SU604479A3 - Способ получени производных пинана в виде оптически активных изомеров - Google Patents
Способ получени производных пинана в виде оптически активных изомеровInfo
- Publication number
- SU604479A3 SU604479A3 SU752101430A SU2101430A SU604479A3 SU 604479 A3 SU604479 A3 SU 604479A3 SU 752101430 A SU752101430 A SU 752101430A SU 2101430 A SU2101430 A SU 2101430A SU 604479 A3 SU604479 A3 SU 604479A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- mixture
- hydrochloride
- hydrogen
- optically active
- optical rotation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 11
- 150000003048 pinane derivatives Chemical class 0.000 title claims 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 24
- 230000003287 optical effect Effects 0.000 claims description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 11
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 9
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 6
- 238000005984 hydrogenation reaction Methods 0.000 claims description 4
- 238000001953 recrystallisation Methods 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 238000004508 fractional distillation Methods 0.000 claims description 3
- 230000003993 interaction Effects 0.000 claims description 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- GRWFGVWFFZKLTI-YGPZHTELSA-N (5r)-4,6,6-trimethylbicyclo[3.1.1]hept-3-ene Chemical compound C1C2CC=C(C)[C@]1([H])C2(C)C GRWFGVWFFZKLTI-YGPZHTELSA-N 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 238000005065 mining Methods 0.000 claims 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- VUNCLQCPKWLBRY-UHFFFAOYSA-N 4,6,6-trimethylbicyclo[3.1.1]heptane-3-carbaldehyde Chemical compound C1C(C=O)C(C)C2C(C)(C)C1C2 VUNCLQCPKWLBRY-UHFFFAOYSA-N 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 229910052703 rhodium Inorganic materials 0.000 description 5
- 239000010948 rhodium Substances 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- -1 for example Substances 0.000 description 4
- 238000007037 hydroformylation reaction Methods 0.000 description 4
- GRWFGVWFFZKLTI-IUCAKERBSA-N (-)-α-pinene Chemical compound CC1=CC[C@@H]2C(C)(C)[C@H]1C2 GRWFGVWFFZKLTI-IUCAKERBSA-N 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 235000019439 ethyl acetate Nutrition 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 238000000199 molecular distillation Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 3
- GRWFGVWFFZKLTI-UHFFFAOYSA-N α-pinene Chemical compound CC1=CCC2C(C)(C)C1C2 GRWFGVWFFZKLTI-UHFFFAOYSA-N 0.000 description 3
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- MVNCAPSFBDBCGF-UHFFFAOYSA-N alpha-pinene Natural products CC1=CCC23C1CC2C3(C)C MVNCAPSFBDBCGF-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- BJFPYGGTDAYECS-UHFFFAOYSA-N (3-chlorophenyl)methanamine Chemical compound NCC1=CC=CC(Cl)=C1 BJFPYGGTDAYECS-UHFFFAOYSA-N 0.000 description 1
- WNOPIURUTIVUBE-UHFFFAOYSA-N (3-hydroxyphenyl)methylazanium;chloride Chemical compound Cl.NCC1=CC=CC(O)=C1 WNOPIURUTIVUBE-UHFFFAOYSA-N 0.000 description 1
