CN115803309A - 有气味的化合物及其制备方法 - Google Patents
有气味的化合物及其制备方法 Download PDFInfo
- Publication number
- CN115803309A CN115803309A CN202280005362.2A CN202280005362A CN115803309A CN 115803309 A CN115803309 A CN 115803309A CN 202280005362 A CN202280005362 A CN 202280005362A CN 115803309 A CN115803309 A CN 115803309A
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- China
- Prior art keywords
- compound
- formula
- enal
- oil
- methyl
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 170
- 238000000034 method Methods 0.000 title claims abstract description 39
- 239000000203 mixture Substances 0.000 claims abstract description 206
- 230000000873 masking effect Effects 0.000 claims abstract description 27
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 14
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 14
- -1 3, 5-dimethylhex-4-en-1-ol Chemical compound 0.000 claims description 60
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 18
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 claims description 16
- 150000002148 esters Chemical class 0.000 claims description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 12
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 claims description 8
- UUNXWMRKMGMGDU-UHFFFAOYSA-N CC(C)CC(C)=CC(C)CCO Chemical compound CC(C)CC(C)=CC(C)CCO UUNXWMRKMGMGDU-UHFFFAOYSA-N 0.000 claims description 8
- XKBLPPODBHBBDM-UHFFFAOYSA-N CC(CC=O)CC(=CC)C Chemical compound CC(CC=O)CC(=CC)C XKBLPPODBHBBDM-UHFFFAOYSA-N 0.000 claims description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 8
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- IOUPDNRRDRIYHN-UHFFFAOYSA-N CC(C)CC(C)CC(C)CC=O Chemical compound CC(C)CC(C)CC(C)CC=O IOUPDNRRDRIYHN-UHFFFAOYSA-N 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- JSGGOQUKXVGBCS-UHFFFAOYSA-N CC(C)CC(CC(C)C)=CC(C)CC=O Chemical compound CC(C)CC(CC(C)C)=CC(C)CC=O JSGGOQUKXVGBCS-UHFFFAOYSA-N 0.000 claims description 6
- YVKLNMVJGKFOOM-UHFFFAOYSA-N CCC(CC(C)CC=O)=CC Chemical compound CCC(CC(C)CC=O)=CC YVKLNMVJGKFOOM-UHFFFAOYSA-N 0.000 claims description 6
- UVVIUGWQFUUNHV-UHFFFAOYSA-N CCC(CC)=CC(C)CC=O Chemical compound CCC(CC)=CC(C)CC=O UVVIUGWQFUUNHV-UHFFFAOYSA-N 0.000 claims description 6
- FZPZQBMVJQQHIJ-UHFFFAOYSA-N 3,5-dimethylhept-4-enal Chemical compound CC(CC=O)C=C(CC)C FZPZQBMVJQQHIJ-UHFFFAOYSA-N 0.000 claims description 5
- SMBJLQXVNPBQCD-UHFFFAOYSA-N CC(C)C=C(C)CC(C)CC=O Chemical compound CC(C)C=C(C)CC(C)CC=O SMBJLQXVNPBQCD-UHFFFAOYSA-N 0.000 claims description 5
- LSKZWURHIFRZGL-UHFFFAOYSA-N CC(C)CC(C)=CC(C)CC=O Chemical compound CC(C)CC(C)=CC(C)CC=O LSKZWURHIFRZGL-UHFFFAOYSA-N 0.000 claims description 5
- ZPOUFPKZRHWSKB-UHFFFAOYSA-N CCC(CC(C)CC=O)=C Chemical compound CCC(CC(C)CC=O)=C ZPOUFPKZRHWSKB-UHFFFAOYSA-N 0.000 claims description 5
- VXOUDDMVOANEGF-UHFFFAOYSA-N CCC=C(C)CC(C)CCO Chemical compound CCC=C(C)CC(C)CCO VXOUDDMVOANEGF-UHFFFAOYSA-N 0.000 claims description 5
- XCCJVPRPBPFNSM-UHFFFAOYSA-N CCCC(C)=CC(C)CCO Chemical compound CCCC(C)=CC(C)CCO XCCJVPRPBPFNSM-UHFFFAOYSA-N 0.000 claims description 5
- JXFOAFSBNQPYNV-UHFFFAOYSA-N CCCCCC(C)=CC(C)CC=O Chemical compound CCCCCC(C)=CC(C)CC=O JXFOAFSBNQPYNV-UHFFFAOYSA-N 0.000 claims description 5
- VMNHETMUNKCGQC-UHFFFAOYSA-N CCCCCC(CC(C)CC=O)=C Chemical compound CCCCCC(CC(C)CC=O)=C VMNHETMUNKCGQC-UHFFFAOYSA-N 0.000 claims description 5
- JDYJMORGCGHOQV-UHFFFAOYSA-N CCCCCCC(C)=CC(C)CCO Chemical compound CCCCCCC(C)=CC(C)CCO JDYJMORGCGHOQV-UHFFFAOYSA-N 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- WKVNQCMDNVWYJR-UHFFFAOYSA-N 3,5-dimethylheptanal Chemical compound CCC(C)CC(C)CC=O WKVNQCMDNVWYJR-UHFFFAOYSA-N 0.000 claims description 4
- YLGDZVLGSPOMTL-UHFFFAOYSA-N 3,5-dimethylhex-5-en-1-ol Chemical compound OCCC(C)CC(C)=C YLGDZVLGSPOMTL-UHFFFAOYSA-N 0.000 claims description 4
- UPUNRENWKQNARL-UHFFFAOYSA-N 3,5-dimethylhex-5-enal Chemical compound O=CCC(C)CC(C)=C UPUNRENWKQNARL-UHFFFAOYSA-N 0.000 claims description 4
- VWLITJGXNSANSN-UHFFFAOYSA-N 3,5-dimethylhexanal Chemical compound CC(C)CC(C)CC=O VWLITJGXNSANSN-UHFFFAOYSA-N 0.000 claims description 4
- HZNTUZXEPORDRA-UHFFFAOYSA-N 3,5-dimethylnonan-1-ol Chemical compound CCCCC(C)CC(C)CCO HZNTUZXEPORDRA-UHFFFAOYSA-N 0.000 claims description 4
- NDYSYMLYTJHGES-UHFFFAOYSA-N 3,5-dimethylnonanal Chemical compound CCCCC(C)CC(C)CC=O NDYSYMLYTJHGES-UHFFFAOYSA-N 0.000 claims description 4
- DJHNRHOPRVNXHR-UHFFFAOYSA-N 3,5-dimethyloctan-1-ol Chemical compound CCCC(C)CC(C)CCO DJHNRHOPRVNXHR-UHFFFAOYSA-N 0.000 claims description 4
- RRUQQIRORZQAAR-UHFFFAOYSA-N 3,5-dimethyloctanal Chemical compound CCCC(C)CC(C)CC=O RRUQQIRORZQAAR-UHFFFAOYSA-N 0.000 claims description 4
- YMHIOUBTHQIQOB-UHFFFAOYSA-N CC(C)CC(CC(C)C)=CC(C)CCO Chemical compound CC(C)CC(CC(C)C)=CC(C)CCO YMHIOUBTHQIQOB-UHFFFAOYSA-N 0.000 claims description 4
- UKNSOWIGHGQSKS-UHFFFAOYSA-N CC(C)CC(CC(C)CCO)=CC(C)C Chemical compound CC(C)CC(CC(C)CCO)=CC(C)C UKNSOWIGHGQSKS-UHFFFAOYSA-N 0.000 claims description 4
- OKDLXRZPCWJOAK-UHFFFAOYSA-N CC(CCO)C=C(CC)C Chemical compound CC(CCO)C=C(CC)C OKDLXRZPCWJOAK-UHFFFAOYSA-N 0.000 claims description 4
- GOWKXIRBUKZQCB-UHFFFAOYSA-N CC(CCO)CC(C)=CC Chemical compound CC(CCO)CC(C)=CC GOWKXIRBUKZQCB-UHFFFAOYSA-N 0.000 claims description 4
- PFQUBDOIPJDKDP-UHFFFAOYSA-N CCC(CC(C)CCO)=CC Chemical compound CCC(CC(C)CCO)=CC PFQUBDOIPJDKDP-UHFFFAOYSA-N 0.000 claims description 4
- SVIJFUUOUZOMKE-UHFFFAOYSA-N CCC(CC)=CC(C)CCO Chemical compound CCC(CC)=CC(C)CCO SVIJFUUOUZOMKE-UHFFFAOYSA-N 0.000 claims description 4
- JYUWMUYDYQYOHT-UHFFFAOYSA-N CCCC=C(C)CC(C)CCO Chemical compound CCCC=C(C)CC(C)CCO JYUWMUYDYQYOHT-UHFFFAOYSA-N 0.000 claims description 4
- DJUIFSBEKZFGAT-UHFFFAOYSA-N CCCCC=C(C)CC(C)CC=O Chemical compound CCCCC=C(C)CC(C)CC=O DJUIFSBEKZFGAT-UHFFFAOYSA-N 0.000 claims description 4
- JDYITQRTGYHCSJ-UHFFFAOYSA-N CCCCCC(C)=CC(C)CCO Chemical compound CCCCCC(C)=CC(C)CCO JDYITQRTGYHCSJ-UHFFFAOYSA-N 0.000 claims description 4
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 4
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000003444 phase transfer catalyst Substances 0.000 claims description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 4
- LSLGWIFKKYBKLE-UHFFFAOYSA-N CC(C)CC(CC(C)C)CC(C)CC=O Chemical compound CC(C)CC(CC(C)C)CC(C)CC=O LSLGWIFKKYBKLE-UHFFFAOYSA-N 0.000 claims description 3
- SOWJSMOVZRNDGP-UHFFFAOYSA-N CC(C)CC(CC(C)C)CC(C)CCO Chemical compound CC(C)CC(CC(C)C)CC(C)CCO SOWJSMOVZRNDGP-UHFFFAOYSA-N 0.000 claims description 3
- GNKFDHVZZPHMBH-UHFFFAOYSA-N CC(C)CC(CC(C)CCO)=C Chemical compound CC(C)CC(CC(C)CCO)=C GNKFDHVZZPHMBH-UHFFFAOYSA-N 0.000 claims description 3
- SPNPJSBDWIDZFX-UHFFFAOYSA-N CC(CCO)CC(CC)CC Chemical compound CC(CCO)CC(CC)CC SPNPJSBDWIDZFX-UHFFFAOYSA-N 0.000 claims description 3
