novel glun2b selective nmda receptor antagonists: relative configuration of 7-methoxy-2-methyl-2,3,4,5-tetrahydro-1h-3-benzazepin-1-ols

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ID: 133323
2016
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Abstract
The title compounds, C22H29NO2 (3) and C22H29NO2 (4) [systematic names: (1S*,2R*)-7-methoxy-2-methyl-3-(4-phenylbutyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-1-ol and (1R*,2R*)-7-methoxy-2-methyl-3-(4-phenylbutyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-1-ol, are diastereomers with the relative configuration of the adjacent hydroxyl and methyl groups at the seven-membered azepine ring being trans in (3) and cis in (4). In the crystals the orientation of these groups is −anti-periplanar (3) and +syn-clinal (4). In both cases, the crystals studied proved to be of a racemic mixture, with relative configurations (R*,S*)-3 and (R*,R*)-4. In both compounds, the seven-membered azepine ring has a chair-like conformation, and the 4-phenylbutyl side chain adopts a extended conformation in (R*,S*)-3, but a twisted conformation in (R*,R*)-4. In the crystal of (S*,R*)-3, molecules are linked via C—H...O hydrogen bonds, forming slabs parallel to the ac plane. In the crystal of (R*,R*)-4, molecules are linked via O—H...N hydrogen bonds, forming chains propagating along the c-axis direction. The chains are linked by C—H...O hydrogen bonds, forming slabs parallel to the ac plane.
Reference Key
tewes2016actanovel Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors ;Bastian Tewes;Bastian Frehland;Roland Fröhlich;Bernhard Wünsch
Journal Disability and rehabilitation
Year 2016
DOI
10.1107/S2056989016005843
URL
http://scripts.iucr.org/cgi-bin/paper?S2056989016005843
Keywords
crystal structure conformational restrictionchemistry

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