CN112930335A - 烷氧基苯甲醛衍生物及其前体 - Google Patents
烷氧基苯甲醛衍生物及其前体 Download PDFInfo
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- CN112930335A CN112930335A CN201980071569.8A CN201980071569A CN112930335A CN 112930335 A CN112930335 A CN 112930335A CN 201980071569 A CN201980071569 A CN 201980071569A CN 112930335 A CN112930335 A CN 112930335A
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- Prior art keywords
- group
- alkyl
- substituted
- benzene
- butoxy
- Prior art date
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- 239000002243 precursor Substances 0.000 title claims abstract description 32
- -1 4- (3-butoxyphenyl) -2-methylbut-3-en-1-yl Chemical group 0.000 claims description 70
- 150000001875 compounds Chemical class 0.000 claims description 68
- 238000000034 method Methods 0.000 claims description 30
- 125000003118 aryl group Chemical group 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 239000003205 fragrance Substances 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 125000001033 ether group Chemical group 0.000 claims description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- UXAZIOBKGOMERJ-BABZSUFTSA-N 1-butoxy-3-[(1E,4Z)-hepta-1,4-dienyl]benzene Chemical compound C(CCC)OC1=CC(=CC=C1)\C=C\C\C=C/CC UXAZIOBKGOMERJ-BABZSUFTSA-N 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 238000006467 substitution reaction Methods 0.000 claims description 7
- SFSXGGMNFUGTRR-UHFFFAOYSA-N 1-[4-(3-butoxyphenyl)but-3-enyl]-4-methyl-2-(2-methylpropyl)benzene Chemical compound C(CCC)OC=1C=C(C=CC=1)C=CCCC1=C(C=C(C=C1)C)CC(C)C SFSXGGMNFUGTRR-UHFFFAOYSA-N 0.000 claims description 5
- VKVLDEJWCPLEBY-UHFFFAOYSA-N 1-[4-(3-butoxyphenyl)but-3-enyl]-2-methyl-4-(2-methylpropyl)benzene Chemical compound C(CCC)OC=1C=C(C=CC=1)C=CCCC1=C(C=C(C=C1)CC(C)C)C VKVLDEJWCPLEBY-UHFFFAOYSA-N 0.000 claims description 4
- TXISUJXRDRTCBV-SXWITGCCSA-N 1-butan-2-yloxy-3-[(1E,4Z)-hepta-1,4-dienyl]benzene Chemical compound CC/C=C\C/C=C/C1=CC(=CC=C1)OC(C)CC TXISUJXRDRTCBV-SXWITGCCSA-N 0.000 claims description 4
- VLEPEYAUBWPIFZ-UHFFFAOYSA-N 1-butoxy-3-(3-methyldodec-1-enyl)benzene Chemical compound C(CCC)OC1=CC(=CC=C1)C=CC(CCCCCCCCC)C VLEPEYAUBWPIFZ-UHFFFAOYSA-N 0.000 claims description 4
- YHZUVACZKWYOKL-UHFFFAOYSA-N 1-butoxy-3-(3-phenylprop-1-enyl)benzene Chemical compound C(CCC)OC1=CC(=CC=C1)C=CCC1=CC=CC=C1 YHZUVACZKWYOKL-UHFFFAOYSA-N 0.000 claims description 4
- ILFQFXIGBLWNIR-UHFFFAOYSA-N 1-butoxy-3-(7-methoxy-3,7-dimethylnon-1-enyl)benzene Chemical compound C(CCC)OC1=CC(=CC=C1)C=CC(CCCC(CC)(C)OC)C ILFQFXIGBLWNIR-UHFFFAOYSA-N 0.000 claims description 4
- CKPAMKGJJQPRBD-OARRTAFWSA-N 1-butoxy-3-[(5E)-undeca-1,5-dienyl]benzene Chemical compound C(CCC)OC1=CC(=CC=C1)C=CCC\C=C\CCCCC CKPAMKGJJQPRBD-OARRTAFWSA-N 0.000 claims description 4
- MAXXCESLSCEHDI-UHFFFAOYSA-N 1-butoxy-3-[4-(3-propan-2-ylphenyl)pent-1-enyl]benzene Chemical compound C(CCC)OC1=CC(=CC=C1)C=CCC(C)C1=CC(=CC=C1)C(C)C MAXXCESLSCEHDI-UHFFFAOYSA-N 0.000 claims description 4
- WXDORHIADHLHPL-UHFFFAOYSA-N 1-butoxy-3-[4-(4-ethylphenyl)-3,3-dimethylbut-1-enyl]benzene Chemical compound C(CCC)OC1=CC(=CC=C1)C=CC(CC1=CC=C(C=C1)CC)(C)C WXDORHIADHLHPL-UHFFFAOYSA-N 0.000 claims description 4
- WZYCELHRMDRWKC-UHFFFAOYSA-N 1-butoxy-3-[4-(4-tert-butylphenyl)-3-methylbut-1-enyl]benzene Chemical compound C(CCC)OC1=CC(=CC=C1)C=CC(CC1=CC=C(C=C1)C(C)(C)C)C WZYCELHRMDRWKC-UHFFFAOYSA-N 0.000 claims description 4
- ZXUAQJLKJJEHBW-UHFFFAOYSA-N 1-butoxy-3-[4-(4-tert-butylphenyl)but-1-enyl]benzene Chemical compound C(CCC)OC1=CC(=CC=C1)C=CCCC1=CC=C(C=C1)C(C)(C)C ZXUAQJLKJJEHBW-UHFFFAOYSA-N 0.000 claims description 4
- AKMJZBWRCHWZLP-UHFFFAOYSA-N 1-butoxy-3-[4-[4-(2-methylpropyl)phenyl]but-1-enyl]benzene Chemical compound C(CCC)OC1=CC(=CC=C1)C=CCCC1=CC=C(C=C1)CC(C)C AKMJZBWRCHWZLP-UHFFFAOYSA-N 0.000 claims description 4
- LELAJTDKLPCFOJ-UHFFFAOYSA-N 1-butoxy-3-tetradeca-1,3-dienylbenzene Chemical compound C(CCC)OC1=CC(=CC=C1)C=CC=CCCCCCCCCCC LELAJTDKLPCFOJ-UHFFFAOYSA-N 0.000 claims description 4
- RSLMQUKBSVXFBW-UHFFFAOYSA-N 11-(3-butoxyphenyl)-2,6-dimethylundeca-6,10-dien-2-ol Chemical compound C(CCC)OC=1C=C(C=CC=1)C=CCCC=C(CCCC(C)(O)C)C RSLMQUKBSVXFBW-UHFFFAOYSA-N 0.000 claims description 4
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 4
- SJHOSAKFUQGIPU-UGXDAERVSA-N CC/C=C\C/C=C/C1=CC(OC(C)C)=CC=C1 Chemical compound CC/C=C\C/C=C/C1=CC(OC(C)C)=CC=C1 SJHOSAKFUQGIPU-UGXDAERVSA-N 0.000 claims description 4
- CARMBADQUYPMJB-MHBAEANFSA-N CCCCCOC1=CC=CC(/C=C/C/C=C\CC)=C1 Chemical compound CCCCCOC1=CC=CC(/C=C/C/C=C\CC)=C1 CARMBADQUYPMJB-MHBAEANFSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000005394 methallyl group Chemical group 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- 230000002269 spontaneous effect Effects 0.000 claims description 4
- 125000006592 (C2-C3) alkenyl group Chemical group 0.000 claims description 3
- FTNJQNQLEGKTGD-UHFFFAOYSA-N 1,3-benzodioxole Chemical compound C1=CC=C2OCOC2=C1 FTNJQNQLEGKTGD-UHFFFAOYSA-N 0.000 claims description 3
- RIIFYVWJPCZVPX-LJRDKERCSA-N 1-butoxy-3-[(1E,7Z)-deca-1,7-dienyl]benzene Chemical compound CCCCOC1=CC=CC(=C1)/C=C/CCCC/C=C\CC RIIFYVWJPCZVPX-LJRDKERCSA-N 0.000 claims description 3
- 150000002430 hydrocarbons Chemical group 0.000 claims description 3
- BSFFHHPGSJXWFP-UHFFFAOYSA-N 7-methyl-1h-indene Chemical compound CC1=CC=CC2=C1CC=C2 BSFFHHPGSJXWFP-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 238000004140 cleaning Methods 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims 8
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims 4
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 239000000203 mixture Substances 0.000 abstract description 31
- 239000002304 perfume Substances 0.000 abstract description 23
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 60
- 239000000047 product Substances 0.000 description 42
- 239000000243 solution Substances 0.000 description 41
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- 235000019645 odor Nutrition 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- UKZXPOJABTXLMK-UHFFFAOYSA-N 3-[2-methyl-4-(2-methylpropyl)phenyl]propanal Chemical compound CC(C)CC1=CC=C(CCC=O)C(C)=C1 UKZXPOJABTXLMK-UHFFFAOYSA-N 0.000 description 15
- JDCFJMZIEBNQRQ-UHFFFAOYSA-N 3-[4-methyl-2-(2-methylpropyl)phenyl]propanal Chemical compound C(C(C)C)C1=C(C=CC(=C1)C)CCC=O JDCFJMZIEBNQRQ-UHFFFAOYSA-N 0.000 description 14
- 241000207199 Citrus Species 0.000 description 14
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 14
- 235000020971 citrus fruits Nutrition 0.000 description 14
- 239000012043 crude product Substances 0.000 description 14
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 14
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 13
- 238000005160 1H NMR spectroscopy Methods 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
- 239000007788 liquid Substances 0.000 description 13
- IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 description 12
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 12
- 238000003818 flash chromatography Methods 0.000 description 11
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 11
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 11
- 239000000796 flavoring agent Substances 0.000 description 10
- 235000019634 flavors Nutrition 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 235000019198 oils Nutrition 0.000 description 10
- YESCIRFCEGIMED-UHFFFAOYSA-N 3-butoxybenzaldehyde Chemical compound CCCCOC1=CC=CC(C=O)=C1 YESCIRFCEGIMED-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 239000004615 ingredient Substances 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 7
- 239000003599 detergent Substances 0.000 description 7
- 239000004744 fabric Substances 0.000 description 7
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- 239000003570 air Substances 0.000 description 6
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- HKEUNLNJRSTCMJ-UHFFFAOYSA-N 3-(2-methylprop-2-enoxy)benzaldehyde Chemical compound CC(=C)COC1=CC=CC(C=O)=C1 HKEUNLNJRSTCMJ-UHFFFAOYSA-N 0.000 description 5
- VDZAJWUUHHMPCY-UHFFFAOYSA-N 3-butan-2-yloxybenzaldehyde Chemical compound CCC(C)OC1=CC=CC(C=O)=C1 VDZAJWUUHHMPCY-UHFFFAOYSA-N 0.000 description 5
- AMTVZBSJJCTNNT-UHFFFAOYSA-N 3-pentoxybenzaldehyde Chemical compound CCCCCOC1=CC=CC(C=O)=C1 AMTVZBSJJCTNNT-UHFFFAOYSA-N 0.000 description 5
- NOBKCEXLDDGYID-UHFFFAOYSA-N 3-propan-2-yloxybenzaldehyde Chemical compound CC(C)OC1=CC=CC(C=O)=C1 NOBKCEXLDDGYID-UHFFFAOYSA-N 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- LQPIWLJUUYUXQO-XNOMRPDFSA-M C(C\C=C/CC)[Mg]Cl Chemical compound C(C\C=C/CC)[Mg]Cl LQPIWLJUUYUXQO-XNOMRPDFSA-M 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L magnesium sulphate Substances [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- XTOBUABQVGTVRJ-UHFFFAOYSA-N (3-butoxyphenyl)methanol Chemical compound CCCCOC1=CC=CC(CO)=C1 XTOBUABQVGTVRJ-UHFFFAOYSA-N 0.000 description 3
- OOCCDEMITAIZTP-QPJJXVBHSA-N (E)-cinnamyl alcohol Chemical compound OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-N 0.000 description 3
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical group OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 244000068485 Convallaria majalis Species 0.000 description 3
- 235000009046 Convallaria majalis Nutrition 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 235000000484 citronellol Nutrition 0.000 description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 description 3
- WPFVBOQKRVRMJB-UHFFFAOYSA-N hydroxycitronellal Chemical compound O=CCC(C)CCCC(C)(C)O WPFVBOQKRVRMJB-UHFFFAOYSA-N 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 238000007347 radical substitution reaction Methods 0.000 description 3
- CZCBTSFUTPZVKJ-UHFFFAOYSA-N rose oxide Chemical compound CC1CCOC(C=C(C)C)C1 CZCBTSFUTPZVKJ-UHFFFAOYSA-N 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 2
- CRDAMVZIKSXKFV-GNESMGCMSA-N (2-trans,6-cis)-farnesol Chemical compound CC(C)=CCC\C(C)=C/CC\C(C)=C\CO CRDAMVZIKSXKFV-GNESMGCMSA-N 0.000 description 2
- AVJMJMPVWWWELJ-DHZHZOJOSA-N (2e)-1-methoxy-3,7-dimethylocta-2,6-diene Chemical compound COC\C=C(/C)CCC=C(C)C AVJMJMPVWWWELJ-DHZHZOJOSA-N 0.000 description 2
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 2
- KRLBLPBPZSSIGH-CSKARUKUSA-N (6e)-3,7-dimethylnona-1,6-dien-3-ol Chemical compound CC\C(C)=C\CCC(C)(O)C=C KRLBLPBPZSSIGH-CSKARUKUSA-N 0.000 description 2