- SZOMYOIMTWWYKO-UHFFFAOYSA-N CC(CCO)CC(CCCCC)C Chemical compound CC(CCO)CC(CCCCC)C SZOMYOIMTWWYKO-UHFFFAOYSA-N 0.000 claims description 3
- XYYYOQNXJBXQRU-UHFFFAOYSA-N CCC(CC)CC(C)CC=O Chemical compound CCC(CC)CC(C)CC=O XYYYOQNXJBXQRU-UHFFFAOYSA-N 0.000 claims description 3
- GNODSRWUMBLMTB-UHFFFAOYSA-N CCCCC(CC(C)CCO)=C Chemical compound CCCCC(CC(C)CCO)=C GNODSRWUMBLMTB-UHFFFAOYSA-N 0.000 claims description 3
- JIIFGRYFJXWOBX-UHFFFAOYSA-N CCCCCC(CC(C)CCO)=C Chemical compound CCCCCC(CC(C)CCO)=C JIIFGRYFJXWOBX-UHFFFAOYSA-N 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- UWDMKTDPDJCJOP-UHFFFAOYSA-N 4-hydroxy-2,2,6,6-tetramethylpiperidin-1-ium-4-carboxylate Chemical compound CC1(C)CC(O)(C(O)=O)CC(C)(C)N1 UWDMKTDPDJCJOP-UHFFFAOYSA-N 0.000 claims 1
- XRDSPRLTHJHTNM-UHFFFAOYSA-N CCCC(CC(C)CCO)=C Chemical compound CCCC(CC(C)CCO)=C XRDSPRLTHJHTNM-UHFFFAOYSA-N 0.000 claims 1
- 239000003921 oil Substances 0.000 description 65
- 235000019198 oils Nutrition 0.000 description 65
- 239000003205 fragrance Substances 0.000 description 53
- 230000015572 biosynthetic process Effects 0.000 description 47
- 238000003786 synthesis reaction Methods 0.000 description 47
- 239000000047 product Substances 0.000 description 45
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 38
- 238000005481 NMR spectroscopy Methods 0.000 description 32
- 239000000796 flavoring agent Substances 0.000 description 28
- 239000011541 reaction mixture Substances 0.000 description 25
- 150000001299 aldehydes Chemical class 0.000 description 24
- 239000002304 perfume Substances 0.000 description 24
- 235000019634 flavors Nutrition 0.000 description 23
- 230000001877 deodorizing effect Effects 0.000 description 21
- 240000000560 Citrus x paradisi Species 0.000 description 19
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 19
- 239000000243 solution Substances 0.000 description 19
- 239000012044 organic layer Substances 0.000 description 16
- 241000207199 Citrus Species 0.000 description 14
- 235000020971 citrus fruits Nutrition 0.000 description 14
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000003960 organic solvent Substances 0.000 description 12
- GVONPEQEUQYVNH-SNAWJCMRSA-N 2-Methyl-3-(2-pentenyl)-2-cyclopenten-1-one Chemical compound CC\C=C\CC1=C(C)C(=O)CC1 GVONPEQEUQYVNH-SNAWJCMRSA-N 0.000 description 11
- 239000001725 2-hexylcyclopent-2-en-1-one Substances 0.000 description 11
- 239000012043 crude product Substances 0.000 description 11
- 241000220317 Rosa Species 0.000 description 10
- 239000000463 material Substances 0.000 description 10
- 239000011347 resin Substances 0.000 description 10
- 229920005989 resin Polymers 0.000 description 10
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 9
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 229930002839 ionone Natural products 0.000 description 9
- 150000002499 ionone derivatives Chemical class 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 8
- LHXDLQBQYFFVNW-UHFFFAOYSA-N Fenchone Chemical compound C1CC2(C)C(=O)C(C)(C)C1C2 LHXDLQBQYFFVNW-UHFFFAOYSA-N 0.000 description 8
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 239000010642 eucalyptus oil Substances 0.000 description 8
- 229940044949 eucalyptus oil Drugs 0.000 description 8
- 239000004615 ingredient Substances 0.000 description 8
- QVDTXNVYSHVCGW-ONEGZZNKSA-N isopentenol Chemical compound CC(C)\C=C\O QVDTXNVYSHVCGW-ONEGZZNKSA-N 0.000 description 8
- 230000003647 oxidation Effects 0.000 description 8
- 238000007254 oxidation reaction Methods 0.000 description 8
- 150000001241 acetals Chemical class 0.000 description 7
- 150000001298 alcohols Chemical class 0.000 description 7
- POIARNZEYGURDG-FNORWQNLSA-N beta-damascenone Chemical compound C\C=C\C(=O)C1=C(C)C=CCC1(C)C POIARNZEYGURDG-FNORWQNLSA-N 0.000 description 7
- 150000002576 ketones Chemical class 0.000 description 7
- 239000007800 oxidant agent Substances 0.000 description 7
- 229930007850 β-damascenone Natural products 0.000 description 7
- ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 2-octanone Chemical compound CCCCCCC(C)=O ZPVFWPFBNIEHGJ-UHFFFAOYSA-N 0.000 description 6
- ULZTUGHPDQMHOQ-UHFFFAOYSA-N CC(C)C=C(C)CC(C)CCO Chemical compound CC(C)C=C(C)CC(C)CCO ULZTUGHPDQMHOQ-UHFFFAOYSA-N 0.000 description 6
- WQGFUOWFBJRJOA-UHFFFAOYSA-N CC(C)CC1(C)OCCC(C)C1 Chemical compound CC(C)CC1(C)OCCC(C)C1 WQGFUOWFBJRJOA-UHFFFAOYSA-N 0.000 description 6
- 241000402754 Erythranthe moschata Species 0.000 description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
- 244000299790 Rheum rhabarbarum Species 0.000 description 6
- 235000009411 Rheum rhabarbarum Nutrition 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000001444 canarium indicum l. oil Substances 0.000 description 6
- 239000010632 citronella oil Substances 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 description 6
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000002453 shampoo Substances 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- WJUFSDZVCOTFON-UHFFFAOYSA-N veratraldehyde Chemical compound COC1=CC=C(C=O)C=C1OC WJUFSDZVCOTFON-UHFFFAOYSA-N 0.000 description 6
- OXYRENDGHPGWKV-UHFFFAOYSA-N 3-methyl-5-phenylpentan-1-ol Chemical compound OCCC(C)CCC1=CC=CC=C1 OXYRENDGHPGWKV-UHFFFAOYSA-N 0.000 description 5
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 description 5
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- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 5
- 239000007868 Raney catalyst Substances 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 5
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 150000002825 nitriles Chemical class 0.000 description 5
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 5
- KMPQYAYAQWNLME-UHFFFAOYSA-N undecanal Chemical compound CCCCCCCCCCC=O KMPQYAYAQWNLME-UHFFFAOYSA-N 0.000 description 5
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- IAIHUHQCLTYTSF-UHFFFAOYSA-N 2,2,4-trimethylbicyclo[2.2.1]heptan-3-ol Chemical compound C1CC2(C)C(O)C(C)(C)C1C2 IAIHUHQCLTYTSF-UHFFFAOYSA-N 0.000 description 4
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 4
- XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 235000007173 Abies balsamea Nutrition 0.000 description 4
- ROWKJAVDOGWPAT-UHFFFAOYSA-N Acetoin Chemical compound CC(O)C(C)=O ROWKJAVDOGWPAT-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000004857 Balsam Substances 0.000 description 4
- 241000717739 Boswellia sacra Species 0.000 description 4
- FKUPPRZPSYCDRS-UHFFFAOYSA-N Cyclopentadecanolide Chemical compound O=C1CCCCCCCCCCCCCCO1 FKUPPRZPSYCDRS-UHFFFAOYSA-N 0.000 description 4
