FR2499071A1 - Nouveaux derives de l'acide cyclopropane carboxylique substitue en 3 par une chaine vinylique, leur procede de preparation et leur application comme agents parfumants - Google Patents
Nouveaux derives de l'acide cyclopropane carboxylique substitue en 3 par une chaine vinylique, leur procede de preparation et leur application comme agents parfumants Download PDFInfo
- Publication number
- FR2499071A1 FR2499071A1 FR8102236A FR8102236A FR2499071A1 FR 2499071 A1 FR2499071 A1 FR 2499071A1 FR 8102236 A FR8102236 A FR 8102236A FR 8102236 A FR8102236 A FR 8102236A FR 2499071 A1 FR2499071 A1 FR 2499071A1
- Authority
- FR
- France
- Prior art keywords
- cyclopropane
- methyl
- carbon
- radical
- dimethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000000034 method Methods 0.000 title abstract description 11
- 238000002360 preparation method Methods 0.000 title abstract description 10
- -1 VINYL CHAIN Chemical group 0.000 title description 78
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical group OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 title description 27
- 239000003795 chemical substances by application Substances 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 abstract description 33
- 239000000203 mixture Substances 0.000 abstract description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 7
- 150000002576 ketones Chemical group 0.000 abstract description 3
- 229910052717 sulfur Inorganic materials 0.000 abstract description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229950011148 cyclopropane Drugs 0.000 description 93
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 91
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 87
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- 239000000047 product Substances 0.000 description 69
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- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 25
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- YMGUBTXCNDTFJI-UHFFFAOYSA-M cyclopropanecarboxylate Chemical compound [O-]C(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-M 0.000 description 16
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
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- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
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- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 4
- 150000007942 carboxylates Chemical class 0.000 description 4
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 4
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- 235000000126 Styrax benzoin Nutrition 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- MOLRJCRTZIEBKH-UHFFFAOYSA-N cyclopropane propanoic acid Chemical compound C(CC)(=O)O.C1CC1 MOLRJCRTZIEBKH-UHFFFAOYSA-N 0.000 description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- XOLBXXZZQLVKRU-UHFFFAOYSA-N C1CC1.[C] Chemical compound C1CC1.[C] XOLBXXZZQLVKRU-UHFFFAOYSA-N 0.000 description 2
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- VONGZNXBKCOUHB-UHFFFAOYSA-N Phenylmethyl butanoate Chemical compound CCCC(=O)OCC1=CC=CC=C1 VONGZNXBKCOUHB-UHFFFAOYSA-N 0.000 description 2
- 241000220317 Rosa Species 0.000 description 2
- 235000008411 Sumatra benzointree Nutrition 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 238000007239 Wittig reaction Methods 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 2
- 229960002130 benzoin Drugs 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
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- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
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- LDDOSDVZPSGLFZ-UHFFFAOYSA-N ethyl cyclopropanecarboxylate Chemical compound CCOC(=O)C1CC1 LDDOSDVZPSGLFZ-UHFFFAOYSA-N 0.000 description 2
