Alkyl ether and enol analogs of (Z)-5-decenyl acetate, a pheromone component of the turnip moth, Agrotis segetum: probing a proposed bioactive conformation for chain-elongated analogs was written by Gustavsson, Anna-Lena;Liljefors, Tommy;Hansson, Bill S.. And the article was included in Journal of Chemical Ecology in 1995.Reference of 4457-67-4 This article mentions the following:
To test a previous conclusion that chain-elongated analogs of (Z)-5-decenyl acetate, a pheromone component of the turnip moth, Agrotis segetum, adopt a loop conformation of the terminal alkyl chain in the bioactive conformation, a series of alkyl ether and enol ether analogs of 1 and (Z)-5-dodecenyl acetate have been synthesized and tested using single-cell electrophysiol. In these analogs a methylene group in positions 7 and 9 of (Z)-5-decenyl acetate and in positions 7 and 11 in (Z)-5-dodecenyl acetate have been replaced by an oxygen atom to energetically facilitate the formation of a loop conformation in the chain-elongated analogs. The electrophysiol. results in conformation with mol. mechanisms (MM2 and MM3) calculated conformational energies show that the activity decreases of the chain-elongated ether analogs are significantly smaller than that for (Z)-5-dodecenyl acetate and that these activity decreases parallel the conformational energies for a loop formation of the terminal chains in the analogs. The results support the previous conclusion that the terminal chain of chain-elongated analogs of (Z)-5-decenyl acetate adopts a loop conformation in their bioactive conformations. In the experiment, the researchers used many compounds, for example, 1-Bromo-4-methoxybutane (cas: 4457-67-4Reference of 4457-67-4).
1-Bromo-4-methoxybutane (cas: 4457-67-4) belongs to organobromine compounds. Bromine is more electronegative than carbon (2.9 vs 2.5). Consequently, the carbon in a carbon–bromine bond is electrophilic, i.e. alkyl bromides are alkylating agents. When the molecular ion is detected, the bromine and chlorine isotope patterns are very distinct, but caution is to be exercised for certain mixed chlorinated/brominated compounds, which can look similar to homohalogen patterns.Reference of 4457-67-4
Referemce:
Bromide – Wikipedia,
bromide – Wiktionary