WO2017071871A1 - Synthèse de photo-cages libérant des cétones - Google Patents

Synthèse de photo-cages libérant des cétones Download PDF

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Publication number
WO2017071871A1
WO2017071871A1 PCT/EP2016/071685 EP2016071685W WO2017071871A1 WO 2017071871 A1 WO2017071871 A1 WO 2017071871A1 EP 2016071685 W EP2016071685 W EP 2016071685W WO 2017071871 A1 WO2017071871 A1 WO 2017071871A1
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WO
WIPO (PCT)
Prior art keywords
group
substituted
branched
linear
formula
Prior art date
Application number
PCT/EP2016/071685
Other languages
German (de)
English (en)
Inventor
Thomas Gerke
Christian Kropf
Ursula Huchel
Axel Griesbeck
Agnieszka LANDES
Original Assignee
Henkel Ag & Co. Kgaa
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from DE102015220926.1A external-priority patent/DE102015220926A1/de
Priority claimed from DE102015224955.7A external-priority patent/DE102015224955A1/de
Application filed by Henkel Ag & Co. Kgaa filed Critical Henkel Ag & Co. Kgaa
Publication of WO2017071871A1 publication Critical patent/WO2017071871A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C67/347—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to unsaturated carbon-to-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
    • C07C45/676—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton by elimination of carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Definitions

