JP2022514862A - 香料としての使用するための二環式及び三環式化合物 - Google Patents
香料としての使用するための二環式及び三環式化合物 Download PDFInfo
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- JP2022514862A JP2022514862A JP2021535279A JP2021535279A JP2022514862A JP 2022514862 A JP2022514862 A JP 2022514862A JP 2021535279 A JP2021535279 A JP 2021535279A JP 2021535279 A JP2021535279 A JP 2021535279A JP 2022514862 A JP2022514862 A JP 2022514862A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 367
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- 125000002619 bicyclic group Chemical group 0.000 title abstract description 21
- 239000000203 mixture Substances 0.000 claims abstract description 466
- 239000001257 hydrogen Substances 0.000 claims abstract description 79
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 79
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 70
- 238000000034 method Methods 0.000 claims abstract description 67
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 16
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims abstract description 11
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract description 11
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- 239000002904 solvent Substances 0.000 claims description 27
- 150000002431 hydrogen Chemical class 0.000 claims description 25
- 238000005984 hydrogenation reaction Methods 0.000 claims description 20
- 239000004094 surface-active agent Substances 0.000 claims description 19
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 14
- 239000012038 nucleophile Substances 0.000 claims description 10
- 238000006722 reduction reaction Methods 0.000 claims description 10
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
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- PUTMRZPJEVQBNJ-NAJBLILTSA-N 1-[(7R)-2,3,7-trimethyl-2,3,4,5,6,7,8,8a-octahydro-1H-naphthalen-4a-yl]ethanone Chemical compound CC1CC2C[C@@H](CCC2(CC1C)C(C)=O)C PUTMRZPJEVQBNJ-NAJBLILTSA-N 0.000 description 5
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 5
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- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000457 mentha pulegium l. herb oil Substances 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 150000005309 metal halides Chemical group 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- DILOFCBIBDMHAY-UHFFFAOYSA-N methyl 2-(3,4-dimethoxyphenyl)acetate Chemical compound COC(=O)CC1=CC=C(OC)C(OC)=C1 DILOFCBIBDMHAY-UHFFFAOYSA-N 0.000 description 1
- IPWBXORAIBJDDQ-UHFFFAOYSA-N methyl 2-hexyl-3-oxocyclopentane-1-carboxylate Chemical compound CCCCCCC1C(C(=O)OC)CCC1=O IPWBXORAIBJDDQ-UHFFFAOYSA-N 0.000 description 1
- 229960001047 methyl salicylate Drugs 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 235000019426 modified starch Nutrition 0.000 description 1
- 230000003020 moisturizing effect Effects 0.000 description 1
- 235000021281 monounsaturated fatty acids Nutrition 0.000 description 1
- 210000000214 mouth Anatomy 0.000 description 1
- 239000002324 mouth wash Substances 0.000 description 1
- 229940051866 mouthwash Drugs 0.000 description 1
- XMWRWTSZNLOZFN-UHFFFAOYSA-N musk xylene Chemical compound CC1=C(N(=O)=O)C(C)=C(N(=O)=O)C(C(C)(C)C)=C1N(=O)=O XMWRWTSZNLOZFN-UHFFFAOYSA-N 0.000 description 1
- DUNCVNHORHNONW-UHFFFAOYSA-N myrcenol Chemical compound CC(C)(O)CCCC(=C)C=C DUNCVNHORHNONW-UHFFFAOYSA-N 0.000 description 1
- 239000001627 myristica fragrans houtt. fruit oil Substances 0.000 description 1
- 229940078812 myristyl myristate Drugs 0.000 description 1
- 239000002088 nanocapsule Substances 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- WASNIKZYIWZQIP-AWEZNQCLSA-N nerolidol Natural products CC(=CCCC(=CCC[C@@H](O)C=C)C)C WASNIKZYIWZQIP-AWEZNQCLSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 150000007823 ocimene derivatives Chemical class 0.000 description 1
- WRPMUZXHQKAAIC-CZIZESTLSA-N octadecyl (e)-octadec-9-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCCCCCC\C=C\CCCCCCCC WRPMUZXHQKAAIC-CZIZESTLSA-N 0.000 description 1
- GAQPWOABOQGPKA-UHFFFAOYSA-N octadecyl docosanoate Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCCCCCCCCC GAQPWOABOQGPKA-UHFFFAOYSA-N 0.000 description 1
- NKBWPOSQERPBFI-UHFFFAOYSA-N octadecyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCCCCCC NKBWPOSQERPBFI-UHFFFAOYSA-N 0.000 description 1
- IEDOGKKOPNRRKW-UHFFFAOYSA-N octadecyl tetradecanoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCC IEDOGKKOPNRRKW-UHFFFAOYSA-N 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-M oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC([O-])=O ZQPPMHVWECSIRJ-KTKRTIGZSA-M 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- BARWIPMJPCRCTP-UHFFFAOYSA-N oleic acid oleyl ester Natural products CCCCCCCCC=CCCCCCCCCOC(=O)CCCCCCCC=CCCCCCCCC BARWIPMJPCRCTP-UHFFFAOYSA-N 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- VWMVAQHMFFZQGD-UHFFFAOYSA-N p-Hydroxybenzyl acetone Natural products CC(=O)CC1=CC=C(O)C=C1 VWMVAQHMFFZQGD-UHFFFAOYSA-N 0.000 description 1
- OJEQSSJFSNLMLB-UHFFFAOYSA-N p-Tolyl phenylacetate Chemical compound C1=CC(C)=CC=C1OC(=O)CC1=CC=CC=C1 OJEQSSJFSNLMLB-UHFFFAOYSA-N 0.000 description 1
- ZYTMANIQRDEHIO-UHFFFAOYSA-N p-menth-8-en-3-ol Chemical compound CC1CCC(C(C)=C)C(O)C1 ZYTMANIQRDEHIO-UHFFFAOYSA-N 0.000 description 1
- JYTMDBGMUIAIQH-ZPHPHTNESA-N palmityl oleate Chemical compound CCCCCCCCCCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC JYTMDBGMUIAIQH-ZPHPHTNESA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- JYVLIDXNZAXMDK-UHFFFAOYSA-N pentan-2-ol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 description 1
- 239000001024 permanent hair color Substances 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- JDQVBGQWADMTAM-UHFFFAOYSA-N phenethyl isobutyrate Chemical compound CC(C)C(=O)OCCC1=CC=CC=C1 JDQVBGQWADMTAM-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 229940100595 phenylacetaldehyde Drugs 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000010665 pine oil Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000001738 pogostemon cablin oil Substances 0.000 description 1
- 229920001522 polyglycol ester Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229940068965 polysorbates Drugs 0.000 description 1
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- GTVITUZSWANKRK-UHFFFAOYSA-N propan-2-yloxycyclododecane Chemical compound CC(C)OC1CCCCCCCCCCC1 GTVITUZSWANKRK-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 239000001327 prunus amygdalus amara l. extract Substances 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- JSASXSHMJYRPCM-UHFFFAOYSA-N r-3-(methylthio)-1-hexanol Chemical compound CCCC(SC)CCO JSASXSHMJYRPCM-UHFFFAOYSA-N 0.000 description 1
- NJGBTKGETPDVIK-UHFFFAOYSA-N raspberry ketone Chemical compound CC(=O)CCC1=CC=C(O)C=C1 NJGBTKGETPDVIK-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 229930007790 rose oxide Natural products 0.000 description 1
- 239000010668 rosemary oil Substances 0.000 description 1
- 229940058206 rosemary oil Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 238000009991 scouring Methods 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000001026 semi permanent hair color Substances 0.000 description 1