- PXIKRTCSSLJURC-UHFFFAOYSA-N Dihydroeugenol Chemical compound CCCC1=CC=C(O)C(OC)=C1 PXIKRTCSSLJURC-UHFFFAOYSA-N 0.000 description 4
- 239000004863 Frankincense Substances 0.000 description 4
- 229910019093 NaOCl Inorganic materials 0.000 description 4
- 238000010478 Prins reaction Methods 0.000 description 4
- MOYAFQVGZZPNRA-UHFFFAOYSA-N Terpinolene Chemical compound CC(C)=C1CCC(C)=CC1 MOYAFQVGZZPNRA-UHFFFAOYSA-N 0.000 description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/02—Saturated compounds having —CHO groups bound to acyclic carbon atoms or to hydrogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/02—Acyclic alcohols with carbon-to-carbon double bonds
- C07C33/025—Acyclic alcohols with carbon-to-carbon double bonds with only one double bond
-
- 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
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
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- C07—ORGANIC CHEMISTRY
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- C07C47/00—Compounds having —CHO groups
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- C07C47/21—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0007—Aliphatic compounds
- C11B9/0015—Aliphatic compounds containing oxygen as the only heteroatom
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- Oil, Petroleum & Natural Gas (AREA)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Cosmetics (AREA)
Abstract
本发明涉及式(I)的化合物,其中A代表‑CH2OH或‑CHO、‑CH2OAc,R1是烷基基团或亚烷基基团,R2是烷基基团或亚烷基基团,虚线代表双键或单键。本发明还涉及制备该化合物的方法和包含该化合物的组合物,所述组合物被用于发香组合物、调味组合物、除臭组合物、掩蔽组合物。
Description
发明领域
本发明涉及由式(I)表示的有气味的化合物(odorous compound)、包含由式(I)表示的有气味的化合物的组合物,以及用于制备式(I)的化合物的工艺。
发明背景
对天然香料成分(natural fragrance ingredient)的供应的越来越多的限制已经彻底改变了合成香料成分领域。如今,对新颖的气味剂(odorant)/化合物和/或包含所述气味剂/化合物的新颖的香料、调味剂(flavor)和/或除臭/掩蔽组合物存在越来越多的需求。
Kraft等人(Angew.Chem.Int.Ed.Eng.39(2000)2980-3010)已经讨论了葡萄柚气味剂的列表。如Kraft在上文的文章中所报告的,葡萄柚气味剂具有许多方面:柑橘样的(柑橘香(hesperidic))、水果味-大黄(fruity-rhubarb)、黑醋栗酒型香调(cassis-typenote)以及绿香调(green note)。葡萄柚调合物(grapefruit accord)被广泛地用于向香料赋予清新和振奋(lift)。诺卡酮(nootkatone),一种由朱栾倍半萜(valencene)合成的天然存在的葡萄柚气味剂,对于广泛使用来说过于昂贵。其他重要的葡萄柚气味剂包括圆柚甲烷(Methyl Pamplemousse)(二甲基乙缩醛)、二甲基辛烯酮(酮)、Floralate(酯)、弗罗派(Floropal)(乙缩醛)和大黄呋喃(Rhubafuran)(四氢吡喃衍生物)。在这些气味剂中,典型地,乙缩醛在许多产品中形成的酸性条件下易于水解,而酯在碱性条件下可以经历水解。
另一种强烈的葡萄柚气味剂是1-对薄荷烯-8-硫醇,其在葡萄柚汁中被发现并且容易环化成2,8-环硫-对薄荷烷衍生物(2,8-epi-thio-p-menthane derivative)。另一种葡萄柚气味剂是Corps Guava,其呈现绿香、葡萄柚和黑醋栗的特征。许多基于硫醇的气味剂由于其氧化倾向而不稳定。因此,高度期望具有葡萄柚和相关气味特征并且在产品中非常稳定的新颖的化合物。
本发明的优点是,由式(I)表示的新颖的有气味的化合物可用作香料或调味剂材料,特别是可用于为香水、芳香剂(aroma)或除臭/掩蔽组合物提供花香(floral)型、葡萄柚型、柑橘型和/或大黄型的香调。
概述:
本发明涉及包含式(I)的化合物的香料、调味剂和/或除臭/掩蔽组合物;这里,式(I)的化合物选自其立体异构体中的任一种或这些立体异构体中的一种或更多种的混合物。此外,式(I)的化合物选自其区域异构体(regioisomer)中的一种或其区域异构体中的一种或更多种的混合物。
本发明还公开了式(I)的有气味的化合物。特别地,本发明公开了式(I)的香料、调味剂和/或除臭/掩蔽化合物。
其中A代表-CH2OAc、-CH2OH或-CHO
R1是烷基基团或亚烷基基团,
R2是烷基基团或亚烷基基团,
虚线代表双键或单键,
条件是(I)不是:
a.3,5-二甲基己-5-烯-1-醇;
b.3,5-二甲基己-4-烯-1-醇;
c.3,5-二甲基己-1-醇;
d.3,5-二甲基己醛;
e.3,5-二甲基己-5-烯醛;
f.3,5-二甲基己-4-烯醛;
g.3,5-二甲基庚-1-醇;
h.3,5-二甲基庚醛;
i.5-乙基-3-甲基辛-5-烯-1-醇;
j.3,5-二甲基辛-1-醇;
k.3,5-二甲基辛醛;
l.3,5-二甲基壬-4-烯-1-醇;
m.3,5-二甲基壬-1-醇;
n.3,5-二甲基壬醛;
o.3,5-二甲基壬-4-烯醛;
p.3,5-二甲基癸-5-烯-1-醇;以及
q.3,5-二甲基癸-5-烯醛。
根据本发明,基团R1和R2是分开的基团,即它们不一起形成环。对于本领域技术人员来说还将清楚的是,两条虚线不能同时是双键。因此,如果R1用双键键合,则R2将用单键键合;并且如果R2用双键键合,则R1将用单键键合。
优选地,R1和/或R2选自具有多达6个碳原子的烷基基团或亚烷基基团。R1和R2独立地选自包括以下的组:甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、正戊基、正己基、亚甲基、亚乙基、亚丙基、亚异丙基、亚丁基、亚异丁基、亚戊基和亚己基。
在另一种实施方案中,本发明的式(I)的化合物是手性的,例如,它们作为纯的对映异构体或非对映异构体或作为立体异构体的(对映异构体的或非对映异构体的)混合物来使用,更具体地作为对映异构体或非对映异构体的混合物来使用;例如,作为R异构体、S异构体、外消旋混合物和/或非外消旋混合物来使用。此外,式(I)的化合物有利地作为RR异构体、SS异构体、RS异构体、SR异构体、外消旋混合物和/或非外消旋混合物来使用。此外,本发明的式(I)的化合物作为其区域异构体中的任一种或其区域异构体的混合物来使用。
通过表述“其区域异构体中的任一种或其区域异构体的混合物”,本领域技术人员应当理解,区域异构体的存在是由于双键在式(I)的结构中的不同位置造成的。
此外,本发明的式(I)的化合物作为纯的化合物或作为几何异构体(非对映异构体)的混合物来使用;例如,它们是顺式异构体和反式异构体的混合物或作为E异构体和Z异构体的混合物。
详述
本发明涉及式(I)的化合物:
其中A代表-CH2OH或-CHO、-CH2OAc
R1是烷基基团或亚烷基基团,
R2是烷基基团或亚烷基基团,
虚线代表双键或单键。
条件是(I)不是:
a.3,5-二甲基己-5-烯-1-醇;
b.3,5-二甲基己-4-烯-1-醇;
c.3,5-二甲基己-1-醇;
d.3,5-二甲基己醛;
e.3,5-二甲基己-5-烯醛;
f.3,5-二甲基己-4-烯醛;
g.3,5-二甲基庚-1-醇;
h.3,5-二甲基庚醛;
i.5-乙基-3-甲基辛-5-烯-1-醇;
j.3,5-二甲基辛-1-醇;
k.3,5-二甲基辛醛;
l.3,5-二甲基壬-4-烯-1-醇;
m.3,5-二甲基壬-1-醇;
n.3,5-二甲基壬醛;
o.3,5-二甲基壬-4-烯醛;
p.3,5-二甲基癸-5-烯-1-醇;以及
q.3,5-二甲基癸-5-烯醛。
优选地,R1和R2独立地选自包括以下的组:甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、正戊基、正己基、亚甲基、亚乙基、亚丙基、亚异丙基、亚丁基、亚异丁基、亚戊基、亚己基。
优选地,该化合物选自以下化合物:
1)3-甲基-5-亚甲基庚-1-醇;
2)3,5-二甲基庚-4-烯-1-醇;
3)3,5-二甲基庚-5-烯-1-醇;
4)3-甲基-5-亚甲基庚醛;
5)3,5-二甲基庚-4-烯醛;
6)3,5-二甲基庚-5-烯醛;
7)3-甲基-5-亚甲基辛-1-醇;
8)3,5-二甲基辛-4-烯-1-醇;
9)3,5-二甲基辛-5-烯-1-醇;
10)3-甲基-5-亚甲基辛醛;
11)3,5-二甲基辛-4-烯醛;
12)3,5-二甲基辛-5-烯醛;
13)5-乙基-3-甲基庚-4-烯-1-醇;
14)5-乙基-3-甲基庚-5-烯-1-醇;
15)5-乙基-3-甲基庚-1-醇;
16)5-乙基-3-甲基庚-5-烯醛;
17)5-乙基-3-甲基庚-4-烯醛;
18)5-乙基-3-甲基庚醛;
19)3-甲基-5-亚甲基壬-1-醇;
20)3,5-二甲基壬-5-烯-1-醇;
21)3,7-二甲基-5-亚甲基辛-1-醇;
22)3,5,7-三甲基辛-4-烯-1-醇;
23)3,5,7-三甲基辛-5-烯-1-醇;
24)3,5,7-三甲基辛-1-醇;
25)3,7-二甲基-5-亚甲基辛醛;
26)3,5,7-三甲基辛-4-烯醛;
27)3,5,7-三甲基辛-5-烯醛;
28)3,5,7-三甲基辛醛;
29)3-甲基-5-亚甲基癸-1-醇;
30)3,5-二甲基癸-1-醇;
31)3-甲基-5-亚甲基癸醛;
32)3,5-二甲基癸-4-烯醛;
33)3,5-二甲基癸醛;
34)3-甲基-5-亚甲基十一-1-醇;
35)3,5-二甲基十一-4-烯-1-醇;
36)3,5-二甲基癸-4-烯-1-醇;
37)3,5-二甲基十一醛;
38)5-异丁基-3,7-二甲基辛-4-烯-1-醇;
39)5-异丁基-3,7-二甲基辛-5-烯-1-醇;
40)5-异丁基-3,7-二甲基辛-1-醇;
41)3,7-二甲基-5-(2-甲基丙基)辛-5-烯醛;
42)3,7-二甲基-5-(2-甲基丙基)辛-4-烯醛;和
43)3,7-二甲基-5-(2-甲基丙基)辛醛。
本发明的另一种实施方案涉及包含至少两种本发明的化合物的混合物的组合物。
优选地,式(I)的化合物在组合物中的含量是至少0.00001wt.%或至少0.00001wt.%至99.9wt.%。
更优选地,式(I)的化合物在组合物中的含量是至少1wt.%或从至少1wt.%至25wt.%。
在另一种实施方案中,组合物包含至少一种酯和/或至少一种醇,优选地至少酯和醇的混合物,其中一种或更多种式(I)的化合物连同一种或更多种酯和一种或更多种醇的总含量是25wt%或大于25wt%或者50wt%或大于50wt%。
在实施方案中,根据本发明的组合物被用于发香组合物(perfumedcomposition)、调味组合物、除臭组合物或掩蔽组合物中。
在实施方案中,根据本发明的化合物被用于发香组合物、调味组合物、除臭组合物或掩蔽组合物中。
本发明的另一种实施方案涉及用于制备式(I)的化合物的工艺。
该工艺包括以下步骤:
a.使式(II)的化合物
与下式的醇反应
以得到式(III)的化合物
b.使式(III)的化合物与Ra-Ni和氢反应,以得到式(IV)的化合物
c.使式(IV)的化合物与乙酸酐反应,以得到式(V)的化合物
d.使式(V)的化合物与氢氧化钠在水中反应,以得到式(VI)的化合物
e.使用(2,2,6,6-四甲基哌啶-1-基)氧基(TEMPO)连同N-氯代琥珀酰亚胺和相转移催化剂来氧化式(VI)的化合物,以获得式(VII)的化合物
表征根据本发明的化合物的术语“气味剂”意指其在人类中触发气味感觉,优选地,该气味感觉是令人愉快的;因此,其常规地被用于使工业物品和卫生物品、洗涤剂、清洁剂、个人卫生产品、化妆品等发香。出于本发明和所附权利要求的目的,术语“气味剂”包括“芳香物质”。芳香物质是通常用来指示向食品提供气味和/或风味的物质的术语。
式(I)的化合物可以单独使用、作为其混合物使用,或者与基材组合使用。
如本文使用的,“基材”包括选自如以下的广泛范围的天然产物的所有已知的香料/调味剂材料:精油、提取物、类树脂或分离物以及目前可获得的合成材料,诸如:烃、醇、醛和酮、醚和缩醛、酯和内酯、腈、肟或杂环化合物,和/或与以下常规地与香料和/或调味组合物中的气味剂结合使用的一种或更多种成分或赋形剂/辅料混合,例如:溶剂/稀释剂、稳定剂、载体材料和本领域常用的其他助剂。
式(I)的化合物可以用于宽范围的香料应用,例如用于精细的和功能性香料的任何领域,诸如香水、空气护理产品(air care product)、家用产品、洗衣产品、身体护理产品和化妆品。化合物以宽泛变化的量使用,这取决于具体的应用以及其他气味剂成分的性质和量。
根据本发明的优选的实施方案,根据本发明的香料、调味剂和/或除臭/掩蔽组合物包含至少一种根据如先前描述的式(I)的化合物,该化合物的量在0.00001wt.%和99.9wt.%之间,例如在0.0001wt.%和95wt.%之间,例如在0.001wt.%和25wt.%之间,优选地在0.01wt.%和15wt.%之间,更有利地在0.1wt.%和10wt.%之间,特别是在1wt.%和5wt.%之间,在每种情况下都相对于整个组合物。
根据本发明的特别优选的实施方案,除了根据本发明的式(I)的化合物之外,根据本发明的香料、调味剂和/或除臭/掩蔽组合物还包含另外的气味剂,例如该另外的气味剂的量相对于整个香料和/或调味组合物为0.1wt.%至99.9wt.%,优选地5wt.%-90wt.%,特别地15wt.%-70wt.%。
