JPH058689B2 - - Google Patents
Info
- Publication number
- JPH058689B2 JPH058689B2 JP59242209A JP24220984A JPH058689B2 JP H058689 B2 JPH058689 B2 JP H058689B2 JP 59242209 A JP59242209 A JP 59242209A JP 24220984 A JP24220984 A JP 24220984A JP H058689 B2 JPH058689 B2 JP H058689B2
- Authority
- JP
- Japan
- Prior art keywords
- carbon atoms
- group
- formula
- aliphatic group
- saturated aliphatic
- 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 - Lifetime
Links
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 30
- 125000001931 aliphatic group Chemical group 0.000 claims description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims description 12
- 125000004185 ester group Chemical class 0.000 claims description 10
- 125000004036 acetal group Chemical class 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 150000002170 ethers Chemical class 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 8
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 6
- 239000003446 ligand Substances 0.000 claims 4
- 229910052763 palladium Inorganic materials 0.000 claims 4
- 239000003054 catalyst Substances 0.000 claims 3
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims 1
- 229910052787 antimony Inorganic materials 0.000 claims 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 claims 1
- 229910000074 antimony hydride Inorganic materials 0.000 claims 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims 1
- RBFQJDQYXXHULB-UHFFFAOYSA-N arsane Chemical compound [AsH3] RBFQJDQYXXHULB-UHFFFAOYSA-N 0.000 claims 1
- 229910052785 arsenic Inorganic materials 0.000 claims 1
- RQNWIZPPADIBDY-UHFFFAOYSA-N arsenic atom Chemical compound [As] RQNWIZPPADIBDY-UHFFFAOYSA-N 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- -1 methanesulfonyloxy, phenylsulfonyloxy, p-toluenesulfonyloxy Chemical group 0.000 claims 1
- 150000002940 palladium Chemical class 0.000 claims 1
- 150000003017 phosphorus Chemical class 0.000 claims 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 1
- 239000003880 polar aprotic solvent Substances 0.000 claims 1
- OUULRIDHGPHMNQ-UHFFFAOYSA-N stibane Chemical compound [SbH3] OUULRIDHGPHMNQ-UHFFFAOYSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 235000019165 vitamin E Nutrition 0.000 abstract description 2
- 239000011709 vitamin E Substances 0.000 abstract description 2
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 abstract 2
- 229920006395 saturated elastomer Polymers 0.000 abstract 2
- 229930003427 Vitamin E Natural products 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 abstract 1
- 229940046009 vitamin E Drugs 0.000 abstract 1
- 238000001819 mass spectrum Methods 0.000 description 10
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 8
- 238000002329 infrared spectrum Methods 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/185—Saturated compounds having only one carboxyl group and containing keto groups
-
- 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
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8318392A FR2555170B1 (fr) | 1983-11-18 | 1983-11-18 | Nouveaux derives insatures, leur preparation et leur emploi |
| FR8318392 | 1983-11-18 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60116640A JPS60116640A (ja) | 1985-06-24 |
| JPH058689B2 true JPH058689B2 (https=) | 1993-02-02 |
Family
ID=9294282
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59242209A Granted JPS60116640A (ja) | 1983-11-18 | 1984-11-16 | 新規な不飽和化合物類およびそれらの製造 |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US4615838A (https=) |
| EP (1) | EP0145555B1 (https=) |
| JP (1) | JPS60116640A (https=) |
| AT (1) | ATE23147T1 (https=) |
| CA (1) | CA1250312A (https=) |
| DE (1) | DE3461079D1 (https=) |
| FR (1) | FR2555170B1 (https=) |
| RU (1) | RU2017720C1 (https=) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2034261A1 (en) * | 1990-01-17 | 1991-07-18 | Mitsubishi Chemical Corporation | Acyclic terpenes |
| US5298655A (en) * | 1991-09-27 | 1994-03-29 | Merck & Co., Inc. | Farnesyl pyrophosphate analogs |
| US5574025A (en) * | 1994-10-26 | 1996-11-12 | Merck & Co., Inc. | Inhibitors of prenyl-protein transferases |
| EP1327620A1 (en) * | 2002-01-14 | 2003-07-16 | Aventis Animal Nutrition S.A. | Process for the preparation of phytone |
| US20100121057A1 (en) * | 2007-04-17 | 2010-05-13 | Merck Serono Sa | Process for the Preparation of Piperazine Benzothiazoles |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1008729B (de) * | 1955-06-02 | 1957-05-23 | Basf Ag | Verfahren zur Herstellung von konjugiert-ungesaettigten Oxocarbonsaeureestern |
| US3032491A (en) * | 1958-07-23 | 1962-05-01 | Polaroid Corp | Irradiation of cyclohexadienones |
| US3781313A (en) * | 1971-01-20 | 1973-12-25 | Rhone Poulenc Sa | Sulfone intermediates for the synthesis of vitamin a |
| US4016178A (en) * | 1975-06-17 | 1977-04-05 | Hoffmann-La Roche Inc. | Synthesis of vitamin E |
| JPS601283B2 (ja) * | 1976-06-08 | 1985-01-14 | 帝人株式会社 | 包接化合物並びにその製造法 |
| US4221742A (en) * | 1977-12-29 | 1980-09-09 | Scm Corporation | Coupling reaction involving a Grignard and allylic halide |
| DE3013672A1 (de) * | 1980-04-09 | 1981-10-15 | Consortium für elektrochemische Industrie GmbH, 8000 München | 2,4-dialkyl-2.6-heptadienal-derivate, verfahren zu deren herstellung und ihre anwendung als geruchs- und geschmacksstoffe |
| US4564477A (en) * | 1982-02-19 | 1986-01-14 | Kuraray Co., Ltd. | Polyprenyl compounds and method of producing the same |
-
1983
- 1983-11-18 FR FR8318392A patent/FR2555170B1/fr not_active Expired
-
1984
- 1984-11-13 DE DE8484402298T patent/DE3461079D1/de not_active Expired
- 1984-11-13 AT AT84402298T patent/ATE23147T1/de not_active IP Right Cessation
- 1984-11-13 EP EP84402298A patent/EP0145555B1/fr not_active Expired
- 1984-11-15 CA CA000467918A patent/CA1250312A/fr not_active Expired
- 1984-11-16 JP JP59242209A patent/JPS60116640A/ja active Granted
- 1984-11-16 RU SU843813106A patent/RU2017720C1/ru active
- 1984-11-16 US US06/671,963 patent/US4615838A/en not_active Expired - Fee Related
-
1985
- 1985-09-13 US US06/775,835 patent/US4693849A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0145555B1 (fr) | 1986-10-29 |
| JPS60116640A (ja) | 1985-06-24 |
| CA1250312A (fr) | 1989-02-21 |
| FR2555170B1 (fr) | 1986-07-18 |
| DE3461079D1 (en) | 1986-12-04 |
| RU2017720C1 (ru) | 1994-08-15 |
| US4693849A (en) | 1987-09-15 |
| ATE23147T1 (de) | 1986-11-15 |
| FR2555170A1 (fr) | 1985-05-24 |
| US4615838A (en) | 1986-10-07 |
| EP0145555A3 (en) | 1985-08-07 |
| EP0145555A2 (fr) | 1985-06-19 |
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