- 230000008786 sensory perception of smell Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 230000009759 skin aging Effects 0.000 description 1
- 239000002884 skin cream Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 229940087124 spike lavender oil Drugs 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940094908 stearyl myristate Drugs 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- OHEFFKYYKJVVOX-UHFFFAOYSA-N sulcatol Natural products CC(O)CCC=C(C)C OHEFFKYYKJVVOX-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 229960003080 taurine Drugs 0.000 description 1
- 239000010677 tea tree oil Substances 0.000 description 1
- 229940111630 tea tree oil Drugs 0.000 description 1
- AVKVDDQTHIQFSC-UHFFFAOYSA-N tetradecyl docosanoate Chemical compound CCCCCCCCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCCCCC AVKVDDQTHIQFSC-UHFFFAOYSA-N 0.000 description 1
- DHZWALZKPWZSMA-UHFFFAOYSA-N tetradecyl oleate Natural products CCCCCCCCCCCCCCOC(=O)CCCCCCCC=CCCCCCCCC DHZWALZKPWZSMA-UHFFFAOYSA-N 0.000 description 1
- DZKXJUASMGQEMA-UHFFFAOYSA-N tetradecyl tetradecanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCC DZKXJUASMGQEMA-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 239000001789 thuja occidentalis l. leaf oil Substances 0.000 description 1
- 239000010678 thyme oil Substances 0.000 description 1
- 229940098465 tincture Drugs 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000015961 tonic Nutrition 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 229960000716 tonics Drugs 0.000 description 1
- 239000000606 toothpaste Substances 0.000 description 1
- 229940034610 toothpaste Drugs 0.000 description 1
- MBDOYVRWFFCFHM-UHFFFAOYSA-N trans-2-hexenal Natural products CCCC=CC=O MBDOYVRWFFCFHM-UHFFFAOYSA-N 0.000 description 1
- CRDAMVZIKSXKFV-UHFFFAOYSA-N trans-Farnesol Natural products CC(C)=CCCC(C)=CCCC(C)=CCO CRDAMVZIKSXKFV-UHFFFAOYSA-N 0.000 description 1
- XJPBRODHZKDRCB-UHFFFAOYSA-N trans-alpha-ocimene Natural products CC(=C)CCC=C(C)C=C XJPBRODHZKDRCB-UHFFFAOYSA-N 0.000 description 1
- DKZBBWMURDFHNE-UHFFFAOYSA-N trans-coniferylaldehyde Natural products COC1=CC(C=CC=O)=CC=C1O DKZBBWMURDFHNE-UHFFFAOYSA-N 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000000165 tricyclic carbocycle group Chemical group 0.000 description 1
- WKSPQBFDRTUGEF-UHFFFAOYSA-N tridec-2-enenitrile Chemical compound CCCCCCCCCCC=CC#N WKSPQBFDRTUGEF-UHFFFAOYSA-N 0.000 description 1
- DBWSGRFEGVADLQ-UHFFFAOYSA-N trideca-3,12-dienenitrile Chemical compound C=CCCCCCCCC=CCC#N DBWSGRFEGVADLQ-UHFFFAOYSA-N 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- FAGMGMRSURYROS-UHFFFAOYSA-M trihexadecyl(methyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(CCCCCCCCCCCCCCCC)CCCCCCCCCCCCCCCC FAGMGMRSURYROS-UHFFFAOYSA-M 0.000 description 1
- HETFMJQWNWIBPN-UHFFFAOYSA-N undec-2-enenitrile Chemical compound CCCCCCCCC=CC#N HETFMJQWNWIBPN-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 239000001846 viola odorata l. leaf absolute Substances 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 239000001529 viverra civetta schreber and viverra zibeth a schreber absolute Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
- 239000009637 wintergreen oil Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- ZFNVDHOSLNRHNN-UHFFFAOYSA-N xi-3-(4-Isopropylphenyl)-2-methylpropanal Chemical compound O=CC(C)CC1=CC=C(C(C)C)C=C1 ZFNVDHOSLNRHNN-UHFFFAOYSA-N 0.000 description 1
- QRPLZGZHJABGRS-UHFFFAOYSA-N xi-5-Dodecanolide Chemical compound CCCCCCCC1CCCC(=O)O1 QRPLZGZHJABGRS-UHFFFAOYSA-N 0.000 description 1
- WGPCZPLRVAWXPW-UHFFFAOYSA-N xi-Dihydro-5-octyl-2(3H)-furanone Chemical compound CCCCCCCCC1CCC(=O)O1 WGPCZPLRVAWXPW-UHFFFAOYSA-N 0.000 description 1
