Odoriferous Cyclic Ethers via Co‐Halogenation Reaction: Facile Preparation of Nerol Oxide, Florol^®, Florol^® Methyl Ether, and Pityol^® Methyl Ether

Abstract

A series of odoriferous cyclic ethers, including nerol oxide (1), Florol (2), Florol methyl ether (3), and Pityol methyl ether (4b), were prepared by a versatile synthetic protocol based on co-halogenation with 1,3-dibromo-5,5-dimethylhydantoin (= 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; DDH) as the key step. The methodology provides a facile access to important perfumery molecules from abundantly available monoterpene alcohols.

Characterization of Volatiles and Aroma-Active Compounds in Honeybush (Cyclopia subternata) by GC-MS and GC-O Analysis

“…The following compounds were synthesized according to the literature cited (experimental details and NMR data are given in the Supporting Information): 2,6,6-trimethylcyclohex-2-enone, ( E , E )- and ( Z , E )-3,5-octadien-2-one, 5,6-epoxy-β-ionone, hexyl tiglate, benzyl tiglate, 3,4-dehydro-β-ionone, octan-5-olide, hexahydrofarnesylacetone, nerol oxide, (+)- p -menth-1-en-9-al, and cis - and trans -dehydroxylinalool oxide …”

“…The majority of identified or tentatively identified compounds were terpenoids (103; 56%), comprising terpene ketones (27 constituents), terpenes (24), terpene ethers (20), terpene alcohols (18), terpene aldehydes (7), terpene esters (6), and a terpene lactone (1). Of the nonterpenoid compound classes found in the headspace of the brews of fermented C. subternata, aldehydes (20) are the most well represented, followed by ketones (12), hydrocarbons (11), esters (9), alcohols (6), lactones (5), furans (5), carboxylic acids (4), ethers (2), and a thiazole compound (1) (Table 1).…”

A New Monoterpenoid and a New Flavonoid Glycoside from the Peels of Clausena lansium

“…The HMBC spectrum also showed that  H 7.30 (H-7) had correlations with  C 81.8 (C-2), 130.5 (C-8) and 176.4 (C-9), and  H 5.11 (H-2) had correlations with  C 130.5 (C-8) (Figure 2). The NMR data of 1 were similar to those of nerol oxide[17]. The major difference was that CH 3 -10 in nerol oxide had been Natural Product Communications Vol.…”