Synthese von Haschisch‐Inhaltsstoffen. 4. Mitteilung

Petrzilka, Th.; Haefliger, W.; Sikemeier, C.

doi:10.1002/hlca.19690520427

Cited by 172 publications

(85 citation statements)

References 38 publications

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“…Die dabei auftretende intensive Färbung ist für die Alkoxyderivate 3b-g, 9 a, b sowie 6 und 7 rotorange, für 4, 3 a und h mehr braun-violett und orange für das CBD (5). Eine Unterscheidung der C=C-Doppelbindungsisomerend 8 -und zl 9 Ist der Pyranring wie beim CBD-Derivat (5) nicht geschlossen, wird das NMR-Spektrum (Benzol-Dß) in charakteristischer Weise verändert. So findet man jetzt zwei vinylische Methylgruppen als verbreiterte Singuletts bei <5=1,65 und 1,78.…”

Section: -Runclassified

“…Unter dem Triplett des Butoxyrestes bei <5 = 3,85 liegt das benzylische Proton als breites Multiplett in einer für Cannabidiole typischen Lage. Das Singulett bei <5 = 5,95 der beiden aromatischen Protonen beweist die Substitution des Menthadienylrestes zwischen den Hydroxylgruppen, da sie anderenfalls aufspalten wür-den 9 .…”

Section: -Runclassified

“…Auf Grund ihrer pharmakologischen Wirkung besteht schon seit langem ein starkes Interesse an der Struktur-Wirkungsbeziehung dieser Stoffklasse 1 . Hierzu wurden zahlreiche strukturelle Änderungen und Variationen am THC-Molekülgerüst vorgenommen, jedoch in der überwiegenden Zahl an den isomeren Zl 6a ( 10a )-THC und weniger am A 8 -oder zl 9 -THC. Desweiteren erfolgten auch Synthesen heteroanaloger Cannabisderivate, bei denen im Molekülgerüst oder im Alkylsubstituenten Heteroatome wie Stickstoff 3 , Schwefel 4 oder Sauerstoff eingebaut sind.…”

unclassified

“…Nach der Umsetzung von 6 konnte das gewünschte Produkt 3 c zwar dünnschichtchromatographisch in Spuren nachgewiesen werden, als einziges Hauptprodukt entstand jedoch durch völlige Bromreduktion das zl 8 -THC (7). Dieses Produkt 7 wird auch bei der Kondensation von Menthadienol (1) mit Resorcin direkt erhalten 9 .…”

unclassified

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Sauerstoffanaloge Δ⁸- und Δ⁹-Tetrahydrocannabinole.

Kraatz

Körte

1976

Zeitschrift Für Naturforschung B

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Sauerstoffanaloge Δ⁸- und Δ⁹-Tetrahydrocannabinole.

Kraatz

Körte

1976

Zeitschrift Für Naturforschung B

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“…Syntheses of many plant products including cannabinoids (1)(2)(3)(4) and their ho~nologues depend largely on the availability of I-alkyl-3,5-dihydroxybenzenes (1) (5). Although syntheses of S L I C~ resorcinol homologues were described several years ago (6-lo), they remain somewhat inaccessible and thecurrent interest in cannabinoids and other plant products has spurred further investigations (2,(11)(12)(13).…”

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A Synthesis of 1-Alkyl-3,5-dimethoxybenzenes

Bailey¹

1974

Can. J. Chem.

