Synthesis and physical properties of C18 azido-oxygenated and N-heterocyclic fatty acid derivatives

Rahmatullah, Syed I.

doi:10.5353/th_b3123238

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“…Hence, a pure sample of methyl 12-oxo-10E-octadecenoate was prepared from methyl ricinoleate (methyl 12-hydroxy-9Z-octadecenoate) (29). With reference to the proton and carbon shifts of the pure sample of methyl 12-oxo-10E-octadecenoate, the proton and carbon signals arising from compound 3a in the mixture of 3a/3b could be readily identified (by assigning the more intense signals to compound 3a, as the ratio of 3a/3b was found to be 3:2 as described above).…”

Section: Resultsmentioning

confidence: 99%

Reaction of mono‐epoxidized conjugated linoleic acid ester with boron trifluoride etherate complex

Jie

Lam

2004

Lipids

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The reaction of methyl 11,12-E-epoxy-9Z-octadecenoate (1) with boron trifluoride etherate furnished a mixture of methyl 12-oxo-10E-octadecenoate (3a) and methyl 11-oxo-9E-octadecenoate (3b) in 66% yield. Methyl 9,10-Z-epoxy-11E-octadecenoate (2) with boron trifluoride etherate furnished a mixture of methyl 9-oxo-10E-octadecenoate (4a, 45%) and methyl 10-oxo-11E-octadecenoate (4b, 19%). A plausible mechanism is proposed for these reactions, which involves the attack on the epoxy ring system by BF3, followed by deprotonation, oxo formation, and double bond migration to give a mixture of two positional alpha,beta-unsaturated C18 enone ester derivatives (3a/3b, 4a/4b). The structures of these C18 enone ester derivatives (3a/3b, 4a/4b) were identified by a combination of NMR spectroscopic and mass spectrometric analyses.

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Section: Resultsmentioning

confidence: 99%