  • the present invention is in the field of the synthesis of fragrance storage materials, as for example in the field of detergents or cleaners, cosmetic products and
  • the invention relates to the preparation of specific ketones which function as photolabile fragrance storage materials.
  • Detergents or cleaners or cosmetic products usually contain fragrances that give the products a pleasant smell. In most cases, the fragrances mask the odor of the other ingredients, resulting in a pleasant odor impression for the consumer.
  • Fragrances are important constituents of the composition, in particular in the area of detergents, since the laundry should have a pleasant and if possible fresh fragrance both in the moist and in the dry state.
  • the use of fragrances is fundamentally problematic, since these are more or less volatile compounds, but nevertheless a long-lasting fragrant effect is sought.
  • those fragrances that represent the fresh and light notes of the perfume and are particularly volatile due to their high vapor pressure the desired longevity of the fragrance impression is hardly achievable.
  • Delayed fragrance release may be e.g. by carrier-bound preform of perfumes.
  • a carrier-bound preform of a fragrance is also referred to as a "pro-fragrance" or fragrance storage material
  • US Patent 6,949,680 discloses the use of certain phenyl or pyridyl ketones as photoactivatable substances that in the presence of light in a photochemical fragmentation form a terminal
  • the active substance mentioned has, for example, a fragrant or antimicrobial activity which is delayed by the photochemically induced decomposition and released over a longer period of time on a specific surface.
  • WO 2009/1 18219 A1 discloses photoactivatable substances which enable a release of cyclic terpenes or cyclic terpenoids.
  • WO 201 1/101 180 discloses the use of certain ketones as photoactivatable substances which release an active substance in the presence of light in a photochemical fragmentation.
  • the active substance mentioned has, for example, a fragrant activity, which is delayed by the photochemically induced decomposition and released over a longer period of time on a certain surface.
  • Known processes for the preparation of the herein described fragrance precursors have significant disadvantages, for example, low temperatures of -78 ° C are required, which requires a high technical effort, and on the other costly and difficult to dispose chemicals such as butyl lithium and cerium chloride must be used.
  • the object of the present invention was therefore an improved process for the preparation of photoactivatable substances which can be used as fragrance storage materials which permit the delayed release of fragrance ketones, in particular of damascone.
  • R is a hydrocarbon radical, preferably having 2 to 20 C atoms, which has at least one keto group or an ester group, preferably a keto group;
  • R1 is a linear or branched, substituted or unsubstituted alkyl, aryl or
  • Alkenyl group all of which may optionally contain one or more heteroatom (s), preferably 1 to 6 heteroatoms selected from N, O and S;
  • R 2 is hydrogen, a halogen atom, an aryl radical, -NO 2, a linear or branched, substituted or unsubstituted alkoxy group having up to 15 C atoms or a linear or branched, substituted or unsubstituted alkenyl group having up to 15 C atoms or a linear or branched, substituted or unsubstituted alkyl group having up to 15 carbon atoms or a substituted or unsubstituted aryl radical;
  • R3, R4, R5, R6 and R7 each independently represent hydrogen, a halogen atom, an amino group, -NO2, -NH-alkyl, -N (alkyl) 2, a linear or branched, substituted or unsubstituted alkoxy group having up to 15C -Atomen or a linear or branched, substituted or unsubstituted alkyl group having up to 15 C atoms, a cycloalkyl radical, an acyl radical, an aryl radical, -OH, -COY group or a quaternary ammonium radical of the formula (IV)
  • Y is hydrogen, alkyl, cycloalkyl, aryl, acyl, -OH, -Oalkyl, -NH 2 , -NH-alkyl, -N (alkyl) 2 or halogen,
  • R8, R9, R10 each independently represent H or a substituted or unsubstituted alkyl, cycloalkyl, alkenyl, aryl or acyl groups-containing radical and wherein in each case two of the radicals R8, R9, R10 may be connected to each other by ring closure; and
  • R1 1 represents a linear or branched, substituted or unsubstituted alkyl, aryl, alkylaryl, arylalkyl or alkenyl group, all optionally heteroatoms, preferably 1 to 6
  • Heteroatoms selected from N, O and S may contain, preferably a linear or branched alkyl, aryl, alkylaryl, arylalkyl or alkenyl group, or a
  • the reaction of the compounds of the formulas (II) and (III) takes place via 2 stages, in a first step the compound of the formula (II) having a strong base being able to exchange the carbon atom between the both
  • a suitable strong base is, for example, sodium hydride.
  • the reaction may be carried out in a suitable organic aprotic solvent such as dimethylsulfoxide (DMSO).
  • DMSO dimethylsulfoxide