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Reserirch Lrrborntor.ies, Healtlr Protection Brrrtrch, Healtlr rrtrrl We!fcrre Ccinrrdrr, Ottrrtva KIAOL2Received January 28, 1974 KEITH BAILEY. Can. J. Chern. 52, 2136 (1974). The reaction of 3,4,5-trimethoxybenzaldehyde or 3,4,5-trimethoxyphenyl methyl ketone with alkyl magnesium halides gives secondary or tertiary carbinols. These are converted i n good yields into 1-alkyl-3,s-dimethoxybenzenes by reaction with dissolving sodium in alcohols.KEITH BAILEY. Can. J. Chem. 52, 2136Chem. 52, (1974.Les reactions du trimCthoxy-3,4,5 benzaldehyde OLI de la trimetlioxy-3,4,5 pliCnyl methyl cCtone avec les halogenures de nietliylniagnCsi~~m conduisent aux alcools secondaires ou testiaires correspondants. La staction dc ces derniers avec du sodi~lm dissous dans les alcools conduit avec de bons rendements aux alkyl-l dirnithoxy-3,5 benzene.[Traduit par le journal]Syntheses of many plant products including cannabinoids (1-4) and their ho~nologues depend largely on the availability of I-alkyl-3,5-dihydroxybenzenes (1) (5). Although syntheses of S L I C~ resorcinol homologues were described several years ago (6-lo), they remain somewhat inaccessible and thecurrent interest in cannabinoids and other plant products has spurred further investigations (2,(11)(12)(13). A simple synthesis of 1-alkyl-3,5-dimethoxybenzenes (2), which are readily demethylatecl to the 3,5-dihydroxybenzenes (2, 9, 1 I), is described here. It involves the Grignard reaction of an alkyl magnesium halide CH3O OCH I 0 C t l 3 with 3,4,5-trirnethoxybenzaldehyde or 3,4,5-trimethoxyphenyl methyl ketone (which are more readily available than their 3,5-dirnethoxy counterparts) to give a carbinol (3; R1 = H or CH,) which is sin~ultaneously 4-demethoxylated and reduced in the side chain t o give the dirnethoxybenzenes (2; R 1 = H or CH,) by the action of dissolving s o d i~~r n in t-butanol, The last step is an extension and ilnproverne~lt of a reaction described by Asahina (6) in which dirnethoxybenzenes (2; R ' = H) were prepared from 3,4,5-tri~nethoxyphenyl alkyl ketones with dissolving sodium in alcohol. If the resorcinol derivatives (I) are desired, it is 1101 generally necessary to purify the intermediates 2 and 3. Typical procedures are described in the ~xperimentalsection.When the reaction was 'first investigated, Asahina's procedure (6) (add sodiuni pieces and ethanol or isopropanol to 3,4,5-trin~ethoxy-phenyl alkyl ketones) was applied to the carbinol.A number of I -alkyl-3,5-di1iietl1oxybenzenes were prepared (2; R ' = H, R2 = CH,; RI = H, R2 = JI-C3H7; R 1 = M. R2 = t7-C,H,; R1 = H, R2 = 17-C5t1,,; R L = H, R2 = C6H5; R1 = CH,, RZ = JI-C,H,; R1 = CH,, R~ = 17-C,H,; R' = CH,, R2 = 17-C6HI3; R 1 = CH,, R2 = cyclohexyl; R1 = CH,, R2 = C6Hj) but the yields were only fair (about 7 5 z isolated, about 607, pure). A more satisfactory practice (see T A B L E I. ElTect of change in alcohol on reduction" of 3 ( R 1 = H, R 2 = tr-C5Hll)

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Addition and elimination of HCl to tetrahydrocannabinol isomers. A method for the preparation of stereospecifically 2H-labeled cannabinoids

Banijamali

Schyf

Makriyannis

1998

J Label Compd Radiopharm

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Addition of HCl gas to (−)Δ8‐, (−)Δ9‐, or (−)Δ9,11‐THC solutions at −60°C results in the formation of 9α‐ and 9β‐chlorohexahydrocannabinol (Cl‐HHC). The addition appears to involve initial protonation of the double bond in the form of a bridged hydrogen cation followed by attack of the chloride anion at the most substituted 9‐position. For both steps in the addition reaction the stereochemistry is dependent on the double bond position in the THC isomer. Elimination of HCl from each of the two addition products using potassium‐tert‐amylate leads exclusively to Δ9‐THC in the case of 9β‐Cl‐HHC and to Δ9,11‐THC in the case of 9α‐Cl‐HHC. The individual addition products can be separated and used to obtain regio‐ and stereochemically 2H‐isotopically labeled tetrahydrocannabinols which can be used in biophysical and biochemical studies. © 1998 John Wiley & Sons, Ltd.

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Synthese von Haschisch‐Inhaltsstoffen. 4. Mitteilung

Abstract: Summary The synthesis of a new ( -)-ds-6a, 10s-tvans-tetrahydrocannabinol analogue, containing a N-mcthyl-3-propyl-pyrrol1din-3-yl side-chain, is reported.

Cited by 172 publications

References 38 publications

Sauerstoffanaloge Δ⁸- und Δ⁹-Tetrahydrocannabinole.

Sauerstoffanaloge Δ⁸- und Δ⁹-Tetrahydrocannabinole.

A Synthesis of 1-Alkyl-3,5-dimethoxybenzenes

Addition and elimination of HCl to tetrahydrocannabinol isomers. A method for the preparation of stereospecifically 2H-labeled cannabinoids

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Synthese von Haschisch‐Inhaltsstoffen. 4. Mitteilung

Abstract: Summary The synthesis of a new ( -)-ds-6a, 10s-tvans-tetrahydrocannabinol analogue, containing a N-mcthyl-3-propyl-pyrrol1din-3-yl side-chain, is reported.

Cited by 172 publications

References 38 publications

Sauerstoffanaloge Δ8- und Δ9-Tetrahydrocannabinole.

Sauerstoffanaloge Δ8- und Δ9-Tetrahydrocannabinole.

A Synthesis of 1-Alkyl-3,5-dimethoxybenzenes

Addition and elimination of HCl to tetrahydrocannabinol isomers. A method for the preparation of stereospecifically 2H-labeled cannabinoids

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Sauerstoffanaloge Δ⁸- und Δ⁹-Tetrahydrocannabinole.

Sauerstoffanaloge Δ⁸- und Δ⁹-Tetrahydrocannabinole.