Ab initio calculations on (Z)-5-decenyl acetate, a component of the pheromone complex of Agrotis segetum (Lepidoptera: Noctuidae) and electrophysiological studies with chain elongated analogues.
Conformational analyses of (Z)-5-decenylacetate, a sex pheromone component of the turnip moth, Agrotis segetum, and double unsaturated pheromone analogues 4 and 5 have been performed by ab initio calculations using Gaussian 92. Two minima were found for a cisoid and a transoid conformer, differing for 0.03 kcal/mol only. Conformational energies of diene analogues (5Z,7E)-5,7-decadienyl acetate (4) and (3E,5Z)-3,5,-decadienyl acetate (5) were determined for conformers required to mimic spatial relationships of the cisoid conformation of the natural pheromone 2. Finally, single sensillum recording studies were carried out with chain elongated C11- to C16-pheromone analogues 6.
Bestmann
H J
HJ
Organic Chemistry Institute, University Erlangen-Nürnberg, Germany.
Roth
K D
KD
Rehefeld
C
C
Leinemann
B
B
Kern
F
F
Vostrowsky
O
O
D000085:Acetates / Q000737:chemistry*; D000200:Action Potentials; D000818:Animals; D004594:Electrophysiology; D008958:Models, Molecular; D009036:Moths / Q000737:chemistry*; D012724:Sex Attractants / Q000737:chemistry*; D013329:Structure-Activity Relationship
D000085:Acetates; D012724:Sex Attractants; C101383:5-decenyl acetate