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- VNXBKJFUJUWOCW-UHFFFAOYSA-N methylcyclopropane Chemical compound CC1CC1 VNXBKJFUJUWOCW-UHFFFAOYSA-N 0.000 description 2
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- 210000000988 bone and bone Anatomy 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-M carbamimidate Chemical compound NC([NH-])=O XSQUKJJJFZCRTK-UHFFFAOYSA-M 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 235000000484 citronellol Nutrition 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- MSQDVGOEBXMPRF-UHFFFAOYSA-N cyclohexane;propan-2-one Chemical compound CC(C)=O.C1CCCCC1 MSQDVGOEBXMPRF-UHFFFAOYSA-N 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 1
- 239000000551 dentifrice Substances 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000005680 ethenylethyl group Chemical group [H]C([H])=C([H])C([H])([H])C([H])([H])* 0.000 description 1
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000000816 ethylene group Chemical class [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- LJJVZJSGXHJIPP-UHFFFAOYSA-N ethylpentyl Chemical group [CH2+]CCC[CH]C[CH2-] LJJVZJSGXHJIPP-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000834 fixative Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- ORDVEJHCXIDYEF-UHFFFAOYSA-N formyl cyclopropanecarboxylate Chemical compound O=COC(=O)C1CC1 ORDVEJHCXIDYEF-UHFFFAOYSA-N 0.000 description 1
- HIGQPQRQIQDZMP-UHFFFAOYSA-N geranil acetate Natural products CC(C)=CCCC(C)=CCOC(C)=O HIGQPQRQIQDZMP-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229930002839 ionone Natural products 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- UWKAYLJWKGQEPM-UHFFFAOYSA-N linalool acetate Natural products CC(C)=CCCC(C)(C=C)OC(C)=O UWKAYLJWKGQEPM-UHFFFAOYSA-N 0.000 description 1
- JILPJDVXYVTZDQ-UHFFFAOYSA-N lithium methoxide Chemical compound [Li+].[O-]C JILPJDVXYVTZDQ-UHFFFAOYSA-N 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- KVWWIYGFBYDJQC-UHFFFAOYSA-N methyl dihydrojasmonate Chemical compound CCCCCC1C(CC(=O)OC)CCC1=O KVWWIYGFBYDJQC-UHFFFAOYSA-N 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 101150035983 str1 gene Proteins 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 235000012222 talc Nutrition 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
- 239000001993 wax Substances 0.000 description 1
Classifications
-
- 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
- C11B9/0092—Heterocyclic compounds containing only N as heteroatom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
- C11B9/003—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing less than six carbon atoms
-
- 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
- C11B9/0076—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing less than six atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Furan Compounds (AREA)
- Cosmetics (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8102236A FR2499071A1 (fr) | 1981-02-05 | 1981-02-05 | Nouveaux derives de l'acide cyclopropane carboxylique substitue en 3 par une chaine vinylique, leur procede de preparation et leur application comme agents parfumants |
| US06/343,348 US4431576A (en) | 1981-02-05 | 1982-01-27 | Perfumant cyclopropane-carboxylic acid derivatives |
| IT47671/82A IT1147810B (it) | 1981-02-05 | 1982-01-28 | Derivati di acido diclopropancarbossilico sostituiti in posizione 3 da una catena vinilica,loro procedimento di preparazione,loro applicazione come agenti profumati e composizioni che li contengono |
| NL8200342A NL8200342A (nl) | 1981-02-05 | 1982-01-29 | Nieuwe, op plaats 3 door een vinylketen gesubstitueerde, cyclopropaancarbonzuurverbindingen, hun bereiding, hun toepassing als reukmiddelen en de samenstellingen die zij bevatten. |