  • the invention therefore also relates to a process which comprises the preparation of a compound of the general formula (VI)
  • the two process steps are combined, so that the invention also relates to a process for the preparation of a compound of general formula (VI), which comprises:
  • R is a hydrocarbon radical, preferably having 2 to 20 C atoms, which has at least one keto group or an ester group, preferably a keto group;
  • R1 is a linear or branched, substituted or unsubstituted alkyl, aryl or
  • Alkenyl group all of which may optionally contain one or more heteroatom (s), preferably 1 to 6 heteroatoms selected from N, O and S;
  • R 2 is hydrogen, a halogen atom, an aryl radical, -NO 2, a linear or branched, substituted or unsubstituted alkoxy group having up to 15 C atoms or a linear or branched, substituted or unsubstituted alkenyl group having up to 15 C atoms or a linear or branched chain branched, substituted or unsubstituted alkyl group having up to 15 carbon atoms or a substituted or unsubstituted aryl radical;
  • R3, R4, R5, R6 and R7 each independently represent hydrogen, a halogen atom, an amino group, -NO2, -NH-alkyl, -N (alkyl) 2, a linear or branched, substituted or unsubstituted alkoxy group having up to 15C -Atomen or a linear or branched, substituted or unsubstituted alkyl group having up to 15 C atoms, a cycloalkyl radical, an acyl radical, an aryl radical, -OH, -COY group or a quaternary ammonium radical of the formula (IV)
  • Y is hydrogen, alkyl, cycloalkyl, aryl, acyl, -OH, -Oalkyl, -NH 2 , -NH-alkyl, -N (alkyl) 2 or halogen,
  • R8, R9, R10 each independently represent H or a substituted or unsubstituted alkyl, cycloalkyl, alkenyl, aryl or acyl groups-containing radical and wherein in each case two of the radicals R8, R9, R10 may be connected to each other by ring closure; and
  • R1 1 represents a linear or branched, substituted or unsubstituted alkyl, aryl, alkylaryl, arylalkyl or alkenyl group, all optionally heteroatoms, preferably 1 to 6
  • Heteroatoms selected from N, O and S may contain, preferably a linear or branched alkyl, aryl, alkylaryl, arylalkyl or alkenyl group, or a
  • I stands for iodine
  • Fragrance storage are effective to allow the delayed release of fragrance ketones, in particular Damascone, and thereby easily accessible without the use of consuming reagents to dispose of, without low reaction temperatures and with few synthetic steps.
  • Fragrance storage materials according to the invention in a laundry treatment agent such as e.g. Detergent and fabric softener, an improved long-term odor effect of the treated laundry can be found. Furthermore, corresponding products have a particularly good storage stability.
  • the compositions according to the invention make it possible to reduce the total amount of perfume contained on average, and nevertheless to achieve odor advantages on the laundered textiles, especially with regard to the sensation of freshness.
  • the fragrance according to the invention prepared according to the general formula (I) is suitable as a fragrance for all customary fragrance ketones, in particular selected from buccoxime, iso-jasmone, methyl-beta-naphthyl ketone, musk indanone, Tonalid / musk plus, alpha Damascon, beta Damascon, delta-damascon, gamma-damascon, damascenon, damarose, methyldihydrojasmonate, menthone, carvone, camphor, fenchone, alpha-ionone, beta-ionone, gamma-methylionone called lonon, fleuramon, dihydrojasmon, cis-jasmone, 1 - (1 .2.3 .4.5.6.7.8-octahydro-2.3.8.8, -tetramethyl-2-naphthyl) ethan-1-one (Iso-E Super®
  • Methylcedrylon acetophenone, methylacetophenone, para-methoxyacetophenone, methyl-betaphthyl ketone, benzylacetone, benzophenone, para-hydroxyphenylbutanone, 3-methyl-5-propyl-2-cyclohexene-1-one (celery ketone or livescone), 6-isopropyldecahydro -2-naphton,
  • Methylheptenone 2- (2- (4-methyl-3-cyclohexen-1-yl) -propyl) cyclopentanone, 1- (p-menthene-6 (2) yl) -1-propanone, 4- (4-hydroxy-3 -methoxyphenyl) -2-butanone, 2-acetyl-3,3-dimethylnorbornane, 6,7-dihydro-1,1,2,3,3-pentamethyl-4 (5H) -indanone, 4-damascol, dulcinyl or cassion, gelson, hexalon, isocyclone E, methylcyclocitron , Methyllavendelketon, Orivon, para-tertiary
  • the ketones may preferably be selected from the damascones, carvone, gamma methyl ionone, Iso-E-Super ®, 2.4.4.7- tetramethyl-oct-6-en-3-one, Benzyl Acetone, Damascenone, methyl dihydrojasmonate, methyl, hedione, and mixtures from that. Most preferred are all damascone and damascenone.
  • the abovementioned fragrances can be bonded as the radical R to the compound of the formula (I).
  • the substituent R in the formula (I) is a hydrocarbon radical having 2 to 20 carbon atoms and having at least one keto group or an ester group.
  • the hydrocarbon radical may have, in addition to the at least one keto or ester group, further substituents.
  • the perfume ketone can be selected from those mentioned above.
  • the substituent R 2 in the formula (I) is a linear or branched, substituted or unsubstituted alkyl group having up to 6 C atoms, preferably up to 3 C atoms, in particular is a methyl radical.
