Efficient syntheses of insect sex pheromones emitted by the boll weevil and the red bollworm moth was written by Wollenberg, Robert H.;Peries, Rohan. And the article was included in Tetrahedron Letters in 1979.Quality Control of (E)-Dodeca-9,11-dien-1-yl acetate The following contents are mentioned in the article:
Dimedone on sequential hydrazidation, treatment with aqueous K2CO3, hydrogenation, reaction with Z-LiCH:CHOEt (I), and rearrangement gave 44% of a 1:1 mixture of male boll weevil pheromones E– and Z-cyclohexylidene monoterpenoids II. CH2:CHCH:CH(CH2)8OAc, a potent sex pheromone of the virgin female red bollworm moth, was prepared (36%) from CH2:CH(CH2)8OH by sequential tetrahydropyranylation, OsO4/NaIO4 oxidation, reaction with I, rearrangement, Wittig methylenation, deprotection, and acetylation. This study involved multiple reactions and reactants, such as (E)-Dodeca-9,11-dien-1-yl acetate (cas: 50767-78-7Quality Control of (E)-Dodeca-9,11-dien-1-yl acetate).
(E)-Dodeca-9,11-dien-1-yl acetate (cas: 50767-78-7) belongs to esters. Esters are also usually derived from carboxylic acids. It may also be obtained by reaction of acid anhydride or acid halides with alcohols or by the reaction of salts of carboxylic acids with alkyl halides. Many esters have the potential for conformational isomerism, but they tend to adopt an s-cis (or Z) conformation rather than the s-trans (or E) alternative, due to a combination of hyperconjugation and dipole minimization effects. The preference for the Z conformation is influenced by the nature of the substituents and solvent, if present. Lactones with small rings are restricted to the s-trans (i.e. E) conformation due to their cyclic structure.Quality Control of (E)-Dodeca-9,11-dien-1-yl acetate
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics