KR20080103961A - 유기금속 루테늄 착물, 및 사치환 및 기타 입체장애된올레핀의 제조를 위한 관련 방법 - Google Patents
유기금속 루테늄 착물, 및 사치환 및 기타 입체장애된올레핀의 제조를 위한 관련 방법 Download PDFInfo
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- KR20080103961A KR20080103961A KR1020087017250A KR20087017250A KR20080103961A KR 20080103961 A KR20080103961 A KR 20080103961A KR 1020087017250 A KR1020087017250 A KR 1020087017250A KR 20087017250 A KR20087017250 A KR 20087017250A KR 20080103961 A KR20080103961 A KR 20080103961A
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- South Korea
- Prior art keywords
- substituted
- unsubstituted
- nhc
- catalyst
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- Prior art date
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- -1 Organometallic ruthenium complexes Chemical class 0.000 title claims abstract description 82
- 150000001336 alkenes Chemical class 0.000 title claims description 37
- 238000000034 method Methods 0.000 title claims description 34
- 238000002360 preparation method Methods 0.000 title abstract description 32
- ADLVDYMTBOSDFE-UHFFFAOYSA-N 5-chloro-6-nitroisoindole-1,3-dione Chemical compound C1=C(Cl)C([N+](=O)[O-])=CC2=C1C(=O)NC2=O ADLVDYMTBOSDFE-UHFFFAOYSA-N 0.000 claims abstract description 103
- 239000003446 ligand Substances 0.000 claims abstract description 93
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 57
- 238000006798 ring closing metathesis reaction Methods 0.000 claims abstract description 42
- 238000005865 alkene metathesis reaction Methods 0.000 claims abstract description 41
- 229910052707 ruthenium Inorganic materials 0.000 claims abstract description 41
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 22
- 239000001257 hydrogen Substances 0.000 claims abstract description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 16
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 12
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims abstract description 8
- 239000003054 catalyst Substances 0.000 claims description 201
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 38
- 238000005649 metathesis reaction Methods 0.000 claims description 37
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 33
- 125000003118 aryl group Chemical group 0.000 claims description 31
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 29
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 23
- 238000005686 cross metathesis reaction Methods 0.000 claims description 20
- 125000005842 heteroatom Chemical group 0.000 claims description 20
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 125000000743 hydrocarbylene group Chemical group 0.000 claims description 16
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 claims description 16
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 15
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 12
- 125000001624 naphthyl group Chemical group 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 150000004820 halides Chemical class 0.000 claims description 11
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 claims description 11
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- 125000000524 functional group Chemical group 0.000 claims description 8
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 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 7
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 150000002390 heteroarenes Chemical class 0.000 claims description 6
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 230000007935 neutral effect Effects 0.000 claims description 6
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 150000007942 carboxylates Chemical class 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
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000000129 anionic group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 125000002837 carbocyclic group Chemical group 0.000 claims description 3
- 150000002466 imines Chemical class 0.000 claims description 3
- 150000003003 phosphines Chemical class 0.000 claims description 3
- 238000006467 substitution reaction Methods 0.000 claims description 3
- 150000003568 thioethers Chemical class 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 2
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical group O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 claims description 2
- RBFQJDQYXXHULB-UHFFFAOYSA-N arsane Chemical compound [AsH3] RBFQJDQYXXHULB-UHFFFAOYSA-N 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000005538 phosphinite group Chemical group 0.000 claims description 2
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 claims description 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 2
- 150000003462 sulfoxides Chemical class 0.000 claims description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 2
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims 1
- 125000000707 boryl group Chemical group B* 0.000 claims 1
- 235000013557 nattō Nutrition 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 2
- 238000006243 chemical reaction Methods 0.000 description 105
- 239000007787 solid Substances 0.000 description 31
- 239000000243 solution Substances 0.000 description 24
- 239000002243 precursor Substances 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 20
- 239000011550 stock solution Substances 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 17
- 239000011541 reaction mixture Substances 0.000 description 15
- 239000000047 product Substances 0.000 description 14
- 239000000758 substrate Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 150000004985 diamines Chemical class 0.000 description 13
- 230000000694 effects Effects 0.000 description 13
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 12
- 229940125904 compound 1 Drugs 0.000 description 12
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 12
- 0 *c1ccccc1N(CC1)CN1c1ccccc1* Chemical compound *c1ccccc1N(CC1)CN1c1ccccc1* 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- 238000004440 column chromatography Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- 238000013480 data collection Methods 0.000 description 8
- 238000007363 ring formation reaction Methods 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- LXFXSRBNTGMCPR-UHFFFAOYSA-N n,n'-bis(2-ethylphenyl)oxamide Chemical compound CCC1=CC=CC=C1NC(=O)C(=O)NC1=CC=CC=C1CC LXFXSRBNTGMCPR-UHFFFAOYSA-N 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000003197 catalytic effect Effects 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 238000007429 general method Methods 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 229940015043 glyoxal Drugs 0.000 description 6
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 6
- 238000007152 ring opening metathesis polymerisation reaction Methods 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 5
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 5
- 150000001448 anilines Chemical class 0.000 description 5
- 238000006555 catalytic reaction Methods 0.000 description 5
- 229940125758 compound 15 Drugs 0.000 description 5
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical group 0.000 description 5
- 125000005394 methallyl group Chemical group 0.000 description 5
- MJKNHXCPGXUEDO-UHFFFAOYSA-N 3,5-ditert-butylaniline Chemical compound CC(C)(C)C1=CC(N)=CC(C(C)(C)C)=C1 MJKNHXCPGXUEDO-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 125000003342 alkenyl group Chemical group 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Substances ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- 235000019439 ethyl acetate Nutrition 0.000 description 4
- 238000003818 flash chromatography Methods 0.000 description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 4
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
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- 125000006850 spacer group Chemical group 0.000 description 4
- 241000894007 species Species 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 3
- YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical class NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 description 3
- 239000012327 Ruthenium complex Substances 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 229940126214 compound 3 Drugs 0.000 description 3
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 3
- 229940073769 methyl oleate Drugs 0.000 description 3
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- 239000011733 molybdenum Substances 0.000 description 3
- 125000002524 organometallic group Chemical group 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 150000003222 pyridines Chemical class 0.000 description 3
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- FYOKZZNUNQUQRW-UHFFFAOYSA-N CCOC(C1(CC(C)=C(C)C1)C(OCC)=O)=O Chemical compound CCOC(C1(CC(C)=C(C)C1)C(OCC)=O)=O FYOKZZNUNQUQRW-UHFFFAOYSA-N 0.000 description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- UURSXESKOOOTOV-UHFFFAOYSA-N dec-5-ene Chemical compound CCCCC=CCCCC UURSXESKOOOTOV-UHFFFAOYSA-N 0.000 description 2
