Two stereoisomers of the rat toxicant norbormide.
The structures of two diastereoisomers of norbormide [systematic name: 5-[hydroxy(phenyl)(2-pyridyl)methyl]-8-[phenyl(2-pyridyl)methylene]-3a,4,7,7a-tetrahydro-4,7-methano-1H-isoindole-1,3(2H)-dione], viz. the unsolvated molecule, C(33)H(25)N(3)O(3), and the ethyl acetate hemisolvate, C(33)H(25)N(3)O(3).0.5C(4)H(8)O(2), have been determined unambiguously. They differ in the relative stereochemistry about the exocyclic double bond and the relative conformations of the aryl rings. Each compound exhibits both intra- and intermolecular hydrogen bonding.
Steel
Peter J
PJ
Department of Chemistry, University of Canterbury, Christchurch, New Zealand. peter.steele@canterbury.ac.nz
Brimble
Margaret A
MA
Hopkins
Brian
B
Rennison
David
D
D000818:Animals; D006860:Hydrogen Bonding; D008956:Models, Chemical; D009636:Norbornanes / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity; D051381:Rats; D013237:Stereoisomerism
D009636:Norbornanes; C005321:norbormide