CA2424225C - Phosphines tertiaires et leurs methodes de preparation - Google Patents
Phosphines tertiaires et leurs methodes de preparation Download PDFInfo
- Publication number
- CA2424225C CA2424225C CA 2424225 CA2424225A CA2424225C CA 2424225 C CA2424225 C CA 2424225C CA 2424225 CA2424225 CA 2424225 CA 2424225 A CA2424225 A CA 2424225A CA 2424225 C CA2424225 C CA 2424225C
- Authority
- CA
- Canada
- Prior art keywords
- unsubstituted
- compound
- substituted
- heteroatoms
- phosphabicyclo
- 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
- 238000000034 method Methods 0.000 title claims description 25
- 150000003003 phosphines Chemical group 0.000 title description 21
- 238000002360 preparation method Methods 0.000 title description 12
- 239000003054 catalyst Substances 0.000 claims abstract description 20
- 239000003446 ligand Substances 0.000 claims abstract description 12
- 150000001728 carbonyl compounds Chemical class 0.000 claims abstract description 11
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 10
- 229910052751 metal Inorganic materials 0.000 claims abstract description 7
- 239000002184 metal Substances 0.000 claims abstract description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 42
- 150000001875 compounds Chemical class 0.000 claims description 40
- -1 3-oxo-cyclopentyl Chemical group 0.000 claims description 21
- 125000004437 phosphorous atom Chemical group 0.000 claims description 18
- 229910052698 phosphorus Inorganic materials 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical compound O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 claims description 7
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000000923 (C1-C30) alkyl group Chemical group 0.000 claims description 5
- VBKOPLXNMXIFAO-UHFFFAOYSA-N 3-(9-phosphabicyclo[3.3.1]nonan-9-yl)cyclohexan-1-one Chemical compound C1C(=O)CCCC1P1C2CCCC1CCC2 VBKOPLXNMXIFAO-UHFFFAOYSA-N 0.000 claims description 5
- BZKFMUIJRXWWQK-UHFFFAOYSA-N Cyclopentenone Chemical compound O=C1CCC=C1 BZKFMUIJRXWWQK-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 5
- 125000004475 heteroaralkyl group Chemical group 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 4
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 claims description 4
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims description 4
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 3
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical group [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229910052707 ruthenium Inorganic materials 0.000 claims description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
- NVWNUCAKKNRYLY-UHFFFAOYSA-N 3-[bis(2-methylpropyl)phosphanyl]cyclohexan-1-one Chemical compound CC(C)CP(CC(C)C)C1CCCC(=O)C1 NVWNUCAKKNRYLY-UHFFFAOYSA-N 0.000 claims description 2
- QOTKBUMPAOPTGK-UHFFFAOYSA-N 3-[cyclohexyl-(3-oxocyclohexyl)phosphanyl]cyclohexan-1-one Chemical compound C1C(=O)CCCC1P(C1CC(=O)CCC1)C1CCCCC1 QOTKBUMPAOPTGK-UHFFFAOYSA-N 0.000 claims description 2
- AZHWSDQJWRSYKE-UHFFFAOYSA-N 3-dicyclohexylphosphanylcyclohexan-1-one Chemical compound C1C(=O)CCCC1P(C1CCCCC1)C1CCCCC1 AZHWSDQJWRSYKE-UHFFFAOYSA-N 0.000 claims description 2
- QJCMAJXWIAFFED-UHFFFAOYSA-N 9-phosphabicyclo[3.3.1]nonane Chemical compound C1CCC2CCCC1P2 QJCMAJXWIAFFED-UHFFFAOYSA-N 0.000 claims description 2
- RTWRUXIOIPQRRE-UHFFFAOYSA-N 9-phosphabicyclo[4.2.1]nonane Chemical compound C1CCCC2CCC1P2 RTWRUXIOIPQRRE-UHFFFAOYSA-N 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 4