- PHXATPHONSXBIL-UHFFFAOYSA-N xi-gamma-Undecalactone Chemical compound CCCCCCCC1CCC(=O)O1 PHXATPHONSXBIL-UHFFFAOYSA-N 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 229910000859 α-Fe Inorganic materials 0.000 description 1
- PFSTYGCNVAVZBK-KVDYQJCMSA-N α-sinensal Chemical compound O=CC(\C)=C/CCC(/C)=C/C\C=C(\C)C=C PFSTYGCNVAVZBK-KVDYQJCMSA-N 0.000 description 1
- NOPLRNXKHZRXHT-PVMFERMNSA-N β-sinensal Chemical compound O=CC(\C)=C/CCC(/C)=C/CCC(=C)C=C NOPLRNXKHZRXHT-PVMFERMNSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/29—Saturated compounds containing keto groups bound to rings
- C07C49/313—Saturated compounds containing keto groups bound to rings polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/29—Saturated compounds containing keto groups bound to rings
- C07C49/313—Saturated compounds containing keto groups bound to rings polycyclic
- C07C49/323—Saturated compounds containing keto groups bound to rings polycyclic having keto groups bound to condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/527—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings
- C07C49/553—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/14—All rings being cycloaliphatic
- C07C2602/26—All rings being cycloaliphatic the ring system containing ten carbon atoms
- C07C2602/28—Hydrogenated naphthalenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/60—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members
- C07C2603/66—Ring systems containing bridged rings containing three rings containing at least one ring with less than six members containing five-membered rings
- C07C2603/68—Dicyclopentadienes; Hydrogenated dicyclopentadienes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
Abstract
Description
の基を表し、
R1a及びR1bは、互いに独立して、水素若しくはメチルから選択され、又はR1aは、R1bと一緒になってメチレン若しくはエチレン基を形成し、
R2、R3a、R3b、R4、R5a及びR5bは、互いに独立して、水素又はメチルから選択され、
R6は、水素、メチル又はエチルから選択され、
R7は、選択されたメチル又はエチルである)
の化合物に関する。
(i)一般式(II)
の基を表し、
R2、R5a及びR5bは、互いに独立して、水素又はメチルから選択され、
R6は、水素、メチル又はエチルから選択される)
の化合物を、一般式(III)
R1a及びR1bは、互いに独立して、水素若しくはメチルから選択され、又はR1aは、R1bと一緒になってメチレン若しくはエチレン基を形成し、
R3a、R3b及びR4は、互いに独立して、水素又はメチルから選択される)
のジエン化合物と、触媒の存在下で反応させて、一般式(I)(式中、R3a及びR3b基を有する炭素原子の間の破線は、二重結合であり、XはX1基を表す)の化合物を得る工程、
並びに任意選択で以下の工程:
(ii.a)工程(i)で得られた化合物のC=C二重結合を、水素化触媒の存在下で、水素で選択的触媒水素化して、一般式(I)(式中、破線は単結合を表し、XはX1基を表す)の化合物を得る工程、
又は
(ii.b)工程(i)で得られた化合物のC=C二重結合及びC=O二重結合を、水素化触媒の存在下で、水素で触媒水素化して、一般式(I)(式中、破線は単結合を表し、XはX2基を表す)の化合物を得る工程、
(iii.a)工程(i)で得られた化合物、若しくは工程(ii.a)で得られた化合物を、カルボニル基のヒドロキシル基への還元反応に供して、一般式(I)(式中、破線は、互いに独立して単結合又は二重結合を表し、XはX2基を表す)の化合物を得る工程、
又は
(iii.b)工程(i)で得られた化合物、若しくは工程(ii.a)で得られた化合物を、メチル求核試薬若しくはエチル求核試薬と反応させて、一般式(I)(式中、破線は、互いに独立して単結合又は二重結合を表し、XはX3基を表す)の化合物を得る工程
のうちの1つ又は2つを含む、方法に関する。
(i')一般式(II')
の基を表し、
R1a及びR1bは、互いに独立して、水素若しくはメチルから選択され、又はR1aは、R1bと一緒になってメチレン若しくはエチレン基を形成し、
R3a、R3b及びR4は、互いに独立して、水素又はメチルから選択され、
R6は、水素、メチル又はエチルから選択される)
の化合物を、一般式(III')
R2、R5a及びR5bは、互いに独立して、水素又はメチルから選択される)
のジエン化合物と触媒の存在下で反応させて、一般式(I)(式中、R2及びR5b基を有する炭素原子の間の破線は、二重結合であり、XはX1基を表す)の化合物を得る工程、
並びに任意選択で以下の工程:
(ii'.a)工程(i')で得られた化合物のC=C二重結合を、水素化触媒の存在下で、水素で選択的触媒水素化して、一般式(I)(式中、破線は単結合を表し、XはX1基を表す)の化合物を得る工程、
又は
(ii'.b)工程(i')で得られた化合物のC=C二重結合及びC=O二重結合を、水素化触媒の存在下で、水素で触媒水素化して、一般式(I)(式中、破線は単結合を表し、XはX2基を表す)の化合物を得る工程、
(iii'.a)工程(i')で得られた化合物、若しくは工程(ii'.a)で得られた化合物を、カルボニル基のヒドロキシル基への還元反応に供して、一般式(I)(式中、破線は、互いに独立して単結合又は二重結合を表し、XはX2基を表す)の化合物を得る工程、
又は
(iii'.b)工程(i')で得られた化合物、若しくは工程(ii'.a)で得られた化合物を、メチル求核試薬若しくはエチル求核試薬と反応させて、一般式(I)の化合物(式中、破線は、互いに独立して単結合又は二重結合を表し、XはX3基を表す)を得る工程
のうちの1つ又は2つを含む、方法に関する。
XはX1基、特に-(C=O)CH3を表し、
R2はメチルであり、
R6は、メチル又はエチル、特にメチルであり、
R5a及びR5b基の両方が水素である。
R3a及びR3b基を有する炭素原子の間の破線が、単結合又は二重結合を表し、