  • the substituents R3, R4, R5, R6 and R7 in the formula (I) independently of one another represent hydrogen or a linear or branched, substituted or unsubstituted alkoxy group having up to 6 C atoms or a linear one or branched, substituted or unsubstituted alkyl group having up to 6 C atoms, preferably hydrogen or an alkyl group having up to 6 C atoms.
  • alkyl is in the definition of Y as well as in the
  • Cycloalkyl is corresponding cyclic alkyl radicals, preferably having 3 to 15 carbon atoms.
  • Aryl is preferably a substituted or unsubstituted aryl radical, where the aryl radical may also comprise 1 to 6 heteroatoms, such as N, O or S, as ring atoms, thus forming a heteroaryl radical, preferably C6 to C14 aryl.
  • the term also includes 5-membered heteroaryl radicals which can not be derived directly from an aryl radical by exchange of a ring C atom by a heteroatom, such as furan, thiophene or pyrrole radicals.
  • Acyl is preferably -C (O) alkyl, wherein alkyl is as defined above.
  • Substituted as used herein in reference to alkyl, alkenyl, alkoxy and acyl groups means that the corresponding group has one or more substituents replacing one or more hydrogen atoms and selected from -OR ', -NR 'R', -SR ', - C (O) R', - C (O) OR ', -C (O) NR'R', -NR'-C (O) -R ', and halogen, where R 'and R "are hydrogen or unsubstituted C1 to C10 alkyl.
  • the alkyl, aryl, acyl, alkylaryl, arylalkyl and alkenyl groups or moieties contain up to 20, preferably up to 12, carbon atoms.
  • fragrance storage substances according to the following formula (V) are particularly preferred: (V)
  • R 16 is a hydrocarbon radical having at least 5 C atoms, which in particular comprises a cyclic, optionally substituted hydrocarbon radical, preferably a cyclic, substituted alkenyl radical, in particular
  • a fragrance storage substance according to the formula (III) is particularly preferred, in which R1 is ethyl, R1 is methyl and R16 is
  • the fragrance storage materials according to the invention can be incorporated in the usual washing or makesmittelmatnces, in cosmetics and existing fragrance compositions stable. They allow a delayed release of the stored fragrances, including damascone in the alpha, beta, gamma or delta form and damascenone, in particular delta-damascenone.
  • These fragrance storage agents give usual washing or cleaning agents as well as cosmetics a particularly long lasting freshness impression. In particular, the dried, washed textile benefits from the good long-term freshness effect.
  • the slow release of the stored fragrance takes place after exposure to light (electromagnetic radiation) comprising the wavelengths of 200 to 600 nm.
  • the invention relates to a process which comprises the preparation of a compound of general formula (VI)
  • R 1 and R 2 are methyl, R 3 to R 7 are hydrogen, and R is -CH 2 -C (O) -R 17 where R 17 is a cyclic, optionally substituted Hydrocarbon radical, preferably represents a cyclic, substituted alkenyl radical, i , preferably
  • the base may be any base suitable for this purpose and known to those skilled in the art.
  • the base is a Lewis base and thus a
  • the base in aqueous solution is capable of forming hydroxide ions (OH " ), ie increasing the pH of a solution
  • the base is selected from the group consisting of
  • potassium hydroxide (KOH) Potassium hydroxide (KOH) and sodium hydroxide (NaOH).
  • the base is potassium hydroxide (KOH).
  • the invention thus also relates to processes for the preparation of a compound of the formula (VI) which comprises preparing a compound of the formula (I) by reacting a compound of the formula (II) with an iodide of the formula (III) and then reacting the compound of the formula (I) with a base to obtain the compound of the formula (VI).
  • the preferred radicals R and R 1 to R 7 listed above in connection with the compounds of the formula (I) are also preferred in the context of the compound of the formula (VI).
  • the compound of the formula (I) prepared by the process according to the invention can, according to preferred embodiments of the invention, be extracted with an organic solvent, for example cyclohexane, and / or purified by column chromatography.
  • an organic solvent for example cyclohexane
  • the product of formula (VI) obtained by reacting the compound of formula (I) with a base is reacted with a suitable organic solvent, e.g. Diethyl ester, extracted and / or purified by column chromatography.
  • a suitable organic solvent e.g. Diethyl ester
  • the processes described herein are preferably carried out at temperatures in the range of 0 to 40 ° C, preferably at room temperature, i. about 20 ° C, performed.
  • fragrance storage materials The preparation according to the invention of the fragrance storage materials is described in the example part by way of example with reference to the preparation of a fragrance containing delta-damascone fragrance. about This basic synthesis route can also be represented by the other fragrance storage substances of the general formulas (I) and (VI).