| CH691/82A CH657846A5 (fr) | 1981-02-05 | 1982-02-04 | Derives de l'acide cyclopropane carboxylique substitue en 3 par une chaine vinylique, leur preparation et les compositions parfumantes les renfermant. |
| GB8203193A GB2093022B (en) | 1981-01-24 | 1982-02-04 | Derivatives of cyclopropane carboxylic acid |
| JP57016462A JPS57154147A (en) | 1981-02-05 | 1982-02-05 | Novel derivatives substituted with vinyl chain at 3-position, manufacture, use as perfume and composition containing same |
| DE19823203977 DE3203977A1 (de) | 1981-02-05 | 1982-02-05 | Neue, in 3-stellung durch eine vinylkette substituierte cyclopropancarbonsaeurederivate, deren herstellung, deren verwendung als duftverleihende mittel und die sie enthaltenden zusammensetzungen |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8102236A FR2499071A1 (fr) | 1981-02-05 | 1981-02-05 | Nouveaux derives de l'acide cyclopropane carboxylique substitue en 3 par une chaine vinylique, leur procede de preparation et leur application comme agents parfumants |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2499071A1 true FR2499071A1 (fr) | 1982-08-06 |
| FR2499071B1 FR2499071B1 (cg-RX-API-DMAC10.html) | 1984-10-19 |
Family
ID=9254870
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8102236A Granted FR2499071A1 (fr) | 1981-01-24 | 1981-02-05 | Nouveaux derives de l'acide cyclopropane carboxylique substitue en 3 par une chaine vinylique, leur procede de preparation et leur application comme agents parfumants |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4431576A (cg-RX-API-DMAC10.html) |
| JP (1) | JPS57154147A (cg-RX-API-DMAC10.html) |
| CH (1) | CH657846A5 (cg-RX-API-DMAC10.html) |
| DE (1) | DE3203977A1 (cg-RX-API-DMAC10.html) |
| FR (1) | FR2499071A1 (cg-RX-API-DMAC10.html) |
| IT (1) | IT1147810B (cg-RX-API-DMAC10.html) |
| NL (1) | NL8200342A (cg-RX-API-DMAC10.html) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4522749A (en) * | 1981-12-21 | 1985-06-11 | National Distillers And Chemical Corporation | Process for augmenting or enhancing the aroma of a fragrance by adding a vinylcyclopropane compound |
| FR2534252A1 (fr) * | 1982-10-12 | 1984-04-13 | Roussel Uclaf | Nouveaux derives de l'acide cyclopropane carboxylique substitues en 3 par une chaine vinylique elle-meme substituee, leur procede de preparation et leur application comme pesticides |
| US6576247B1 (en) * | 1994-11-10 | 2003-06-10 | Kanebo Ltd. And T. Hasegawa Co. Ltd. | Sustained-release aromatic and method of detecting micro-organism by using the same |
| US5767305A (en) * | 1997-04-03 | 1998-06-16 | International Flavors & Fragrances Inc. | Cyclopropyl carboxylic acid esters and uses thereof in imparting, augmenting and enhancing aromas |
| ES2621903T3 (es) * | 2012-01-18 | 2017-07-05 | International Flavors & Fragrances Inc. | Nuevos compuestos organolépticos |
| EP4402230A1 (en) * | 2021-09-13 | 2024-07-24 | Symrise AG | Cyclopropanated fragrance compounds |
| CN116375604B (zh) * | 2022-02-22 | 2024-10-22 | 江苏扬农化工股份有限公司 | 一种双键含氰基的拟除虫菊酯化合物及合成方法与应用 |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2045177A5 (cg-RX-API-DMAC10.html) * | 1969-06-13 | 1971-02-26 | Roussel Uclaf | |
| US3714153A (en) * | 1970-06-22 | 1973-01-30 | Roussel Uclaf | Novel cyclopropanecarboxylic acids |
| FR2232273A1 (cg-RX-API-DMAC10.html) * | 1973-06-07 | 1975-01-03 | Nat Res Dev | |
| US3926860A (en) * | 1974-01-28 | 1975-12-16 | Int Flavors & Fragrances Inc | Fragrance materials containing cis-2-n-pentyl cyclopropane-1-carboxylic acid |
| FR2413820A1 (fr) * | 1977-12-29 | 1979-07-27 | Sony Corp | Appareil d'accord, notamment pour recepteur de radiophonie |