- MUOITVAMHSVXLO-UHFFFAOYSA-N (4,6,6-trimethyl-3-bicyclo[3.1.1]heptanyl)methanamine Chemical compound C1C(CN)C(C)C2C(C)(C)C1C2 MUOITVAMHSVXLO-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 101100522841 Drosophila melanogaster pygo gene Proteins 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- WTARULDDTDQWMU-UHFFFAOYSA-N Pseudopinene Natural products C1C2C(C)(C)C1CCC2=C WTARULDDTDQWMU-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- ADGFUTSPEKVFKD-UHFFFAOYSA-N carbonyl dichloride;rhodium Chemical compound [Rh].ClC(Cl)=O ADGFUTSPEKVFKD-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 1
- 239000004914 cyclooctane Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- RMLOZYVMENRVSS-UHFFFAOYSA-N formaldehyde;rhodium Chemical compound [Rh].O=C RMLOZYVMENRVSS-UHFFFAOYSA-N 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- SJLOMQIUPFZJAN-UHFFFAOYSA-N oxorhodium Chemical compound [Rh]=O SJLOMQIUPFZJAN-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic 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
- 150000003003 phosphines Chemical class 0.000 description 1
- XOKSLPVRUOBDEW-UHFFFAOYSA-N pinane group Chemical group C12C(CCC(C1(C)C)C2)C XOKSLPVRUOBDEW-UHFFFAOYSA-N 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 150000003283 rhodium Chemical class 0.000 description 1
- 229910003450 rhodium oxide Inorganic materials 0.000 description 1
- SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
- C07D295/02—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
- C07D295/03—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
- C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2404306A DE2404306C3 (de) | 1974-01-30 | 1974-01-30 | Optisch aktive Pinanderivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU604479A3 true SU604479A3 (ru) | 1978-04-25 |
Family
ID=5906041
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU752101430A SU604479A3 (ru) | 1974-01-30 | 1975-01-28 | Способ получени производных пинана в виде оптически активных изомеров |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4081477A (en, 2012) |
| JP (2) | JPS5918376B2 (en, 2012) |
| AT (1) | AT337671B (en, 2012) |
| BE (1) | BE824827A (en, 2012) |
| CA (1) | CA1058183A (en, 2012) |
| CH (1) | CH617651A5 (en, 2012) |
| DD (1) | DD119573A5 (en, 2012) |
| DE (1) | DE2404306C3 (en, 2012) |
| DK (1) | DK162280C (en, 2012) |
| FR (1) | FR2259087B1 (en, 2012) |
| GB (1) | GB1487867A (en, 2012) |
| HU (1) | HU170374B (en, 2012) |
| NL (1) | NL180656C (en, 2012) |
| SU (1) | SU604479A3 (en, 2012) |
| ZA (1) | ZA75603B (en, 2012) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2725878C1 (ru) * | 2019-12-30 | 2020-07-07 | Федеральное государственное бюджетное учреждение науки Федеральный исследовательский центр "КОМИ научный центр Уральского отделения Российской академии наук" | Хиральные миртанилсульфонамиды |
| RU2802954C1 (ru) * | 2022-10-17 | 2023-09-05 | Федеральное государственное бюджетное учреждение науки Федеральный исследовательский центр "КОМИ научный центр Уральского отделения Российской академии наук" | Трифторметилированные монотерпеновые аминоспирты на основе нопинона, камфорохинона или вербанона |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4139559A (en) * | 1976-07-02 | 1979-02-13 | Merck & Co., Inc. | Process for preparation of 1-[1,5-di-(3,3-dimethylnorborn-2-yl)-3-pentyl]-1,5,9-triazanonane and novel intermediates |
| DE2849742B2 (de) * | 1978-11-16 | 1980-10-16 | Henkel Kgaa, 4000 Duesseldorf | Verfahren zur Herstellung von Aldehyden und Verwendung der Verfahrensprodukte als Riechstoffe |
| DE69204660T2 (de) * | 1991-12-05 | 1996-04-18 | Givaudan Roure Int | Pinane. |