Xが、式X1からX3
の基を表し、
Xが、特にX1、とりわけ-(C=O)CH3であり、
R1aが、水素又はメチルから選択され、
R1bが水素であり、又は
R1aが、R1bと一緒になってメチレン若しくはエチレン基を形成し、
1、2又は3個のR2、R3a、R3b、R4、R5a及びR5b基が、互いに独立して、メチルである一方、その他が水素であり、
R6が、メチル又はエチル、特にメチルであり、
R7が、メチル又はエチル、特にメチルである、
一般式(I')の化合物、その混合物、その立体異性体及びその立体異性体の混合物が好ましい。
R3a及びR3b基を有する炭素原子の間の破線は、単結合又は二重結合を表し、
Xは、-(C=O)CH3又は-CH(OH)CH3、特に-(C=O)CH3から選択され、
R1a及びR1bは水素であり、又はR1aは、R1bと一緒になってメチレン若しくはエチレン基を形成し、
R2、R3a、R3b及びR4は、互いに独立して、水素又はメチルから選択され、
R5a及びR5bは水素であり、
R6は、メチル又はエチルである)
の化合物及びその混合物、その立体異性体及びその立体異性体の混合物に関する。
Xが、-(C=O)CH3又は-CH(OH)CH3から選択され、
R1a及びR1bが水素であり、又はR1aが、R1bと一緒になってメチレン基を形成し、
R3a、R3b及びR4が、互いに独立して、水素及びメチルからなる群から選択される、
化合物及びその混合物、その立体異性体及びその立体異性体の混合物が特に好ましい。
破線は、単結合又は二重結合を表し、
Xは、-(C=O)CH3又は-CH(OH)CH3から選択され、
R1a及びR1bは水素であり、又はR1aは、R1bと一緒になってメチレン基を形成し、
R3a、R3b及びR4は、互いに独立して、水素及びメチルからなる群から選択される)
の化合物、その混合物、その立体異性体及びその立体異性体の混合物に関する。
破線が、単結合又は二重結合を表し、
Xが、-(C=O)CH3又は-CH(OH)CH3から選択され、特に-(C=O)CH3であり、
R1a及びR1bが水素であり、又はR1aが、R1bと一緒になってメチレン基を形成し、
R3a及びR3bが、互いに独立して、水素又はメチルであり、
R4が水素である、
一般式(I.a-R)の化合物、その混合物、その立体異性体及びその立体異性体の混合物に関する。
1-(7-メチル-1,5,6,7,8,8a-ヘキサヒドロ-1,4-メタノナフタレン-4a(4H)-イル)エタン-1-オン、
1-(7-メチルオクタヒドロ-1,4-メタノナフタレン-4a(2H)-イル)エタン-1-オン、
1-(2,7-ジメチル-1,3,4,5,8,8a-ヘキサヒドロナフタレン-4a(2H)-イル)エタン-1-オン、
1-(2,7-ジメチルオクタヒドロナフタレン-4a(2H)-イル)エタン-1-オン、
1-(2,6,7-トリメチル-1,3,4,5,8,8a-ヘキサヒドロナフタレン-4a(2H)-イル)エタン-1-オン、
1-(2,3,7-トリメチルオクタヒドロナフタレン-4a(2H)-イル)エタン-1-オン及び
1-(1,5,6,7,8,8a-ヘキサヒドロ-1,4-メタノナフタレン-4a(4H)-イル)エタン-1-オン、
特に
1-((7-メチル-1,5,6,7,8,8a-ヘキサヒドロ-1,4-メタノナフタレン-4a(4H)-イル)エタン-1-オン、
1-(7-メチルオクタヒドロ-1,4-メタノナフタレン-4a(2H)-イル)エタン-1-オン、
1-(2,7-ジメチル-1,3,4,5,8,8a-ヘキサヒドロナフタレン-4a(2H)-イル)エタン-1-オン、
1-(2,7-ジメチルオクタヒドロナフタレン-4a(2H)-イル)エタン-1-オン、
1-(2,6,7-トリメチル-1,3,4,5,8,8a-ヘキサヒドロナフタレン-4a(2H)-イル)エタン-1-オン及び
1-(2,3,7-トリメチルオクタヒドロナフタレン-4a(2H)-イル)エタン-1-オン
である。
1-((7R)-7-メチル-1,5,6,7,8,8a-ヘキサヒドロ-1,4-メタノナフタレン-4a(4H)-イル)エタン-1-オン、
1-((7R)-7-メチルオクタヒドロ-1,4-メタノナフタレン-4a(2H)-イル)エタン-1-オン、
1-((2R)-2,7-ジメチル-1,3,4,5,8,8a-ヘキサヒドロナフタレン-4a(2H)-イル)エタン-1-オン、
1-((2R)-2,7-ジメチルオクタヒドロナフタレン-4a(2H)-イル)エタン-1-オン、
1-((2R)-2,6,7-トリメチル-1,3,4,5,8,8a-ヘキサヒドロナフタレン-4a(2H)-イル)エタン-1-オン、
1-((7R)-2,3,7-トリメチルオクタヒドロナフタレン-4a(2H)-イル)エタン-1-オン及び
1-(1,5,6,7,8,8a-ヘキサヒドロ-1,4-メタノナフタレン-4a(4H)-イル)エタン-1-オンであり、
特に
1-((7R)-7-メチル-1,5,6,7,8,8a-ヘキサヒドロ-1,4-メタノナフタレン-4a(4H)-イル)エタン-1-オン、
1-((7R)-7-メチルオクタヒドロ-1,4-メタノナフタレン-4a(2H)-イル)エタン-1-オン、
1-((2R)-2,7-ジメチル-1,3,4,5,8,8a-ヘキサヒドロナフタレン-4a(2H)-イル)エタン-1-オン、
1-((2R)-2,7-ジメチルオクタヒドロナフタレン-4a(2H)-イル)エタン-1-オン、
1-((2R)-2,6,7-トリメチル-1,3,4,5,8,8a-ヘキサヒドロナフタレン-4a(2H)-イル)エタン-1-オン及び
1-((7R)-2,3,7-トリメチルオクタヒドロナフタレン-4a(2H)-イル)エタン-1-オン
である。
- 式(I)の化合物若しくは2種以上の一般式(I)の化合物の混合物、又はその立体異性体若しくは2種以上のその立体異性体の混合物、並びに
- 少なくとも1種のさらなる香料及び/又は非香料キャリア、ここで非香料キャリアが、界面活性剤、油成分、及び溶媒からなる群から特に選択される、
を含む。
ゲラニルアセテート(3,7-ジメチル-2,6オクタジエン-1イルアセテート)、アルファ-ヘキシルシンナムアルデヒド、2-フェノキシエチルイソブチレート(Phenirat1)、ジヒドロミルセノール(2,6-ジメチル-7-オクテン-2-オール)、メチルジヒドロジャスモネート(好ましくは、シス型異性体の含量が60重量%超である)(Hedione9、Hedione HC9)、4,6,6,7,8,8-ヘキサメチル-1,3,4,6,7,8-ヘキサヒドロシクロペンタ[g]ベンゾピラン(Galaxolid3)、テトラヒドロリナロオール(3,7-ジメチルオクタン-3-オール)、エチルリナロオール、ベンジルサリチレート、2-メチル-3-(4-tert-ブチルフェニル)プロパナール(Lysmeral2)、シンナミルアルコール、4,7-メタノ-3a,4,5,6,7,7a-ヘキサヒドロ-5-インデニルアセテート及び/又は4,7-メタノ-3a,4,5,6,7,7a-ヘキサヒドロ-6-インデニルアセテート(Herbaflorat1)、シトロネロール、シトロネリルアセテート、テトラヒドロゲラニオール、バニリン、リナリルアセテート、スチロリルアセテート(1-フェニルエチルアセテート)、オクタヒドロ-2,3,8,8-テトラメチル-2-アセトナフトン及び/又は2-アセチル-1,2,3,4,6,7,8-オクタヒドロ-2,3,8,8-テトラメチルナフタレン(Iso E Super3)、ヘキシルサリチレート、4-tert-ブチルシクロヘキシルアセテート(Oryclone1)、2-tert-ブチルシクロヘキシルアセテート(Agrumex