| EP0006354A1 (en) * | 1978-06-21 | 1980-01-09 | Ici Australia Limited | Fluoro-substituted pyrethroid-type esters, processes for their preparation, intermediates for use in such processes, compositions for insecticidal use, and methods of combating insect pests |
| EP0018894A1 (fr) * | 1979-04-26 | 1980-11-12 | Roussel-Uclaf | Esters de dérivés de l'alléthrolone et d'acides carboxyliques, leur procédé de préparation et les compositions les renfermant |
| EP0019719A1 (de) * | 1979-05-02 | 1980-12-10 | Bayer Ag | Verfahren zur Herstellung von Alkenen, neue Zwischenprodukte zu ihrer Herstellung und Verfahren zu deren Herstellung |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU432259B1 (en) * | 1970-02-26 | 1972-08-24 | Sumitomo Chemical Company, Limited | Novel substituted chrysanthemates |
| JPS5111171B1 (cg-RX-API-DMAC10.html) * | 1971-06-28 | 1976-04-09 | Sumitomo Chemical Co | |
| DE2710174A1 (de) * | 1977-03-09 | 1978-09-14 | Bayer Ag | Verfahren zur herstellung von dihalogenvinyl-cyclopropancarbonsaeuren und deren ester |
| DE2819788A1 (de) * | 1978-05-05 | 1979-11-08 | Bayer Ag | Benzylester mit fluorsubstituierten aether- und/oder thioaethergruppen und ihre verwendung als insektizide |
| DE2961566D1 (en) * | 1978-12-15 | 1982-02-04 | Ciba Geigy Ag | Process for the preparation of optically active 3-substituted 2-(2',2'-dihalovinyl)-cyclopropane-1-carboxylic acids and their derivatives; 4-(2',2',2'-trihaloethyl)-cyclobutane-1-sulphonic acid salts and their preparation |
| US4335252A (en) * | 1979-05-24 | 1982-06-15 | Fmc Corporation | Insecticidal pyrethroid enantiomer pair |
-
1981
- 1981-02-05 FR FR8102236A patent/FR2499071A1/fr active Granted
-
1982
- 1982-01-27 US US06/343,348 patent/US4431576A/en not_active Expired - Fee Related
- 1982-01-28 IT IT47671/82A patent/IT1147810B/it active
- 1982-01-29 NL NL8200342A patent/NL8200342A/nl not_active Application Discontinuation
- 1982-02-04 CH CH691/82A patent/CH657846A5/fr not_active IP Right Cessation
- 1982-02-05 JP JP57016462A patent/JPS57154147A/ja active Pending
- 1982-02-05 DE DE19823203977 patent/DE3203977A1/de not_active Withdrawn
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2045177A5 (cg-RX-API-DMAC10.html) * | 1969-06-13 | 1971-02-26 | Roussel Uclaf | |
| US3714153A (en) * | 1970-06-22 | 1973-01-30 | Roussel Uclaf | Novel cyclopropanecarboxylic acids |
| FR2232273A1 (cg-RX-API-DMAC10.html) * | 1973-06-07 | 1975-01-03 | Nat Res Dev | |
| US3926860A (en) * | 1974-01-28 | 1975-12-16 | Int Flavors & Fragrances Inc | Fragrance materials containing cis-2-n-pentyl cyclopropane-1-carboxylic acid |
| FR2413820A1 (fr) * | 1977-12-29 | 1979-07-27 | Sony Corp | Appareil d'accord, notamment pour recepteur de radiophonie |
| EP0006354A1 (en) * | 1978-06-21 | 1980-01-09 | Ici Australia Limited | Fluoro-substituted pyrethroid-type esters, processes for their preparation, intermediates for use in such processes, compositions for insecticidal use, and methods of combating insect pests |
| EP0018894A1 (fr) * | 1979-04-26 | 1980-11-12 | Roussel-Uclaf | Esters de dérivés de l'alléthrolone et d'acides carboxyliques, leur procédé de préparation et les compositions les renfermant |
| EP0019719A1 (de) * | 1979-05-02 | 1980-12-10 | Bayer Ag | Verfahren zur Herstellung von Alkenen, neue Zwischenprodukte zu ihrer Herstellung und Verfahren zu deren Herstellung |
Also Published As
| Publication number | Publication date |
|---|---|
| IT1147810B (it) | 1986-11-26 |
| JPS57154147A (en) | 1982-09-22 |
| FR2499071B1 (cg-RX-API-DMAC10.html) | 1984-10-19 |
| NL8200342A (nl) | 1982-09-01 |
| CH657846A5 (fr) | 1986-09-30 |
| DE3203977A1 (de) | 1982-09-02 |
| IT8247671A0 (it) | 1982-01-28 |
| US4431576A (en) | 1984-02-14 |
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