- GLZPCOQZEFWAFX-JXMROGBWSA-N (E)-Geraniol Chemical compound CC(C)=CCC\C(C)=C\CO GLZPCOQZEFWAFX-JXMROGBWSA-N 0.000 description 2
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 2
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 2
- JFTSYAALCNQOKO-UHFFFAOYSA-N 3-(4-ethylphenyl)-2,2-dimethylpropanal Chemical compound CCC1=CC=C(CC(C)(C)C=O)C=C1 JFTSYAALCNQOKO-UHFFFAOYSA-N 0.000 description 2
- XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 description 2
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 2
- GHBSPIPJMLAMEP-UHFFFAOYSA-N 6-pentyloxan-2-one Chemical compound CCCCCC1CCCC(=O)O1 GHBSPIPJMLAMEP-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 2
- 240000006927 Foeniculum vulgare Species 0.000 description 2
- 235000004204 Foeniculum vulgare Nutrition 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 235000011430 Malus pumila Nutrition 0.000 description 2
- 235000015103 Malus silvestris Nutrition 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 description 2
- 239000002250 absorbent Substances 0.000 description 2
- 230000002745 absorbent Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- HMKKIXGYKWDQSV-KAMYIIQDSA-N alpha-Amylcinnamaldehyde Chemical compound CCCCC\C(C=O)=C\C1=CC=CC=C1 HMKKIXGYKWDQSV-KAMYIIQDSA-N 0.000 description 2
- WUOACPNHFRMFPN-UHFFFAOYSA-N alpha-terpineol Chemical compound CC1=CCC(C(C)(C)O)CC1 WUOACPNHFRMFPN-UHFFFAOYSA-N 0.000 description 2
- 239000012080 ambient air Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
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- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229940043353 maltol Drugs 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- KVWWIYGFBYDJQC-UHFFFAOYSA-N methyl dihydrojasmonate Chemical compound CCCCCC1C(CC(=O)OC)CCC1=O KVWWIYGFBYDJQC-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- BOPPSUHPZARXTH-UHFFFAOYSA-N ocean propanal Chemical compound O=CC(C)CC1=CC=C2OCOC2=C1 BOPPSUHPZARXTH-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- WCVRQHFDJLLWFE-UHFFFAOYSA-N pentane-1,2-diol Chemical compound CCCC(O)CO WCVRQHFDJLLWFE-UHFFFAOYSA-N 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000001738 pogostemon cablin oil Substances 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 235000019719 rose oil Nutrition 0.000 description 1
- 239000010666 rose oil Substances 0.000 description 1
- 239000010671 sandalwood oil Substances 0.000 description 1
- 230000007017 scission Effects 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
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000012438 synthetic essential oil Substances 0.000 description 1
- 229940116411 terpineol Drugs 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
- MBDOYVRWFFCFHM-UHFFFAOYSA-N trans-2-hexenal Natural products CCCC=CC=O MBDOYVRWFFCFHM-UHFFFAOYSA-N 0.000 description 1
- LVBXEMGDVWVTGY-UHFFFAOYSA-N trans-2-octenal Natural products CCCCCC=CC=O LVBXEMGDVWVTGY-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
- VMUNAKQXJLHODT-UHFFFAOYSA-N tridec-2-enal Chemical compound CCCCCCCCCCC=CC=O VMUNAKQXJLHODT-UHFFFAOYSA-N 0.000 description 1
- CMSYDJVRTHCWFP-UHFFFAOYSA-N triphenylphosphane;hydrobromide Chemical compound Br.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 CMSYDJVRTHCWFP-UHFFFAOYSA-N 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 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
- DCSCXTJOXBUFGB-UHFFFAOYSA-N verbenone Natural products CC1=CC(=O)C2C(C)(C)C1C2 DCSCXTJOXBUFGB-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- PHXATPHONSXBIL-UHFFFAOYSA-N xi-gamma-Undecalactone Chemical compound CCCCCCCC1CCC(=O)O1 PHXATPHONSXBIL-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
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- 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
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- C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring
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- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/215—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring having unsaturation outside the six-membered aromatic rings
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- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
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- C07D257/04—Five-membered rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
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- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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Abstract
本发明涉及烷氧基苯甲醛衍生物及其前体。本发明还涉及包含它们的香料组合物和加香制品。
Description
本公开涉及具有持久的柑橘类气味特征的烷氧基苯甲醛衍生物。本发明还涉及其生产方法和包含它们的香料组合物。
随着商业和法规要求的不断变化,人们一直在寻找新的分子来增强香味香型或拥有新近可用的香味香型,特别是持久的柑橘类气味香型。
具有柑橘类气味香型的化合物特别受关注,因为消费者将其与新鲜度和/或清洁度相关联。
烷氧基苯甲醛,例如对甲氧基苯甲醛(也称作茴香醛)及其作为香料成分的用途是已知的。描述它们具有极为典型的苯甲醛样气味,通常将其描述为芳香、茴香与辛香美味香调。
尽管文献中报道了式(I)的间烷氧基苯甲醛,但是例如据我们所知,其作为制备药物的中间体,但没有关于它们的任何感官特性或用作香料成分的报道或建议。
现已令人惊奇地发现,如下文定义的式(I)的间烷氧基苯甲醛确实具有柑橘样的气味特征,基本上不含会降低期望的新鲜感印象的辛香美味副香型(side note)。
因此,在一个方面,提供了式(I)的化合物作为香料的用途,
其中R1选自直链或支链C3-、C4-和C5-烷基和C3-、C4-和C5-烯基(例如丁基、戊基、丁-2-基)。
作为式(I)的的化合物的具体实例,作为非限制性实例可以举出3-丁氧基苯甲醛,其具有新鲜的柑橘类气味与青香香调。这种类型的气味香型合并了特别良好的其他青香和/或花香-醛香香型,从而生成或改善了清洁度和/或新鲜度的印象。