- 150000002431 hydrogen Chemical group 0.000 claims 2
- PIMCCWAFWVLTFJ-UHFFFAOYSA-N 9-phosphabicyclo[3.3.1]nonan-4-one Chemical compound C1CCC2C(=O)CCC1P2 PIMCCWAFWVLTFJ-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 abstract description 51
- 229910000073 phosphorus hydride Inorganic materials 0.000 abstract description 26
- 239000007858 starting material Substances 0.000 abstract description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract description 6
- 150000004714 phosphonium salts Chemical class 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 description 27
- 229910052757 nitrogen Inorganic materials 0.000 description 19
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 125000001424 substituent group Chemical group 0.000 description 12
- 125000001183 hydrocarbyl group Chemical group 0.000 description 11
- 150000003254 radicals Chemical class 0.000 description 10
- 239000000047 product Substances 0.000 description 9
- 238000007792 addition Methods 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000009835 boiling Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 125000000753 cycloalkyl group Chemical group 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 238000007341 Heck reaction Methods 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 238000006069 Suzuki reaction reaction Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000005865 alkene metathesis reaction Methods 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- HDULBKVLSJEMGN-UHFFFAOYSA-N dicyclohexylphosphane Chemical compound C1CCCCC1PC1CCCCC1 HDULBKVLSJEMGN-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 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 2
- 238000010926 purge Methods 0.000 description 2
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 2
- DCSCXTJOXBUFGB-JGVFFNPUSA-N (R)-(+)-Verbenone Natural products CC1=CC(=O)[C@@H]2C(C)(C)[C@H]1C2 DCSCXTJOXBUFGB-JGVFFNPUSA-N 0.000 description 1
- DCSCXTJOXBUFGB-SFYZADRCSA-N (R)-(+)-verbenone Chemical compound CC1=CC(=O)[C@H]2C(C)(C)[C@@H]1C2 DCSCXTJOXBUFGB-SFYZADRCSA-N 0.000 description 1
- WPGPCDVQHXOMQP-UHFFFAOYSA-N (r)-carvotanacetone Chemical compound CC(C)C1CC=C(C)C(=O)C1 WPGPCDVQHXOMQP-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- REHMYGKLHCUEHZ-UHFFFAOYSA-N 2-[bis(2-methylpropyl)phosphanyl]cyclohexan-1-one Chemical compound CC(C)CP(CC(C)C)C1CCCCC1=O REHMYGKLHCUEHZ-UHFFFAOYSA-N 0.000 description 1
- RQAXPYMCBYIMAG-UHFFFAOYSA-N 2-dicyclohexylphosphanylcyclohexan-1-one Chemical compound O=C1CCCCC1P(C1CCCCC1)C1CCCCC1 RQAXPYMCBYIMAG-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-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
- FSNTUMYJRNVIAU-UHFFFAOYSA-N 3-[cyclohexyl-(3-oxocyclohexyl)phosphanyl]cyclohexan-1-one cyclohexylphosphane Chemical compound C1(CCCCC1)P.C1(CC(CCC1)P(C1CCCCC1)C1CC(CCC1)=O)=O FSNTUMYJRNVIAU-UHFFFAOYSA-N 0.000 description 1
- 238000004679 31P NMR spectroscopy Methods 0.000 description 1
- FDPJLUXFPVJWEV-UHFFFAOYSA-N 9-phosphabicyclo[3.3.1]nonan-3-one Chemical compound C1CCC2CC(=O)CC1P2 FDPJLUXFPVJWEV-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 238000007355 Double Michael addition reaction Methods 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- PNPBGYBHLCEVMK-UHFFFAOYSA-N benzylidene(dichloro)ruthenium;tricyclohexylphosphanium Chemical compound Cl[Ru](Cl)=CC1=CC=CC=C1.C1CCCCC1[PH+](C1CCCCC1)C1CCCCC1.C1CCCCC1[PH+](C1CCCCC1)C1CCCCC1 PNPBGYBHLCEVMK-UHFFFAOYSA-N 0.000 description 1
- LREAZWJEBORMTB-UHFFFAOYSA-N bis(2-methylpropyl)phosphane Chemical compound CC(C)CPCC(C)C LREAZWJEBORMTB-UHFFFAOYSA-N 0.000 description 1
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000006315 carbonylation Effects 0.000 description 1
- 238000005810 carbonylation reaction Methods 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- ULDHMXUKGWMISQ-UHFFFAOYSA-N carvone Chemical compound CC(=C)C1CC=C(C)C(=O)C1 ULDHMXUKGWMISQ-UHFFFAOYSA-N 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- DYBHXFFCBKDNBD-UHFFFAOYSA-N cyclohex-2-en-1-one 3-(9-phosphabicyclo[3.3.1]nonan-9-yl)cyclohexan-1-one Chemical compound C1(C=CCCC1)=O.C12CCCC(CCC1)P2C2CC(CCC2)=O DYBHXFFCBKDNBD-UHFFFAOYSA-N 0.000 description 1
- ZBCKWHYWPLHBOK-UHFFFAOYSA-N cyclohexylphosphane Chemical compound PC1CCCCC1 ZBCKWHYWPLHBOK-UHFFFAOYSA-N 0.000 description 1
- NSHQAIKRVDXIMX-UHFFFAOYSA-N cyclooct-2-en-1-one Chemical compound O=C1CCCCCC=C1 NSHQAIKRVDXIMX-UHFFFAOYSA-N 0.000 description 1
- VZZJVOCVAZHETD-UHFFFAOYSA-N diethylphosphane Chemical compound CCPCC VZZJVOCVAZHETD-UHFFFAOYSA-N 0.000 description 1
- YOTZYFSGUCFUKA-UHFFFAOYSA-N dimethylphosphine Chemical compound CPC YOTZYFSGUCFUKA-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- JLHMVTORNNQCRM-UHFFFAOYSA-N ethylphosphine Chemical compound CCP JLHMVTORNNQCRM-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 239000011984 grubbs catalyst Substances 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000007037 hydroformylation reaction Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- SAWKFRBJGLMMES-UHFFFAOYSA-N methylphosphine Chemical compound PC SAWKFRBJGLMMES-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000001421 myristyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 description 1
- 150000002900 organolithium compounds Chemical class 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 238000001394 phosphorus-31 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- 229940093635 tributyl phosphate Drugs 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- CGRJOQDFNTYSGH-UHFFFAOYSA-N tritylphosphane Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(P)C1=CC=CC=C1 CGRJOQDFNTYSGH-UHFFFAOYSA-N 0.000 description 1
- DCSCXTJOXBUFGB-UHFFFAOYSA-N verbenone Natural products CC1=CC(=O)C2C(C)(C)C1C2 DCSCXTJOXBUFGB-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6568—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms
- C07F9/65683—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms the ring phosphorus atom being part of a phosphine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/5018—Cycloaliphatic phosphines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/505—Preparation; Separation; Purification; Stabilisation
- C07F9/5059—Preparation; Separation; Purification; Stabilisation by addition of phosphorus compounds to alkenes or alkynes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Des phosphines tertiaires sont préparées en faisant réagir une phosphine (PH3 ou phosphine primaire ou secondaire) avec un composé carbonylé cyclique alpha, bêta-insaturé comptant au plus une liaison double C=C conjuguée avec le groupement carbonyle. Les phosphines tertiaires visées par l'invention peuvent avoir des groupements R semblables ou différents entre eux. Les phosphines tertiaires visées par l'invention peuvent être utilisées comme ligands dans les catalyseurs métalliques ou comme produits de départ dans la préparation de sels ou d'ylures de phosphonium.
