BR112012008069B1 - compostos fragrantes à base de dioxanos bicíclicos e composições compreendendo os mesmos - Google Patents
compostos fragrantes à base de dioxanos bicíclicos e composições compreendendo os mesmos Download PDFInfo
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- BR112012008069B1 BR112012008069B1 BR112012008069-5A BR112012008069A BR112012008069B1 BR 112012008069 B1 BR112012008069 B1 BR 112012008069B1 BR 112012008069 A BR112012008069 A BR 112012008069A BR 112012008069 B1 BR112012008069 B1 BR 112012008069B1
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- Prior art keywords
- methyl
- dioxin
- butyl
- ethyl
- group
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 90
- 239000000203 mixture Substances 0.000 title claims description 71
- -1 bicyclic dioxanes Chemical class 0.000 title claims description 32
- 239000003205 fragrance Substances 0.000 claims abstract description 30
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 9
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 9
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 37
- UCZQXJKDCHCTAI-UHFFFAOYSA-N 4h-1,3-dioxine Chemical compound C1OCC=CO1 UCZQXJKDCHCTAI-UHFFFAOYSA-N 0.000 claims description 26
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 25
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 18
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 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 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 239000002585 base Substances 0.000 claims description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 239000002304 perfume Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
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- 238000002360 preparation method Methods 0.000 abstract description 45
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract description 10
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- 238000005160 1H NMR spectroscopy Methods 0.000 description 58
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- IIQFBBQJYPGOHJ-UHFFFAOYSA-N 4-(cyclohexen-1-yl)morpholine Chemical compound C1CCCC(N2CCOCC2)=C1 IIQFBBQJYPGOHJ-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 125000005594 diketone group Chemical group 0.000 description 13
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 12
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- 229910000033 sodium borohydride Inorganic materials 0.000 description 11
- 125000003118 aryl group Chemical group 0.000 description 10
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- 238000000034 method Methods 0.000 description 8
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- XXDOKDGDIMZUJO-UHFFFAOYSA-N 2-(3-methylbutanoyl)cyclohexan-1-one Chemical compound CC(C)CC(=O)C1CCCCC1=O XXDOKDGDIMZUJO-UHFFFAOYSA-N 0.000 description 4
- CJBGXBKIDRIJOB-UHFFFAOYSA-N 2-[hydroxy(phenyl)methyl]cyclohexan-1-ol Chemical compound C=1C=CC=CC=1C(O)C1CCCCC1O CJBGXBKIDRIJOB-UHFFFAOYSA-N 0.000 description 4
- OEKATORRSPXJHE-UHFFFAOYSA-N 2-acetylcyclohexan-1-one Chemical compound CC(=O)C1CCCCC1=O OEKATORRSPXJHE-UHFFFAOYSA-N 0.000 description 4
- YTVQIZRDLKWECQ-UHFFFAOYSA-N 2-benzoylcyclohexan-1-one Chemical compound C=1C=CC=CC=1C(=O)C1CCCCC1=O YTVQIZRDLKWECQ-UHFFFAOYSA-N 0.000 description 4
- PFDJPXDSJBDMCC-UHFFFAOYSA-N 2-propanoylcyclohexan-1-one Chemical compound CCC(=O)C1CCCCC1=O PFDJPXDSJBDMCC-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
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- MVYIQVQYQBTWRR-UHFFFAOYSA-N 2-(1-hydroxyethyl)cyclohexan-1-ol Chemical compound CC(O)C1CCCCC1O MVYIQVQYQBTWRR-UHFFFAOYSA-N 0.000 description 1
- ZVLLAZFFOOZKQC-UHFFFAOYSA-N 2-(1-hydroxypropyl)-4,4-dimethylcyclohexan-1-ol Chemical compound CCC(O)C1CC(C)(C)CCC1O ZVLLAZFFOOZKQC-UHFFFAOYSA-N 0.000 description 1
- DTYXJMMASRYUTP-AATRIKPKSA-N 2-[(e)-but-2-enoyl]-4-tert-butylcyclohexan-1-one Chemical compound C\C=C\C(=O)C1CC(C(C)(C)C)CCC1=O DTYXJMMASRYUTP-AATRIKPKSA-N 0.000 description 1
- WKFJEERVXCIQBM-UHFFFAOYSA-N 2-acetyl-4,4-dimethylcyclohexan-1-one Chemical compound CC(=O)C1CC(C)(C)CCC1=O WKFJEERVXCIQBM-UHFFFAOYSA-N 0.000 description 1
- JKKVIIBTROLMFL-UHFFFAOYSA-N 2-acetyl-4-tert-butylcyclohexan-1-one Chemical compound CC(=O)C1CC(C(C)(C)C)CCC1=O JKKVIIBTROLMFL-UHFFFAOYSA-N 0.000 description 1
- LFJRMBAJZUHFNC-UHFFFAOYSA-N 2-benzoyl-4-tert-butylcyclohexan-1-one Chemical compound C1C(C(C)(C)C)CCC(=O)C1C(=O)C1=CC=CC=C1 LFJRMBAJZUHFNC-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- ISULZYQDGYXDFW-UHFFFAOYSA-N 3-methylbutanoyl chloride Chemical compound CC(C)CC(Cl)=O ISULZYQDGYXDFW-UHFFFAOYSA-N 0.000 description 1
- ZXJGOLMRNGHJCU-UHFFFAOYSA-N 4,4-dimethyl-2-propanoylcyclohexan-1-one Chemical compound CCC(=O)C1CC(C)(C)CCC1=O ZXJGOLMRNGHJCU-UHFFFAOYSA-N 0.000 description 1
- PXQMSTLNSHMSJB-UHFFFAOYSA-N 4,4-dimethylcyclohexan-1-one Chemical compound CC1(C)CCC(=O)CC1 PXQMSTLNSHMSJB-UHFFFAOYSA-N 0.000 description 1
- OLOGTUJODZYHCO-AATRIKPKSA-N 4,6,6-trimethyl-2-[(e)-prop-1-enyl]-4,4a,5,7,8,8a-hexahydrobenzo[d][1,3]dioxine Chemical compound C1C(C)(C)CCC2OC(/C=C/C)OC(C)C21 OLOGTUJODZYHCO-AATRIKPKSA-N 0.000 description 1
- KGWNHIBAVCUIHP-UHFFFAOYSA-N 4-(4,4-dimethylcyclohexen-1-yl)morpholine Chemical compound C1C(C)(C)CCC(N2CCOCC2)=C1 KGWNHIBAVCUIHP-UHFFFAOYSA-N 0.000 description 1
- CFLBVNHHOOZJGH-UHFFFAOYSA-N 4-(4-tert-butylcyclohexen-1-yl)morpholine Chemical compound C1C(C(C)(C)C)CCC(N2CCOCC2)=C1 CFLBVNHHOOZJGH-UHFFFAOYSA-N 0.000 description 1
- VGBBHJFPJMUSFO-UHFFFAOYSA-N 4-ethyl-6,6-dimethyl-2-propan-2-yl-4,4a,5,7,8,8a-hexahydrobenzo[d][1,3]dioxine Chemical compound C1CC(C)(C)CC2C(CC)OC(C(C)C)OC21 VGBBHJFPJMUSFO-UHFFFAOYSA-N 0.000 description 1
- HEXKZEFWQJYPFE-UHFFFAOYSA-N 4-tert-butyl-2-(1-hydroxybutyl)cyclohexan-1-ol Chemical compound CCCC(O)C1CC(C(C)(C)C)CCC1O HEXKZEFWQJYPFE-UHFFFAOYSA-N 0.000 description 1
- HFPLZKCJQIXIFR-UHFFFAOYSA-N 4-tert-butyl-2-(1-hydroxyethyl)cyclohexan-1-ol Chemical compound CC(O)C1CC(C(C)(C)C)CCC1O HFPLZKCJQIXIFR-UHFFFAOYSA-N 0.000 description 1
- UCTXVQWYBSUIGO-UHFFFAOYSA-N 4-tert-butyl-2-[hydroxy(phenyl)methyl]cyclohexan-1-ol Chemical compound C1C(C(C)(C)C)CCC(O)C1C(O)C1=CC=CC=C1 UCTXVQWYBSUIGO-UHFFFAOYSA-N 0.000 description 1
- UUOALHMQTJPKOY-UHFFFAOYSA-N 4-tert-butyl-2-propanoylcyclohexan-1-one Chemical compound CCC(=O)C1CC(C(C)(C)C)CCC1=O UUOALHMQTJPKOY-UHFFFAOYSA-N 0.000 description 1
- RDHNTAXPFZIMDN-UHFFFAOYSA-N 6,6-Dimethoxy-2,5,5-trimethyl-2-hexene Chemical compound COC(OC)C(C)(C)CC=C(C)C RDHNTAXPFZIMDN-UHFFFAOYSA-N 0.000 description 1
- HAFWAVOMECONDC-UHFFFAOYSA-N 6-tert-butyl-2,4-dimethyl-4a,5,6,7,8,8a-hexahydro-4h-benzo[d][1,3]dioxine Chemical compound C1C(C(C)(C)C)CCC2OC(C)OC(C)C21 HAFWAVOMECONDC-UHFFFAOYSA-N 0.000 description 1
- YZIWHKHXPUIDLI-UHFFFAOYSA-N 6-tert-butyl-2-methyl-4-phenyl-4a,5,6,7,8,8a-hexahydro-4h-benzo[d][1,3]dioxine Chemical compound O1C(C)OC2CCC(C(C)(C)C)CC2C1C1=CC=CC=C1 YZIWHKHXPUIDLI-UHFFFAOYSA-N 0.000 description 1
- SJOGWQIHALUVJA-UHFFFAOYSA-N 6-tert-butyl-4-ethyl-2-propan-2-yl-4a,5,6,7,8,8a-hexahydro-4h-benzo[d][1,3]dioxine Chemical compound C1CC(C(C)(C)C)CC2C(CC)OC(C(C)C)OC21 SJOGWQIHALUVJA-UHFFFAOYSA-N 0.000 description 1
- 240000007087 Apium graveolens Species 0.000 description 1
