60428-80-0

Upstream product

• 29541-97-7 9-acetoxynonal 
• 112-19-6 10-undecenyl acetate 
• 256235-74-2 methyl dodeca-9,11-dienoate 
• 124388-99-4 1-acetoxy-9-hydroxy-dodec-11-ene 
• 108-24-7 acetic anhydride 
• 114073-59-5 (E,Z)-9,11-dodecadien-1-ol 
• 35153-10-7 11-Dodecenyl acetate 
• 85363-39-9 12-acetoxy-4-hydroxy-3-phenylseleno-1-dodecene 
• 84143-40-8 12-acetoxy-3-dodecen-1-ol 

Relevant academic research and scientific papers

Combined Lewis acid catalysts in shotgun process: A convenient synthesis of the female sex pheromone of the red-bollworm moth

The combined use of Lewis acid and distannoxane catalysts gives rise to a new variant of the shotgun process. The unwanted acetylation of a secondary homoallyl alcohol by the former catalyst is suppressed through hybridization with the latter resulting in one-pot aldehyde allylation and primary alcohol acetylation of ω-hydroxy alkanal without protection/deprotection procedures.

Synthesis of 9,11-dodecadien-1-yl acetate from aleuritic acid

9,11-Dodecadien-1-yl acetate (7), the sex pheromone of Diparopsis castanea (red bollworm moth) has been synthesized from aleuritic acid (1).

Tellurolate-Induced 1,4-Elimination of 1,4-Dibromo-2-Enes. Syntheses of 1,3-Dienes

Sodium 2-thienyltellurolate, generated in catalytic amounts from sodium borohydride and bis(2-thienyl) ditelluride, was found to efficiently debrominate 1,4-dibromo-2-olefins to 1,3-dienes under very mild reaction conditions.The required 1,4-dibromo-2-olefins were usually synthesized by allylic α,α'-bromination of olefins.Terminal olefins yielded, via allylic rearrangement, a mixture of 1,4-dibromo-2-olefins and 1,2-dibromo-3-olefins.Both these isomers were converted to 1,3-dienes (E/Z ca. 9/1) by the tellurolate reagent.The syntetic utility of the tellurolate-induced debromination reaction was demonstrated in a two-step synthesis of the main component of the red bollworm moth sex pheromone.

Ethylaluminum Dichloride Catalyzed Ene Reactions of Aldehydes with Nonnucleophilic Alkenes

Ethylaluminum dichloride, which is a strong Lewis acid and a proton scavenger, catalyzes the ene reactions of aliphatic aldehydes with nonnucleophilic alkenes.Higher aldehydes give good yields of ene adducts with terminal alkenes.Formaldehyde gives good yields of adducts with electron-deficient alkenes.This reaction has been used for the synthesis of recifeiolide, ricinelaidic acid, and the insect pheromones (E,E)-8,10-dodecadienyl acetate and (E)-9,11-dodecadienyl acetate.

REGIOREVERSED REACTIONS OF TRIMETHYLSILYL OR PHENYLSELENYL ALLYLIC CARBANION WITH CARBONYL COMPOUNDS VIA ALLYLIC ALUMINUM "ATE" COMPLEXES

Triethylaluminum "ate" complexes of trimethylsilyl and phenylselenyl allylic carbanion react with carbonyl compounds at the α-position either exclusively or predominantly.