此外,非限制性实例为选自如下的式(I)的化合物:
3-(仲丁氧基)苯甲醛,
3-戊氧基苯甲醛,
3-((2-甲基烯丙基)氧基)苯甲醛,和
3-异丙氧基苯甲醛。
可以将式(I)的化合物添加到香料组合物中,即,合并了单个香料成分以提供期望的享乐效果的制品。它们可以选自本领域可利用的大量此类材料中的任何一种。
香料成分的典型的非限制性实例包括:
-精油和提取物,例如,海狸,木香根油,橡苔净油,香叶油,树苔净油,罗勒油,果油如香柠檬油和橘子油,香桃木油,玫瑰草油,广藿香油,橙叶油,茉莉油,玫瑰油,檀香油,苦艾油,熏衣草油和/或依兰-依兰油;
-醇类,例如肉桂醇((E)-3-苯基丙-2-烯-1-醇);顺式-3-己烯醇((Z)-己-3-烯-1-醇);香茅醇(3,7-二甲基辛-6-烯-1-醇);二氢月桂烯醇(2,6-二甲基辛-7-烯-2-醇);EbanolTM((E)-3-甲基-5-(2,2,3-三甲基环戊-3-烯-1-基)戊-4-烯-2-醇);丁香酚(4-烯丙基-2-甲氧基苯酚);乙基芳樟醇((E)-3,7-二甲基壬-1,6-二烯-3-醇);金合欢醇((2E,6Z)-3,7,11-三甲基十二碳-2,6,10-三烯-1-醇);香叶醇((E)-3,7-二甲基辛-2,6-二烯-1-醇);Super MuguetTM((E)-6-乙基-3-甲基辛-6-烯-1-醇);芳樟醇(3,7-二甲基辛-1,6-二烯-3-醇);薄荷醇(2-异丙基-5-甲基环己醇);橙花醇(3,7-二甲基-2,6-辛二烯-1-醇);苯乙醇(2-苯乙醇);RhodinolTM(3,7-二甲基辛-6-烯-1-醇);SandaloreTM(3-甲基-5-(2,2,3-三甲基环戊-3-烯-1-基)戊-2-醇);松油醇(2-(4-甲基环己-3-烯-1-基)丙-2-醇);或TimberolTM(1-(2,2,6-三甲基环己基)己-3-醇);2,4,7-三甲基辛-2,6-二烯-1-醇;和/或[1-甲基-2(5-甲基己-4-烯-2-基)环丙基]-甲醇;
-醛类和酮类,例如茴香醛(4-甲氧基苯甲醛);α戊基肉桂醛(2-亚苄基庚醛);GeorgywoodTM(1-(1,2,8,8-四甲基-1,2,3,4,5,6,7,8-八氢萘-2-基)乙酮);羟基香茅醛(7-羟基-3,7-二甲基辛醛);Iso E(1-(2,3,8,8-四甲基-1,2,3,4,5,6,7,8-八氢萘-2-基)乙酮);((E)-3-甲基-4-(2,6,6-三甲基环己-2-烯-1-基)丁-3-烯-2-酮);(3-氧代-2-戊基环戊烷乙酸甲酯);3-(4-异丁基-2-甲基苯基)丙醛;麦芽酚;甲基柏木基酮;甲基紫罗兰酮;马鞭草烯酮;2,6,10-三甲基十一碳-5,9-二烯醛;3-(4-乙基苯基)-2,2-二甲基丙醛;1-甲基-4-(4-甲基戊-3-烯-1-基)环己-3-烯-1-甲醛;己-2-烯醛和/或香草醛;
-醚类和缩醛类,例如(3a,6,6,9a-四甲基-2,4,5,5a,7,8,9,9b-八氢-1H-苯并[e][1]苯并呋喃);香叶基甲基醚((2E)-1-甲氧基-3,7-二甲基辛-2,6-二烯);玫瑰醚(4-甲基-2-(2-甲基丙-1-烯-1-基)四氢-2H-吡喃);和/或(2',2',3,7,7-五甲基螺[二环[4.1.0]庚烷-2,5'-[1,3]二噁烷]);
-酯类和内酯类,例如乙酸苄酯;乙酸柏木酯(乙酸(1S,6R,8aR)-1,4,4,6-四甲基八氢-1H-5,8a-亚甲基甘菊环-6-基酯);γ-癸内酯(6-戊基四氢-2H-吡喃-2-酮);(丙酸2-(1-(3,3-二甲基环己基)乙氧基)-2-甲基丙酯);γ-十一烷酸内酯(5-庚基氧杂戊环-2-酮);和/或乙酸岩兰草酯(乙酸(4,8-二甲基-2-丙-2-亚基-3,3a,4,5,6,8a-六氢-1H-甘菊环-6-基)酯);
-杂环类,例如异丁基喹啉(2-异丁基喹啉)。
式(I)的化合物可以通过将化合物本身或包含该化合物的香料组合物与香料用品直接混合而简单地用于香料应用,和/或它们可在较早的步骤中被截留材料俘获,例如聚合物,胶囊,微胶囊和纳米胶囊,脂质体,成膜剂,吸收剂,例如碳或沸石,环状寡糖及其混合物,和/或它们可以化学键合到底物上,这些底物适合于在施加外部刺激例如光、空气、湿气、升温、酶等时释放香味分子,然后与所述用品混合。
尽管如上述定义的式(I)的化合物自身可能不具有特定的强烈香味,但是它们有用地与其他香料成分合并,从而得到有用的具有持久柑橘类效果的香味特性。
因此,在一个具体的实施方案中,可以以前体形式添加式(I)的化合物,这种前体适合于在施加外部刺激时释放两种香料成分,其中之一为式(I)的化合物。
在一个具体的实施方案中,前体具有通式(II)
其中
R1具有与对式(I)所定义的相同含义,且
R2选自
C4-C14烷基,例如C5-C12,例如C8、C9、C10或C11烷基;
C4-C14烷基,例如C5-C12,例如C8、C9、C10或C11烷基,其被一个-OH基团和/或至多两个(即0、1或2个)醚基团取代(例如R2为6-甲氧基-6-甲基辛-2-基);
C4-C14烯基,例如C5-C12,例如C8、C9、C10或C11烯基,其包含例如一个或两个碳-碳双键;
C4-C14烯基,其被一个-OH基团或醚基团取代,例如C5-C12,例如C8、C9、C10或C11烯基,其被一个-OH基团或醚基团取代,其包含例如一个或两个碳-碳双键(例如R2为(E)-8-羟基-4,8-二甲基壬-3-烯-1-基或戊-2-烯基);
C5-C6环烷基,例如环己基或环戊基;
C5-C8环烷基(例如环己基、环戊基),其被1、2或3个基团取代,所述基团选自C1-C6烷基(例如乙基、异丙基、叔戊基)和C2-C4亚烷基(例如异丙烯基);
C5-C8环烯基,例如C6环烯基,例如环己-2,4-二烯基、环己-1-烯基、环辛-3-烯基;
C5-C8环烯基,例如环辛-3-烯基,其中环烯基-环被1、2或3个基团取代,所述基团选自C1-C4烷基(例如乙基或异丙基)、C2-C4亚烷基(例如异丙烯基)和C3-C5环烷基(例如R2为7-甲基-螺[4.5]癸-8-烯-6-基、螺[4.5]癸-7-烯-7-基、5,5-二甲基环己-1-烯基、2,6,6-三甲基环己-1,3-二烯基、2,4-二甲基环己-3-烯基或4-异丙烯基(环己-1烯-1基);
(C1-C3)烷基(C5-C6)环烷基,其中环烷基-环任选地被一个选自-OH基团和=O基团的基团和/或一个或两个醚基团和/或至多四个C1-C5烷基基团取代(例如R2为(3-叔丁基环己基)乙基或4-(1,1-二甲基丙基)环己基)甲基、(3-氧代-2-戊基环戊基)甲基);
(C1-C4)烷基(C5-C6)环烯基,其中环烯基-环任选地被一个-OH基团和/或一个或两个醚基团和/或至多四个(即0、1、2、3或4个)C1-C5烷基基团取代(例如R2为(2,6,6-三甲基环己-1-烯-1-基)乙基、1-(2,6,6-三甲基环己-2-烯-1-基)丁-3-基);
(C2-C3)烯基(C5-C6)环烯基,其中环烯基-环任选地被一个-OH基团和/或一个或两个醚基团和/或至多四个(即0、1、2、3或4个)C1-C5烷基基团取代(例如R2为(2,6,6-三甲基环己-1-烯-1-基)乙烯基、(2,6,6-三甲基环己-2-烯-1-基)乙烯基、(2,6,6-三甲基环己-2-烯-1-基)丙-2-烯-2-基、(2,6,6-三甲基环己-1-烯-1-基)丙-2-烯-2-基);
C6-C14芳基,例如苯基;
C6-C14芳基,其中芳基环被至多3个(即0、1、2或3个)基团取代,所述基团选自C1-C4烷基(例如乙基、异丙基、叔丁基)、-O-CH2-O-和-OR11,其中R11独立地选自氢和C1-C4烷基(例如乙基、异丙基、叔丁基);
(C1-C4)烷基(C6-C14)芳基,例如苄基、2-苯基乙基;
(C1-C4)烷基(C6-C14)芳基,例如苄基或2-苯基乙基,其中芳基-环被至多2个基团(例如1个基团)取代,所述基团选自C1-C4烷基(例如乙基、异丙基、叔丁基)、-O-CH2-O-和-OR12,其中R12独立地选自氢和C1-C4烷基(例如乙基、异丙基、叔丁基);
(C2-C8)烯基(C6-C14)芳基,例如2-苯基乙烯-1-基(2-phenylethylene-1-yl)、1-苯基庚-1-烯-2-基;
(C2-C8)烯基(C6-C14)芳基,其中芳基-环被至多2个基团(例如1个基团)取代,所述基团选自C1-C4烷基(例如乙基、异丙基、叔丁基)、-O-CH2-O-和-OR13,其中R13独立地选自氢和C1-C4烷基(例如乙基、异丙基、叔丁基);
包含C8-C12碳原子的二-、三或四环烃环,其任选地被至多6个基团取代,所述基团选自C1-C4烷基(例如乙基、异丙基、叔丁基)、-O-CH2-O-和-OR14,其中R14独立地选自氢和C1-C4烷基(例如乙基、异丙基、叔丁基),例如R2为1,1,6,7-四甲基-1,2,3,4,5,6,7,8-八氢萘-7-基、2-((1,1-二甲基-(2,3-二氢-1H-茚))-6-基)-乙-1-基、3,6,8,8-四甲基-2,3,4,7,8,8a-六氢-1H-3a,7-亚甲基甘菊环-5(4H)-亚基或1,1,2,4,4,7-六甲基-1,2,3,4-四氢萘-6-基;
R3选自氢、C1-C5烷基和C2-C5烯基(例如丁-3-烯基)。
除非另有指示,否则本文涉及式(II)的化合物使用的“烷基”是指直链或支链烃基;“烯基”是指包含至少一个碳-碳双键例如2或3个双键的直链或支链烃基;“烃环”是指饱和和不饱和环系,优选包含至多两个碳-碳双键/环,其中所述环可以被至多3个(例如1个或2个)C1-C3烷基取代;且“醚基团”是指连接至两个碳原子的氧原子。
在某些实施方案中,R3为氢。
在具体的实施方案中,R3为氢,且R2选自
C4-C14烷基,例如C5-C12,例如C8、C9、C10或C11烷基;C4-C14烯基,例如C5-C12,例如C8、C9、C10或C11烯基,其包含例如一个或两个碳-碳双键;(E)-4,8-二甲基壬-3-烯-8-醇-1-基);和6-甲氧基-6-甲基辛-2-基。
在其他具体的实施方案中,R3为氢,R2为包含一个碳-碳双键的C5-C12烯基,例如R2选自Z-戊-2-烯-1-基、Z-辛-5-烯-1-基、十二碳-1-烯-1-基、壬-3-烯-1-基(例如E-壬-3-烯-1-基)、癸-8-烯-1-基。
在另外的具体的实施方案中,R3为氢,且R2为(C1-C4)烷基(C6)芳基,例如苄基、2-苯基乙基或3-苯基丙基,其中芳基-环被至多2个基团(例如1个基团)取代,所述基团选自C1-C4烷基(例如乙基、异丙基、叔丁基、异-丁基),例如R2为
在另外的具体的实施方案中,R1选自丁基、戊基、(1-甲基)丙烯基和2-甲基丁-2-烯基,R2选自C4-C14烷基,例如C6-C12,例如C8、C9、C10或C11烷基;和C5-C14烯基,例如C6-C12,例如C8、C9、C10或C11烯基,其包含例如一个或两个碳-碳双键,且R3为氢。
在另一个具体的实施方案中,R2为戊-2-烯基(例如Z-戊-2-烯基),且R3为氢。
式(II)的化合物作为前体用以通过自发空气氧化释放式(I)的烷氧基苯甲醛和式(III)的香味酮或醛(R2-C(O)-R3,其中R2和R3具有与对式(II)的化合物所定义的相同的含义)。
式(II)的化合物在不暴露于环境空气中(即原样保存)或在通常与芳香剂结合使用的稀释剂中时非常稳定,所述稀释剂例如一缩二丙二醇(DPG),肉豆蔻酸异丙酯(IPM),柠檬酸三乙酯(TEC),戊-1,2-二醇和醇(例如乙醇)和已知的香料成分。当掺入消费品例如洗涤剂、香波和织物调理剂中时,也证明了极为良好的存储稳定性。因此,式(II)的化合物可用于广泛的消费品中,其中期望延长的和确定的释放香味化合物。
空气中氧气的浓度足以以这种方式裂解式(II)的化合物,使得可以通过嗅觉或顶空样品的GC-MS分析在环境空气中检测裂解产物。
式(II)的化合物(其中R2为戊-2-烯基且R3为氢)通过自发空气氧化释放己-3-烯醛(例如顺式-3-己烯醛),其自身并不稳定,且由此不能照此在香料制造中使用。