- 235000015849 Apium graveolens Dulce Group Nutrition 0.000 description 1
- 235000010591 Appio Nutrition 0.000 description 1
- 235000017060 Arachis glabrata Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 235000010777 Arachis hypogaea Nutrition 0.000 description 1
- 235000018262 Arachis monticola Nutrition 0.000 description 1
- 235000003092 Artemisia dracunculus Nutrition 0.000 description 1
- 240000001851 Artemisia dracunculus Species 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- 240000000560 Citrus x paradisi Species 0.000 description 1
- 240000009226 Corylus americana Species 0.000 description 1
- 235000001543 Corylus americana Nutrition 0.000 description 1
- 235000007466 Corylus avellana Nutrition 0.000 description 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
- 244000000626 Daucus carota Species 0.000 description 1
- 235000002767 Daucus carota Nutrition 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 235000010254 Jasminum officinale Nutrition 0.000 description 1
- 240000005385 Jasminum sambac Species 0.000 description 1
- 229910010084 LiAlH4 Inorganic materials 0.000 description 1
- 235000011430 Malus pumila Nutrition 0.000 description 1
- 235000015103 Malus silvestris Nutrition 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- 235000014443 Pyrus communis Nutrition 0.000 description 1
- 241000533293 Sesbania emerus Species 0.000 description 1
- 244000223014 Syzygium aromaticum Species 0.000 description 1
- 235000016639 Syzygium aromaticum Nutrition 0.000 description 1
- 235000012308 Tagetes Nutrition 0.000 description 1
- 241000736851 Tagetes Species 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- 240000007316 Xerochrysum bracteatum Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 235000021438 curry Nutrition 0.000 description 1
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical compound O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
- YKFKEYKJGVSEIX-UHFFFAOYSA-N cyclohexanone, 4-(1,1-dimethylethyl)- Chemical compound CC(C)(C)C1CCC(=O)CC1 YKFKEYKJGVSEIX-UHFFFAOYSA-N 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000000834 fixative Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 235000014571 nuts Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 229940100595 phenylacetaldehyde Drugs 0.000 description 1
- 230000001105 regulatory effect 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
- 230000001953 sensory effect Effects 0.000 description 1
- 230000008786 sensory perception of smell Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/08—1,3-Dioxanes; Hydrogenated 1,3-dioxanes condensed with carbocyclic rings or ring systems
-
- 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
- C11B9/0069—Heterocyclic compounds
- C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
- C11B9/008—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing six atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Furan Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP09305713.1 | 2009-07-29 | ||
| EP09305713A EP2287159A1 (en) | 2009-07-29 | 2009-07-29 | New bicyclic dioxanes, their preparation and their use as organoleptic compounds |
| PCT/IB2010/053424 WO2011013077A1 (en) | 2009-07-29 | 2010-07-28 | New bicyclic dioxanes, their preparation and their use as fragrant compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| BR112012008069A2 BR112012008069A2 (pt) | 2016-03-01 |
| BR112012008069B1 true BR112012008069B1 (pt) | 2020-12-01 |
Family
ID=41350300