HC1)、アルファ-イオノン(4-(2,2,6-トリメチル-2-シクロヘキセン-1-イル)-3-ブテン-2-オン)、n-アルファ-メチルイオノン、アルファ-イソメチルイオノン、クマリン、テルピニルアセテート、2-フェニルエチルアルコール、4-(4-ヒドロキシ-4-メチルペンチル)-3-シクロヘキセンカルボキサルデヒド(Lyral3)、アルファ-アミルシンナムアルデヒド、エチレンブラシレート、(E)-及び/又は(Z)-3-メチルシクロペンタデカ-5-エノン(Muscenon9)、15-ペンタデカ-11-エノリド及び/又は15-ペンタデカ-12-エノリド(Globalide1)、15-シクロペンタデカノリド(Macrolide1)、1-(5,6,7,8-テトラヒドロ-3,5,5,6,8,8-ヘキサメチル-2-ナフタレニル)エタノン(Tonalid10)、2-イソブチル-4-メチルテトラヒドロ-2H-ピラン-4-オール(Florol9)、2-エチル-4-(2,2,3-トリメチル-3-シクロペンテン-1-イル)-2-ブテン-1-オール(Sandolen1)、cis-3-ヘキセニルアセテート、trans-3-ヘキセニルアセテート、trans-2/cis-6-ノナジエノール、2,4-ジメチル-3-シクロヘキセンカルボキサルデヒド(Vertocitral1)、2,4,4,7-テトラメチルオクタ-6-エン-3-オン(Claritone1)、2,6-ジメチル-5-ヘプテン-1-アール(Melonal2)、ボルネオール、3-(3-イソプロピルフェニル)ブタナール(Florhydral2)、2-メチル-3-(3,4-メチレンジオキシフェニル)プロパナール(Helional3)、3-(4-エチルフェニル)-2,2-ジメチルプロパナール(Florazon1)、7-メチル-2H-1,5-ベンゾジオキセピン-3(4H)-オン(Calone)、3,3,5-トリメチルシクロヘキシルアセテート(好ましくは、シス型異性体の含量が、70重量%以上である)及び2,5,5-トリメチル-1,2,3,4,4a,5,6,7-オクタヒドロナフタレン-2-オール(Ambrinol S1)からなる群から選択される1種の香料、好ましくは2種、3種、4種、5種、6種、7種又は8種以上の香料であってよい。したがって、本発明の文脈において、上記香料(複数可)は、好ましくは、上に定義されたような、式(I)の化合物若しくは2種以上の式(I)の化合物の混合物、又はその立体異性体若しくはその立体異性体の混合物と組み合わせられる。
1ドイツ、Symrise GmbHの商標、
2BASF SEの商標、
3アメリカ、International Flavors & Fragrances Inc.の商標、
9スイス、Firmenich S.A.の商標、
10オランダ、PFW Aroma Chemicals B.V.の商標。
を挙げることができる。
GC:ガスクロマトグラフィー
MTBE:メチルtert-ブチルエーテル
EtOAc:酢酸エチル
生成物の純度及び同一性は、GC、1H-NMR(CDCl3、500MHz)及び/又は13C-NMR(125MHz、CDCl3)により判定された。
1.1 1-((2R)-2,6,7-トリメチル-1,3,4,5,8,8a-ヘキサヒドロナフタレン-4a(2H)-イル)エタン-1-オンの調製
温度計及び250ml滴下漏斗を備えた500mL三口丸底フラスコ中で、15g(108.5mmol)の1-[(4R)-4-メチルシクロヘキセン-1-イル]エタノンを、AlCl3(1.5g)及びトルエン(200mL)と合わせた。トルエン(100mL)中の2,3-ジメチル-1,3-ブタジエン(18.2g、221.6mmol)の溶液を、滴下漏斗を通し、4hかけてゆっくり添加した。反応を室温でさらに48時間撹拌した。水(100mL)を、反応混合物に添加して、これをクエンチし、すべてのゲル状材料が溶解するまで酢酸(50%)を添加した。MTBE(100mL)を添加し、続いて相分離した。MTBEをさらに100mLを使用して、再び水相を抽出した。合わせた有機相を水/ブライン(1/1、100mL)で再び洗浄し、続いてNa2CO3(10%)でpH8まで中和した。有機相をNa2SO4固体で乾燥させた。濾過後、濃縮により、粗生成物32gを得た。純粋な生成物を、カラムクロマトグラフィー(シリカゲル、EtOAc/ヘキサン)を通して収率13gの無色液体として得た。生成物の同定は、1H-NMR及び13C-NMRにより確認した。
1H-NMR (CDCl3, 500 MHz): δ 1.69 (d, J = 6.5Hz, 3H, -CH3), 0.88-0.95 (m, 1H, -CH-), 1.15-1.20 (m, 1H, -CH-), 1.42-1.51 (m, 2H, -CH2-), 1.59 (s, J = 11Hz, 6H, -CH3), 1.62-1.79 (m, 4H, -CH2-), 1.88-2.01 (m, 4H, -CH2-), 2.14 (d, J = 2.5Hz, 3H, -CH3).
13C-NMR (125 MHz, CDCl3): δ 18.7, 18.9, 21.6, 24.8, 26.0, 28.0, 31.2, 31.3, 34.2, 36.1, 39.4, 51.1, 121.4, 124.0, 213.7.
500mLオートクレーブParr反応器中で、3.1g(14.1mmol)の例1.1のディールス-アルダー付加体、Pd(C)(150mg)及びMeOH(50mL)を合わせた。反応器に、次いで水素を30barの圧力まで入れた。反応をGCによりモニターし、反応の撹拌を室温で36時間、50~60℃でさらに3時間続けた。反応混合物は、セライトを通して濾過し、濃縮して粗還元生成物2.6gを得た。
2種の主異性体の混合物:1H-NMR (CDCl3, 500 MHz): δ 0.71-0.91 (m, 9H, -CH3), 0.93-1.02 (m, 2H, -CH2-), 1.08-1.58 (m, 9H, -CH-, -CH2-), 1.70-1.89 (m, 3H, -CH2-,-CH-,), 2.12 (s, 3H, -CH3).
13C-NMR (125 MHz, CDCl3): δ 11.5, 16.4, 19.4, 19.7, 19.8, 22.6, 24.6, 24.7, 26.0, 26.1, 26.8, 26.9, 27.0, 28.3, 29.5, 32.8, 33.0, 33.8, 34.9, 35.6, 37.0, 37.1, 37.9, 37,94, 39.0, 44.2, 52.7, 52.9, 214.1, 224.1.
1-((2R)-2,7-ジメチル-1,3,4,5,8,8a-ヘキサヒドロナフタレン-4a(2H)-イル)エタン-1-オンは、1-[(4R)-4-メチルシクロヘキセン-1-イル]エタノンを2-メチル-1,3-ブタジエンと反応させることを除いて、例1.1に従って調製した。生成物の同定は、1H-NMR及び13C-NMRにより確認した。
1H-NMR (CDCl3, 500 MHz): δ 0.85 (d, J = 8.5Hz, 3H, -CH3), 0.91-0.98 (m, 1H, -CH-), 1.16-1.27 (m, 2H, -CH2-), 1.41-1.53 (m, 2H, -CH2-), 1.56-1.60 (m, 1H, -CH-), 1.63 (s, 3H, -CH3), 1.67-1.76 (m, 2H, -CH2-), 1.87-1.92 (m, 2H, -CH2-), 2.03-2.10 (m, 1H, -CH-), 2.15 (s, 3H, -CH3), 2.37 (m, 1H, -CH-), 5.24-5.26 (m, 1H, -CH=).
13C-NMR (125 MHz, CDCl3): δ 21.6, 23.3, 24.8, 26.0, 28.0, 30.9, 31.3, 31.6, 32.4, 36.2, 50.0, 116.9, 132.4, 213.8.
1-((2R)-2,7-ジメチルオクタヒドロナフタレン-4a(2H)-イル)エタン-1-オンは、例1.2に記載されている反応手順を使用することにより、例1.3で得られた反応生成物から調製した。望ましい生成物を、2種の主異性体の混合物として得た。生成物の同定は、1H-NMR及び13C-NMRにより確認した。
主異性体:1H-NMR (CDCl3, 500 MHz): δ 0.76 (d, J = 6.5Hz, 3H, -CH3), 0.90 (d, J = 6.5Hz, 3H, -CH3), 1.04-1.21 (m, 3H, -CH-, -CH2-), 1.28-1.41 (m, 4H, -CH2-,), 1.47-1.64 (m, 5H, -CH2-, -CH-), 1.70-1.82 (m, 2H, -CH2-), 2.13 (s, 3H, -CH3), 2.20-2.23 (m, 1H, -CH-).