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fats And Perfumes (AREA)

Abstract

La présente invention concerne la production de cétones spéciales ayant les formules (I) et (VI), telles que définies dans la description, et fonctionnant comme des substances photolabiles renfermant un parfum.
PCT/EP2016/071685 2015-10-27 2016-09-14 Synthèse de photo-cages libérant des cétones WO2017071871A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
DE102015220926.1A DE102015220926A1 (de) 2015-10-27 2015-10-27 Ketone freisetzende Photocages
DE102015220926.1 2015-10-27
DE102015224955.7A DE102015224955A1 (de) 2015-12-11 2015-12-11 Synthese von Ketonen freisetzenden Photocages
DE102015224955.7 2015-12-11

Publications (1)

Publication Number Publication Date
WO2017071871A1 true WO2017071871A1 (fr) 2017-05-04

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011101180A1 (fr) * 2010-02-17 2011-08-25 Henkel Ag & Co. Kgaa Substances photolabiles renfermant un parfum
WO2015124671A1 (fr) * 2014-02-24 2015-08-27 Henkel Ag & Co. Kgaa Substances odoriférantes photolabiles
WO2015144484A1 (fr) * 2014-03-24 2015-10-01 Henkel Ag & Co. Kgaa Substances photolabiles de stockage de parfum

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011101180A1 (fr) * 2010-02-17 2011-08-25 Henkel Ag & Co. Kgaa Substances photolabiles renfermant un parfum
WO2015124671A1 (fr) * 2014-02-24 2015-08-27 Henkel Ag & Co. Kgaa Substances odoriférantes photolabiles
WO2015144484A1 (fr) * 2014-03-24 2015-10-01 Henkel Ag & Co. Kgaa Substances photolabiles de stockage de parfum

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
ADOLF BAEYER ET AL: "Ueber Benzoylessigsäure", BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, vol. 16, no. 2, 1 July 1883 (1883-07-01), DE, pages 2128 - 2135, XP055317191, ISSN: 0365-9496, DOI: 10.1002/cber.188301602118 *
BUNCE R A ET AL: "Functionalised carbocycles by tandem dealkoxycarbonylation-Michael addition reactions", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, US, vol. 58, no. 25, 3 December 1993 (1993-12-03), pages 7143 - 7148, XP002273309, ISSN: 0022-3263, DOI: 10.1021/JO00077A043 *
CHIU PAK-KAN ET AL: "The synthesis and chemistry of azolenines. Part 18. Preparation of 3-ethoxycarbonyl-3-pyrroles the paal-knorr reaction, and sigmatropic rearrangements involving competitive ester migrations to c-2, c-4 and n.", TETRAHEDRON, vol. 46, no. 10, 1 January 1990 (1990-01-01), AMSTERDAM, NL, pages 3439 - 3456, XP055316846, ISSN: 0040-4020, DOI: 10.1016/S0040-4020(01)81514-3 *
OLIVIER ROY ET AL: "Access to optically active linear ketones by one-pot catalytic deprotection, decarboxylation, asymmetric tautomerization from racemic benzyl [beta]-ketoesters", CHEMICAL COMMUNICATIONS - CHEMCOM., no. 6, 1 January 2001 (2001-01-01), pages 533 - 534, XP055317113, ISSN: 1359-7345, DOI: 10.1039/b009828k *
OLIVIER ROY ET AL: "Catalysed Asymmetric Protonation of Simple Linear Keto-Enolic Species - A Route to Chiral [alpha]-Arylpropionic Acids", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 2002, no. 23, 1 December 2002 (2002-12-01), DE, pages 3986 - 3994, XP055316848, ISSN: 1434-193X, DOI: 10.1002/1099-0690(200212)2002:23<3986::AID-EJOC3986>3.0.CO;2-L *

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