如本文上文描述的式(I)的化合物可以简单地通过将至少一种式(I)的化合物或包含一种或更多种所述式(I)的化合物的香料组合物与消费产品基质(consumer productbase)直接地混合而被用于消费产品基质中;或者,它们可以在较早的步骤中用包埋材料(entrapment material)包埋,所述包埋材料例如聚合物、胶囊、微胶囊和/或纳米胶囊、脂质体、成膜剂、吸收剂诸如活性炭或沸石、环状寡糖、环状甘脲以及它们的两种或更多种的混合物;或者它们可以化学键合到底物上,并且然后与消费产品基质混合,该底物适于在施加外部刺激诸如光、酶、空气、水等时释放香料分子。
因此,本发明可用于制造香料、调味剂和/或除臭/掩蔽组合物的现有方法,包括使用常规的技术和方法将一种或更多种式(I)的化合物作为香料、调味剂和/或除臭/掩蔽成分并入,该并入是通过将化合物直接混合到消费产品基质中,或者通过混合包含所述一种或更多种式(I)的化合物的香料、调味剂和/或除臭/掩蔽组合物,然后可以将其与消费产品基质混合。通过添加嗅觉可接受的量的至少一种如上文描述的本发明的式(I)的化合物,消费产品基质的气味香调被改善、增强和/或修改。
本发明涉及包含式(I)的化合物的香料、调味剂和/或除臭/掩蔽组合物,
本发明涉及式(I)的有气味的化合物。特别地,本发明公开了式(I)的香料、调味剂和/或除臭/掩蔽化合物。
其中A代表-CH2OAc、-CH2OH或-CHO
R1是烷基基团或亚烷基基团,
R2是烷基基团或亚烷基基团,
虚线代表双键或单键,
条件是(I)不是:
a.3,5-二甲基己-5-烯-1-醇;
b.3,5-二甲基己-4-烯-1-醇;
c.3,5-二甲基己-1-醇;
d.3,5-二甲基己醛;
e.3,5-二甲基己-5-烯醛;
f.3,5-二甲基己-4-烯醛;
g.3,5-二甲基庚-1-醇;
h.3,5-二甲基庚醛;
i.5-乙基-3-甲基辛-5-烯-1-醇;
j.3,5-二甲基辛-1-醇;
k.3,5-二甲基辛醛;
l.3,5-二甲基壬-4-烯-1-醇;
m.3,5-二甲基壬-1-醇;
n.3,5-二甲基壬醛;
o.3,5-二甲基壬-4-烯醛;
p.3,5-二甲基癸-5-烯-1-醇;以及
q.3,5-二甲基癸-5-烯醛。
根据本发明,基团R1和R2是分开的基团,即它们不一起形成环。
优选地,R1和/或R2选自具有多达6个碳原子的烷基或亚烷基。R1和R2独立地选自包括以下的组:甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、正戊基、正己基、亚甲基、亚乙基、亚丙基、亚异丙基、亚丁基、亚异丁基、亚戊基、亚己基。
在另一种实施方案中,本发明的式(I)的化合物是手性的,例如,它们作为纯的对映异构体或非对映异构体或作为立体异构体的(对映异构体的或非对映异构体的)混合物来使用,更具体地作为对映异构体或非对映异构体的混合物来使用;例如作为R异构体、S异构体、外消旋混合物和/或非外消旋混合物来使用。此外,式(I)的化合物还有利地作为RR异构体、SS异构体、RS异构体、SR异构体、外消旋混合物和/或非外消旋混合物来使用。此外,本发明的式(I)的化合物作为其区域异构体中的任一种或其区域异构体的混合物来使用。此外,本发明的式(I)的化合物作为纯的化合物或作为几何异构体(非对映异构体)的混合物来使用;例如,它们是顺式异构体和反式异构体的混合物或作为E异构体和Z异构体的混合物。
本发明的优点是所公开的化合物表现出花香气味、葡萄柚气味、柑橘气味和/或大黄气味的特征。此外,具有本文描述的这些新颖化合物的香料组合物表现出花香气味、葡萄柚气味、柑橘气味和/或大黄气味的特征。另一个优点是,与常规的基于硫醇的或基于缩醛或酯的葡萄柚气味剂相比,这些化合物表现出增加的化学稳定性。由于这种增加的稳定性,香料组合物的保存期被增加。此外,这种增加的稳定性导致由香料组合物释放的芳香的持久性的对应的增加,并且因此与常规的香料组合物相比,促进了具有降低的气味剂浓度的香料组合物提供持续更久的芳香。
本发明的实施方案涉及包含式(I)的化合物的有气味的组合物。特别地,本发明公开了包含一种或更多种式(I)的化合物和一种或更多种辅料的香料、调味剂和/或除臭/掩蔽组合物。
一般而言,除了本文描述的新颖的气味剂和/或香料、调味剂和/或除臭/掩蔽组合物之外,合适的香料、调味剂或除臭组合物可以有利地包含常规的辅料,诸如,例如溶剂、载体、稳定剂、乳化剂、保湿剂、分散剂、稀释剂(diluent)、增稠剂、稀释剂(thinner)、其他气味剂和/或其他辅料,及类似物。
在实施方案中,可用于香料、调味剂和/或除臭/掩蔽组合物的式(I)的化合物选自以下化合物:
1)3-甲基-5-亚甲基庚-1-醇;
2)3,5-二甲基庚-4-烯-1-醇;
3)3,5-二甲基庚-5-烯-1-醇;
4)3-甲基-5-亚甲基庚醛;
5)3,5-二甲基庚-4-烯醛;
6)3,5-二甲基庚-5-烯醛;
7)3-甲基-5-亚甲基辛-1-醇;
8)3,5-二甲基辛-4-烯-1-醇;
9)3,5-二甲基辛-5-烯-1-醇;
10)3-甲基-5-亚甲基辛醛;
11)3,5-二甲基辛-4-烯醛;
12)3,5-二甲基辛-5-烯醛;
13)5-乙基-3-甲基庚-4-烯-1-醇;
14)5-乙基-3-甲基庚-5-烯-1-醇;
15)5-乙基-3-甲基庚-1-醇;
16)5-乙基-3-甲基庚-5-烯醛;
17)5-乙基-3-甲基庚-4-烯醛;
18)5-乙基-3-甲基庚醛;
19)3-甲基-5-亚甲基壬-1-醇;
20)3,5-二甲基壬-5-烯-1-醇;
21)3,7-二甲基-5-亚甲基辛-1-醇;
22)3,5,7-三甲基辛-4-烯-1-醇;
23)3,5,7-三甲基辛-5-烯-1-醇;
24)3,5,7-三甲基辛-1-醇;
25)3,7-二甲基-5-亚甲基辛醛;
26)3,5,7-三甲基辛-4-烯醛;
27)3,5,7-三甲基辛-5-烯醛;
28)3,5,7-三甲基辛醛;
29)3-甲基-5-亚甲基癸-1-醇;
30)3,5-二甲基癸-1-醇;
31)3-甲基-5-亚甲基癸醛;
32)3,5-二甲基癸-4-烯醛;
33)3,5-二甲基癸醛;
34)3-甲基-5-亚甲基十一-1-醇;
35)3,5-二甲基十一-4-烯-1-醇;
36)3,5-二甲基癸-4-烯-1-醇
37)3,5-二甲基十一醛
38)5-异丁基-3,7-二甲基辛-4-烯-1-醇
39)5-异丁基-3,7-二甲基辛-5-烯-1-醇
40)5-异丁基-3,7-二甲基辛-1-醇
41)3,7-二甲基-5-(2-甲基丙基)辛-5-烯醛
42)3,7-二甲基-5-(2-甲基丙基)辛-4-烯醛;
43)3,7-二甲基-5-(2-甲基丙基)辛醛。
在根据本发明的实施方案中,香料、调味剂和/或除臭/掩蔽组合物包含式(I)的化合物,其选自上文给出的所述化合物中的任何化合物和/或选自上文给出的所述化合物中的两种或更多种的混合物。
本发明人已经令人惊讶地发现,从嗅觉的角度来看,式(I)的化合物具有葡萄柚气味。事实上,式(I)的化合物呈现清新的柑橘香调和大黄香调的平衡的共混物。此外,式(I)的化合物显示出强的花香调(floral facet)。由式(I)代表的化合物在吸墨纸(blotter)上是非常有保持力的,并且是非常高扩散性的。当在洗发水组合物中使用时,式(I)的化合物在玫瑰和柑橘类调合物中表现得非常好,而当在包含馥奇(fougère)和玫瑰调合物的织物软化剂组合物中使用时,式(I)的化合物比基准化合物呈现更好的性能。
在本发明的实施方案中,所要求保护的香料、调味剂和/或除臭/掩蔽组合物有利地作为香料组合物被使用。根据本发明的香料组合物通常包括香水、古龙水、淡香水(eaude toilette)和/或淡香精(eau de parfum)。在本发明的实施方案中,所要求保护的香料、调味剂和/或除臭/掩蔽组合物有利地被用于化妆品制剂、个人护理产品、清洁产品、织物软化剂和/或空气清新剂及类似物。此外,本文描述的新颖的香料、调味剂和/或除臭/掩蔽组合物和/或新颖的式(I)的化合物可以被整合到建筑材料、墙壁和地板覆盖物、交通工具部件等中,这在本发明的实施方案的范围内。
在实施方案中,式(I)的化合物与许多已知的天然的或合成的香料、调味剂和/或除臭/掩蔽材料组合,由此天然成分的范围不仅包括易挥发性组分,还包括半挥发性组分和微挥发性组分,并且合成的成分的范围包括来自许多类别的物质的代表,诸如在SteffenArctander,Perfume and Flavor Chemicals,第1和2卷,Montclair,N.J.,1969;SteffenArctander,Perfume and Flavor Materials of Natural Origin,Elizabeth,N.J.,1960或Horst Surburg,Johannes Panten,Common Fragrance and Flavor Materials,Wiley-VCH,Weinheim,2016中描述的,并且如从以下非限制性汇编中将是明显的:
天然产物,诸如:
香旱芹油(Ajowan oil)、香树油(Amyris oil)、艾蒿油(Armoise oil)、青蒿油(Artemisia oil)、罗勒油(Basil oil)、蜂蜡净油(Bees wax absolute)、香柠檬油(Bergamot oil)、桦木焦油(Birch tar oil)、黑胡椒油(Black pepper oil)、黑胡椒油树脂(Black pepper oleoresin)、白樟油(Camphor oil)、依兰油(Cananga oil)、藏茴香油(Caraway oil)、小豆蔻油(Cardamom oil)、胡萝卜籽油、海狸香净油(Castoreumabsolute)、雪松叶油(Cedar leaf oil)、雪松木油(Cedarwood oil)、芹菜籽油(Celeryseed oil)、春黄菊油(Chamomile oil)、桂皮油(Cinnamon bark oil)、桂叶油、岩蔷薇净油(Cistus absolute)、岩蔷薇油(Cistus oil)、香茅油(Citronella oil)、香茅萜(Citronella terpenes)、香紫苏油(Clary sage oil)、精馏丁香油(Clove oilrectified)、康酿克油(白)(Cognac oil white)、芫荽籽油(Coriander seed oil)、枯茗籽油(Cumin seed oil)、柏树油(Cypress oil)、印蒿油(Davana oil)、莳萝籽油(Dill seedoil)、榄香脂油(Elemi oil)、榄香树脂(Elemi resinoid)、桉树油(Eucalyptus oil)、松针油(Fir needle oil)、白松香油(Galbanum oil)、天竺葵油(Geranium oil)、印度姜油(Ginger oil Indian)、葡萄柚油(Grapefruit oil)、愈创木油(Guaiacwood oil)、古芸香胶(Gurjun balsam)、茉莉净油(Jasmin absolute)、甘松油(Jatamansi oil)、杜松籽油(Juniper berry oil)、杜松叶油(Juniper leaf oil)、卡胡尔油(Kachur oil)、赖百当净油(Labdanum absolute)、赖百当树脂(Labdanum resinoid)、熏衣草油(Lavender oil)、柠檬油、柠檬油萜、柠檬草油(Lemongrass oil)、酸橙油(Lime oil)、山苍子油(Litseacubeba oil)、山苍子萜(Litsea cubeba terpenes)、Lobhan choya树脂型物、橘油(Mandarin oil)、薄荷油(Mentha arvensis oil)、柠檬薄荷油(Mentha citrata oil)、含羞草净油(Mimosa absolute)、没药树脂(Myrrh resinoid)、莎草油(Nagarmothaoil)、肉豆蔻油(Nutmeg oil)、橡苔净油(Oakmoss absolute)、橡苔树脂(Oakmoss resinoid)、乳香油(Olibanum oil)、乳香树脂(Olibanum resinoid)、橙油、牛至油(Origanum oil)、玫瑰草油(Palma rosa oil)、广藿香油(Patchouli oil)、胡椒薄荷油(Peppermint oil)、秘鲁香脂树脂(Peru Balsam resinoid)、橙叶油(Petitgrain oil)、松叶油(Pine needle oil)、粉红胡椒油(Pink pepper oil)、玫瑰净油(Rose absolute)、玫瑰油(Rose oil)、迷迭香油、檀香木油(Sandalwood oil)、海草净油(Seaweed absolute)、留兰香油(Spearmint oil)、印度苏刚达油(Sugandh kokila oil)、印度苏刚达香薰油(Sugandh mantri oil)、万寿菊油(Tagete oil)、妥鲁香脂树脂(Tolu Balsam resinoid)、晚香玉净油(Tuberoseabsolute)、姜黄油(Turmeric oil)、松节油(Turpentine oil)、缬草油(Valerian oil)、香根油(Vetiver oil)、香根萜(Vetiverterpenes)。
合成的原材料,例如:
酯类,诸如:C16醛、格蓬酯、己酸烯丙酯、环己基丙酸烯丙酯、庚酸烯丙酯、苯氧基乙酸烯丙酯、乙酸异戊酯、苯甲酸戊酯、丁酸戊酯、己酸戊酯、肉桂酸戊酯、异戊酸戊酯、苯基乙酸戊酯、丙酸戊酯、水杨酸异戊酯、乙酰化香树油(Amyris acetate)、乙酸茴香酯、乙酸苄酯、苯甲酸苄酯、丁酸苄酯、肉桂酸苄酯、甲酸苄酯、异丁酸苄酯、苄基异丁香酚、丙酸苄酯、水杨酸苄酯、惕各酸苄酯、乙酸丁酯、丁酸丁酯、丁酰乳酸丁酯、乙酸石竹烯酯(Caryophyllene acetate)、乙酸柏木酯(Cedryl acetate)、乙酸肉桂酯、丁酸肉桂酯、顺式-3-己烯基乙酸酯、顺式-3-己烯基苯甲酸酯、顺式-3-己烯基己酸酯、顺式-3-己烯基甲酸酯、顺式-3-己烯基异丁酸酯、顺式-3-己烯基-2-甲基丁酸酯、顺式-3-己烯基丙酸酯、顺式-3-己烯基水杨酸酯、顺式-3-己烯基惕各酸酯、乙酸香茅酯(Citronellyl acetate)、丁酸香茅酯、甲酸香茅酯、异丁酸香茅酯、丙酸香茅酯、惕各酸香茅酯、异丁酸三环癸烯酯(Cyclabute)、环格蓬酯(Cyclogalbanate)、环己基乙基乙酸酯、乙酸癸酯、邻苯二甲酸二丁酯、丙二酸二乙酯、邻苯二甲酸二乙酯、乙酸二氢月桂烯酯(Dihydromyrcenyl acetate)、乙酸二甲基辛酯、乙酸二甲基苯乙基原酯(Dimethyl phenyl ethyl carbinyl acetate)、己二酸二辛酯、邻苯二甲酸二辛酯、乙酸二甲基苄基原酯、丁酸二甲基苄基原酯、乙酸乙基芳樟酯(Ethyl linalyl acetate)、2-甲基丁酸乙酯、3-苯基丙酸乙酯、乙酸乙酯、乙酰乙酸乙酯、苯甲酸乙酯、丁酸乙酯、癸酸乙酯、己酸乙酯、辛酸乙酯、肉桂酸乙酯、庚酸乙酯、乙基己基乙酸酯、异丁酸乙酯、月桂酸乙酯、壬酸乙酯(Ethyl pelargonate)、苯氧基乙酸乙酯、乙基苯基乙酸酯、乙基苯基环氧乙烷甲酸酯(Ethyl phenyl glycidate)、丙酸乙酯、藏红花酸乙酯(Ethyl saf ranate)、水杨酸乙酯、戊酸乙酯、乙酸丁香酚酯(Eugenyl acetate)、Evernyl、乙酸小茴香酯(Fenchyl acetate)、Floramat、Frescolat