| WO2023061894A1 (en) | 2021-10-13 | 2023-04-20 | Basf Se | Use of acetoxymethyl -pinane isomers and mixtures thereof as aroma ingredient |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3584045A (en) * | 1967-12-28 | 1971-06-08 | Nat Distillers Chem Corp | Cycloaliphatic di(aminoalkanes) |
| DE1945007A1 (de) * | 1969-09-05 | 1971-03-11 | Basf Ag | N-Arylsulfonyl-N'-2-tetrahydrodicyclopentadienylharnstoffe |
| US3845048A (en) * | 1971-07-06 | 1974-10-29 | Berri Balzac | Terpene derivatives |
| DE2208155A1 (de) * | 1972-02-22 | 1973-08-30 | Basf Ag | Verfahren zur herstellung von 4-endotricyclo(5,2,1,0 hoch 2,6-endo)-decylamin |
-
1974
- 1974-01-30 DE DE2404306A patent/DE2404306C3/de not_active Expired
- 1974-12-19 DK DK665474A patent/DK162280C/da not_active IP Right Cessation
-
1975
- 1975-01-27 US US05/544,306 patent/US4081477A/en not_active Expired - Lifetime
- 1975-01-27 BE BE152747A patent/BE824827A/xx not_active IP Right Cessation
- 1975-01-28 DD DD183865A patent/DD119573A5/xx unknown
- 1975-01-28 FR FR7502555A patent/FR2259087B1/fr not_active Expired
- 1975-01-28 SU SU752101430A patent/SU604479A3/ru active
- 1975-01-28 HU HUBA3195A patent/HU170374B/hu unknown
- 1975-01-29 ZA ZA00750603A patent/ZA75603B/xx unknown
- 1975-01-29 AT AT67775A patent/AT337671B/de not_active IP Right Cessation
- 1975-01-29 NL NLAANVRAGE7501041,A patent/NL180656C/xx not_active IP Right Cessation
- 1975-01-29 CA CA218,884A patent/CA1058183A/en not_active Expired
- 1975-01-29 GB GB3843/75A patent/GB1487867A/en not_active Expired
- 1975-01-29 CH CH104475A patent/CH617651A5/de not_active IP Right Cessation
- 1975-01-30 JP JP50011965A patent/JPS5918376B2/ja not_active Expired
-
1983
- 1983-08-18 JP JP58149720A patent/JPS5951227A/ja active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2725878C1 (ru) * | 2019-12-30 | 2020-07-07 | Федеральное государственное бюджетное учреждение науки Федеральный исследовательский центр "КОМИ научный центр Уральского отделения Российской академии наук" | Хиральные миртанилсульфонамиды |
| RU2802954C1 (ru) * | 2022-10-17 | 2023-09-05 | Федеральное государственное бюджетное учреждение науки Федеральный исследовательский центр "КОМИ научный центр Уральского отделения Российской академии наук" | Трифторметилированные монотерпеновые аминоспирты на основе нопинона, камфорохинона или вербанона |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS616059B2 (en, 2012) | 1986-02-24 |
| JPS5951227A (ja) | 1984-03-24 |
| DK162280C (da) | 1992-03-16 |
| NL180656C (nl) | 1987-04-01 |
| NL7501041A (nl) | 1975-08-01 |
| DE2404306B2 (de) | 1980-02-28 |
| DK665474A (en, 2012) | 1975-09-29 |
| CH617651A5 (en, 2012) | 1980-06-13 |
| FR2259087B1 (en, 2012) | 1980-01-04 |
| FR2259087A1 (en, 2012) | 1975-08-22 |
| JPS50131958A (en, 2012) | 1975-10-18 |
| AT337671B (de) | 1977-07-11 |
| ZA75603B (en) | 1976-02-25 |
| CA1058183A (en) | 1979-07-10 |
| DK162280B (da) | 1991-10-07 |
| AU7728975A (en) | 1976-07-15 |
| DE2404306C3 (de) | 1980-10-23 |
| DE2404306A1 (de) | 1975-07-31 |
| BE824827A (fr) | 1975-07-28 |
| GB1487867A (en) | 1977-10-05 |
| ATA67775A (de) | 1976-11-15 |
| JPS5918376B2 (ja) | 1984-04-26 |
| HU170374B (en, 2012) | 1977-06-28 |
| US4081477A (en) | 1978-03-28 |
| DD119573A5 (en, 2012) | 1976-05-05 |
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