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US 2018/0170849 A1Published application
Photolabile pro-fragrances
AssigneeHenkel AG & Co. KGaA
InventorsThomas GERKE, Christian KROPF, Ursula HUCHEL, Axel GRIESBECK, Björn PORSCHEN
Life of this patent
Estimating the term…
Abstract
A method for producing photo-cleavable fragrance pre-cursors is described, which includes potential stereoselective method steps, agents containing the fragrance pre-cursors and the use of the fragrance pre-cursors for prolonging the scent impression in the agent and on surfaces treated with said agent.
Claims17
A method for producing a ketone of the general formula (I)
- wherein R1 to R5, in each case independently of one another, stand for hydrogen, halogen, NO2—, —OH, —NR′R″R′″, or for linear, branched, or cyclic, saturated or unsaturated radicals with up to 15 carbon atoms, wherein R′, R″, and R′″, in each case independently of one another, are selected from hydrogen and up to 15 carbon atoms, wherein the carbon atoms are linear, branched, cyclic, saturated, unsaturated alkyl radicals, or combinations thereof, and wherein
- the carbon atoms of the ring of formula (I) linked to R1 and R2 or R2 and R3 can be a common component of an annealed five-, six- or seven-membered cycloalkyl, aryl, heteroaliphatic or heteroaryl ring, wherein the radicals R1 and R2 or R2 and R3, in each case independently of one another, are completely or partly an integral component of the annealed ring;
- and wherein one or more hydrogen atoms, methyl groups, methylene groups, methine groups, quaternary carbon atoms, or combinations thereof of the radicals R1 to R5 can, in each case independently of one another, be substituted by heteroatoms;
- and
- wherein R6 to R7, in each case independently of one another, stand for a secondary, tertiary, or quaternary carbon atom;
- and wherein
- Q stands for an R6 to R7-bridging substituted or unsubstituted group with up to 11 carbon atoms;
- wherein the method comprises:
- a) obtaining a ketone of the general formula (II)
- wherein the radicals R6, R7 and Q are identical to the general formula (I), with a phosphonate of the general formula (III)
- wherein R8 and R9, in each case independently of one another, stand for an alkoxy group with up to 15 carbon atoms, and R10 stands for an alkyl group with up to 10 carbon atoms, is converted to an alpha,beta-unsaturated ester of the general formula (IV)
- wherein one or more hydrogen atoms, methyl groups, methylene groups, methine groups, or quaternary carbon atoms of the radicals R8 and R9 can, in each case independently of one another, be substituted by heteroatoms,
- b) reducing the alpha,beta-unsaturated ester of the general formula (IV) obtained in step a) to an alcohol of the general formula (V)
- c) oxidizing the allyl alcohol of the general formula (V) obtained in step b) to an alpha,beta-unsaturated aldehyde of the general formula (VI)
- d) reducing the alpha,beta-unsaturated aldehyde of the general formula (VI) obtained in step c) to an aldehyde of the general formula (VII)
- e) converting the aldehyde of the general formula (VII) obtained in step d) to an alcohol of the general formula (VIII)
- wherein the radicals R1 to R5 are identical to the general formula (I) and
- f) oxidizing the alcohol of the general formula (VIII) obtained in step e) to the ketone of the general formula (I).
15 more elements
A ketone of one of the general formulae (X) or (XI),
- wherein R1 to R5, in each case independently of one another, stand for hydrogen, halogen, NO2—, —OH, —NR′R″R′″, or for linear, branched, or cyclic, saturated or unsaturated radicals with up to 15 carbon atoms, wherein R′, R″, and R′″, in each case independently of one another, are selected from hydrogen and up to 15 carbon atoms, wherein the carbon atoms are linear, branched, cyclic, saturated, unsaturated alkyl radicals, or combinations thereof, and wherein the carbon atoms of the ring of formula (I) linked to R1 and R2 or R2 and R3 can be a common component of an annealed five-, six- or seven-membered cycloalkyl, aryl, heteroaliphatic or heteroaryl ring, wherein the radicals R1 and R2 or R2 and R3, in each case independently of one another, are completely or partly an integral component of the annealed ring;
- and wherein one or more hydrogen atoms, methyl groups, methylene groups, methine groups, quaternary carbon atoms, or combinations thereof of the radicals R1 to R5 can, in each case independently of one another, be substituted by heteroatoms;
- and
- wherein R6 to R7, in each case independently of one another, stand for a secondary, tertiary, or quaternary carbon atom;
- wherein Q stands for an R6 to R7-bridging substituted or unsubstituted group with up to 11 carbon atoms, and * indicates a stereocenter, and the proportion of the represented epimer in relation to the corresponding other epimer is greater than 50%.
2 more elements
An agent comprising a ketone of the general formula (X) or (XI),
- wherein R1 to R5, in each case independently of one another, stand for hydrogen, halogen, NO2—, —OH, —NR′R″R′″, or for linear, branched, or cyclic, saturated or unsaturated radicals with up to 15 carbon atoms, wherein R′, R″, and R′″, in each case independently of one another, are selected from hydrogen and up to 15 carbon atoms, wherein the carbon atoms are linear, branched, cyclic, saturated, unsaturated alkyl radicals, or combinations thereof, and wherein the carbon atoms of the ring of formula (I) linked to R1 and R2 or R2 and R3 can be a common component of an annealed five-, six- or seven-membered cycloalkyl, aryl, heteroaliphatic or heteroaryl ring, wherein the radicals Wand R2 or R2 and R3, in each case independently of one another, are completely or partly an integral component of the annealed ring;
- and wherein one or more hydrogen atoms, methyl groups, methylene groups, methine groups, quaternary carbon atoms, or combinations thereof of the radicals R1 to R5 can, in each case independently of one another, be substituted by heteroatoms;
- and
- wherein R6 to R7, in each case independently of one another, stand for a secondary, tertiary, or quaternary carbon atom;
- wherein Q stands for an R6 to R7-bridging substituted or unsubstituted group with up to 11 carbon atoms, and * indicates a stereocenter, and the proportion of the represented epimer in relation to the corresponding other epimer is greater than 50%.
2 more elements
Dependencies are inferred from the claim text.