作为式(I)的化合物的前体的具体实例可以举出式(II)的化合物,其中R1为C4-C5烷基(例如丁基),R2为氢,且R3为戊-2-烯-1-基(例如Z-戊-2-烯-1-基),该化合物产生具有特别理想特性的前体,即在暴露于空气中裂解时,既提供柑橘类香型又提供青香香型,这是许多商品、例如洗衣洗涤剂中非常期望的组合。
在另一个具体的实施方案中,式(II)的前体选自
1-丁氧基-3-((1E,4Z)-庚-1,4-二烯-1-基)苯;
1-丁氧基-3-((1E,7Z)-癸-1,7-二烯-1-基)苯;
1-(4-(3-丁氧基苯基)丁-3-烯-1-基)-4-异丁基-2-甲基苯;
1-(4-(3-丁氧基苯基)丁-3-烯-1-基)-2-异丁基-4-甲基苯;
1-(仲丁氧基)-3-((1E,4Z)-庚-1,4-二烯-1-基)苯;
1-((1E,4Z)-庚-1,4-二烯-1-基)-3-(戊氧基)苯;
1-((1E,4Z)-庚-1,4-二烯-1-基)-3-((2-甲基烯丙基)氧基)苯;
1-((1E,4Z)-庚-1,4-二烯-1-基)-3-异丙氧基苯;
1-丁氧基-3-(4-(4-(叔丁基)苯基)丁-1-烯-1-基)苯;
1-丁氧基-3-(4-(4-(叔丁基)苯基)-3-甲基丁-1-烯-1-基)苯;
1-丁氧基-3-(4-(3-异丙基苯基)戊-1-烯-1-基)苯;
11-(3-丁氧基苯基)-2,6-二甲基十一碳-6,10-二烯-2-醇;
1-丁氧基-3-(3-甲基十二碳-1-烯-1-基)苯;
5-(4-(3-丁氧基苯基)-2-甲基丁-3-烯-1-基)苯并[d][1,3]间二氧杂环戊烯;
1-丁氧基-3-(十四碳-1,3-二烯-1-基)苯;
1-丁氧基-3-(3-苯基丙-1-烯-1-基)苯;
1-丁氧基-3-((5E)-十一碳-1,5-二烯-1-基)苯;
5-(5-(3-丁氧基苯基)戊-4-烯-1-亚基)八氢-1H-4,7-亚甲基茚;
1-丁氧基-3-(4-(4-乙基苯基)-3,3-二甲基丁-1-烯-1-基)苯;
1-丁氧基-3-(7-甲氧基-3,7-二甲基壬-1-烯-1-基)苯;和
1-丁氧基-3-(4-(4-异丁基苯基)丁-1-烯-1-基)苯。
还提供了给消费品加香的方法,所述方法包括向消费品基质中添加式(I)的化合物或其前体,例如式(II)的化合物。
式(I)的化合物或其前体、例如式(II)的化合物可以用于广泛的香料应用,例如任何精细和功能性香料领域,例如香料,家用产品,洗衣产品,身体护理产品和化妆品。
式(I)的化合物或其前体(例如式(II)的化合物)可以以广泛不同的量使用,这取决于特定的应用以及其他芳香剂成分的性质和数量。该比例典型地占用品的0.0001-2重量%。在一个实施方案中,化合物可以0.0001-0.005重量%的量用于织物柔软剂中。在另一个实施方案中,化合物可以0.01-3重量%、更特别地0.5-2重量%的量在醇溶液中使用。然而,这些值仅作为实例给出,因为有经验的调香师也可以以更低或更高的浓度达到效果或可以产生新颖的谐香(accords),例如基于香料组合物至多约20重量%。
式(I)的化合物或其前体(例如式(II)的化合物)可以通过直接混合式(I)的化合物或其前体(例如式(II)的化合物)或包含式(I)的化合物或其前体(例如式(II)的化合物)的香料组合物或消费品基质的香料组合物而用于消费品基质中,或者可以在较早的步骤中用截留材料俘获它们,例如聚合物,胶囊,微胶囊和纳米胶囊,脂质体,成膜剂,吸收剂,例如碳或沸石,环状寡糖及其混合物,然后与消费品基质混合。
因此,本发明还提供了一种制造加香制品的方法,所述方法包括通过将式(I)的化合物或其前体(例如式(II)的化合物)直接混合到消费品基质中,或通过混合包含式(I)的化合物或其前体(例如式(II)的化合物)的香料组合物将作为香料成分的式(I)的化合物或其前体(例如式(II)的化合物)掺入,然后可以使用常规技术和方法将其与消费品基质混合。通过添加嗅觉上可接受量的式(I)的化合物或其前体(例如式(II)的化合物),将改善、增强或改变消费品基质的气味香型。
因此,本发明还提供了改善、增强或改变消费品基质的方法,所述方法通过向其中添加嗅觉上可接受量的式(I)的化合物或其前体(例如式(II)的化合物)来进行。
本发明还提供了加香制品,其包含:
a)作为芳香剂的式(I)的化合物、其混合物或其前体(例如式(II)的化合物);和
b)消费品基质、
如本文所用,‘消费品基质’是指用作消费品以完成特定功能(例如清洁,软化和护理等)的组合物。这种产品的实例包括精细香料,例如香水和淡香水;织物护理剂,家用产品和个人护理产品,例如化妆品,洗衣护理清洁剂,漂洗调理剂,个人清洁组合物,洗碗机用清洁剂,表面清洁剂;洗衣产品,例如柔软剂,漂白剂,洗涤剂;身体护理产品,例如香波,沐浴露;空气护理产品(包括优选包含挥发性和通常令人愉悦的化合物的产品,这些化合物甚至可以非常少量地掩盖令人不愉快的气味)。用于居住区的空气清新剂尤其包含天然和合成的精油,例如松针油,柑橘油,桉叶油,薰衣草油等,其用量为例如至多50%重量。作为气雾剂,作为实例,它们倾向于包含较少量的这种精油,例如少于5%或少于2%重量,但是另外包括化合物,例如乙醛(特别是<0.5%重量),异丙醇(特别是<5%重量),矿物油(特别是<5%重量)和推进剂。
在一个具体的实施方案中,消费品基质(例如漂白产品)基本上不含芳香酰亚胺。
该产品列表通过示例方式给出,并且不应以任何方式视为限制性的。
式(I)的化合物可以通过在适当的溶剂例如四氢呋喃或二甲基甲酰胺中,在碱例如钾或钠的碳酸盐或氢氧化物存在下,使3-羟基苯甲醛与烷基卤R1-X(X为氯,溴,碘或甲苯磺酸酯基)进行醚化反应来制备。可以使用有机合成领域普通技术人员已知的其他形成苯基醚的条件。
式(II)的化合物可以通过在溶剂如四氢呋喃或乙醚中,使-R2R3CHMgBr和式(I)的烷氧基苯甲醛发生格氏反应,然后在本领域技术人员已知的条件下进行标准后处理和在催化剂例如对甲苯磺酸存在下使得到的仲苄醇脱水来制备。可以使用其他双键形成反应,例如维悌希反应。
参考以下描述特定实施方案的非限制性实施例进一步描述本公开。
实施例1:3-丁氧基苯甲醛及其前体
1.1:3-丁氧基苯甲醛
用碳酸钾(27.2g,197mmol,1.2当量)处理3-羟基苯甲醛(20g,164mmol,1.0当量)在DMF(100mL)中的溶液。将得到的混合物加热至80℃,然后缓慢地用1-溴丁烷(21.2ml,197mmol,1.2eq.)处理。将该混合物在80℃搅拌1h,然后冷却至25℃,过滤以除去固体,用MTBE(500mL)稀释,用水(3x100mL)洗涤。将有机层用MgSO4干燥,过滤,浓缩。用5cm Vigreux柱真空蒸馏得到的油状物,在135-137℃在25mbar下采集,得到3-丁氧基苯甲醛(25.3g,142mmol,87%),为澄清无色液体。
1H NMR(CDCl3,400MHz):δ=9.99(s,1H),7.44-7.47(m,2H),7.39-7.42(m,1H),7.17-7.21(m,1H),4.04(t,J=6.5Hz,2H),1.76-1.85(m,2H),1.46-1.58(m,2H),1.00ppm(t,J=7.3Hz,3H)。
13C NMR(CDCl3,101MHz):δ=192.3,159.7,137.8,130.0,123.3,122.0,112.8,68.0,31.2,19.2,13.8ppm。
MS(EI,70eV):178(30,[M]+·),123(11),122(100),121(100),77(9),65(13),41(18),39(12),29(22),27(9)。
气味描述(在吸墨纸上10%的DPG溶液,24h):新鲜柑橘香,柠檬醛香,柠檬草香,马鞭草香,青香,轻度热铁味,轻度脂肪味。
1.2:1-丁氧基-3-((1E,4Z)-庚-1,4-二烯-1-基)苯
在用氮气吹扫的烧瓶中放入镁粉(0.750g,31mmol,1.3当量)和THF(2mL)。回流滴加在THF(60mL)中的(Z)-1-氯己-3-烯(3.66g,31mmol,1.3当量),进一步将该反应混合物加热至回流12h,然后冷却至0℃。加入3-丁氧基苯甲醛(4.00g,22mmol,1.0当量),将该反应混合物在25℃搅拌30min,并倾倒在冰冷的1M HCl-水溶液(100mL)上。用MTBE(2x50mL)萃取水层。用盐水(50mL)洗涤合并的有机相,用MgSO4干燥,过滤,浓缩。将得到的油状物溶于甲苯(50mL),在25℃用对甲苯磺酸一水合物(0.21g,1.12mmol,0.05当量)处理,用迪安-斯达克装置加热至回流3h。将得到的混合物冷却至25℃,用MTBE(100mL)稀释,用饱和NaHCO3水溶液(50mL)、盐水(50mL)洗涤,将有机层用MgSO4干燥,过滤,浓缩。通过快速柱色谱法纯化得到的粗物质,用1-7%MTBE的己烷溶液梯度洗脱,得到1-丁氧基-3-((1E,4Z)-庚-1,4-二烯-1-基)苯(2.06g,8.43mmol,37.6%),为澄清无色液体。
1H-NMR(CDCl3,400MHz):δ=7.22(dd,J=8.2,7.6Hz,1H),6.90-6.98(m,2H),6.77(ddd,J=8.2,2.6,0.7Hz,1H),6.39(dt,J=15.9,1.5Hz,1H),6.22(dt,J=15.9,6.4Hz,1H),5.39-5.58(m,2H),3.99(t,J=6.5Hz,2H),2.94-3.01(m,2H),2.08-2.18(m,2H),1.75-1.84(m,2H),1.46-1.56(m,2H),1.02(t,J=7.6Hz,6H),1.00ppm(t,J=7.6Hz,3H)。
13C-NMR(CDCl3,101MHz):δ=159.4,139.2,133.0,129.9,129.4,129.3,126.0,118.5,113.1,111.9,67.6,31.4,30.6,20.6,19.3,14.3,13.9ppm
MS(EI,70eV):244(34,[M]+·),159(49),145(100),133(16),131(24),128(18),120(39),115(27),41(20),29(21)。
气味描述(在吸墨纸上1%的EtOH溶液,24h):青香,柑橘香,苹果香,来檬香,碎叶味。
1.3:1-丁氧基-3-((1E,7Z)-癸-1,7-二烯-1-基)苯
使用在THF(150mL)中的来源于Z-9-溴壬-3-烯(13.8g,67mmol,1.2当量)和镁(1.64g,67mmol,1.2当量)的格氏试剂和3-丁氧基苯甲醛(实施例1.1)重复实施例1.2中所述的方法,然后将粗产物使用在甲苯(100mL)中的对甲苯磺酸(500mg)进行脱水。将粗产物通过硅胶快速色谱法与庚烷100%-庚烷/MTBE 50:1梯度纯化,得到(2.18g,28%),为淡黄色液体。
1H-NMR(CDCl3,400MHz):δ=7.18(t,J=7.9Hz,1H),6.86-6.94(m,2H),6.73(ddd,J=8.2,2.4,0.7Hz,1H),6.29-6.37(m,1H),6.14-6.26(m,1H),5.28-5.48(m,2H),3.96(t,J=6.5Hz,2H),2.15-2.25(m,2H),1.94-2.10(m,4H),1.72-1.82(m,2H),1.33-1.57(m,6H),0.96(td,J=7.5,6.4Hz,6H)。
13C-NMR(CDCl3,101MHz):δ=159.4(s),139.4(s),131.8(s),131.3(s),129.8(s),129.4(s),129.0(s),118.5(s),113.0(s),112.9-113.0(m),111.9(s),67.6(s),32.9(s),31.4(s),29.3(s),29.0(s),27.0(s),20.5(s),19.3(s),14.4(s),13.9(s)。
MS(EI,70eV):286(16),257(13),230(6),176(18),164(46),145(69),127(100),108(58),107(58),55(54),41(92),29(50)。
气味描述(在吸墨纸上1%的EtOH溶液,24h)):甜瓜香,青香,柑橘香,花香。
