JPS5942658B2 - シクロペンテン誘導体 - Google Patents
シクロペンテン誘導体Info
- Publication number
- JPS5942658B2 JPS5942658B2 JP51033676A JP3367676A JPS5942658B2 JP S5942658 B2 JPS5942658 B2 JP S5942658B2 JP 51033676 A JP51033676 A JP 51033676A JP 3367676 A JP3367676 A JP 3367676A JP S5942658 B2 JPS5942658 B2 JP S5942658B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- atom
- compound
- tables
- cyclopentene derivative
- 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.)
- Expired
Links
- 125000002433 cyclopentenyl group Chemical class C1(=CCCC1)* 0.000 title claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 239000012320 chlorinating reagent Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 150000001804 chlorine Chemical class 0.000 description 4
- 230000002140 halogenating effect Effects 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000003205 fragrance Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000039 hydrogen halide Inorganic materials 0.000 description 3
- 239000012433 hydrogen halide Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000012459 cleaning agent Substances 0.000 description 2
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- 150000001941 cyclopentenes Chemical class 0.000 description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 2
- 239000012336 iodinating agent Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000001371 (5E)-3,5-dimethylocta-1,5,7-trien-3-ol Substances 0.000 description 1
- OJRUSAPKCPIVBY-KQYNXXCUSA-N C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N Chemical compound C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N OJRUSAPKCPIVBY-KQYNXXCUSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003172 aldehyde group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125758 compound 15 Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 229940076286 cupric acetate Drugs 0.000 description 1
- 229940045803 cuprous chloride Drugs 0.000 description 1
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 1
- ZJIQIJIQBTVTDY-SREVYHEPSA-N dehydrolinalool Chemical compound CC(=C)\C=C/CC(C)(O)C=C ZJIQIJIQBTVTDY-SREVYHEPSA-N 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 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
- 150000004820 halides Chemical class 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229910000043 hydrogen iodide Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C22/00—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom
- C07C22/02—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom having unsaturation in the rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2513995A DE2513995C2 (de) | 1975-03-29 | 1975-03-29 | Cyclopentenderivate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS51131854A JPS51131854A (en) | 1976-11-16 |
| JPS5942658B2 true JPS5942658B2 (ja) | 1984-10-16 |
Family
ID=5942718
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51033676A Expired JPS5942658B2 (ja) | 1975-03-29 | 1976-03-29 | シクロペンテン誘導体 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4038330A (enExample) |
| JP (1) | JPS5942658B2 (enExample) |
| CH (1) | CH620184A5 (enExample) |
| DE (1) | DE2513995C2 (enExample) |
| FR (1) | FR2306184A1 (enExample) |
| GB (1) | GB1532091A (enExample) |
| NL (1) | NL7603220A (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT360401B (de) * | 1978-09-05 | 1980-01-12 | Tyrolia Freizeitgeraete | Skibindung |
| US4686310A (en) * | 1985-02-06 | 1987-08-11 | International Flavors & Fragrances Inc. | 2-isopropenyl-5-methylcyclopentanealkanols derivatives and organoleptic uses or same |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2721160A (en) * | 1951-05-21 | 1955-10-18 | Pennsylvania Salt Mfg Co | Pesticidal compositions and their use |
| CH565728A5 (enExample) * | 1972-03-17 | 1975-08-29 | Givaudan & Cie Sa |
-
1975
- 1975-03-29 DE DE2513995A patent/DE2513995C2/de not_active Expired
-
1976
- 1976-03-08 US US05/665,064 patent/US4038330A/en not_active Expired - Lifetime
- 1976-03-23 FR FR7608345A patent/FR2306184A1/fr active Granted
- 1976-03-24 CH CH368276A patent/CH620184A5/de not_active IP Right Cessation
- 1976-03-26 GB GB12201/76A patent/GB1532091A/en not_active Expired
- 1976-03-26 NL NL7603220A patent/NL7603220A/xx not_active Application Discontinuation
- 1976-03-29 JP JP51033676A patent/JPS5942658B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2306184A1 (fr) | 1976-10-29 |
| DE2513995C2 (de) | 1984-04-12 |
| NL7603220A (nl) | 1976-10-01 |
| US4038330A (en) | 1977-07-26 |
| JPS51131854A (en) | 1976-11-16 |
| GB1532091A (en) | 1978-11-15 |
| DE2513995A1 (de) | 1976-10-07 |
| CH620184A5 (enExample) | 1980-11-14 |
| FR2306184B1 (enExample) | 1979-01-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH02125A (ja) | フルオル置換ベンジルアルコール | |
| Ortiz et al. | Silver (II) oxide as a reagent. Reactions with aromatic amines and miscellaneous related compounds | |
| EP0405427B1 (fr) | Nouveaux composés aromatiques, leur procédé de préparation et leur utilisation à titre d'ingrédients parfumants | |
| US4097531A (en) | Substituted cyclopropane process and product | |
| JPS5942658B2 (ja) | シクロペンテン誘導体 | |
| JP2837210B2 (ja) | 香料組成物又は賦香製品の芳香特性を授与、促進、改良又は変更する方法、香料組成物、賦香製品、脂環式エステル及びその製法 | |
| JPH03184938A (ja) | エチレン性ケトンの製造方法 | |
| JP2000219651A (ja) | 新規なテトラヒドロナフタレン | |
| Sardessai et al. | THE BROMINATION OF 2, 5-DIMETHOXYBENZALDEHYDE. STRUCTURAL PROOF OF THE 6-BROMO ISOMER via 3, 6-DIMETHOXYBENZOCYCLOBUTENE | |
| Kugatova-Shemyakina et al. | The stereochemistry and reactivity of unsaturated compounds—III: Reactivity of the double bond in Δ30cyclohexene and Δ4-octalin derivatives relative to their conformations | |
| Jonczyk et al. | Convenient synthesis of t-butyl Z-3-substituted glycidates under conditions of phase-transfer catalysis | |
| Kashima et al. | The reaction of 3, 5-dimethylisoxazole with carbonyl compounds. | |
| JP2630470B2 (ja) | ２―シクロヘキシルプロピルアセテートを含有する香料組成物 | |
| JPH05286902A (ja) | α−クロロ−β−ケトエステル誘導体の製造方法 | |
| JPS6313975B2 (enExample) | ||
| EP0102066A1 (en) | Process for preparing 2-cyclopentenone esters | |
| JPH0131495B2 (enExample) | ||
| US2665297A (en) | Process of producing organic unsaturated nitriles | |
| US2750397A (en) | Production of halogenated polycyclic alcohols | |
| JPS6159286B2 (enExample) | ||
| JPH05229981A (ja) | 芳香族アセトアルデヒドの製造方法 | |
| US3953520A (en) | Chemical compounds and processes | |
| JPS6310934B2 (enExample) | ||
| JPH046697B2 (enExample) | ||
| Rogovik et al. | Fluoroaliphatic esters of fluorosulfonic acid. 5. Conjugate radical fluorosulfatohalogenation of higher fluoroolefins |