16620-79-4

Upstream product

• 83759-48-2 C₁₁H₁₆O₂ 
• 694-98-4 norborn-5-en-2-one 
• 83759-48-2 C₁₁H₁₆O₂ 

Downstream Products

• 83759-48-2 C₁₁H₁₆O₂ 
• 694-97-3 (1S,2S,4S)-bicyclo[2.2.1]hept-5-en-2-ol 
• 2890-98-4 exo-5-norbornen-2-ol 
• 694-97-3 endo-5-norbornen-2-ol 
• 497-38-1 (1R,4S)-bicyclo[2.2.1]heptan-2-one 
• 202335-52-2 Toluene-4-sulfonic acid 2-((1S,4R)-4-propyl-cyclopent-2-enyl)-ethyl ester 
• 20350-15-6 (+)-brefeldin A 
• 120052-54-2 (1S,3S)-1-hydroxy-3-(methyl-carboxymethyl)-4-cyclopentene 
• 83759-48-2 C₁₁H₁₆O₂ 

Relevant academic research and scientific papers

Enantiomers of cis- and trans-3-(4-propyl-cyclopent-2-enyl) propyl acetate. A study on the bioactive conformation and chiral recognition of a moth sex pheromone component

The enantiomers of cis- and trans-3-(4-propyl-cyclopent-2-enyl) propyl acetate, which are conformationally constrained analogues of (Z)-5-decenyl acetate (1), a sex pheromone component of the turnip moth, Agrotis segetum, have been synthesized and tested using the elcctrophysiological single-sensillum technique. The analogues mimic a cisoid and transoid conformation of 1, respectively. In addition, the enantiomers of each of the cis- and trans-isomers are conformationally constrained analogues of enantiomeric cisoid and transoid conformations of 1. Thus, the compounds prepared and tested are well suited to investigate the nature of the bioactive conformation of the natural pheromone component 1 and the chiral sense of its interaction with the receptor. Electrophysiological single-sensillum recordings show that the activity of the most active cis-isomer, which has a (1S,4R)-configuration, is more than two orders of magnitude higher than that of the most active trans-isomer. Furthermore, the (1S,4R)-isomer is at least 100 times more active than its enantiomer. These results strongly support a previously proposed cisoid bioactive conformation of 1. Furthermore, the (1S,4R)-configuration of most active stereoisomer identifies the chiral sense of the interaction between the natural pheromone component 1 and its receptor.

DETERMINATION DE PURETE ENANTIOMERIQUE PAR RMN13C DANS LES SERIES DES BICYCLO(2.2.1.)-HEPTANE ET BICYCLO(2.2.1.)-HEPTENE

N.M.R.13C peak assignments were established for each diastereoisomeric ketal form of norbornanone (+/-), or norbornenone (+/-).This method offers an attractive route for the determination of the optical purity of these ketones.