13C-NMR (125 MHz, CDCl3): δ 22.5, 22.6, 24.7, 26.1, 26.2, 30.0, 32.7, 32.8, 35.2, 35.5, 36.5, 38.3, 51.7, 214.5.
1-((7R)-7-メチル-1,5,6,7,8,8a-ヘキサヒドロ-1,4-メタノナフタレン-4a(4H)-イル)エタン-1-オンは、1-[(4R)-4-メチルシクロヘキセン-1-イル]エタノンをシクロペンタ-1,3-ジエンと反応させることを除いて、例1.1に従って調製した。望ましい生成物を、2種の異性体の混合物として得た。生成物の同定は、1H-NMR及び13C-NMRにより確認した。
主異性体:1H-NMR (CDCl3, 500 MHz): δ 0.55-0.60 (m, 1H, -CH-), 0.86 (dd, J = 7.0Hz, J = 1.5Hz, 3H, -CH2-), 1.00-1.06 (m, 1H, -CH-), 1.12-1.18 (m, 2H, -CH2-), 1.29-1.35 (m, 2H, -CH2-), 1.64-1.68 (m, 2H, -CH3),1.78 (d, J = 13.0Hz, 1H, -CH-), 2.21 (d, J = 1.0Hz, 3H, -CH3), 2.67 (s, 1H, -CH-), 2.84-2.87 (m, 1H, -CH-), 2.92 (s, 1H, -CH-), 6.15-6.17 (m, 1H, -CH=), 6.25-6.26 (m, 1H, -CH=).
13C-NMR (125 MHz, CDCl3): δ 22.5, 25.4, 25.9, 28.0, 28.2, 33.0, 34.4, 46.8, 47.3, 50.0, 60.1, 134.6, 138.5, 212.3.
1-((7R)-7-メチルオクタヒドロ-1,4-メタノナフタレン-4a(2H)-イル)エタン-1-オンは、例1.2に記載されている反応手順を使用することにより、例1.5で得られた反応生成物から調製した。望ましい生成物を、異性体の混合物として得た。生成物の同定は、1H-NMR及び13C-NMRにより確認した。
主異性体:1H-NMR (CDCl3, 500 MHz): δ 0.52-0.61 (m, 1H, -CH-), 0.84-0.90 (m, 3H, -CH3), 1.07-1.25 (m, 4H, -CH2-), 1.34-1.43 (m, 1H, -CH-), 1.47-1.55 (m, 3H, -CH2-), 1.63-1.72 (m, 4H, -CH2-), 2.07-2.11 (m, 1H, -CH-), 2.12-2.14 (m, 3H, -CH3), 2.29 (s, 1H, -CH-), 2.64-2.68 (m, 1H, -CH-).
13C-NMR (125 MHz, CDCl3) δ 22.1, 22.6, 23.3, 24.5, 25.3, 26.1, 28.3, 29.5, 33.1, 37.0, 41.6, 44.0, 57.6, 212.7.
1-(1,5,6,7,8,8a-ヘキサヒドロ-1,4-メタノナフタレン-4a(4H)-イル)エタン-1-オンは、1-(シクロヘキセン-1-イル)エタノンをシクロペンタ-1,3-ジエンと反応させることを除いて、例1.1に従って調製した。望ましい生成物を2種の主異性体の混合物として得た。生成物の同定は、1H-NMR及び13C-NMRにより確認した。
2種の異性体の混合物(約1/1):1H-NMR (CDCl3, 500 MHz): δ 0.55-0.66 (m, 1H, -CH-), 0.81-0.88 (m, 1H, -CH-), 1.02-1.70 (m, 16H, -CH2-, -CH- ), 1.73-1.83 (m, 3H, -CH-), 2.01-2.06 (m, 1H, -CH-), 2.09 (s, 3H, -CH3), 2.20 (s, 3H, -CH3), 2.46 (s, 1H, -CH-), 2.69-2.74(m, 2H, -CH-, -CH2-), 2.90 (d, J = 1.5Hz, 1H, -CH-), 5.87 (dd, (m, J = 3.5Hz, J = 7.0Hz, 1H, -CH=), 6.13-6.16 (m, 2H, -CH=), 6.21 (dd, m, J = 3.5Hz, J = 7.0Hz, 1H, -CH=).
13C-NMR (125 MHz, CDCl3): δ 17.6, 18.2, 19.0, 19.2, 24.9, 25.7, 25.9, 26.3, 26.5, 28.3, 38.5, 39.0, 44.3, 46.4, 46.6, 48.0, 49.9, 50.8, 59.4, 60.0, 132.3, 134.3, 137.6, 138.9, 211.3, 212.6.