1.4:1-(4-(3-丁氧基苯基)丁-3-烯-1-基)-4-异丁基-2-甲基苯和1-(4-(3-丁氧基苯基)丁-3-烯-1-基)-2-异丁基-4-甲基苯
A)(3-丁氧基苯基)甲醇
在25℃向在THF(80mL)中的3-丁氧基苯甲醛(18.5g,104mmol,1.0当量)中滴加LiAlH4(1.26g,31.5mmol,0.304eq.)在THF(120mL)中的混悬液。1h后,将该混合物冷却至0℃,谨慎地用水(1.25mL)、然后用15%NaOH水溶液(1.25mL)且最终用水(3.75mL)处理。将该混合物温热至40℃,用MgSO4处理,然后过滤。浓缩滤液至得到(3-丁氧基苯基)甲醇(17.3g,96mmol,92%),为淡黄色油。
1H-NMR(CDCl3,400MHz):δ=7.23-7.30(m,1H),6.89-6.95(m,2H),6.82-6.87(m,1H),4.62(s,2H),3.98(t,J=6.6Hz,2H),2.64(br s,1H),1.74-1.84(m,2H),1.46-1.59(m,2H),1.02ppm(t,J=7.3Hz,3H)。
13C-NMR(CDCl3,101MHz):δ=159.4,142.6,129.5,118.9,113.7,112.9,67.7,65.1,31.4,19.3,13.9ppm。
MS(EI,70eV):180(52,[M]+·),124(100),123(39),107(19),106(37),105(25),95(50),78(18),77(20),41(13)。
B)1-(4-(3-丁氧基苯基)丁-3-烯-1-基)-4-异丁基-2-甲基苯和1-(4-(3-丁氧基苯基)丁-3-烯-1-基)-2-异丁基-4-甲基苯
合并(3-丁氧基苯基)甲醇(17.0g,94mmol,1.0当量)与三苯膦氢溴酸盐(32.4g,94mmol,1.0当量)和乙腈(100mL),并在氮气气氛中将得到的混合物加热至回流20h。将得到的混合物浓缩,然后混悬于Et2O(70mL)中,并放入冷冻机(4℃)中5h。将沉淀的固体过滤,用Et2O(2x50mL)洗涤,然后在25℃高度真空干燥2h。将得到的固体混悬于THF(350mL),冷却至5℃,分批用KOtBu(10.38g,92mmol,0.98当量)处理,维持温度在0-5℃。将得到的亮红色混合物在5℃搅拌20min,然后通过滴加3-(4-异丁基-2-甲基苯基)丙醛(16.1g,78mmol,0.83当量)和3-(2-异丁基-4-甲基苯基)丙醛(2.84g,14mmol,0.15当量)在THF(50mL)中的溶液处理,历时40min。将得到的混合物温热至25℃,搅拌2h。然后将该混合物倾入乙酸(20mL)和冰水(500mL)的混合物,用庚烷(2x200mL)萃取,将萃取物依次用70%甲醇(3x100mL)、饱和KHCO3水溶液(2x100mL)、水(2x100mL)洗涤,用MgSO4干燥,过滤,蒸发。将得到的粗物质通过快速柱色谱法纯化,用1-7%MTBE的庚烷溶液梯度洗脱,得到1-(4-(3-丁氧基苯基)丁-3-烯-1-基)-4-异丁基-2-甲基苯和1-(4-(3-丁氧基苯基)丁-3-烯-1-基)-2-异丁基-4-甲基苯(22.3g,63.6mmol,68%)异构体混合物,为澄清、淡绿色液体(得到异构体1-4,比例为3:25:9:63(GC)(异构体1:异构体2:异构体3:异构体4))
1H NMR(氯仿-d,400MHz):δ=7.11-7.23(m),7.01-7.09(m),6.86-6.98(m),6.67-6.84(m),6.34-6.44(m),6.21-6.33(m),5.66-5.75(m),3.89-3.99(m),2.67-2.77(m),2.54-2.64(m),2.36-2.50(m),2.31(s),2.30(s),2.28(s),2.25(s),1.69-1.90(m),1.42-1.56(m),0.86-1.01ppm(m)
13C NMR(苯-d6,101MHz):δ=159.7,159.7,159.5,159.4,139.3,139.4,139.3,139.3,139.1,139.1,139.0,139.0,137.1,136.9,136.6,136.5,135.3,135.2,134.8,134.8,132.1,131.0,131.0,130.9,130.9,130.5,130.5,130.1,129.6,129.4,129.2,129.2,129.1,129.1,128.7,128.7,128.7,128.7,126.8,126.8,126.7,126.7,121.3,121.1,118.6,115.4,115.1,115.0,113.2,113.1,112.8,112.8,112.3,111.5,67.1,67.1,67.1,67.0,45.0,41.9,41.9,34.9,33.8,33.0,32.8,32.4,32.2,31.3,31.3,30.4,30.2,30.2,30.1,29.9,29.8,29.3,22.4,22.4,22.2,21.2,20.8,20.8,19.2,19.2,19.1,19.1,13.6,13.6ppm。
MS(EI,70eV)(异构体1):350(12,[M]+·),189(9),161(58),133(29),120(10),119(100),117(9),115(9),105(17),55(15)。
MS(EI,70eV)(异构体2):350(8,[M]+·),189(6),162(13),161(100),133(19),119(25),118(9),117(5),115(6),105(11)。
MS(EI,70eV)(异构体3):350(11,[M]+·),189(10),162(8),161(62),133(35),120(10),119(100),115(8),105(18),55(16)。
MS(EI,70eV)(异构体4):350(9,[M]+·),189(8),162(13),161(100),133(23),119(25),118(9),115(6),105(11),43(5)。
气味描述(在吸墨纸上1%的EtOH溶液,24h):柑橘香,醛香,铃兰香,轻度脂肪味。
实施例2:3-(仲丁氧基)苯甲醛及其前体
2.1:3-(仲丁氧基)苯甲醛
使用在DMF(60mL)中的3-羟基苯甲醛(6.0g,49.1mmol,1当量)、碳酸钾(13.6g,98mmol,2当量)和2-溴丁烷(10.1g,73.7mmol,1.5当量)重复实施例1.1中的方法。将粗产物通过使用己烷/MTBE 93:7的硅胶快速色谱法纯化,然后在114℃/0.03mbar下进行真空球管-球管蒸馏(vacuum bulb-to-bulb distillation),得到3-(仲丁氧基)苯甲醛(6.8g,77%),为无色液体。
1H-NMR(CDCl3,400MHz):δ=9.80-10.16(m,1H),7.42-7.46(m,2H),7.38-7.41(m,1H),7.14-7.20(m,1H),4.40(sxt,J=6.0Hz,1H),1.61-1.84(m,2H),1.33(d,J=5.9Hz,3H),1.00(t,J=7.5Hz,3H)。
13C-NMR(CDCl3,101MHz):δ192.2(d),158.8(s),137.8(s),130.1(d),123.1(d),123.0(d),114.2(d),75.3(d),29.1(t),19.1(q),9.7(q)。
MS(EI,70eV):178(15,M+),122(100),121(95),93(8),77(7),65(11),57(7),41(9),29(18)。
气味描述(在吸墨纸上10%的DPG溶液,4h):柑橘香,果香,酚香。
2.2:1-(仲丁氧基)-3-((1E,4Z)-庚-1,4-二烯-1-基)苯
使用在THF(50mL)中的(Z)-己-3-烯-1-基镁氯化物(0.65M的THF溶液,26mL,16.9mmol,1.2当量)和3-(仲丁氧基)苯甲醛(2.5g,14.3mmol,1当量)重复实施例1.2中的方法,然后将粗产物通过使用在甲苯(100mL)中的对甲苯磺酸(286mg,1.5mmol,0.1当量)进行脱水。将粗产物通过使用己烷/MTBE 100:1的硅胶快速色谱法纯化,得到1-(仲丁氧基)-3-((1E,4Z)-庚-1,4-二烯-1-基)苯(1.43g,39%),为无色液体。
1H-NMR(CDCl3,400MHz):δ=7.22(t,J=7.8Hz,1H),6.91-6.98(m,2H),6.78(ddd,J=8.1,2.5,0.9Hz,1H),6.36-6.44(m,1H),6.18-6.27(m,1H),5.41-5.59(m,2H),4.34(sxt,J=6.1Hz,1H),2.99(br.t,J=6.7Hz,2H),2.14(quind,J=7.4,1.2Hz,2H),1.60-1.85(m,2H),1.33(d,J=6.1Hz,3H),1.03(q,J=7.6Hz,3H),1.00(q,J=7.3Hz,3H)。
13C-NMR(CDCl3,101MHz):δ158.4(s),139.3(s),133.0(d),129.9(d),129.4(d),129.2(d),126.0(d),118.5(d),114.4(d),113.6(d),75.0(d),30.6(t),29.3(t),20.6(t),19.3(q),14.3(q),9.8(q)。
MS(EI,70eV):244(16,M+),159(62),146(17),145(100),131(22),120(56),115(27),81(19),41(18),29(16)。
气味描述(在吸墨纸上1%的EtOH溶液,24h)):青香,柑橘香,碎叶味。
实施例3:3-戊氧基苯甲醛及其前体
3.1:3-戊氧基苯甲醛
使用在DMF(60mL)中的3-羟基苯甲醛(6.0g,49.1mmol,1当量)、碳酸钾(13.6g,98mmol,2当量)和1-溴丁烷(8.9g,59.0mmol,1.2当量)重复实施例1.1中的方法。将粗产物通过使用己烷/MTBE 93:7的硅胶快速色谱法纯化,然后在130℃/0.03mbar下进行真空球管-球管蒸馏,得到3-戊氧基苯甲醛(8.0g,84%),为无色液体。
1H-NMR(CDCl3,400MHz):δ9.98(s,1H),7.43-7.47(m,2H),7.38-7.42(m,1H),7.15-7.22(m,1H),4.03(t,J=6.6Hz,2H),1.78-1.88(m,2H),1.35-1.52(m,4H),0.96(t,J=7.3Hz,3H)。
13C-NMR(CDCl3,101MHz):δ192.2(d),159.7(s),137.8(s),130.0(d),123.3(d),121.9(d),112.8(d),68.3(t),28.8(t),28.2(t),22.4(t),14.0(d)。
MS(EI,70eV):192(21,M+),122(100),121(78),105(5),93(6),77(9),71(3),70(8),65(9),55(10),43(30),29(23)。
气味描述(在吸墨纸上10%的DPG溶液,4h):花香,水样味,柑橘香,脂肪味。
3.2:1-((1E,4Z)-庚-1,4-二烯-1-基)-3-(戊氧基)苯
使用在THF(50mL)中的(Z)-己-3-烯-1-基镁氯化物(0.65M的THF溶液,38.4mL,25.0mmol,1.2当量)和3-(戊氧基)苯甲醛(4.0g,20.8mmol,1当量)重复实施例1.2中的方法,然后将粗产物通过使用在甲苯(100mL)中的对甲苯磺酸(432mg,2.3mmol,0.1当量)进行脱水。将粗产物通过使用己烷/MTBE 100:1的硅胶快速色谱法纯化,得到1-((1E,4Z)-庚-1,4-二烯-1-基)-3-(戊氧基)苯(2.84g,47%),为无色液体。
