73264-90-1

Upstream product

• 71720-83-7 (Z,Z)11,13-hexadecadien, 1-ol 
• 1214742-94-5 (Z)-1,1-diethoxyhexadec-13-en-11-yne 
• 71685-56-8 (Z,Z)-1-(2-Tetrahydropyranyloxy)-11,13-hexadiene 
• 85416-30-4 (Z)-12-Iodo-1-(2-tetrahydropyranyloxy)-11-dodecene 
• 85416-27-9 12-Iodo-1-(2-tetrahydropyranyloxy)-11-dodecyne 
• 51795-88-1 1-bromo-10-(tetrahydropyranyloxy)decane 
• 152488-40-9 1-(2-tetrahydropyranyloxy)-2-dodecyne 
• 71084-07-6 1-tetrahydropyranyloxy 11-dodecyne 
• 18202-10-3 11-dodecyn-1-ol 
• 693-58-3 1-Bromononane 
• 69064-46-6 dodec-2-yn-1-ol 
• 80625-62-3 (11E,13Z)-hexadeca-11,13-dien-1-ol 

Relevant academic research and scientific papers

New synthesis of (11Z,13Z)-11,13-Hexadecadienal, the female sex pheromone of the navel orangeworm

(11Z,13Z)-11,13-Hexadecadienal, the female sex pheromone of the navel orangeworm (Amyelois transitella), was synthesized from commercially available 10-bromo-1-decanol in a 27% overall yield (8 steps). The synthesis was achieved by using 10-iododecanal, trimethylsilylacetylene and (Z)-1-bromo-12-butene as the key building blocks, employing Sonogashira-Hagihara coupling and Brown's hydroboration-protonolysis as the key reactions. The terminal formyl group was installed in the earlier stage of the synthesis rather than in the final step. This procedure enabled the multi-gram-scale preparation of this economically important pheromone.

Synthetic pheromone compositions

The present invention provides compounds useful for preparing synthetic pheromone compositions that can be used as attractants or inhibitors of insect species. The compositions are useful in the control of navel orangeworm or meal moth insect pests.