本発明の化合物(I)の匂いの質及び強さを試験するために、香りストリップ試験(scent strip test)を実施した。
例1.1、1.2、1.3、1.4、1.5、1.6及び1.7の化合物は、表2及び3に従って芳香組成物に配合した。表2及び3における数値は、重量部を意味する。
Claims (17)
- 1、2又は3個のR2、R3a、R3b、R4、R5a及びR5b基が、互いに独立してメチルであり、その他が水素である、請求項1に記載の化合物。
- XがX1基を表す、請求項1又は2に記載の化合物。
- R2及びR5b基を有する炭素原子の間の破線が、単結合を表す、請求項1から3のいずれか一項に記載の化合物。
- 式(I)の化合物が、以下の特徴a)からf)
a)R6がメチルである、
b)R7が、存在する場合メチルである、
c)R1a及びR1bが水素であり、又はR1aが、R1bと一緒になってメチレン基を形成する、
d)R2がメチルである、
e)R4が水素である、
f)R5a及びR5bが水素である
のうちの少なくとも1つを有する、請求項1から4のいずれか一項に記載の化合物。 - 一般式(I.a-R)の化合物が、以下の特徴a)及び/又はb)
a)Xが-(C=O)CH3である、
b)R4が水素である、
のうちの少なくとも1つを有する、請求項6又は7に記載の化合物。 - Xが-(C=O)CH3である、請求項8に記載の化合物。
- 請求項1から10のいずれか一項に記載の、一般式(I)の化合物若しくは2種以上の一般式(I)の化合物の混合物、又はその立体異性体若しくは2種以上のその立体異性体の混合物を調製する方法であって:
(i)一般式(II)
破線は、単結合又は二重結合を表し、
X'は、式X1
の基を表し、
R2、R5a及びR5bは、互いに独立して、水素又はメチルから選択され、
R6は、水素、メチル又はエチルから選択される)
の化合物を、一般式(III)
R1a及びR1bは、互いに独立して、水素若しくはメチルから選択され、又はR1aは、R1bと一緒になってメチレン若しくはエチレン基を形成し、
R3a、R3b及びR4は、互いに独立して、水素又はメチルから選択される)
のジエン化合物と触媒の存在下で反応させて、一般式(I)(式中、R3a及びR3b基を有する炭素原子の間の破線は、二重結合であり、XはX1基を表す)の化合物を得る工程、
及び任意選択で以下の工程:
(ii.a)工程(i)で得られた化合物のC=C二重結合を、水素化触媒の存在下で、水素で選択的触媒水素化して、一般式(I)(式中、破線は単結合を表し、XはX1基を表す)の化合物を得る工程、
又は
(ii.b)工程(i)で得られた化合物のC=C二重結合及びC=O二重結合を、水素化触媒の存在下で、水素で触媒水素化して、一般式(I)(式中、破線は単結合を表し、XはX2基を表す)の化合物を得る工程、
(iii.a)工程(i)で得られた化合物、若しくは工程(ii.a)で得られた化合物を、カルボニル基のヒドロキシル基への還元反応に供して、一般式(I)(式中、破線は、互いに独立して単結合又は二重結合を表し、XはX2基を表す)の化合物を得る工程、
又は
(iii.b)工程(i)で得られた化合物、若しくは工程(ii.a)で得られた化合物を、メチル求核試薬若しくはエチル求核試薬と反応させて、一般式(I)(式中、破線は、互いに独立して単結合又は二重結合を表し、XはX3基を表す)の化合物を得る工程
のうちの1つ又は2つを含む、方法。 - 請求項1から10のいずれか一項に記載の、一般式(I)の化合物若しくは2種以上の一般式(I)の化合物の混合物、又はその立体異性体若しくは2種以上のその立体異性体の混合物を調製する方法であって、
(i')一般式(II')
破線は、単結合又は二重結合を表し、
X'は、式X1
の基を表し、
R1a及びR1bは、互いに独立して、水素若しくはメチルから選択され、又はR1aは、R1bと一緒になってメチレン若しくはエチレン基を形成し、
R3a、R3b及びR4は、互いに独立して、水素又はメチルから選択され、
R6は、水素、メチル又はエチルから選択される)
の化合物を、一般式(III')
のジエン化合物と触媒の存在下で反応させて、一般式(I)(式中、R2及びR5b基を有する炭素原子の間の破線は、二重結合であり、XはX1基を表す)の化合物を得る工程、
及び任意選択で以下の工程:
(ii'.a)工程(i')で得られた化合物のC=C二重結合を、水素化触媒の存在下で、水素で選択的触媒水素化して、一般式(I)(式中、破線は単結合を表し、XはX1基を表す)の化合物を得る工程、
又は
(ii'.b)工程(i')で得られた化合物のC=C二重結合及びC=O二重結合を、水素化触媒の存在下で、水素で触媒水素化して、一般式(I)(式中、破線は単結合を表し、XはX2基を表す)の化合物を得る工程、
(iii'.a)工程(i')で得られた化合物、若しくは工程(ii'.a)で得られた化合物を、カルボニル基のヒドロキシル基への還元反応に供して、一般式(I)(式中、破線は、互いに独立して単結合又は二重結合を表し、XはX2基を表す)の化合物を得る工程、
又は
(iii'.b)工程(i')で得られた化合物、若しくは工程(ii'.a)で得られた化合物を、メチル求核試薬若しくはエチル求核試薬と反応させて、一般式(I)(式中、破線は、互いに独立して単結合又は二重結合を表し、XはX3基を表す)の化合物を得る工程
のうちの1つ又は2つを含む、方法。 - 請求項1から10のいずれか一項に記載の、式(I)の化合物若しくは2種以上の一般式(I)の化合物の混合物、又はその立体異性体若しくは2種以上のその立体異性体の混合物の、香料としての使用。
- 請求項1から10のいずれか一項に記載の、式(I)の化合物若しくは2種以上の式(I)の化合物の混合物、又はその立体異性体若しくは2種以上のその立体異性体の混合物の、フレグランス組成物の香り特性を変更するための使用。
- - 請求項1から10のいずれか一項に記載の、式(I)の化合物若しくは2種以上の一般式(I)の化合物の混合物、又はその立体異性体若しくは2種以上のその立体異性体の混合物、並びに
- 少なくとも1種のさらなる香料及び/又は非香料キャリア、ここで非香料キャリアが、界面活性剤、油成分、及び溶媒からなる群から特に選択される、
を含む香料組成物。 - フレグランス組成物を調製する方法であって、請求項1から10のいずれか一項に記載の、式(I)の化合物若しくは2種以上の一般式(I)の化合物の混合物、又はその立体異性体若しくは2種以上のその立体異性体の混合物を、前記組成物に組み込む工程を含む、方法。
- フレグランス組成物の香り特性を変更する方法であって、請求項1から10のいずれか一項に記載の、式(I)の化合物若しくは2種以上の一般式(I)の化合物の混合物、又はその立体異性体若しくは2種以上のその立体異性体の混合物を、前記組成物に組み込む工程を含む、方法。
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