Vanilla oceanics: Synthesis and olfactory properties of (1E)-7-(prop-1-enyl)-2H-benzo[b][1,4]dioxepin-3(4H)-ones and homologues

Philip Kraft, Kasim Popaj, Peter Müller, Michael Schär

Research output: Contribution to journalArticlepeer-review

Abstract

(1E)-7-(Prop-1-enyl)-2H-benzo[b][1,4]dioxepin-3(4H)-one was synthesized from dimethyl 2,2-[(4-allyl-1,2-phenylene)bis(oxy)]diacetate by isomerization of the double bond and Dieckmann condensation followed by saponification and decarboxylation. It possessed an intense marine, spicy-vanillic odor, and served as starting material for the synthesis of homologues by protection as 1,3-dioxolane, Katsuki-Sharpless oxidation of the benzylic double bond, Grignard reaction, and dehydration/deprotection with 50% aqueous sulfuric acid. The olfactory properties and the extremely low odor thresholds of these resulting homologues are rationalized with an improved olfactophore model.

Original languageEnglish (US)
Article numberT06910SS
Pages (from-to)3029-3036
Number of pages8
JournalSynthesis
Issue number17
DOIs
StatePublished - Sep 1 2010
Externally publishedYes

Keywords

  • Grignard reaction
  • benzodioxepinones
  • heterocycles
  • isomerization
  • odorants

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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