Synthesis and Olfactory Properties of 2‐Substituted and 2,3‐Annulated 1,4‐Dioxepan‐6‐ones

Plummer, Christopher M.; Kraft, Philip; Froese, Jordan; Hudlický, Tomáš; Rook, Trevor J.; Jones, Oliver A.H.; Hügel, Helmut

doi:10.1002/ajoc.201500233

Cited by 4 publications

(2 citation statements)

References 29 publications

(35 reference statements)

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“…Among the four diastereomers of LMdiols (Fig. 2), 2b and 2c have already been reported [14,17–20]. Conversely, the distinct characterisations of 2a and 2d remain unreported.…”

Section: Introductionmentioning

confidence: 96%

Systematic synthetic study of four diastereomerically distinct limonene-1,2-diols and their corresponding cyclic carbonates

Morikawa¹,

Yamaguchi²,

Sugimura³

et al. 2019

Beilstein J. Org. Chem.

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In order to produce versatile and potentially functional terpene-based compounds, a (R)-limonene-derived diol and its corresponding five-membered cyclic carbonate were prepared. The diol (cyclic carbonate) comprises four diastereomers based on the stereochemical configuration of the diol (and cyclic carbonate) moiety. By choosing the appropriate starting compounds (trans- and cis-limonene oxide) and conditions, the desired diastereomers were synthesised in moderate to high yields with, in most cases, high stereoselectivity. Comparison of the NMR data of the obtained diols and carbonates revealed that the four different diastereomers of each compound could be distinguished by reference to their characteristic signals.

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“…Among the four diastereomers of LMdiols (Fig. 2), 2b and 2c have already been reported [14,17–20]. Conversely, the distinct characterisations of 2a and 2d remain unreported.…”

Section: Introductionmentioning

confidence: 96%

Systematic synthetic study of four diastereomerically distinct limonene-1,2-diols and their corresponding cyclic carbonates

Morikawa¹,

Yamaguchi²,

Sugimura³

et al. 2019

Beilstein J. Org. Chem.

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“…Already, the parent skeleton 1,4-dioxepan-6-one and the analogue 2-methyl-1,4-dioxepan-6-one display a marine odor [205]. According to the hypothesis [197,206], the seven-membered ring geometry is crucial for the marine odor, which is promoted by pseudo-twisted boat conformations. A revised olfactophore model [203] has been suggested for a compound with an intense marine odor (2t) and a pseudo-half chair conformation.…”

Section: Synthetic Ingredients Of Marine Fragrancementioning

confidence: 99%

Occurrence of Marine Ingredients in Fragrance: Update on the State of Knowledge

et al. 2021

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The fragrance field of perfumes has attracted considerable scientific, industrial, cultural, and civilizational interest. The marine odor is characterized by the specific smell of sea breeze, seashore, algae, and oyster, among others. Marine odor is a more recent fragrance and is considered as one of the green and modern fragrances. The smells reproducing the marine environment are described due to their content of Calone 1951 (7-methyl-2H-1,5-benzodioxepin-3(4H)-one), which is a synthetic compound. In addition to the synthetic group of benzodioxepanes, such as Calone 51 and its derivatives, three other groups of chemical compounds seem to represent the marine smell. The first group includes the polyunsaturated cyclic ((+)-Dictyopterene A) and acyclic (giffordene) hydrocarbons, acting as pheromones. The second group corresponds to polyunsaturated aldehydes, such as the (Z,Z)-3,6-nonadienal, (E,Z)-2,6-nonadienal, which are most likely derived from the degradation of polyunsaturated fatty acids. The third group is represented by small molecules such as sulfur compounds and halogenated phenols which are regarded as the main flavor compounds of many types of seafood. This review exposes, most notably, the knowledge state on the occurrence of marine ingredients in fragrance. We also provide a detailed discussion on several aspects of essential oils, which are the most natural ingredients from various marine sources used in fragrance and cosmetics, including synthetic and natural marine ingredients.

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ChemInform Abstract: Synthesis and Olfactory Properties of 2‐Substituted and 2,3‐Annulated 1,4‐Dioxepan‐6‐ones.

et al. 2016

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Synthesis and Olfactory Properties of 2‐Substituted and 2,3‐Annulated 1,4‐Dioxepan‐6‐ones

Cited by 4 publications

References 29 publications

Systematic synthetic study of four diastereomerically distinct limonene-1,2-diols and their corresponding cyclic carbonates

Systematic synthetic study of four diastereomerically distinct limonene-1,2-diols and their corresponding cyclic carbonates

Occurrence of Marine Ingredients in Fragrance: Update on the State of Knowledge

ChemInform Abstract: Synthesis and Olfactory Properties of 2‐Substituted and 2,3‐Annulated 1,4‐Dioxepan‐6‐ones.

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