YAKUGAKU ZASSHI
Online ISSN : 1347-5231
Print ISSN : 0031-6903
ISSN-L : 0031-6903
Studies on the Syntheses of Decahydroisoquinoline Derivatives. VI
Studies on the Structures of 2-Methyl-4-anisoyl-10-hydroxy-decahydroisoquinoline and its Isomer. (2). On the Stereo-chemical Configuration from Infrared Absorption Spectra
Toshikazu Omoto
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1960 Volume 80 Issue 2 Pages 137-144

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Abstract
Infrared absorption spectra of the synthesized N-methyl-4-anisoyl-10-hydroxy-decahydroisoquinoline (IVα), its stereoisomer (IVβ), and their derivatives are indicated in Figs. 1-12. From the assignment of these infrared absorptions, it is clear that the alpha type (IVα) compounds take a configuration in which the side chain at C-4 and nitrogen in the parent ring are in sterical proximity and the beta type compounds (IVβ) take the steric configuration with the side chain in C-4 and the angular hydroxyl in close proximity. Such observations of infrared absorption spectra and examinations by the Stuart model suggested the structure (A) for the alpha type and (IVα) was assumed to be dl-2-methyl-4α (or β)-anisoyl-10β(or α)-hydroxy-trans-decahydroiso-quinoline. In the case of beta type, however, it was difficult to conclude the structure from their infrared absorption spectra and the possible structures (B), (B′), and (B″) were forwarded for (IVβ).
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