ML、乙酸乙基甲基二茂烷酯(Fructone)、三环癸烷羧酸乙酯(Fruitate)、乙酸香叶酯(Geranylacetate)、丁酸香叶酯、甲酸香叶酯、丙酸香叶酯、惕各酸香叶酯、2-乙基-6,6-二甲基-2-环己烯-1-甲酸乙酯(Givescone)、乙酸愈创木醇酯(Guaiol acetate)、二氢茉莉酮酸酯(Hedionate)、二氢茉莉酮酸甲酯(Hedione)、海菲麝香(Helvetolide)、香菠酯(Herbanate)、乙酸己酯、苯甲酸己酯、丁酸正己酯、己酸己酯、异丁酸己酯、丙酸己酯、水杨酸己酯、乙酸异冰片酯、乙酸异丁酯、异丁基苯基乙酸酯、水杨酸异丁酯、乙酸异丁香酚酯(Isoeugenyl acetate)、乙酸异壬酯、异戊酸酯、2-甲基丁酸异丙酯、肉豆蔻酸异丙酯、茉莉酯(Jasmonyl)、绿花酚(Liffarome)、乙酸芳樟酯(Linalyl acetate)、藿檀酯(Mahagonate)、母菊酯(Manzanate)、二氢松香醇乙酸酯(Menthanyl acetate)、乙酸薄荷酯、苯甲酸甲酯、2-甲基丁基乙酸酯、2-甲基戊丁酯(Methyl camomille)、肉桂酸甲酯、环香叶酸甲酯(Methyl cyclogeranate)、庚炔羧酸甲酯(Methyl heptine carbonate)、月桂酸甲酯、辛炔羧酸甲酯(Methyl octinecarbonate)、苯基乙酸甲酯、水杨酸甲酯、甲基-2-甲基丁酸酯、新福力酯(Neofolione)、乙酸诺卜酯(Nopyl acetate)、乙酸辛烯基酯、乙酸辛酯、异丁酸辛酯、乙酸对甲酚酯(Paracresyl acetate)、异丁酸对甲酚酯、苯乙酸对甲酚酯、梨酯、2-甲基戊酸2-甲基戊酯(Peranat)、异丁酸苯氧基乙酯、乙酸苯乙酯、丁酸苯乙酯、甲酸苯乙酯、异丁酸苯乙酯、苯乙酸苯乙酯、丙酸苯乙酯、水杨酸苯乙酯、惕各酸苯乙酯、异丁酸苯丙酯、乙酸异戊二烯酯(Prenyl acetate)、罗曼麝香(Romandolide)、Sagecete、乙酸苏合香酯(Styrallylacetate)、丙酸苏合香酯(Styrallylpropionate)、红桔酯(Tangerinol)、乙酸松油酯(Terpinyl acetate)、Thesaron、反式-2-己烯基乙酸酯、Tropicate、乙酸邻叔丁基环己酯(Verdox)、乙酸三环癸烯酯(Verdyl acetate)、丙酸三环癸烯酯(Verdyl propionate)、乙酸对叔丁基环已酯(Vertenex)、乙酸维木酯(Vetikol acetate)、乙酸香根酯(Vetiverylacetate)、Yasmolys。
内酯类,诸如:黄葵内酯(Ambrettolide)、Arova N、3-丙亚基-1-异苯并呋喃酮(Celeriax)、癸内酯δ、癸内酯γ、十二内酯δ、十二内酯γ、巴西酸乙二醇酯(Ethylenebrassylate)、环十五内酯(Exaltolide)、庚内酯γ、己内酯δ、己内酯γ、甲基内酯(Methyllaitone)、甲基辛内酯、壬内酯δ、壬内酯γ、八氢香豆素、辛内酯δ、辛内酯γ、Rootylone、环十六内酯(Silvanone supra)、十一内酯δ、十一内酯γ、戊内酯γ、10-氧杂十六内酯(OHD麝香)、香豆素(Coumarin)、环十五烯内酯(Habanolide)、茉莉内酯(Jasmolactone)。
醛类,诸如:乙醛、阿道克醛(Adoxal)、C10醛、异C11醛(Aldehyde C11iso)、C11moa醛、C11十一碳烯醛(Aldehyde C11 undecylenic)、C11十一烷基醛(Aldehyde C11undecylic)、C12月桂醛、C12 MNA醛、茴香醛(Anisaldehyde)、戊基肉桂醛、苯甲醛、波吉洪醛(Bourgeonal)、樟脑烯醛(Campholenaldehyde)、Cantonal、紫罗兰醛(Cetonal)、肉桂醛、顺式-4-癸烯醛、顺式-6-壬烯醛、柠檬醛、香茅醛、香茅基氧基乙醛(Citronellyloxyacetaldehyde)、可卡醛(Cocal)、枯茗醛(Cuminaldehyde)、Curgix、Cyclal C、兔耳草醛(Cyclamen aldehyde)、铃兰甲醛(Cyclomyral)、女贞醛(Cyclovertal)、癸烯醛9、Dupical、柑青醛(Empetal)、乙基香草醛(Ethyl vanillin)、海风醛(Floralozone)、花青醛(Florhydral)、香叶醛(Geraldehyde)、洋茉莉醛(Heliotropin)、庚醛、己醛、己基肉桂醛、neo、氢化阿托醛(Hydratropaldehyde)、羟基香茅醛、内十一烯醛(Intreleven aldehyde)、异丁酸香兰酯(Isobutavan)、异环柠檬醛(Isocyclocitral)、异戊醛、铃兰醛(Lilial)、新柠檬醛(Limonenal)、马赛醛(Maceal)、梅弗兰醛(Mefranal)、甜瓜醛(Melonal)、甲基肉桂醛、反式-2-顺式-6-壬二烯醛、壬醛、辛醛、Oncidal、对甲苯醛(Para tolyl aldehyde)、苯乙醛、苯丙醛、甲基柑青醛B(Precyclemone B)、藏红花醛(Safranal)、水杨醛、清风醛(Scentenal)、丁香醛(Syringa aldehyde)、反式-4-癸烯醛、反式-2-十二烯醛、反式-2-己烯醛、反式-2-壬烯醛、新女贞醛(Trifernal)、香草醛、藜芦醛(Veratraldehyde)、鲜草醛(Vernaldehyde)。
酮类,诸如:山楂花酮(Acetanisol)、乙偶姻(Acetoin)、苯乙酮、Aldron、烯丙基紫罗兰酮(Allyl ionone)、苯甲酮、苄基丙酮、西瓜酮(Calone)、莰酮(Camphor)、d-香芹酮、l-香芹酮、喀什米尔香(Cashmeran)、柏木基甲基酮(Cedryl methyl ketone)、二氢茉莉酮酸甲酯(Cepionate)、卡瑞酮(Claritone)、天籁麝香(Cosmone)、萨利麝香(Crysolide)、甲基环戊烯醇酮(Cyclotene)、大马烯酮(Damascenone)、大马酮α、大马酮β、大马酮δ、大马酮γ、二乙酰(Diacetyl)、二氢-β-紫罗兰酮、二氢异茉莉酮酸酯(Dihydro isojasmonate)、二甲基辛烯酮、王朝酮(Dynascone)、乙基戊基酮、乙基麦芽酚、葑酮(Fenchone)、榛子酮(Filbertone)、香叶基丙酮(Geranyl acetone)、8-环十六烯-1-酮(Globanone)、庚基环戊酮、紫罗兰酮α(Iononeα)、紫罗兰酮β、纯紫罗兰酮(Ionone pure)、鸢尾木(Iriswood)、鸢尾酮α(Ironeα)、龙涎酮(Iso E Super)、异葑酮(Isof enchone)、异茉莉酮T(Iso ja smoneT)、异洛酮K(Isolone K)、异薄荷酮(Isomenthone)、异佛尔酮、顺式-茉莉酮(Jasmonecis-)、Kambernoir、加菲力士(Kephalis)、高芳烯(Koavone)、Lavendinal、麦芽酚(Maltol)、薄荷酮、甲基苯乙酮、甲基戊基酮、甲基庚烯酮、甲基己基酮、甲基紫罗兰酮γ、甲基萘基酮β、甲基壬基酮、麝香烯酮(Muscenone)、麝香酮(Muscone)、桃酮(Nectaryl)、Orinox、OTBC酮、对叔丁基环己酮、Patchwood、粉檀麝香(Phantolid)、法老酮(Pharaone)、胡椒酮(Piperitone)、普利卡酮(Plicatone)、覆盆子酮(Raspberry ketone)、覆盆子酮甲基醚、藏花茚(Safraleine)、纯螺环格蓬酮(Spirogalbanone pure)、吐纳麝香(Tonalid)、三甲基琥珀酮(Trimofix O)、凡路酮(Veloutone)、Vetikon。
醇类,诸如:氧代C13醇(Alcohol oxo C13)、琥珀芯(Amber core)、Ambermax、龙涎醇(Ambrinol)、戊基乙烯基原醇(Amyl vinyl carbinol)、茴香醇(Anisicalcohol)、白檀醇(Bacdanol)、苄醇、丁醇、结晶柏木醇(Cedrol crystals)、肉桂醇、香茅醇、花冠醇(Coranol)、癸醇(Decanol)、二甲基苄基原醇、二甲基辛醇、二甲基苯乙基原醇、二甲基庚醇(Dimetol)、葑醇(Fenchol)、己醇、异龙脑(Isoborneol)、环己异龙脑酯(Isobornylcyclohexanol)、爪哇檀香(Javanol)、Keflorol、3,5,6,6-四甲基-4-亚甲基-2-庚醇(Kohinool)、月桂醇、风铃醇(Lilyflore)、氧化芳樟醇(Linalool oxide)、五月铃兰醇(Mayol)、薄荷醇、赛木香醇(Norlimbanol)、辛醇、沙针醇(Osyrol)、对叔丁基环己醇、苯基异己醇(Phenoxanol)、苯氧基乙醇、苯乙醇、苯丙醇、丙二醇、甲基苯戊醇(Rosaphen)、玫瑰二醇、苏合香醇(Styrallyl alcohol)、三环癸烷二甲醇、四氢芳樟醇、四氢月桂烯醇、特木倍醇(Timberol)、甲基癸烯醇(Undecavertol)、顺式-3-己烯醇、左旋香茅醇(Citronellollaevo)、环花醇(Cyclofloranol)、二氢芳樟醇(Dihydrolinalool)、二氢月桂烯醇(Dihydromyrcenol)、二聚月桂烯醇(Dimyrcetol)、黑檀醇(Ebanol)、香叶醇(Geraniol)、异蒲勒醇(Isopulegol)、芳樟醇(Linalool)、橙花醇(Nerol)、橙花叔醇(Nerolidol)、反式-2顺式-6壬二烯醇、聚檀香醇(Polysantol)、Rosalva、白雷曼檀香核(Sandalmysore core)、檀香(Sandalore)、萜烯-4-醇(Terpinen-4-ol)、萜品醇(Terpineol)、反式-2-己烯醇。
酚类,诸如:丁羟茴醚、二氢丁香酚(Dihydroeugenol)、二甲基氢醌、二甲基间苯二酚、纯丁香酚(Eugenol pure)、愈创木酚、异丁香酚、间甲酚、甲基丹提力士(Methyldiantilis)、对甲酚、丙烯基乙基愈创木酚(Propenyl guaethol)、麝香草酚(Thymol)、香荚兰醇(Ultravanil)。
醚类,诸如:降龙涎香醚(Ambroxan)、茴香脑(Anethole)、花药(Anther)、苄基异戊基醚、苄基异丙基醚、异戊酸苄酯、鸢尾香木(Boisiris)、柏木甲醚(Cedramber)、降龙涎醚(Cetalox)、癸基甲基醚、二苄基醚、二氢玫瑰醚、二苯醚(Diphenyl oxide)、道立米(Doremox)、草蒿脑(Estragole)、乙基芳樟醇、桉油精、佳乐麝香(Galaxolide)、吉兰吡喃(Gyrane)、Herbavert、酸橙氧化物(Lime oxide)、Madrox、甲基异丁香酚、萘基异丁基醚β、橙花醚(Nerol oxide)、橙花素(Nerolin bromelia)、对甲苯酚丁醚、对甲苯酚甲基醚、Petiole、苯乙基甲基醚、大黄呋喃、玫瑰醚(Roseoxide)、芳香玫瑰醚(Rosyrane)、Trisamber、Vetylbois K、β-萘基甲基醚(Yara yara)。
缩醛类,诸如:乙缩醛CD、乙缩醛R、龙涎缩醛(Amberketal)、乙氧基环十二烷氧基甲烷(Boisambrene forte)、柠檬醛(Citrathal)、1,1-二乙氧基乙烷、翠绿亚胺(Emeraldine)、Freshopal、薰衣草噁烷(Herboxane)、吲哚素(Indoflor)、Jacinthaflor、Magnolan、香辣醚(Spirambrene)、苯乙醛二甲缩醛(Viridine)、爱林塔尔(Elintaal)、克力二噁茂烷(Glycolierral)、卡拉花醛(Karanal)、圆柚甲烷。
烃类,诸如:红没药烯(Bisabolene)、莰烯、蒈烯δ3(Carene delta 3)、石竹烯(Caryophyllene)、柏木烯(Cedrene)、对伞花烃(Cymene para)、二戊烯(Dipentene)、二苯基甲烷、异长叶烯(Isolongifolene)、d-柠檬烯、长叶烯(Longifolene)、月桂烯(Myrcene)、萘、罗勒烯(Ocimene)、蒎烯α、蒎烯β、苯乙烯、萜品烯γ、萜品油烯(Terpinolene)、1,3,5-十一碳三烯、异丙基格篷(Verdoracine)。
硫化合物,诸如:Corps cassis、二丁基硫醚、二甲基硫醚、2-己基-3-氧代环戊羧酸甲酯(Exovert)、西柚硫醇(Grapefruit thiol)、噁烷(Oxane)、巯基马来酮(Ribesmercaptan)、硫噻唑(Sulfurol)、桉叶硫醚(Thiocineol)。
腈类,诸如:肉桂腈(Cinnamyl nitrile)、香茅腈(Citronellyl nitrile)、Citronitrile、Clonal、枯茗腈(Cumin nitrile)、己基环戊酮、鸢尾腈、柠檬腈(Lemonile)、牡丹腈(Peonile)、十三烷基腈、Agrumen腈、正癸腈。
肟类,诸如:布枯肟(Buccoxime)、雷冰诺星(Labienoxime)、榄青酮(Stemone)。
氮杂环类,诸如:2-乙酰基吡嗪、2-乙酰基吡啶、仲丁基喹啉、2-(3-苯丙基)吡啶(Corps racine)、2-乙基-3,5(或6)-二甲基吡嗪、糠基吡咯、吲哚、异丁基喹啉、2-异丁基-3(或6)-甲氧基吡嗪、异丙基喹啉、Maritima、对甲基喹啉、3-甲基吲哚(Skatol)、2,3,5-三甲基吡嗪。
硝基化合物,诸如:麝香酮(Musk Ketone)。
希夫碱类,诸如:橙花素(Aurantiol)、半日花素(Helianthral)、女贞缩醛(ligantraal)、玲兰素(verdantiol)。
其他材料,诸如:乙酰苯胺、Gardamide、水果酰胺(Paradisamide)、邻氨基苯甲酸二甲酯、邻氨基苯甲酸甲酯、正丁酸、癸酸、己酸、辛酸、苯乙酸、石竹烯氧化物、环氧柏木醚(Cedroxyde)、杜柏醇(Tobacarol)。
因此,式(I)的化合物用于产生组合物,并且如从前述汇编中将明显的,用于广泛的已知的气味剂/香料、调味剂和/或除臭/掩蔽材料。在这样的组合物的产生中,根据调香师已知的方法,诸如例如根据W.A.Poucher,Perfumes,Cosmetics and Soaps 2,第7版,Chapman and Hall,London 1974,使用早先提及的已知的香料、调味剂和/或除臭/掩蔽材料。
在本发明的实施方案中,所要求保护的香料、调味剂和/或除臭/掩蔽组合物除了包含式(I)的化合物之外,还包含至少一种酯和/或至少一种醇(如果存在,不同于化合物(I)),优选地至少酯和醇的混合物;所述酯和/或醇优选地选自本文上文定义的列表。在本发明的实施方案中,所要求保护的气味剂组合物的特征是一种或更多种式(I)的化合物与一种或更多种酯和/或一种或更多种醇的总含量大于25wt.%、优选地大于50wt.%、例如大于75wt.%或甚至大于90wt.%。
制备
式(I)的化合物可以指的是立体异构体的和/或区域异构体的混合物或单独地分离的异构体,式(I)的化合物是在5个步骤中制备的。本公开内容中详述的工艺是如WO2012025934A1中描述的早先报告的5步工艺的改进。