1H-NMR(CDCl3,400MHz):δ7.18-7.32(m,1H),6.87-7.00(m,2H),6.78(ddd,J=8.2,2.4,0.9Hz,1H),6.34-6.47(m,1H),6.16-6.29(m,1H),5.40-5.61(m,2H),3.99(t,J=6.6Hz,2H),2.99(br.t,J=6.7Hz,2H),2.10-2.20(m,2H),1.77-1.87(m,2H),1.37-1.54(m,4H),1.04(t,J=7.6Hz,3H),0.98(t,J=7.1Hz,3H)。
13C-NMR(CDCl3,101MHz):δ159.4(s),139.2(s),133.0(d),129.9(d),129.4(d),129.3(d),126.0(d),118.5(d),113.1(d),112.0(d),67.9(t),30.6(t),29.1(t),28.3(t),22.5(t),20.6(t),14.3(q),14.1(q)。
MS(EI,70eV):258(21,M+),159(48),145(100),133(18),131(22),128(18),120(41),115(27),43(25),41(20)。
气味描述(在吸墨纸上1%的EtOH溶液,24h):青香,柑橘香,香叶味
实施例4:3-((2-甲基烯丙基)氧基)苯甲醛及其前体
4.1:3-((2-甲基烯丙基)氧基)苯甲醛
使用在DMF(60mL)中的3-羟基苯甲醛(5.0g,40.9mmol,1当量)、碳酸钾(11.3g,82mmol,2当量)和3-溴-2-甲基丙烯(6.63g,49.1mmol,1.2当量)重复实施例1.1中的方法。将粗产物通过使用己烷/MTBE93:7的硅胶快速色谱法纯化,然后在129℃/0.03mbar下进行真空球管-球管蒸馏,得到3-((2-甲基烯丙基)氧基)苯甲醛(5.2g,72%),为无色液体。
1H-NMR(CDCl3,400MHz):δ9.98(s,1H),7.40-7.50(m,3H),7.21(dt,J=7.0,2.5Hz,1H),5.10-5.15(m,1H),5.02(td,J=2.1,1.0Hz,1H),4.50(s,2H),1.85(br.d,J=0.7Hz,3H)。
13C-NMR(CDCl3,101MHz):δ192.1(d),159.3(s),140.3(s),137.8(s),130.0(d),123.5(d),122.0(d),113.3(d),113.1(t),71.9(t),19.4(q)。
MS(EI,70eV):176(11,M+),161(31),158(8),147(11),133(10),121(18),105(5),92(5),77(8),65(12),55(100),39(33),29(29)。
气味描述(在吸墨纸上10%的DPG溶液,4h):新鲜味,花香,柑橘香,茴香味。
4.2:1-((1E,4Z)-庚-1,4-二烯-1-基)-3-((2-甲基烯丙基)氧基)苯
使用在THF(50mL)中的(Z)-己-3-烯-1-基镁氯化物(0.65M的THF溶液,52.4mL,25.0mmol,1.2当量)和3-((2-甲基烯丙基)氧基)苯甲醛(5.0g,28.4mmol,1当量)重复实施例1.2中的方法,然后将粗产物通过使用在甲苯(100mL)中的对甲苯磺酸(584mg,2.3mmol,0.1当量)进行脱水。将粗产物通过使用己烷/MTBE 100:1的硅胶快速色谱法纯化,得到1-((1E,4Z)-庚-1,4-二烯-1-基)-3-((2-甲基烯丙基)氧基)苯(1.49g,20%),为无色液体。
1H-NMR(CDCl3,400MHz):δ7.23(t,J=7.8Hz,1H),6.94-7.02(m,2H),6.81(ddd,J=8.3,2.5,1.0Hz,1H),6.41(dt,J=15.9,1.5Hz,1H),6.24(dt,J=15.7,6.6Hz,1H),5.41-5.61(m,2H),5.12-5.18(m,1H),4.98-5.06(m,1H),4.48(br.s,2H),3.00(t,J=6.7Hz,2H),2.09-2.22(m,2H),1.88(br.s,3H),1.04(t,J=7.6Hz,3H)。
13C-NMR(CDCl3,101MHz):δ159.0(s),141.0(s),139.2(s),133.1(d),129.8(d),129.4(d),129.4(s),126.0(d),118.8(d),113.4(d),112.7(t),112.3(d),71.7(t),30.6(t),20.6(t),19.5(q),14.3(q)。
MS(EI,70eV):242(15,M+),174(15),159(32),145(61),131(44),129(43),128(42),117(41),115(60),91(33),55(100),29(35)。
气味描述(在吸墨纸上1%的EtOH溶液,24h):青香,柑橘香,茴香味,花香。
实施例5:3-异丙氧基苯甲醛及其前体
5.1:3-异丙氧基苯甲醛
使用在DMF(60mL)中的3-羟基苯甲醛(6.0g,49.1mmol,1当量)、碳酸钾(13.6g,98mmol,2当量)和2-溴丙烷(7.25g,59mmol,1.2当量)重复实施例1.1中的方法。将粗产物通过使用己烷/MTBE 93:7的硅胶快速色谱法纯化,然后在120℃/0.03mbar下进行真空球管-球管蒸馏,得到3-异丙氧基苯甲醛(5.88g,73%),为无色液体。
1H-NMR(CDCl3,400MHz):δ=9.98(s,1H),7.38-7.46(m,3H),7.13-7.19(m,1H),4.64(spt,J=6.1Hz,1H),1.37(d,J=6.1Hz,6H)。
13C-NMR(CDCl3,101MHz):δ=192.2(d),158.5(s),137.8(s),130.1(d),123.1(d),123.0(d),114.2(d),70.2(d),21.9(2q)。
MS(EI,70eV):164(13,M+),122(73),121(100),93(9),77(4),65(11),43(11),39(13),27(7)。
气味描述(在吸墨纸上10%的DPG溶液,4h):青香,酚香,柑橘香,药材味。
5.2:1-((1E,4Z)-庚-1,4-二烯-1-基)-3-异丙氧基苯
使用在THF(50mL)中的(Z)-己-3-烯-1-基镁氯化物(1.3M的THF溶液,29mL,37.5mmol,1.5当量)和3-异丙氧基苯甲醛(4.0g,24.4mmol,1当量)重复实施例1.2中的方法,然后将粗产物通过使用在甲苯(100mL)中的对甲苯磺酸(432mg,2.3mmol,0.1当量)进行脱水。将粗产物通过使用己烷/MTBE 100:1的硅胶快速色谱法纯化,得到1-((1E,4Z)-庚-1,4-二烯-1-基)-3-异丙氧基苯(1.54g,29%),为无色液体。
1H-NMR(CDCl3,400MHz):δ=7.22(t,J=7.8,1H),6.90-6.98(m,2H),6.78(ddd,J=8.1,2.5,0.9Hz,1H),6.39(dt,J=15.7,1.2,1H),6.22(dt,J=15.9,6.6Hz,1H),5.42-5.59(m,2H),4.59(spt,J=5.6Hz,1H),2.99(br.t,J=6.8Hz,2H),2.10-2.20(m,2H),1.37(d,J=5.9Hz,6H),1.04(t,J=7.6Hz,3H)。
13C-NMR(CDCl3,101MHz):δ=158.1(s),139.3(s),133.0(d),129.9(d),129.4(d),129.3(d),126.0(d),118.6(d),114.4(d),113.6(d),69.8(d),30.6(t),22.1(2q),20.6(t),14.3(q)。
MS(EI,70eV):230(18),159(60),145(100),131(26),120(54),115(29),107(18),81(20),43(21),41(19)。
气味描述(在吸墨纸上1%的EtOH溶液,24h):青香,柑橘香,金属味,脂肪味。
实施例6a-6m:
6a:1-丁氧基-3-(4-(4-(叔丁基)苯基)丁-1-烯-1-基)苯
可以通过用相应的3-(4-(叔丁基)苯基)丙醛的溶液替代3-(4-异丁基-2-甲基苯基)丙醛和3-(2-异丁基-4-甲基苯基)丙醛在THF中的溶液来重复实施例1.4中所述的方法,以制备标题产物1-丁氧基-3-(4-(4-(叔丁基)苯基)丁-1-烯-1-基)苯。
6b:1-丁氧基-3-(4-(4-(叔丁基)苯基)-3-甲基丁-1-烯-1-基)苯
可以通过用相应的3-(4-(叔丁基)苯基)-2-甲基丙醛的溶液替代3-(4-异丁基-2-甲基苯基)丙醛和3-(2-异丁基-4-甲基苯基)丙醛在THF中的溶液来重复实施例1.4中所述的方法,以制备标题产物1-丁氧基-3-(4-(4-(叔丁基)苯基)-3-甲基丁-1-烯-1-基)苯。
6c:1-丁氧基-3-(4-(3-异丙基苯基)戊-1-烯-1-基)苯
可以通过用相应的3-(3-异丙基苯基)丁醛的溶液替代3-(4-异丁基-2-甲基苯基)丙醛和3-(2-异丁基-4-甲基苯基)丙醛在THF中的溶液来重复实施例1.4中所述的方法,以制备标题产物1-丁氧基-3-(4-(3-异丙基苯基)戊-1-烯-1-基)苯。
6d:11-(3-丁氧基苯基)-2,6-二甲基十一碳-6,10-二烯-2-醇
可以通过用相应的9-羟基-5,9-二甲基癸-4-烯醛的溶液替代3-(4-异丁基-2-甲基苯基)丙醛和3-(2-异丁基-4-甲基苯基)丙醛在THF中的溶液来重复实施例1.4中所述的方法,以制备标题产物11-(3-丁氧基苯基)-2,6-二甲基十一碳-6,10-二烯-2-醇。
6e:1-丁氧基-3-(3-甲基十二碳-1-烯-1-基)苯
可以通过用相应的2-甲基十一醛的溶液替代3-(4-异丁基-2-甲基苯基)丙醛和3-(2-异丁基-4-甲基苯基)丙醛在THF中的溶液来重复实施例1.4中所述的方法,以制备标题产物1-丁氧基-3-(3-甲基十二碳-1-烯-1-基)苯。
6f:5-(4-(3-丁氧基苯基)-2-甲基丁-3-烯-1-基)苯并[d][1,3]间二氧杂环戊烯
可以通过用相应的3-(苯并[d][1,3]间二氧杂环戊烯-5-基)-2-甲基丙醛的溶液替代3-(4-异丁基-2-甲基苯基)丙醛和3-(2-异丁基-4-甲基苯基)丙醛在THF中的溶液来重复实施例1.4中所述的方法,以制备标题产物5-(4-(3-丁氧基苯基)-2-甲基丁-3-烯-1-基)苯并[d][1,3]间二氧杂环戊烯。
6g:1-丁氧基-3-(十四碳-1,3-二烯-1-基)苯
可以通过用相应的十三碳-2-烯醛的溶液替代3-(4-异丁基-2-甲基苯基)丙醛和3-(2-异丁基-4-甲基苯基)丙醛在THF中的溶液来重复实施例1.4中所述的方法,以制备标题产物1-丁氧基-3-(十四碳-1,3-二烯-1-基)苯。
6h:1-丁氧基-3-(3-苯基丙-1-烯-1-基)苯
可以通过用相应的2-苯基乙醛的溶液替代3-(4-异丁基-2-甲基苯基)丙醛和3-(2-异丁基-4-甲基苯基)丙醛在THF中的溶液来重复实施例1.4中所述的方法,以制备标题产物1-丁氧基-3-(3-苯基丙-1-烯-1-基)苯。
6i:1-丁氧基-3-((5E)-十一碳-1,5-二烯-1-基)苯
可以通过用相应的(E)-癸-4-烯醛溶液替代3-(4-异丁基-2-甲基苯基)丙醛和3-(2-异丁基-4-甲基苯基)丙醛在THF中的溶液来重复实施例1.4中所述的方法,以制备标题产物1-丁氧基-3-((5E)-十一碳-1,5-二烯-1-基)苯。
6j:5-(5-(3-丁氧基苯基)戊-4-烯-1-亚基)八氢-1H-4,7-亚甲基茚
可以通过用相应的4-(八氢-5H-4,7-亚甲基茚-5-亚基)丁醛的溶液替代3-(4-异丁基-2-甲基苯基)丙醛和3-(2-异丁基-4-甲基苯基)丙醛在THF中的溶液来重复实施例1.4中所述的方法,以制备标题产物5-(5-(3-丁氧基苯基)戊-4-烯-1-亚基)八氢-1H-4,7-亚甲基茚。
6k:1-丁氧基-3-(4-(4-乙基苯基)-3,3-二甲基丁-1-烯-1-基)苯