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BR112012008069-5A BR112012008069B1 (pt) | 2009-07-29 | 2010-07-28 | compostos fragrantes à base de dioxanos bicíclicos e composições compreendendo os mesmos |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US8569518B2 (https=) |
| EP (2) | EP2287159A1 (https=) |
| JP (1) | JP5717740B2 (https=) |
| CN (1) | CN102482253B (https=) |
| BR (1) | BR112012008069B1 (https=) |
| DK (1) | DK2459546T3 (https=) |
| ES (1) | ES2451521T3 (https=) |
| MX (1) | MX2012001273A (https=) |
| PL (1) | PL2459546T3 (https=) |
| PT (1) | PT2459546E (https=) |
| RU (1) | RU2562973C2 (https=) |
| WO (1) | WO2011013077A1 (https=) |
| ZA (1) | ZA201200562B (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6713474B2 (ja) * | 2015-01-21 | 2020-06-24 | フイルメニツヒ ソシエテ アノニムＦｉｒｍｅｎｉｃｈ Ｓａ | 活性揮発性カルボニル化合物の制御放出のための光解離性アセタールおよびケタール化合物 |
| CN105044261B (zh) * | 2015-07-02 | 2020-10-16 | 谱尼测试集团深圳有限公司 | 一种个人护理品中卡拉花醛的检测方法 |
| CN115340449B (zh) * | 2022-09-02 | 2024-07-26 | 常州佳德医药科技有限公司 | 一锅法制备2-乙酰基环戊酮的方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2935749A1 (de) * | 1979-09-05 | 1981-03-26 | Henkel KGaA, 40589 Düsseldorf | 4-methyl-2,5-dioxa-bicyclo (4.4.0) decan-3-on, dessen herstellung und verwendung als riechstoff sowie dieses enthaltende riechstoffkompositionen |
| PT1027043E (pt) * | 1996-12-10 | 2005-02-28 | Bristol Myers Squibb Co | Benzodioxole benzofurano di-hidrobenzofurano e benzodioxano como agentes melatonergicos |
| US6303798B1 (en) * | 2001-02-23 | 2001-10-16 | International Flavors & Fragrances Inc. | Methylene dioxy tetrahydroindane derivative |
| DE10225350A1 (de) * | 2002-06-07 | 2003-12-18 | Symrise Gmbh & Co Kg | Aromakompositionen mit Frischewirkung |
-
2009
- 2009-07-29 EP EP09305713A patent/EP2287159A1/en not_active Withdrawn
-
2010
- 2010-07-28 CN CN201080038412.4A patent/CN102482253B/zh active Active
- 2010-07-28 WO PCT/IB2010/053424 patent/WO2011013077A1/en not_active Ceased
- 2010-07-28 ES ES10745409.2T patent/ES2451521T3/es active Active
- 2010-07-28 PL PL10745409T patent/PL2459546T3/pl unknown
- 2010-07-28 PT PT107454092T patent/PT2459546E/pt unknown
- 2010-07-28 US US13/387,214 patent/US8569518B2/en active Active
- 2010-07-28 EP EP10745409.2A patent/EP2459546B1/en active Active
- 2010-07-28 BR BR112012008069-5A patent/BR112012008069B1/pt active IP Right Grant
- 2010-07-28 JP JP2012522325A patent/JP5717740B2/ja active Active
- 2010-07-28 RU RU2012107548/04A patent/RU2562973C2/ru active
- 2010-07-28 DK DK10745409.2T patent/DK2459546T3/en active
- 2010-07-28 MX MX2012001273A patent/MX2012001273A/es active IP Right Grant
-
2012
- 2012-01-24 ZA ZA2012/00562A patent/ZA201200562B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PT2459546E (pt) | 2014-03-20 |
| US8569518B2 (en) | 2013-10-29 |
| ZA201200562B (en) | 2012-10-31 |
| ES2451521T3 (es) | 2014-03-27 |
| PL2459546T3 (pl) | 2014-05-30 |
| JP5717740B2 (ja) | 2015-05-13 |
| RU2012107548A (ru) | 2013-09-10 |
| DK2459546T3 (en) | 2014-03-24 |
| RU2562973C2 (ru) | 2015-09-10 |
| JP2013500327A (ja) | 2013-01-07 |
| EP2459546A1 (en) | 2012-06-06 |
| CN102482253A (zh) | 2012-05-30 |
| WO2011013077A1 (en) | 2011-02-03 |
| US20120165557A1 (en) | 2012-06-28 |
| BR112012008069A2 (pt) | 2016-03-01 |
| EP2287159A1 (en) | 2011-02-23 |
| MX2012001273A (es) | 2012-06-19 |
| EP2459546B1 (en) | 2013-12-18 |
| CN102482253B (zh) | 2014-08-06 |
| HK1169986A1 (en) | 2013-02-15 |
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| B06U | Preliminary requirement: requests with searches performed by other patent offices: procedure suspended [chapter 6.21 patent gazette] | ||
| B06A | Patent application procedure suspended [chapter 6.1 patent gazette] | ||
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