在WO2012025934A1中,在涉及普林斯反应(Prins reaction)的第一步骤中,对甲苯磺酸(PTSA)被用作催化剂。然而,PTSA的使用需要使用有机溶剂,通常是甲苯或甲基环己烷。这样的溶剂与水共沸蒸馏,从而从反应混合物中去除水,因此将普林斯反应中的平衡推向正向。因此,这些反应条件导致有机溶剂的使用,这促成废物管理和流出物处理负荷(effluent treatment load)。虽然所使用的有机溶剂可以通过蒸馏被回收,但这种蒸馏工艺增加了后处理时间并且消耗能量。
在WO2012025934A1中报告的研究工作中,使用了环状酮,而在本公开内容中,反应物是无环酮,已知无环酮是比典型的环状酮反应性更低的。本文中,使用了甲磺酸或三氟甲磺酸。此外,不使用有机溶剂,并且普林斯反应在不存在有机溶剂的情况下进行。使用强酸诸如甲磺酸或三氟甲磺酸以及不存在任何有机溶剂消除了共沸蒸馏的需要。总体而言,由于不再需要有机溶剂回收或处置,工艺的改进导致较少的废物管理的负荷和较少的能量消耗。
在WO2012025934A1中公开的工艺中,在存在在水:甲苯混合物中的NaBr/NaHCO3的情况下,使用催化的TEMPO(0.1当量)作为主要氧化剂连同NaOCl(13%w/w在水中的溶液)作为次要氧化剂将伯醇氧化为对应的醛。由于次氯酸钠(NaOCl)可以容易地分解,并且通常是储存不稳定的,因此不容易每次都获得精确需要的浓度的NaOCl溶液。此外,作为13%w/w在水中的溶液的NaOCl的使用在反应条件下引入了水的大量稀释。这些条件需要大的反应体积,特别是在工厂规模上使用时,并且这导致反应器容量的低效使用。
以显著改进氧化方案为目标,探索了多种次要氧化剂的使用,并且发现当在NaHCO3和K2CO3在水中的缓冲溶液中使用、采用正四丁基氯化铵作为相转移催化剂、采用DCE(二氯乙烷)作为有机溶剂时,N-氯代琥珀酰亚胺(NCS)与作为主要氧化剂的催化的TEMPO一起表现非常好。代替正四丁基氯化铵,还可以有效地使用正四丁基溴化铵作为相转移催化剂。
使用其他次要氧化剂如碘苯二乙酸(Diacetoxyiodobenzene)不是成本有效的。使用DMSO和草酰氯的其他氧化条件(Swern氧化)的使用通常需要低温和惰性反应条件。更重要地,副产物二甲基硫醚是高度易燃的,并且具有极其令人不快的气味。二甲基硫醚作为杂质的存在即使在非常低的水平上也使得有机化合物不可用作气味剂。
在本发明中,已经展示了用于在含水介质中、在短的反应时间1h-2h内将伯醇氧化为醛的有效工艺,该工艺使用催化量(在0.03当量至0.1当量之间)的TEMPO并且使用N-氯代琥珀酰亚胺作为共氧化剂。
可选择地,4-羟基-TEMPO在0.1当量至0.3当量的范围内使用。虽然使用的4-羟基-TEMPO的当量高于TEMPO的当量,但使用4-羟基-TEMPO的优点是因为不存在有色杂质。在许多情况下,由TEMPO的使用而产生的有色杂质不能在蒸馏中与期望的醛产物分离,因为有色杂质和醛具有相似的沸点以及在气相色谱法分析中相似的保留时间。当使用4-羟基-TEMPO时,不存在有色杂质并且因此提高了醛产物的纯度。
工艺包括如下的五个步骤:
步骤1:式(II)的化合物与异戊烯醇的反应,以得到式(III)的化合物。
步骤2:所得到的吡喃类(III)的区域异构体混合物在高温、在压力下使用雷尼镍和氢来氢化,以提供四氢吡喃衍生物(IV)。
步骤3:式(IV)的化合物与乙酸酐反应并且随后开环以获得式(V)的化合物。
步骤4:碱介导的乙酸酯(V)的水解提供不饱和醇(VI)。这里使用的碱选自在水和有机溶剂如甲醇、乙醇、异丙醇中的氢氧化钠或氢氧化钾。
步骤5:用催化量的(2,2,6,6-四甲基哌啶-1-基)氧基(TEMPO)或4-羟基TEMPO以及N-氯代琥珀酰亚胺作为次要氧化剂,在缓冲溶液中氧化式(VI)的化合物,以获得式(VII)的化合物。
可选择地,式(VI)的化合物在高温使用Ra-Ni催化剂来氢化,以得到式(VIII)的化合物。
式(VIII)的化合物的进一步TEMPO介导的氧化提供式(IX)的化合物。
下文给出了一些选定化合物的合成程序和表征数据。
实施例:
实施例-1
使用4-甲基戊-2-酮和异戊烯醇合成3,7-二甲基-5-亚甲基辛醛(化合物25)、3,5,7-三甲基辛-4-烯醛(化合物26)和3,5,7-三甲基辛-5-烯醛(化合物27)的混合物
步骤-1:2-异丁基-2-甲基-4-亚甲基四氢-2H-吡喃、2-异丁基-2,4-二甲基-3,6-二氢-2H-吡喃和6-异丁基-4,6-二甲基-3,6-二氢-2H-吡喃的混合物的合成:
在25℃,经30min向4-甲基戊-2-酮(400g,3.99mol)中添加甲磺酸(115.0g,1.198mol)。将反应混合物搅拌15min,并且在25℃经1.5h向其中添加3-甲基丁-3-烯-1-醇(413g,4.79mol)。在添加期间产生放热,该放热通过采用水的外部冷却来控制。在添加完成之后,将反应混合物在60℃加热持续24h。将反应混合物冷却至25℃。并且将酸层去除。将有机层用120mL的5%碳酸氢钠水溶液洗涤,随后用水(150mL)和饱和盐水(2×150mL)洗涤。将包含根据GC分析的57%产物的粗制残余物(690.0g)蒸馏,以提供275.0g(41%收率)的期望的产物。
IR(纯的):2953.5,1719.0,1609.4,1447.6cm-1
1H NMR(400MHz,CDCl3):δ5.30-5.16(m,1H),4.01-3.97(m,1H),3.73-3.63(m,2H),1.98–1.68(m,3H).1.65(s,2H),1.43–1.20(m,2H),1.10-1.08(m,3H),0.91-0.82(m,6H)。
GC-MS(m/z):168.2(M+),153.1,140.1,111.1
步骤-2:2-异丁基-2,4-二甲基四氢-2H-吡喃(IV)的合成
在高压釜中向来自步骤1的混合物(218g,1.237mol)在2-丙醇(110mL)中的溶液中添加雷尼镍(72.6g,1.24mol)。将反应混合物在200psi氢气压力下在120℃加热并且维持持续18h。将反应混合物冷却至30℃并且通过hyflow床过滤。用2-丙醇(2×10mL)洗涤hyflow床。浓缩有机层,以提供217.0g(96%收率)的期望的产物。
IR(纯的):2951.2,1457.2,1373.2cm-1
1H NMR(400MHz,CDCl3):δ3.66–3.58(m,2H),1.80–1.73(m,3H),1.52–1.34(m,4H),1.21–1.14(m,4H),0.99–0.84(m,9H)。
GC-MS(m/z):171.1(M+),155.2,113.1。
步骤-3:3,5,7-三甲基辛-4-烯-1-基乙酸酯、3,5,7-三甲基辛-5-烯-1-基乙酸酯和3,7-二甲基-5-亚甲基辛基乙酸酯的混合物的合成:
将2-异丁基-2,4-二甲基四氢-2H-吡喃(107.0g,0.58mol)、4-甲基苯磺酸水合物(5.6g,0.029mol)和乙酸酐(90.0g,0.88mol)的溶液在110℃-115℃加热持续5h。将反应混合物冷却至室温,并且向其中添加甲基叔丁基醚(300mL)和水(200mL)。在搅拌持续15min之后,分离两个层,并且将有机层用10%碳酸钠溶液(3×100mL)洗涤,并且然后用水(2×200mL)洗涤,直到中性的pH。将有机层经硫酸钠干燥,过滤并且浓缩,以提供粗制物质(129g),该粗制物质通过在减压下的分馏被纯化,以87%收率获得乙酸酯的区域异构体混合物。
IR(纯的):2955.4,1740.7,1230.6cm-1
1H NMR(400MHz,CDCl3):δ4.78-4.75(m,1H),4.03–3.90(m,2H),2.49–2.42(m,1H),1.96–1.95(m,3H),1.90–1.47(m,8H),0.89–0.47(m,9H)。
GC-MS(m/z):212.2(M+),152.2,137.2,123.1。
步骤-4:区域异构体混合物3,7-二甲基-5-亚甲基辛-1-醇(化合物21)、3,5,7-三甲基辛-4-烯-1-醇(化合物22)和3,5,7-三甲基辛-5-烯-1-醇(化合物23)的合成:
在25℃,经10min将来自步骤-3的乙酸酯的区域异构体混合物(950g,4481mmol)添加至氢氧化钾(453g,8066mmol)和水(1044mL)的溶液中。将反应混合物在100℃加热持续20h,并且然后冷却至25℃。将层分离,并且将有机层用水(2×500mL)和饱和盐水(2×1L)洗涤。将所得到的粗品蒸馏,以提供期望的辛烯醇,其作为区域异构体的混合物(725g,95%收率),呈淡黄色油的形式。
气味特征:绿香,葡萄柚,柑橘类。
IR(纯的):3342.0,2954.9,1713.4,1666.6,1459.3cm-1
1H NMR(400MHz,CDCl3):δ4.88–4.86(m,1H),3.70–3.51(m,2H),2.55–2.43(m,1H),2.36(s,1H),1.95–1.41(m,8H),0.95–0.80(m,9H)。
GC-MS(m/z):170.2(M+),152.2,137.1,125.1,109.1。
步骤-5:3,7-二甲基-5-亚甲基辛醛(化合物25)、3,5,7-三甲基辛-4-烯醛(化合物26)和3,5,7-三甲基辛-5-烯醛(化合物27)的区域异构体混合物的合成:
在室温,向来自步骤-4的辛烯醇的区域异构体混合物(325g,1908mmol)在1,2-二氯乙烷(1800mL)中的溶液中依次添加四正丁基氯化铵水合物(113g,382mmol)和4-羟基TEMPO(65.7g,382mmol)。然后向该反应混合物中添加碳酸氢钠(135g,1603mmol)和碳酸钾(22.16g,160mmol)在水(2500mL)中的缓冲溶液。将反应混合物在室温搅拌持续10min。然后经30分钟分批添加N-氯代琥珀酰亚胺(331g,2481mmol)。将反应混合物在室温搅拌持续3h,并且然后用碳酸氢钠的饱和溶液猝灭。将有机层分离并且用水和盐水洗涤。将有机层经硫酸钠干燥,并且在减压下浓缩以提供粗制醛。在减压下分馏提供了期望的作为区域异构体混合物的辛烯醛(170g,53%收率)。
气味特征:强烈的醛香(strong aldehydic)、水生香(watery)、花香。
IR(纯的):2955.7,2870.1,1725.3,1459.5cm-1
1H NMR(400MHz,CDCl3):δ9.79-9.67(m,1H),5.02–4.91(m,1H),3.01-2.91(m,1H),2.35–2.29(m,2H),1.95-1.57(m,6H),1.02-0.79(m,9H)。
GC-MS(m/z):168.21(M+)。
实施例-2:
由戊-2-酮和异戊烯醇合成3-甲基-5-亚甲基辛醛(化合物10)、3,5-二甲基辛-4-烯醛(化合物11)和3,5-二甲基辛-5-烯醛(化合物12)
步骤-1:2-甲基-4-亚甲基-2-丙基四氢-2H-吡喃、4,6-二甲基-6-丙基-3,6-二氢-2H-吡喃、2,4-二甲基-2-丙基-3,6-二氢-2H-吡喃的混合物的合成:在25℃,经20min向戊-2-酮(200.0g,2.32mol)的溶液中缓慢添加三氟甲磺酸(10.44g,0.070mol),并且将反应混合物搅拌持续15min。然后在室温,经30min添加3-甲基丁-3-烯-1-醇(205.0g,2.32mol)。在添加期间产生放热,该放热通过采用水的外部冷却来控制。在添加之后,将反应混合物加热至75℃-80℃持续15h。将反应混合物冷却至室温,并且然后向其中添加(500mL)甲基叔丁基醚。将有机层用5%碳酸氢钠水溶液(100mL)洗涤,随后用水(4×200mL)洗涤至中性pH。在减压下蒸发有机溶剂,以提供260g的粗制产物。将粗制产物蒸馏(70℃-71℃,以17毫巴-13毫巴),以提供期望的产物的区域异构体混合物(98.0g,31%)。
1H NMR(400MHz,CDCl3):δ5.29–5.16(m,2H),4.04–3.97(m,2H),3.72–3.60(m,2H),1.51-1.14(m,4H),1.08-1.03(m,4H),0.87–0.77(m,4H)。
GC-MS(m/z):154.2(M+)。
步骤-2:2,4-二甲基-2-丙基四氢-2H-吡喃的合成:
在高压釜中,向步骤-1中获得的产物的混合物(122g,0.721mol)在异丙醇(244mL)中的溶液中添加雷尼镍(10.0g,0.170mol)。将反应混合物在200psi氢气压力下在80℃加热持续5h。然后使用300psi氢气压力在120℃加热反应混合物持续16h。在反应完成之后,将反应混合物冷却至室温。将反应混合物过滤并且然后在减压下浓缩。将粗制残余物蒸馏(56℃-58℃,以10毫巴-8毫巴),以提供期望的产物(84.5g,68%)。
1H NMR(400MHz,CDCl3):δ3.63–3.31(m,2H),1.70–1.58(m,2H),1.45–1.15(m,10H),1.08-0.78(m,6H)。
GC-MS(m/z):155.2(M+),113.1。
步骤-3:3,5-二甲基辛-4-烯-1-基乙酸酯、3,5-二甲基辛-5-烯-1-基乙酸酯和3-甲基-5-亚甲基辛基乙酸酯的混合物的合成:将来自步骤-2的2,4-二甲基-2-丙基四氢-2H-吡喃产物(60.0g,0.37mol)、乙酸酐(76.0g,0.74mol)和p-TSA(3.52g,0.18mol)的混合物在110℃加热持续7h。在反应完成之后,将混合物冷却至30℃,然后添加MTBE(400mL),并且将整个混合物用水(200mL)洗涤,随后用10% NaHCO3溶液(200mL)洗涤,并且然后用水(3×200mL)洗涤至中性pH。在减压下蒸发有机溶剂,以提供72.3g的粗制液体,该粗制液体在减压下蒸馏(60℃-62℃,以2.3毫巴-0.5毫巴)以提供作为淡黄色液体的区域异构体乙酸酯的混合物(29.0g,39%)。
气味特征:希蒂莺(Hedione)样的,金属味花香(floral metallic),栀子花。
1H NMR(400MHz,CDCl3):δ5.13–4.77(m,1H),4.08–3.85(m,2H),2.46-3.46(m,1H),1.96–1.86(m,8H),1.57-1.24(m,4H),0.88–0.75(m,6H)。
GC-MS(m/z):198.2(M+)。
步骤-4:3-甲基-5-亚甲基辛-1-醇(化合物7)、3,5-二甲基辛-4-烯-1-醇(化合物8)和3,5-二甲基辛-5-烯-1-醇(化合物9)的混合物的合成:
将来自步骤-3的区域异构体乙酸酯(15g,0.076mol)、氢氧化钾(6.37g,0.11mol)和水(30mL)的混合物在100℃加热至回流持续17h。将反应物质冷却至室温并且用甲基叔丁基醚(350mL)稀释。将有机层用水(3×150mL)洗涤至中性pH。将有机溶剂蒸发,以提供12.5g的粗制产物。粗制产物的蒸馏(83℃-87℃,以5毫巴-7毫巴)提供呈无色液体形式的作为区域异构体的混合物的期望的产物(10.02g,56%)。
气味特征:令人愉快的琥珀花香(floral ambery),海洋希蒂莺样的,辛辣的广藿香香根草大黄(spicy patchouli vetiver rhubarb)。
1H NMR(400MHz,CDCl3):δ5.14–4.83(m,1H),3.62-3.48(m,2H),2.49-2.42(m,1H),2.01-1.85(m,2H),1.74–1.49(m,8H),0.88–0.76(m,6H)。
GC-MS(m/z):156.2(M+)。
步骤-5:3-甲基-5-亚甲基辛醛(化合物10)、3,5-二甲基辛-4-烯醛(化合物11)和3,5-二甲基辛-5-烯醛(化合物12)的混合物的合成:
在室温,向来自步骤-4的区域异构体醇(200.0g,1280mmol)在二氯甲烷(120mL)中的混合物中添加四正丁基氯化铵水合物(152.0g,256mmol)和4-羟基-TEMPO(110.0g,640mmol)。向上述混合物中添加碳酸氢钠(90.0g,1075mmol)和碳酸钾(14.86g,108mmol)在水(200mL)中的溶液。将反应混合物在室温搅拌持续10min,并且然后经10min分批添加N-氯代琥珀酰亚胺(205.0g,1536mmol)。将反应混合物在室温搅拌持续1h,并且然后用碳酸氢钠的饱和水溶液(500mL)猝灭。将有机层分离,用水(2×500mL)和盐水(1×500mL)洗涤。将有机层经无水硫酸钠干燥,并且在减压下浓缩以给出粗制产物。通过在减压下的蒸馏(56℃-58℃,以6毫巴)来纯化粗制产物,以提供呈淡黄色液体形式的作为区域异构体的混合物的期望的产物(125.0g,63%)。
气味特征:水生醛香,铃兰(muguet)
IR(纯的):2960.8,2931.5,1726.4,1457.1cm-1
1H NMR(400MHz,CDCl3):δ9.66-9.65(m,1H),5.06-4.84(m,1H),2.92-2.81(m,2H),2.32–1.81(m,6H),1.56-0.73(m,8H)。
GC-MS(m/z):154.2(M+)。
实施例-3
3-甲基-5-亚甲基壬-1-醇(化合物19)和3,5-二甲基壬-5-烯-1-醇(化合物20)的混合物的合成。该化合物使用实施例-1中描述的方法由己-2-酮和异戊烯醇来合成。
步骤-1:2-丁基-2-甲基-4-亚甲基四氢-2H-吡喃、6-丁基-4,6-二甲基-3,6-二氢-2H-吡喃和2-丁基-2,4-二甲基-3,6-二氢-2H-吡喃的混合物的合成:
该化合物使用实施例-1中的步骤-1中描述的方法由己-2-酮和异戊烯醇来合成:
气味特征:锐利的绿香,茴香样的,浓郁的柑橘类(zesty citrus),香甜的酸橙皮样的(sweet lime peel like)
IR(纯的):2933.5,1683.6,1452.5,1378.4cm-1
1H NMR(400MHz,CDCl3):δ5.38-5.25(m,2H),4.09-4.06(m,2H),3.80-3.71(m,2H),2.07-1.60(m,6H),1.33-1.27(m,5H),1.16–1.15(m,3H)。
GC-MS(m/z):168.1(M+),153.1,140.1,111.1。
步骤-2:2-丁基-2,4-二甲基四氢-2H-吡喃的合成:
该化合物使用实施例-1中的步骤-2中描述的方法,由实施例3中的步骤-1中获得的产物的混合物来合成:
气味特征:芳香清新,桉树,迷迭香样的。
IR(纯的):2954.6,2929.1,1457.1,1375.7,1101.1cm-1
1H NMR(400MHz,CDCl3):δ3.81-3.52(m,2H),1.69-1.27(m,8H),1.14-1.25(m,6H),0.91-0.87(m,6H)。
GC-MS(m/z):170.2(M+)。
步骤-3:3,5-二甲基壬-4-烯-1-基乙酸酯、3,5-二甲基壬-5-烯-1-基乙酸酯和3-甲基-5-亚甲基壬基乙酸酯的混合物的合成:
该产物使用实施例-1中的步骤-3中描述的方法由实施例3中的步骤-2中获得的2-丁基-2,4-二甲基四氢-2H-吡喃来合成:
气味特征:花香,醛香。
IR(纯的):2958.6,2929.1,1741.1,1230.5cm-1
1H NMR(400MHz,CDCl3):δ5.25-4.81(m,1H),4.14-3.92(m,2H),2.04-1.92(m,5H),1.67–1.55(m,6H),1.37-1.27(m,4H),0.95–0.85(m,6H)。
GC-MS(m/z):212.2(M+),152.2,137.1,123.1,110.1,95.1。
步骤-4:3-甲基-5-亚甲基壬-1-醇(化合物19)和(5E)-3,5-二甲基壬-5-烯-1-醇(化合物20)的混合物的合成
该化合物使用实施例-1中给出的步骤-4的程序,由实施例3中的步骤-3中获得的混合物来合成:
气味特征:强烈的绿香,醛花香。
IR(纯的):3326.2,2927.1,1741.1,1455.7,1051.6cm-1
1H NMR(400MHz,CDCl3):δ5.27-4.85(m,1H),3.70-3.59(m,2H),2.65–2.47(m,1H),2.00-1.93(m,4H),1.66-1.55(m,4H),1.38-1.23(m,4H),0.95-0.85(m,6H)。
GC-MS(m/z):170.2(M+),155.1,137.1,125.1,113.1,95.1。
实施例-4
3-甲基-5-亚甲基癸醛(化合物31)和3,5-二甲基癸-4-烯醛(化合物32)的混合物的合成:该化合物使用实施例-1中描述的5-步骤的方案,由庚-2-酮和异戊烯醇来合成。
步骤-1:2-甲基-4-亚甲基-2-戊基四氢-2H-吡喃、4,6-二甲基-6-戊基-3,6-二氢-2H-吡喃和2,4-二甲基-2-戊基-3,6-二氢-2H-吡喃的混合物的合成:
气味特征:花香,金属味,玫瑰绿香
IR(纯的):2932.6,1680.8,1456.3,1378.0cm-1
1H NMR(400MHz,CDCl3):δ5.38-5.25(m,1H),4.09-4.06(m,1H),3.78-3.73(m,2H),2.07-1.79(m,2H),1.60(s,3H),1.36-1.1,14(m,8H),0.90–0.85(m,5H)。
GC-MS(m/z):182.2(M+),167.2,139.1,111.1
步骤-2:2,4-二甲基-2-戊基四氢-2H-吡喃的合成:
该化合物通过使用实施例-1中的步骤-2中描述的方法,由实施例4中的步骤-1的产物来合成。
IR(纯的):2928.5,2860.9,1457.4,1375.1,1094.3cm-1
1H NMR(400MHz,CDCl3):δ3.81-3.52(m,2H),1.75-1.25(m,8H),1.14-1.25(m,8H),0.91-0.87(m,6H)。
GC-MS(m/z):183.2(M+),169.2,113.1。
气味特征:水果,内酯香(lactonic),桃子样的
步骤-3:3,5-二甲基癸-4-烯-1-基乙酸酯、3,5-二甲基癸-5-烯-1-基乙酸酯和3-甲基-5-亚甲基癸基乙酸酯的混合物的合成:
该化合物通过使用实施例-1中的步骤-3中描述的方法,由实施例4中的步骤-2的产物来合成。
IR(纯的):2957.9,2927.5,1741.2,1668.1,1230.3cm-1
1H NMR(400MHz,CDCl3):δ5.26-4.83(m,1H),4.14-3.92(m,2H),2.04-1.92(m,5H),1.65–1.55(m,6H),1.37-1.21(m,6H),0.95–0.85(m,6H)。
GC-MS(m/z):226.3(M+),166.2,151.1,137.1,123.1,109.1,95.1。
气味特征:温和干燥,少许的木质香。
步骤-4:3-甲基-5-亚甲基癸-1-醇(化合物29)和3,5-二甲基癸-4-烯-1-醇(化合物36)的混合物的合成:
该化合物通过使用实施例-1中的步骤-4中描述的方法,由实施例4中的步骤-3的产物来合成:
IR(纯的):3336.8,2926.1,1666.3,1456.2,1051.6cm-1
1H NMR(400MHz,CDCl3):δ5.25-4.87(m,1H),3.78-3.57(m,2H),2.65–2.47(m,1H),2.00-1.92(m,4H),1.69-1.23(m,10H),0.94-0.82(m,6H)。
GC-MS(m/z):184.3(M+)。
气味特征:干燥绿香,轻微的木质香。
步骤-5:3-甲基-5-亚甲基癸醛(化合物31)和3,5-二甲基癸-4-烯醛(化合物32)的混合物的合成:
该化合物通过使用实施例-1中的步骤-5中描述的方法,由实施例4中的步骤-4的产物来合成:
IR(纯的):2957.1,1725.0,1457.7cm-1
1H NMR(400MHz,CDCl3):δ9.75–9.67(m,1H),5.24–4.92(m,1H),2.34–1.91(m,4H),1.67–1.57(m,4H),1.32–1.25(m,6H),1.01-0.85(m,6H)。
GC-MS(m/z):182.2(M+),164.2,138.1,123.1,112.1。
气味特征:清新花香,醛香,水生香。
实施例-5
3-甲基-5-亚甲基十一-1-醇(化合物34)和3,5-二甲基十一-4-烯-1-醇(化合物35)的混合物的合成
该化合物使用实施例-1中的步骤-1中描述的方法由2-辛酮和异戊烯醇来合成:
步骤-1:2-己基-2-甲基-4-亚甲基四氢-2H-吡喃、6-己基-4,6-二甲基-3,6-二氢-2H-吡喃和2-己基-2,4-二甲基-3,6-二氢-2H-吡喃的混合物的合成:
该化合物使用实施例-1中的步骤-1中描述的方法由2-辛酮和异戊烯醇来合成:
气味特征:霉味(musty),花香,少许的绿香。
IR(纯的):2930.4,2859.1,1681.0,1456.9,1376.1cm-1
1H NMR(400MHz,CDCl3):δ5.38-5.25(m,1H),4.08-4.06(m,1H),3.79-3.70(m,1H),2.04-1.52(m,7H),1.48-0.85(m,14H)。
GC-MS(m/z):196.2(M+),181.1,168.2,129.1,111.1。
步骤-2:2-己基-2,4-二甲基四氢-2H-吡喃的合成:
该化合物通过使用实施例-1中的步骤-2中描述的方法,由实施例5中的步骤-1的产物来合成:
IR(纯的):2927.6,2858.2,1457.9,1375.4,1096.5cm-1
1H NMR(400MHz,CDCl3):δ3.79-3.65(m,2H),1.98-1.24(m,15H),1.15-0.85(m,9H)。
GC-MS(m/z):198.2(M+),183.2,113.1。
气味特征:温和的(mild)。
步骤-3:3,5-二甲基十一-4-烯-1-基乙酸酯、3,5-二甲基十一-5-烯-1-基乙酸酯和3-甲基-5-亚甲基十一烷基乙酸酯的合成:
该化合物通过使用实施例-1中的步骤-3中描述的方法,由实施例5中的步骤-2的产物来合成:
IR(纯的):2926.7,2858.4,1741.7,1230.4cm-1
1H NMR(400MHz,CDCl3):δ5.26-4.85(m,1H),4.15-3.92(m,2H),2.04-1.91(m,5H),1.65–1.55(m,6H),1.37-1.21(m,8H),0.95–0.85(m,6H)。
GC-MS(m/z):240.2(M+),180.2,151.2,95.1。
气味特征:温和的气味,木质香。
步骤-4:3-甲基-5-亚甲基十一-1-醇(化合物34)和3,5-二甲基十一-4-烯-1-醇(化合物35)的混合物的合成
该化合物通过使用实施例-1中的步骤-4中描述的方法,由实施例5中的步骤-3的产物来合成:
IR(纯的):3333.0,2924.5,1456.8,1377.9,1052.9cm-1
1H NMR(400MHz,CDCl3):δ5.26-4.89(m,1H),3.72-3.60(m,2H),1.98–1.92(m,1H),1.66-1.23(m,16H),0.95-0.83(m,6H)。
GC-MS(m/z):198.2(M+),180.2,153.2,113.1,95.1。
实施例-6
3,5,7-三甲基辛醛(28)的合成:
步骤-1:3,5,7-三甲基辛-1-醇(24)的合成:
在高压釜中,向实施例-1中的步骤-4的产物3,7-二甲基-5-亚甲基辛-1-醇(化合物21)、3,5,7-三甲基辛-5-烯-1-醇(化合物22)和3,7-二甲基-5-亚甲基辛-1-醇(化合物23)的区域异构体混合物(200g,1.174mol)在2-丙醇(200mL)中的溶液中添加雷尼镍(10g,0.12mol)。将反应混合物在200psi氢气压力下在80℃加热并且维持持续18h。将反应混合物冷却至30℃并且通过hyflow床过滤。用2-丙醇(2×10mL)洗涤hyflow床。浓缩有机层,以提供162.0g(80%收率)的作为淡黄色油的期望的产物。
IR(纯的):3333.6,2955.3,1461.2,1379.9cm-1
1H NMR(400MHz,CDCl3):δ3.71-3.59(m,2H),1.64–1.54(m,4H),1.44-0.78(m,18H)。
GC-MS(m/z):172.2(M+)。
气味特征:水生醛香,花香,绿香。
步骤-2:3,5,7-三甲基辛醛(28)的合成:
该化合物通过使用如实施例-1中的步骤-5中描述的氧化方案,通过3,5,7-三甲基辛-1-醇的氧化来合成。
气味特征:醛香,铁水样的(hot-iron like),水生香。
IR(纯的):3329.2,2957.1,1458.9,1378.3cm-1
1H NMR(400MHz,CDCl3):δ9.77–9.76(m,1H),2.38–2.16(m,3H),1.67–1.55(m,2H),1.23-0.84(m,16H)。
GC-MS(m/z):170.2(M+),126.1,109.1,95.1,83.1。
实施例-7:
5-乙基-3-甲基庚-5-烯醛(化合物16)和5-乙基-3-甲基庚-4-烯醛(化合物17)的混合物的合成
步骤-1:6,6-二乙基-4-甲基-3,6-二氢-2H-吡喃;2,2-二乙基-4-亚甲基四氢-2H-吡喃和2,2-二乙基-4-甲基-3,6-二氢-2H-吡喃的混合物的合成:
该化合物使用实施例-1中的步骤-1中描述的方法,由戊-4-酮和异戊烯醇以31%收率来合成。
GC-MS(m/z):154.2(M+),
步骤-2:2,2-二乙基-4-甲基四氢-2H-吡喃的合成:
在高压釜室中,将雷尼镍(20g,341mmol)添加到在2-丙醇(100mL)中的上文的步骤-1的产物(320g,2102mmol)中,并且在200psi的连续的H2压力下将反应加热至120℃持续18h。在反应完成之后,将混合物冷却至室温并且过滤,以提供(233g,71%)粗制产物,该粗制产物按原样被用于下一反应。
GC-MS(m/z):156.2(M+),
步骤-3:5-乙基-3-甲基庚-4-烯-1-基乙酸酯和5-乙基-3-甲基庚-5-烯-1-基乙酸酯的混合物的合成:
在室温,向搅拌的乙酸酐(272g,2662mmol)和对甲苯磺酸一水合物(12.66g,66.6mmol)的溶液中添加2,2-二乙基-4-甲基四氢-2H-吡喃(208g,1331mmol)并且将反应混合物加热至110℃持续4h。在反应完成之后,将混合物冷却至室温,并且用水(200mL)猝灭。
将含水层用乙酸乙酯(1×200mL)萃取,并且将有机层用水(3×200mL)、碳酸氢钠饱和水溶液(1×200mL)和盐水(1×50mL)洗涤。将有机层经硫酸钠干燥,过滤并且浓缩,以提供240g的粗制化合物。将粗制产物通过蒸馏(97℃-102℃,以3毫巴-8毫巴)纯化以提供期望的产物(158g,60%)。
GC-MS(m/z):198.3(M+),
步骤-4:5-乙基-3-甲基庚-4-烯-1-醇(化合物13)和5-乙基-3-甲基庚-5-烯-1-醇(化合物14)的混合物的合成:
向搅拌的异构体乙酸酯(步骤-3,137g,694mmol)在乙醇(100mL)中的溶液中添加氢氧化钠(41.7g,1042mmol)在水(400mL)中的溶液,并且将反应混合物在室温搅拌持续2h,并且然后在100℃加热持续6h。将反应混合物冷却至室温,分离有机层并且用乙酸乙酯(2×300mL)萃取含水层。将合并的有机层用盐水(1×200mL)洗涤,并且经硫酸钠干燥,过滤,浓缩,以给出粗制产物(140g)。粗制产物通过使用乙酸乙酯:正己烷4%-10%梯度洗脱的柱色谱法(60目-120目)来纯化,以提供作为无色液体的期望的产物(100.0g,66%)。
气味特征:粉香(powdery),泥土香,强烈,芳香前调。
1H NMR(400MHz,CDCl3):δ5.24-5.05(m,1H),3.65-3.47(m,2H),2.05–1.83(m,4H),1.74–1.49(m,4H),0.92–0.76(m,9H)。
GC-MS(m/z):156.2(M+)。
步骤-5:5-乙基-3-甲基庚-5-烯醛(16)和5-乙基-3-甲基庚-4-烯醛(17)的合成:
该化合物通过使用实施例-1中的步骤5中描述的氧化方法,由步骤-4的产物以43%收率来合成。
GCMS(m/z):154.2(M+)。
气味特征:醛香,铁水味,水生香。
实施例-8:
3-甲基-5-亚甲基庚醛(4)、3,5-二甲基庚-4-烯醛(5)、3,5-二甲基庚-5-烯醛(6)的合成:
3,5-二甲基庚-4-烯-1-基乙酸酯、3,5-二甲基庚-5-烯-1-基乙酸酯和3-甲基-5-亚甲基庚基乙酸酯的混合物的合成:该化合物由丁酮和异戊烯醇在如根据实施例1的步骤1至步骤3中描述的3个步骤中合成。
IR(纯的):2961.6,2929.3,1739.9,1670.0cm-1
1H NMR(400MHz,CDCl3):δ5.28–4.84(m,1H),4.15–3.91(m,2H),2.01–1.33(m,11H),0.97–0.82(m,6H)。
GC-MS(m/z):184.2(M+),124.1,109.1。
气味特征:干燥醛香,粉香。
3-甲基-5-亚甲基庚-1-醇(化合物1)、3,5-二甲基庚-4-烯-1-醇(化合物2)和3,5-二甲基庚-5-烯-1-醇(化合物3)的混合物的合成:该化合物通过使用实施例-1中的步骤-4中描述的方法,由上文描述的乙酸酯的混合物来合成:
气味特征:绿叶花香。
IR(纯的):3336.7,2961.5,2925.8,1712.7,1653.4,1456.0cm-1
1H NMR(400MHz,CDCl3):δ5.25-4.83(m,1H),3.70-3.52(m,2H),2.04-1.91(m,3H),1.78–1.29(m,6H),0.97–0.80(m,6H)。
GC-MS(m/z):142.1(M+),127.1,113.1,97.1。
3-甲基-5-亚甲基庚醛(化合物4)、3,5-二甲基庚-4-烯醛(化合物5)和3,5-二甲基庚-5-烯醛(化合物6)的混合物的合成:该化合物通过使用实施例-1中的步骤-5中描述的氧化方案,由上文描述的异构体醇的混合物来合成。
1H NMR(400MHz,CDCl3):δ9.75–9.67(m,1H),5.34–4.92(m,1H),2.37–1.91(m,2H),1.68–1.54(m,6H),1.01–0.91(m,6H)。
GC-MS(m/z):140.1(M+)。
气味特征:绿叶花香。
实施例-9:
3,7-二甲基-5-(2-甲基丙基)辛-5-烯醛(41)和3,7-二甲基-5-(2-甲基丙基)辛-4-烯醛(42)的混合物的合成:
该化合物使用实施例-1中描述的方法,由2,6-二甲基庚-4-酮和异戊烯醇来合成:
步骤-1:2,2-二异丁基-4-亚甲基四氢-2H-吡喃、2,2-二异丁基-4-甲基-3,6-二氢-2H-吡喃和6,6-二异丁基-4-甲基-3,6-二氢-2H-吡喃的混合物的合成:
该化合物使用实施例-1中的步骤-1中描述的方法,由2,6-二甲基庚-4-酮和异戊烯醇以42%收率来合成:
气味特征:温和的柑橘香调。
GC-MS(m/z):210.3(M+)。
步骤-2:2,2-二异丁基-4-甲基四氢-2H-吡喃的合成:
该化合物通过使用实施例-1中的步骤-2中描述的方法,由上文的步骤-1的产物来合成:
IR(纯的):2954.8,2926.1,1455.5,1375.2cm-1
1H NMR(400MHz,CDCl3):δ3.79–3.57(m,2H),1.75–1.15(m,11H),0.94–0.81(m,15H)。
GC-MS(m/z):212.1(M+)。
气味特征:花香,香甜,金属味。
步骤-3:5-异丁基-3,7-二甲基辛-4-烯-1-基乙酸酯和5-异丁基-3,7-二甲基辛-5-烯-1-基乙酸酯的混合物的合成:
该化合物通过使用实施例-1中的步骤-3中描述的方法,由上文的步骤-2的产物来合成:
IR(纯的):2953.6,2925.9,1741.2cm-1
1H NMR(400MHz,CDCl3):δ4.92–4.82(m,1H),4.13-3.97(m,2H),2.51–2.39(m,1H),2.04–1.93(m,3H),1.70–1.41(m,6H),1.12–0.75(m,17H)。
GC-MS(m/z):254.2(M+)。
气味特征:干燥芳香。
步骤-4:5-异丁基-3,7-二甲基辛-4-烯-1-醇(化合物38)和5-异丁基-3,7-二甲基辛-5-烯-1-醇(化合物39)的混合物的合成:该化合物通过使用实施例-1中的步骤-4中描述的方法,由上文的步骤-3的产物来合成:
1H NMR(400MHz,CDCl3):δ4.98–4.84(m,1H),3.73-3.60(m,2H),2.59–2.37(m,1H),1.97–1.43(m,9H),1.12–0.75(m,15H)。
GC-MS(m/z):212.2(M+)。
气味特征:温和的花香。
步骤-5:3,7-二甲基-5-(2-甲基丙基)辛-5-烯醛(化合物41)和3,7-二甲基-5-(2-甲基丙基)辛-4-烯醛(化合物42)的混合物的合成:
气味特征:花香,清新醛香,水生香。
1H NMR(400MHz,CDCl3):δ9.77–9.67(m,1H),5.02-4.86(m,1H),2.35–1.90(m,3H),1.65–1.59(m,6H),1.15–0.73(m,15H)。
GC-MS(m/z):210.2(M+)。
组合物评价实施例:
柑橘组合物的比较:
在以下实施例中,评价了包含两种基准化合物的多种柑橘类组合物调合物,并且与包含来自实施例21、实施例22和实施例23的化合物的组合物调合物进行了比较。组合物A包含来自实施例21、实施例22和实施例23的化合物(即3,7-二甲基-5-亚甲基辛-1-醇、3,5,7-三甲基辛-4-烯-1-醇和3,5,7-三甲基辛-5-烯-1-醇)的混合物,该混合物作为10%w/w的在IPM(肉豆蔻酸异丙酯)中的溶液。组合物B包含商业化合物6,6-二甲氧基-2,5,5-三甲基己-2-烯,组合物C包含商业化合物3-甲基-5-苯基戊-1-醇;并且最后,组合物D仅包含IPM并且用作空白。所有上述组合物在洗发水中进行评价。
添加按重量计0.5%的来自实施例21、实施例22和实施例23的化合物(即3,7-二甲基-5-亚甲基辛-1-醇、3,5,7-三甲基辛-4-烯-1-醇和3,5,7-三甲基辛-5-烯-1-醇)的混合物赋予柑橘类组合物闪亮的(sparkling)和清新的特性。这种特性比在柑橘类组合物B、柑橘类组合物C和柑橘类组合物D中所观察到的在强度上大得多。此外,在前调中还呈现出浓烈香调(tangy note)。组合物A的整体性能被高度增强,并且优于组合物B、组合物C和组合物D的对应性能。
玫瑰组合物的比较:
在另一个评价研究中,评价了包含不同的基准化合物的多种玫瑰组合物调合物,并且与包含来自实施例21、实施例22和实施例23的化合物的混合物的组合物调合物进行了比较。组合物A包含来自实施例21、实施例22和实施例23的化合物(即3,7-二甲基-5-亚甲基辛-1-醇、3,5,7-三甲基辛-4-烯-1-醇和3,5,7-三甲基辛-5-烯-1-醇)的混合物,该混合物作为10%w/w的在IPM(肉豆蔻酸异丙酯)中的溶液。组合物B包含商业化合物6,6-二甲氧基-2,5,5-三甲基己-2-烯,组合物C包含商业化合物3-甲基-5-苯基戊-1-醇;并且最后,组合物D仅包含IPM,并且用作空白。所有上述组合物都用于洗发水以及织物软化剂中。
当来自实施例21、实施例22和实施例23的化合物(即3,7-二甲基-5-亚甲基辛-1-醇、3,5,7-三甲基辛-4-烯-1-醇和3,5,7-三甲基辛-5-烯-1-醇)的混合物以0.5%w/w的剂量添加到洗发水以及织物软化剂中时,如在组合物A中说明的,全面的(well-rounded)并且更丰富的特性被赋予组合物。与分别包含商业化合物6,6-二甲氧基-2,5,5-三甲基己-2-烯和3-甲基-5-苯基戊-1-醇的其他组合物B和组合物C相比,组合物A更有花香、更有玫瑰香,并且具有更丰富的效果。
玫瑰组合物的比较:
在另一个评价研究中,评价了包含两种商业基准化合物的多种玫瑰组合物调合物,并且与包含来自实施例10、实施例11和实施例12的化合物的混合物的组合物调合物进行比较,该混合物是3-甲基-5-亚甲基辛醛、3,5-二甲基辛-4-烯醛和3,5-二甲基辛-5-烯醛的混合物。组合物A包含来自实施例10、实施例11和实施例12的化合物的混合物,该混合物作为10%w/w的在IPM(肉豆蔻酸异丙酯)中的溶液。组合物B包含商业化合物4-(4-羟基-4-甲基戊基)环己-3-烯-1-甲醛,组合物C包含商业化合物1-甲基-4-(4-甲基戊基)环己-3-烯-1-甲醛;并且最后,组合物D仅包含IPM并且用作空白。所有上述组合物在洗发水中被使用。
当来自实施例10、实施例11和实施例12的化合物的混合物以0.5%w/w的剂量添加到洗发水中时,有冲击力的(impactful)花香特性被赋予组合物。与分别包含商业化合物新铃兰醛(Lyral)和鲜草醛(Vernaldehyde)的其他组合物B和组合物C相比,组合物A更具有玫瑰香并且具有更全面的效果。
本文公开了由本发明的范围所涵盖的几种化合物。必须注意的是,所公开的化合物不限制本发明的范围。
本发明的前述描述仅仅是为了说明本发明而设置而不是意图限制。由于对并入本发明的精神和实质的公开的实施方案的修改可以被本领域技术人员想到,因此本发明应当被解释为包括本公开内容的范围内的所有内容。
Claims (10)
1.式(I)的化合物
A=-CH2OAc,-CH2OH,-CHO,
其中A代表-CH2OH或-CHO、-CH2OAc
R1是烷基基团或亚烷基基团,
R2是烷基基团或亚烷基基团,
虚线代表双键或单键,
条件是(I)不是:
a.3,5-二甲基己-5-烯-1-醇;
b.3,5-二甲基己-4-烯-1-醇;
c.3,5-二甲基己-1-醇;
d.3,5-二甲基己醛;
e.3,5-二甲基己-5-烯醛;
f.3,5-二甲基己-4-烯醛;
g.3,5-二甲基庚-1-醇;
h.3,5-二甲基庚醛;
i.5-乙基-3-甲基辛-5-烯-1-醇;
j.3,5-二甲基辛-1-醇;
k.3,5-二甲基辛醛;
l.3,5-二甲基壬-4-烯-1-醇;
m.3,5-二甲基壬-1-醇;
n.3,5-二甲基壬醛;
o.3,5-二甲基壬-4-烯醛;
p.3,5-二甲基癸-5-烯-1-醇;以及
q.3,5-二甲基癸-5-烯醛。
2.根据权利要求1所述的化合物,其中R1和R2独立地选自包括以下的组:甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、正戊基、正己基、亚甲基、亚乙基、亚丙基、亚异丙基、亚丁基、亚异丁基、亚戊基、亚己基。
3.根据权利要求1所述的化合物,选自以下化合物:
1)3-甲基-5-亚甲基庚-1-醇;
2)3,5-二甲基庚-4-烯-1-醇;
3)3,5-二甲基庚-5-烯-1-醇;
4)3-甲基-5-亚甲基庚醛;
5)3,5-二甲基庚-4-烯醛;
6)3,5-二甲基庚-5-烯醛;
7)3-甲基-5-亚甲基辛-1-醇;
8)3,5-二甲基辛-4-烯-1-醇;
9)3,5-二甲基辛-5-烯-1-醇;
10)3-甲基-5-亚甲基辛醛;
11)3,5-二甲基辛-4-烯醛;
12)3,5-二甲基辛-5-烯醛;
13)5-乙基-3-甲基庚-4-烯-1-醇;
14)5-乙基-3-甲基庚-5-烯-1-醇;
15)5-乙基-3-甲基庚-1-醇;
16)5-乙基-3-甲基庚-5-烯醛;
17)5-乙基-3-甲基庚-4-烯醛;
18)5-乙基-3-甲基庚醛;
19)3-甲基-5-亚甲基壬-1-醇;
20)3,5-二甲基壬-5-烯-1-醇;
21)3,7-二甲基-5-亚甲基辛-1-醇;
22)3,5,7-三甲基辛-4-烯-1-醇;
23)3,5,7-三甲基辛-5-烯-1-醇;
24)3,5,7-三甲基辛-1-醇;
25)3,7-二甲基-5-亚甲基辛醛;
26)3,5,7-三甲基辛-4-烯醛;
27)3,5,7-三甲基辛-5-烯醛;
28)3,5,7-三甲基辛醛;
29)3-甲基-5-亚甲基癸-1-醇;
30)3,5-二甲基癸-1-醇;
31)3-甲基-5-亚甲基癸醛;
32)3,5-二甲基癸-4-烯醛;
33)3,5-二甲基癸醛;
34)3-甲基-5-亚甲基十一-1-醇;
35)3,5-二甲基十一-4-烯-1-醇;
36)3,5-二甲基癸-4-烯-1-醇;
37)3,5-二甲基十一醛;
38)5-异丁基-3,7-二甲基辛-4-烯-1-醇;
39)5-异丁基-3,7-二甲基辛-5-烯-1-醇;
40)5-异丁基-3,7-二甲基辛-1-醇;
41)3,7-二甲基-5-(2-甲基丙基)辛-5-烯醛;
42)3,7-二甲基-5-(2-甲基丙基)辛-4-烯醛;和
43)3,7-二甲基-5-(2-甲基丙基)辛醛。
4.一种组合物,包含至少两种根据权利要求1至3中任一项所述的化合物的混合物。
5.根据权利要求4所述的组合物,其中在所述组合物中所述式(I)的化合物的含量是至少0.00001wt.%或至少0.00001wt.%至99.9wt.%。
6.根据权利要求5所述的组合物,其中在所述组合物中所述式(I)的化合物的含量是至少1wt.%或至少1wt.%至25wt.%。
7.根据权利要求4至6中任一项所述的组合物,包含至少一种酯和/或至少一种醇,优选地至少酯和醇的混合物,其中所述式(I)的化合物连同所述酯和所述醇的总含量是25wt%或大于25wt%或者50wt%或大于50wt%。
8.根据权利要求4至7中任一项所述的组合物,在发香组合物、调味组合物、除臭组合物或掩蔽组合物中。
9.根据权利要求1至4中任一项所述的化合物,在发香组合物、调味组合物、除臭组合物或掩蔽组合物中。
10.一种用于制备式(I)的化合物的工艺,所述工艺包括以下步骤:
a.使式(II)的化合物
与下式的醇反应
以得到式(III)的化合物
其中R1是烷基基团或亚烷基基团,
R2是烷基基团或亚烷基基团,
虚线代表双键或单键;
b.使所述式(III)的化合物与Ra-Ni和氢反应,以得到式(IV)的化合物
c.使所述式(IV)的化合物与乙酸酐反应,以得到式(V)的化合物
d.使所述式(V)的化合物与氢氧化钠在水中反应,以得到式(VI)的化合物
e.使用(2,2,6,6-四甲基哌啶-1-基)氧基(TEMPO)或4-羟基-TEMPO(4-羟基-2,2,6,6-四甲基哌啶-1-氧基)连同N-氯代琥珀酰亚胺和相转移催化剂来氧化式(VI)的化合物,以获得式(VII)的化合物
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