydroxy products in positions 11β (9), 12β (3), 7β,11β (4), and 11β,15β (10) as well as the further transformation products 3α-hydroxy- (13), 3α,11β-dihydroxy- (14), 3α,12β-dihydroxy-5β,20α-pregnane-20,18-carbolactone (11), and 11,18-epoxy-3α-hydroxy-5β,20α-pregnane-20,18-carbolactone (16), 1 is transformed by Mycobacterium smegmatis into methyl 3-oxo-pregnane- (18) and 3-oxo-1,4-pregnadiene-20-carboxylate (20).
    Notes: 3α-Acetoxy-5β-pregnan-20-carbonsäure (1) wird durch Fermentation mit Calonectria decora unter Verseifung der 3-Acetylgruppe in 12β- (3), 7β,11β- (4) und 1β,12β-Stellung (5) hydroxyliert. Der Methylester 2 wird analog in 7α,12β- (6), 7β,11α- (7) und 12β, 15α-Position (8) angegriffen. Syncephalastrum racemosum bildet aus 1 die Hydroxylierungsprodukte in den Positionen 11β (9), 12β (3), 7β,11β (4) und 11β,15β (10) sowie die weiteren Umwandlungsprodukte 3α-Hydroxy- (13), 3α,11β-Dihydroxy- (14), 3α,12β-Dihydroxy-5β,20α-pregnan-20,18-carbolacton (11) sowie 11,18-Expoxy-3α-hydroxy-5β,20α-pregnan-20,18-carbolacton (16). Durch Mycobacterium smegmatis wird 1 zu 3-Oxo-4-pregnen- (18) und 3-Oxo-1,4-pregnadien-20-carbonsäure-methylester (20) umgewandelt.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19781110611
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