As an important bridge between the micro and macro material world, chemistry is one of the main methods and means for humans to understand and transform the material world. Category: quinuclidines, 94-53-1, Name is Benzo[d][1,3]dioxole-5-carboxylic acid, SMILES is O=C(C1=CC=C(OCO2)C2=C1)O, in an article , author is BESIDSKY, Y, once mentioned of 94-53-1.
SYNTHESIS AND REACTIVITY OF 6-CARBAMOYL-5-PHENYL-2,3,5,6-TETRAHYDRO-1H-1,4-ETHANOBENZO[F]QUINOLINE – X-RAY MOLECULAR-STRUCTURE OF (4AR-ASTERISK,5S-ASTERISK,6R-ASTERISK,10BR-ASTERISK)-5-PHENYL-2,3,4A,5,6,10B-HEXAHYDRO-1H-1,4-ETHANOBENZO[F]QUINOLIN-6-YL ACETATE
Cyclocondensation of 2-(2-cyano-1,2-diphenylethyl)quinuclidin-3-one 1 in the presence of sulfuric acid gave an intramolecular phenylation instead of lactam formation. The cyclic product was hydrogenated to give 6-carbamoyl-5-phenyl-2,3,4a,5,6,10b-hexahydro-1H-1,4-ethanobenzo- [f]quinoline. On treatment with LiAIH(4) the carbamoyl group was stereospecifically replaced by a hydroxy group. The alcohol was acetylated and the structure was confirmed by X-ray crystallography. The hydroxylation reaction is believed to proceed via a carbonitrile intermediate. In the presence of air the nitrile can be converted to a ketone which is then reduced to the alcohol with an overall retention of configuration.
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Reference:
Quinuclidine – Wikipedia,
,Quinuclidine | C7H13N | ChemSpider