BE1001613A4 - Procede pour la preparation du (+)-13-norfaranal. - Google Patents
Procede pour la preparation du (+)-13-norfaranal. Download PDFInfo
- Publication number
- BE1001613A4 BE1001613A4 BE8700383A BE8700383A BE1001613A4 BE 1001613 A4 BE1001613 A4 BE 1001613A4 BE 8700383 A BE8700383 A BE 8700383A BE 8700383 A BE8700383 A BE 8700383A BE 1001613 A4 BE1001613 A4 BE 1001613A4
- Authority
- BE
- Belgium
- Prior art keywords
- compound
- general formula
- formula
- group
- process according
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 19
- 238000002360 preparation method Methods 0.000 title claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 56
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
- -1 p-toluenesulfonyloxy Chemical group 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 8
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 7
- 229910052744 lithium Inorganic materials 0.000 claims description 7
- 150000001450 anions Chemical class 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 229910052987 metal hydride Inorganic materials 0.000 claims description 4
- 150000004681 metal hydrides Chemical class 0.000 claims description 4
- 125000005948 methanesulfonyloxy group Chemical group 0.000 claims description 4
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- RCBVKBFIWMOMHF-UHFFFAOYSA-L hydroxy-(hydroxy(dioxo)chromio)oxy-dioxochromium;pyridine Chemical compound C1=CC=NC=C1.C1=CC=NC=C1.O[Cr](=O)(=O)O[Cr](O)(=O)=O RCBVKBFIWMOMHF-UHFFFAOYSA-L 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 230000032050 esterification Effects 0.000 claims description 2
- 238000005886 esterification reaction Methods 0.000 claims description 2
- 230000002140 halogenating effect Effects 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- RXBWBMXVYZIXDB-UHFFFAOYSA-N (6E,10Z)-3,4,7,11-tetramethyl-trideca-6,10-dienal Natural products CCC(C)=CCCC(C)=CCC(C)C(C)CC=O RXBWBMXVYZIXDB-UHFFFAOYSA-N 0.000 abstract description 5
- 241000257303 Hymenoptera Species 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 4
- 239000003016 pheromone Substances 0.000 abstract description 4
- 239000000700 radioactive tracer Substances 0.000 abstract description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 17
- 239000000243 solution Substances 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 8
- 239000012047 saturated solution Substances 0.000 description 8
- 239000012230 colorless oil Substances 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- JRLTTZUODKEYDH-UHFFFAOYSA-N 8-methylquinoline Chemical group C1=CN=C2C(C)=CC=CC2=C1 JRLTTZUODKEYDH-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- JSCUZAYKVZXKQE-JXMROGBWSA-N (2e)-1-bromo-3,7-dimethylocta-2,6-diene Chemical compound CC(C)=CCC\C(C)=C\CBr JSCUZAYKVZXKQE-JXMROGBWSA-N 0.000 description 2
- NEXRYLFKZCYFFB-MMJTVPDGSA-N (3s,4r,6e)-3,4,7,11-tetramethyldodeca-6,10-dienal Chemical compound O=CC[C@H](C)[C@H](C)C\C=C(/C)CCC=C(C)C NEXRYLFKZCYFFB-MMJTVPDGSA-N 0.000 description 2
- OBQPKGCVMCIETH-UHFFFAOYSA-N 1-chloro-1-(1-chloroethoxy)ethane Chemical compound CC(Cl)OC(C)Cl OBQPKGCVMCIETH-UHFFFAOYSA-N 0.000 description 2
- NFGXHKASABOEEW-UHFFFAOYSA-N 1-methylethyl 11-methoxy-3,7,11-trimethyl-2,4-dodecadienoate Chemical compound COC(C)(C)CCCC(C)CC=CC(C)=CC(=O)OC(C)C NFGXHKASABOEEW-UHFFFAOYSA-N 0.000 description 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
- 101150041968 CDC13 gene Proteins 0.000 description 2
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000004645 aluminates Chemical class 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- 239000002361 compost Substances 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- 229930002897 methoprene Natural products 0.000 description 2
- 229950003442 methoprene Drugs 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- STLRNDLGNUYBKN-DGRSMZPJSA-N (2E,4R,6E)-3,4,7,11-tetramethyldodeca-2,6,10-trien-1-ol Chemical compound C\C(=C/CO)\[C@@H](C\C=C(\CCC=C(C)C)/C)C STLRNDLGNUYBKN-DGRSMZPJSA-N 0.000 description 1
- NEXRYLFKZCYFFB-BNSCMJDNSA-N (3R,4R,6E)-3,4,7,11-tetramethyldodeca-6,10-dienal Chemical compound C[C@H](CC=O)[C@@H](C\C=C(\CCC=C(C)C)/C)C NEXRYLFKZCYFFB-BNSCMJDNSA-N 0.000 description 1
- YHTLGFCVBKENTE-YFKPBYRVSA-N (4s)-4-methyloxan-2-one Chemical compound C[C@H]1CCOC(=O)C1 YHTLGFCVBKENTE-YFKPBYRVSA-N 0.000 description 1
- AMFDSAVMBKVRFK-CVEARBPZSA-N C[C@@H](CCO)[C@@H](CC=C(CCC=C(C)C)/C)C Chemical compound C[C@@H](CCO)[C@@H](CC=C(CCC=C(C)C)/C)C AMFDSAVMBKVRFK-CVEARBPZSA-N 0.000 description 1
- XIFWHIKDTORZQI-MSOLQXFVSA-N C[C@@H](CCOCOC)[C@@H](CC=C(CCC=C(C)C)/C)C Chemical compound C[C@@H](CCOCOC)[C@@H](CC=C(CCC=C(C)C)/C)C XIFWHIKDTORZQI-MSOLQXFVSA-N 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 239000005792 Geraniol Substances 0.000 description 1
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 102000003960 Ligases Human genes 0.000 description 1