可以通过用相应的3-(4-乙基苯基)-2,2-二甲基丙醛的溶液替代3-(4-异丁基-2-甲基苯基)丙醛和3-(2-异丁基-4-甲基苯基)丙醛在THF中的溶液来重复实施例1.4中所述的方法,以制备标题产物1-丁氧基-3-(4-(4-乙基苯基)-3,3-二甲基丁-1-烯-1-基)苯。
6l:1-丁氧基-3-(7-甲氧基-3,7-二甲基壬-1-烯-1-基)苯
可以通过用相应的6-甲氧基-2,6-二甲基辛醛的溶液替代3-(4-异丁基-2-甲基苯基)丙醛和3-(2-异丁基-4-甲基苯基)丙醛在THF中的溶液来重复实施例1.4中所述的方法,以制备标题产物1-丁氧基-3-(7-甲氧基-3,7-二甲基壬-1-烯-1-基)苯。
6m:1-丁氧基-3-(4-(4-异丁基苯基)丁-1-烯-1-基)苯
可以通过用相应的3-(4-异丁基苯基)丙醛的溶液替代3-(4-异丁基-2-甲基苯基)丙醛和3-(2-异丁基-4-甲基苯基)丙醛在THF中的溶液来重复实施例1.4中所述的方法,以制备标题产物1-丁氧基-3-(4-(4-异丁基苯基)丁-1-烯-1-基)苯。
实施例7:包含式(I)的化合物的香料
1)3E,6E)-2,4,4,7-四甲基壬-6,8-二烯-3-酮肟
上述香料组合物具有经典的新鲜青香柠檬特征。这种香料可以以0.1-1.5wt%(例如0.3wt%)应用于通用清洁剂(APC)。
现在,通过用3-丁氧基苯甲醛即式(I)的化合物替代上述谐香的40份DPG,总体气味特征变得更柔和,更具有花香,更圆润,且总体而言,感觉更轻松,更新鲜,更舒适。
通过用3-丁氧基苯甲醛即式(I)的化合物替代上述谐香的40份DPG,并且用包含1-丁氧基-3-((1E,4Z)-庚-1,4-二烯-1-基)苯(60份)和两种另外的前体(4-(十二烷硫基)-4-甲基戊-2-酮(10份)和N,S-双(4-氧代-4-(2,6,6-三甲基环己-3-烯-1-基)丁-2-基)半胱氨酸乙酯(40份))的混合物替代上述谐香的110份DPG,所述谐香的持久性得到显著改善,从而递送了令人愉悦且非常自然的组合。
实施例8:包含式(II)的化合物的香料
上述香料组合物为新鲜花香青香谐香,让人联想到新鲜青香铃兰香。例如,这种香料可以以0.3-1.5wt%(例如0.6wt%)应用于高密度液体洗涤剂(HDLD)。
通过用1-丁氧基-3-((1E,4Z)-庚-1,4-二烯-1-基)苯即式(I)的化合物的前体替代上述谐香的30份DPG,湿织物上的新鲜青香效果得以明显增强。并且,特别地,当在一或三天后评价干燥织物时,在干燥织物上谐香的持久性明显增强。
通过用1-丁氧基-3-((1E,4Z)-庚-1,4-二烯-1-基)苯替代上述谐香的70份DPG,青香新鲜感将变得非常明显,并在干燥的织物上带来了令人惊讶和异常的新鲜感,让人联想到青香叶和新鲜苹果皮香味。
实施例9:包含式(II)的化合物香料
上述香料组合物是新鲜花香青香谐香,让人联想到新鲜青香铃兰香味。例如,该香料可以以0.1-1.5wt%(例如0.3wt%)应用于高密度粉末洗涤剂(HDPD)。
通过用1-丁氧基-3-((1E,4Z)-庚-1,4-二烯-1-基)苯即式(I)的化合物的前体替代上述谐香的100份DPG,在湿毛巾上的性能和扩散性得到增强,并具有新鲜青香令人愉悦的特征。在干织物上,其直接性得到明显改善,具有不寻常且非常令人愉悦的新鲜青香特征。
通过用包含1-丁氧基-3-((1E,4Z)-庚-1,4-二烯-1-基)苯(70份)和两种另外的前体(4-(十二烷硫基)-4-甲基戊-2-酮(10份)和N,S-双(4-氧代-4-(2,6,6-三甲基环己-3-烯-1-基)丁-2-基)半胱氨酸乙酯(30份))的混合物替代上述谐香的110份DPG,在干燥的织物上递送了非常不寻常和令人愉悦的新鲜青香多汁果香特征。这种新鲜青香多汁果香特征会持续数天,这也是新颖而令人惊讶的。
Claims (9)
2.权利要求1的化合物作为香料的用途,该化合物通过式(II)的化合物的自发空气氧化得到:
其中
R1选自直链或支链C3-、C4-和C5-烷基和C3-、C4-和C5-烯基;
R2选自
C4-C14烷基;被一个-OH基团和/或至多两个醚取代的C4-C14烷基;
C4-C14烯基;被一个-OH基团或醚基团取代的C4-C14烯基;
C5-C6环烷基;被1、2或3个选自C1-C6烷基和C2-C4亚烷基的基团取代的C5-C8环烷基;
C5-C8环烯基;其中环烯基-环被1、2或3个选自C1-C4烷基、C2-C4亚烷基和C3-C5环烷基的基团取代的C5-C8环烯基;
(C1-C3)烷基(C5-C6)环烷基,其中环烷基-环任选地被一个选自-OH基团和=O基团的基团和/或一个或两个醚基团和/或至多四个C1-C5烷基基团取代;
(C1-C4)烷基(C5-C6)环烯基,其中环烯基-环任选地被一个-OH基团和/或一个或两个醚基团和/或至多四个C1-C5烷基基团取代;
(C2-C3)烯基(C5-C6)环烯基,其中环烯基-环任选地被一个-OH基团和/或一个或两个醚基团和/或至多四个C1-C5烷基基团取代;
C6-C14芳基;其中芳基环被至多3个选自C1-C4烷基、-O-CH2-O-和-OR11的基团取代的C6-C14芳基,其中R11独立地选自氢和C1-C4烷基;
(C1-C4)烷基(C6-C14)芳基;其中芳基-环被至多2个选自C1-C4烷基、-O-CH2-O-和-OR12的基团取代的(C1-C4)烷基(C6-C14)芳基,其中R12独立地选自氢和C1-C4烷基;
(C2-C8)烯基(C6-C14)芳基;其中芳基-环被至多2个选自C1-C4烷基、-O-CH2-O-和-OR13的基团取代的(C2-C8)烯基(C6-C14)芳基,其中R13独立地选自氢和C1-C4烷基;
包含C8-C12碳原子的二-、三或四环烃环,其任选地被至多6个选自C1-C4烷基、-O-CH2-O-和-OR14的基团取代,其中R14独立地选自氢和C1-C4烷基;且
R3选自氢、C1-C5烷基和C2-C5烯基。
3.式(II)的化合物
其中
R1选自直链或支链C3-、C4-和C5-烷基和C3-、C4-和C5-烯基;
R2选自
C4-C14烷基;被一个-OH基团和/或至多两个醚取代的C4-C14烷基;
C4-C14烯基;被一个-OH基团或醚基团取代的C4-C14烯基;
C5-C6环烷基;被1、2或3个选自C1-C6烷基和C2-C4亚烷基的基团取代的C5-C8环烷基;
C5-C8环烯基;其中环烯基-环被1、2或3个选自C1-C4烷基、C2-C4亚烷基和C3-C5环烷基的基团取代的C5-C8环烯基;
(C1-C3)烷基(C5-C6)环烷基,其中环烷基-环任选地被一个选自-OH基团和=O基团的基团和/或一个或两个醚基团和/或至多四个C1-C5烷基基团取代;
(C1-C4)烷基(C5-C6)环烯基,其中环烯基-环任选地被一个-OH基团和/或一个或两个醚基团和/或至多四个C1-C5烷基基团取代;
(C2-C3)烯基(C5-C6)环烯基,其中环烯基-环任选地被一个-OH基团和/或一个或两个醚基团和/或至多四个C1-C5烷基基团取代;
C6-C14芳基;其中芳基环被至多3个选自C1-C4烷基、-O-CH2-O-和-OR11的基团取代的C6-C14芳基,其中R11独立地选自氢和C1-C4烷基;
(C1-C4)烷基(C6-C14)芳基;其中芳基-环被至多2个选自C1-C4烷基、-O-CH2-O-和-OR12的基团取代的(C1-C4)烷基(C6-C14)芳基,其中R12独立地选自氢和C1-C4烷基;
(C2-C8)烯基(C6-C14)芳基;其中芳基-环被至多2个选自C1-C4烷基、-O-CH2-O-和-OR13的基团取代的(C2-C8)烯基(C6-C14)芳基,其中R13独立地选自氢和C1-C4烷基;
包含C8-C12碳原子的二-、三或四环烃环,其任选地被至多6个选自C1-C4烷基、-O-CH2-O-和-OR14的基团取代,其中R14独立地选自氢和C1-C4烷基;且
R3选自氢、C1-C5烷基和C2-C5烯基。
4.权利要求3的化合物,选自
1-丁氧基-3-((1E,4Z)-庚-1,4-二烯-1-基)苯;
1-丁氧基-3-((1E,7Z)-癸-1,7-二烯-1-基)苯;
1-(4-(3-丁氧基苯基)丁-3-烯-1-基)-4-异丁基-2-甲基苯;
1-(4-(3-丁氧基苯基)丁-3-烯-1-基)-2-异丁基-4-甲基苯;
1-(仲丁氧基)-3-((1E,4Z)-庚-1,4-二烯-1-基)苯;
1-((1E,4Z)-庚-1,4-二烯-1-基)-3-(戊氧基)苯;
1-((1E,4Z)-庚-1,4-二烯-1-基)-3-((2-甲基烯丙基)氧基)苯;
1-((1E,4Z)-庚-1,4-二烯-1-基)-3-异丙氧基苯;
1-丁氧基-3-(4-(4-(叔丁基)苯基)丁-1-烯-1-基)苯;
1-丁氧基-3-(4-(4-(叔丁基)苯基)-3-甲基丁-1-烯-1-基)苯;
1-丁氧基-3-(4-(3-异丙基苯基)戊-1-烯-1-基)苯;
11-(3-丁氧基苯基)-2,6-二甲基十一碳-6,10-二烯-2-醇;
1-丁氧基-3-(3-甲基十二碳-1-烯-1-基)苯;
5-(4-(3-丁氧基苯基)-2-甲基丁-3-烯-1-基)苯并[d][1,3]间二氧杂环戊烯;
1-丁氧基-3-(十四碳-1,3-二烯-1-基)苯;
1-丁氧基-3-(3-苯基丙-1-烯-1-基)苯;
1-丁氧基-3-((5E)-十一碳-1,5-二烯-1-基)苯;
5-(5-(3-丁氧基苯基)戊-4-烯-1-亚基)八氢-1H-4,7-亚甲基茚;
1-丁氧基-3-(4-(4-乙基苯基)-3,3-二甲基丁-1-烯-1-基)苯;
1-丁氧基-3-(7-甲氧基-3,7-二甲基壬-1-烯-1-基)苯;和
1-丁氧基-3-(4-(4-异丁基苯基)丁-1-烯-1-基)苯。
5.给消费品加香的方法,包括向消费品基质中添加如权利要求1中所定义的式(I)的化合物或其前体。
6.权利要求5的方法,其特征在于式(I)的化合物的前体为如权利要求3中所定义的式(II)的化合物。
7.权利要求5的方法,其特征在于式(I)的化合物通过如权利要求3中所定义的式(II)的化合物在暴露于氧气时自发地空气氧化来生成。
8.消费品,包含如权利要求1中所定义的式(I)的化合物或其前体,优选如权利要求2或权利要求3中所定义的式(II)的化合物,和消费品基质。
9.权利要求8的消费品,其中所述消费品选自家庭护理产品、个人护理产品和清洁产品。
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PCT/EP2019/079605 WO2020089274A1 (en) | 2018-10-31 | 2019-10-30 | Alkoxybenzaldehyde derivatives and precursors thereof |
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EP (1) | EP3873880A1 (zh) |
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CN (1) | CN112930335A (zh) |
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FR2730730B1 (fr) | 1995-02-20 | 1997-04-04 | Rhone Poulenc Chimie | Procede de preparation d'un 4-hydroxybenzaldehyde substitue |
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AU1381800A (en) | 1998-12-16 | 2000-07-03 | Unilever Plc | Bleaching compositions based on air oxidation of aromatic aldehydes at specific ph range |
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