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA 2424225 CA2424225C (fr) | 2003-03-31 | 2003-03-31 | Phosphines tertiaires et leurs methodes de preparation |
| KR1020057018471A KR101075727B1 (ko) | 2003-03-31 | 2004-03-08 | 3차 포스핀과 그 제조 방법 |
| BRPI0408796-8A BRPI0408796A (pt) | 2003-03-31 | 2004-03-08 | composto, método para produzir composto, e, uso de composto |
| CNB2004800081840A CN100567313C (zh) | 2003-03-31 | 2004-03-08 | 叔膦及其制备方法 |
| EP04718546.7A EP1608668B1 (fr) | 2003-03-31 | 2004-03-08 | Phosphines tertiaires et leurs procédés de préparation |
| US10/548,777 US7608713B2 (en) | 2003-03-31 | 2004-03-08 | Tertiary phosphines and their methods of preparation |
| PCT/US2004/007031 WO2004094440A2 (fr) | 2003-03-31 | 2004-03-08 | Phosphines tertiaires et leurs procedes de preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA 2424225 CA2424225C (fr) | 2003-03-31 | 2003-03-31 | Phosphines tertiaires et leurs methodes de preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2424225A1 CA2424225A1 (fr) | 2004-09-30 |
| CA2424225C true CA2424225C (fr) | 2008-08-05 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2424225 Expired - Lifetime CA2424225C (fr) | 2003-03-31 | 2003-03-31 | Phosphines tertiaires et leurs methodes de preparation |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7608713B2 (fr) |
| EP (1) | EP1608668B1 (fr) |
| KR (1) | KR101075727B1 (fr) |
| CN (1) | CN100567313C (fr) |
| BR (1) | BRPI0408796A (fr) |
| CA (1) | CA2424225C (fr) |
| WO (1) | WO2004094440A2 (fr) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2231683B1 (fr) | 2008-01-15 | 2016-03-23 | Dow Global Technologies LLC | Composés d'organophosphine sulfonée et leur utilisation dans des procédés d'hydroformylation |
| US8466306B2 (en) | 2008-01-15 | 2013-06-18 | Dow Global Technologies Llc | Sulfonated organophosphine compounds and use in hydroformylation processes |
| BRPI0905699A2 (pt) | 2008-01-15 | 2015-07-14 | Dow Global Technologies Inc | Composição, catalisador complexo ou composição de precursor de catalisador complexo, solução de catalisador complexo ou solução de percursor de catalisador complexo e processo de hidroformilação |
| US7767862B2 (en) | 2008-08-11 | 2010-08-03 | Shell Oil Company | Ligand, catalyst and process for hydroformylation |
| WO2012072594A1 (fr) | 2010-11-30 | 2012-06-07 | Shell Internationale Research Maatschappij B.V. | Ligand, catalyseur et procédé d'hydroformylation |
| EP3539924A1 (fr) | 2018-03-14 | 2019-09-18 | ETH Zurich | Nouvelles phosphines vinyliques et photo-initiateurs obtenus à partir de celles-ci |
| CN113666961B (zh) * | 2020-05-15 | 2023-05-16 | 湖北大学 | 一种间位取代联芳基型叔膦配体的制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8431551D0 (en) * | 1984-12-13 | 1985-01-23 | Shell Int Research | Tertiary phosphines |
| DE10106348A1 (de) | 2001-02-09 | 2002-08-14 | Basf Ag | Als Katalysator oder zur Herstellung eines Katalysatorsystems geeignete Verbindung |
-
2003
- 2003-03-31 CA CA 2424225 patent/CA2424225C/fr not_active Expired - Lifetime
-
2004
- 2004-03-08 KR KR1020057018471A patent/KR101075727B1/ko active IP Right Grant
- 2004-03-08 BR BRPI0408796-8A patent/BRPI0408796A/pt not_active Application Discontinuation
- 2004-03-08 CN CNB2004800081840A patent/CN100567313C/zh not_active Expired - Fee Related
- 2004-03-08 US US10/548,777 patent/US7608713B2/en not_active Expired - Fee Related
- 2004-03-08 EP EP04718546.7A patent/EP1608668B1/fr not_active Expired - Lifetime
- 2004-03-08 WO PCT/US2004/007031 patent/WO2004094440A2/fr active Application Filing
Also Published As
| Publication number | Publication date |
|---|---|
| CA2424225A1 (fr) | 2004-09-30 |
| KR20050123130A (ko) | 2005-12-29 |
| US7608713B2 (en) | 2009-10-27 |
| EP1608668A2 (fr) | 2005-12-28 |
| EP1608668B1 (fr) | 2018-02-28 |
| US20070037981A1 (en) | 2007-02-15 |
| WO2004094440A2 (fr) | 2004-11-04 |
| KR101075727B1 (ko) | 2011-10-21 |
| BRPI0408796A (pt) | 2006-03-28 |
| CN100567313C (zh) | 2009-12-09 |
| CN1764667A (zh) | 2006-04-26 |
| WO2004094440A3 (fr) | 2005-04-14 |
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