- 108090000364 Ligases Proteins 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 102000004160 Phosphoric Monoester Hydrolases Human genes 0.000 description 1
- 108090000608 Phosphoric Monoester Hydrolases Proteins 0.000 description 1
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 1
- 101100237842 Xenopus laevis mmp18 gene Proteins 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- UZBQIPPOMKBLAS-UHFFFAOYSA-N diethylazanide Chemical compound CC[N-]CC UZBQIPPOMKBLAS-UHFFFAOYSA-N 0.000 description 1
- NKDDWNXOKDWJAK-UHFFFAOYSA-N dimethoxymethane Chemical compound COCOC NKDDWNXOKDWJAK-UHFFFAOYSA-N 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- WZUCXIJQIPPYKF-UHFFFAOYSA-N dodeca-2,6-diene Chemical compound CCCCCC=CCCC=CC WZUCXIJQIPPYKF-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229940113087 geraniol Drugs 0.000 description 1
- FFOWJDCTFSWUMJ-JXMROGBWSA-N geranyl phosphate Chemical compound CC(C)=CCC\C(C)=C\COP(O)(O)=O FFOWJDCTFSWUMJ-JXMROGBWSA-N 0.000 description 1
- 230000003054 hormonal effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229930014550 juvenile hormone Natural products 0.000 description 1
- 239000002949 juvenile hormone Substances 0.000 description 1
- 150000003633 juvenile hormone derivatives Chemical class 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000005905 mesyloxy group Chemical group 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000026731 phosphorylation Effects 0.000 description 1
- 238000006366 phosphorylation reaction Methods 0.000 description 1
- 235000015277 pork Nutrition 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
- PGPCCNUVFLQKFX-UHFFFAOYSA-N trideca-7,11-dienyl methanesulfonate Chemical compound S(=O)(=O)(C)OCCCCCCC=CCCC=CC PGPCCNUVFLQKFX-UHFFFAOYSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D309/30—Oxygen atoms, e.g. delta-lactones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
- C07C45/292—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with chromium derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/20—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms
- C07C47/21—Unsaturated compounds having —CHO groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyrane Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU861526A HU195178B (en) | 1986-04-11 | 1986-04-11 | Process for producing (+)-13-norfaranal of tracer activity for monomorium pharaonis |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE1001613A4 true BE1001613A4 (fr) | 1989-12-19 |
Family
ID=10954878
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE8700383A BE1001613A4 (fr) | 1986-04-11 | 1987-04-10 | Procede pour la preparation du (+)-13-norfaranal. |
Country Status (11)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8097746B2 (en) | 2005-04-05 | 2012-01-17 | Kuraray Co., Ltd. | Method for producing 2-isopropenyl-5-methyl-4-hexen-1-yl 3-methyl-2-butenoate |
| CN102159530A (zh) * | 2008-09-22 | 2011-08-17 | 宝洁公司 | 特殊的多支链多元醛、多元醇和表面活性剂以及基于它们的消费品 |
-
1986
- 1986-04-11 HU HU861526A patent/HU195178B/hu not_active IP Right Cessation
-
1987
- 1987-04-09 CH CH1367/87A patent/CH671013A5/de not_active IP Right Cessation
- 1987-04-10 BE BE8700383A patent/BE1001613A4/fr not_active IP Right Cessation
- 1987-04-10 IT IT20078/87A patent/IT1203879B/it active
- 1987-04-10 SU SU874202347A patent/SU1533625A3/ru active
- 1987-04-10 GB GB8708603A patent/GB2189244B/en not_active Expired
- 1987-04-10 NL NL8700847A patent/NL8700847A/nl not_active Application Discontinuation
- 1987-04-10 FR FR8705145A patent/FR2597094A1/fr active Pending
- 1987-04-10 ES ES8701045A patent/ES2004598A6/es not_active Expired
- 1987-04-11 JP JP62087938A patent/JPS62249943A/ja active Granted
- 1987-04-13 DE DE19873712528 patent/DE3712528A1/de not_active Withdrawn
Non-Patent Citations (2)
| Title |
|---|
| NATURWISSENSCHAFTEN, vol. 70, 1983, pages 469-470, Springer-Verlag; T. KOYAMA et al.: "Congeners of faranal and their trail pheromone activity" * |
| TETRAHEDRON LETTERS, vol. 27, no. 47, 1986, pages 5769-5772, Pergamon Journals Ltd, GB; L. POPPE et al.: "A convenient synthetic route to (+)-faranal: the trail pheromone of Pharaoh's ant" * |
Also Published As
| Publication number | Publication date |
|---|---|
| GB8708603D0 (en) | 1987-05-13 |
| HUT43313A (en) | 1987-10-28 |
| IT1203879B (it) | 1989-02-23 |
| GB2189244B (en) | 1989-11-22 |
| FR2597094A1 (fr) | 1987-10-16 |
| ES2004598A6 (es) | 1989-01-16 |
| GB2189244A (en) | 1987-10-21 |
| DE3712528A1 (de) | 1987-10-15 |
| SU1533625A3 (ru) | 1989-12-30 |
| HU195178B (en) | 1988-04-28 |
| CH671013A5 (enrdf_load_stackoverflow) | 1989-07-31 |
| IT8720078A0 (it) | 1987-04-10 |
| NL8700847A (nl) | 1987-11-02 |
| JPS62249943A (ja) | 1987-10-30 |
| JPH0533930B2 (enrdf_load_stackoverflow) | 1993-05-20 |
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Owner name: EGIS GYOGYSZERGYAR Effective date: 19900430 |