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- 229910052740 iodine Inorganic materials 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- GCDKDLIWAYRURL-UHFFFAOYSA-N n,n'-bis(3,5-ditert-butylphenyl)oxamide Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC(NC(=O)C(=O)NC=2C=C(C=C(C=2)C(C)(C)C)C(C)(C)C)=C1 GCDKDLIWAYRURL-UHFFFAOYSA-N 0.000 description 2
- FTQWRYSLUYAIRQ-UHFFFAOYSA-N n-[(octadecanoylamino)methyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCNC(=O)CCCCCCCCCCCCCCCCC FTQWRYSLUYAIRQ-UHFFFAOYSA-N 0.000 description 2
- 210000003739 neck Anatomy 0.000 description 2
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- 238000010992 reflux Methods 0.000 description 2
- 150000003303 ruthenium Chemical class 0.000 description 2
- 150000003304 ruthenium compounds Chemical class 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000011986 second-generation catalyst Substances 0.000 description 2
- 238000005872 self-metathesis reaction Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- KNCMKWVOMRUHKZ-AATRIKPKSA-N (e)-2,5-dimethylhex-3-ene Chemical compound CC(C)\C=C\C(C)C KNCMKWVOMRUHKZ-AATRIKPKSA-N 0.000 description 1
- SEMZHXXEYIRZAC-UHFFFAOYSA-N 1,3-bis(2-methylphenyl)-4,5-dihydroimidazol-1-ium Chemical compound CC1=CC=CC=C1N1C=[N+](C=2C(=CC=CC=2)C)CC1 SEMZHXXEYIRZAC-UHFFFAOYSA-N 0.000 description 1
- BIPHAXZETHTLLF-UHFFFAOYSA-N 1,3-bis(2-propan-2-ylphenyl)-4,5-dihydroimidazol-1-ium Chemical compound CC(C)C1=CC=CC=C1N1C=[N+](C=2C(=CC=CC=2)C(C)C)CC1 BIPHAXZETHTLLF-UHFFFAOYSA-N 0.000 description 1
- PQVRXLRYFUEHNQ-UHFFFAOYSA-N 1,3-dimethylimidazol-2-ylidene Chemical group CN1[C]N(C)C=C1 PQVRXLRYFUEHNQ-UHFFFAOYSA-N 0.000 description 1
- GPACLCWBWORZEE-UHFFFAOYSA-N 1-ethenyl-3-phenyl-2-propan-2-yloxybenzene Chemical group CC(C)OC1=C(C=C)C=CC=C1C1=CC=CC=C1 GPACLCWBWORZEE-UHFFFAOYSA-N 0.000 description 1
- LIKMAJRDDDTEIG-UHFFFAOYSA-N 1-hexene Chemical compound CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 description 1
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- JCARTGJGWCGSSU-UHFFFAOYSA-N 2,6-dichlorobenzoquinone Chemical compound ClC1=CC(=O)C=C(Cl)C1=O JCARTGJGWCGSSU-UHFFFAOYSA-N 0.000 description 1
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- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 238000006443 Buchwald-Hartwig cross coupling reaction Methods 0.000 description 1
- BHUAHLBDUQGLBQ-UHFFFAOYSA-N CC(C)OC1C(c2ccccc2)=CC=CC1C=C Chemical compound CC(C)OC1C(c2ccccc2)=CC=CC1C=C BHUAHLBDUQGLBQ-UHFFFAOYSA-N 0.000 description 1
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- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
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- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
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- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
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- 125000001118 alkylidene group Chemical group 0.000 description 1
- BIVUUOPIAYRCAP-UHFFFAOYSA-N aminoazanium;chloride Chemical compound Cl.NN BIVUUOPIAYRCAP-UHFFFAOYSA-N 0.000 description 1
- 125000005228 aryl sulfonate group Chemical group 0.000 description 1
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- JCYWCSGERIELPG-UHFFFAOYSA-N imes Chemical compound CC1=CC(C)=CC(C)=C1N1C=CN(C=2C(=CC(C)=CC=2C)C)[C]1 JCYWCSGERIELPG-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
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- 150000002513 isocyanates Chemical class 0.000 description 1
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- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- GPEDLPZUNADVNB-UHFFFAOYSA-N n,n'-bis(2-ethylphenyl)ethane-1,2-diamine;hydrochloride Chemical compound Cl.CCC1=CC=CC=C1NCCNC1=CC=CC=C1CC GPEDLPZUNADVNB-UHFFFAOYSA-N 0.000 description 1
- MMNPEWGRMLABTA-UHFFFAOYSA-N n,n'-bis(2-methylphenyl)ethane-1,2-diamine;hydrochloride Chemical compound Cl.CC1=CC=CC=C1NCCNC1=CC=CC=C1C MMNPEWGRMLABTA-UHFFFAOYSA-N 0.000 description 1
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- LJDZFAPLPVPTBD-UHFFFAOYSA-N nitroformic acid Chemical compound OC(=O)[N+]([O-])=O LJDZFAPLPVPTBD-UHFFFAOYSA-N 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- JDNQPKBFOBQRBN-UHFFFAOYSA-N ruthenium monohydride Chemical compound [RuH] JDNQPKBFOBQRBN-UHFFFAOYSA-N 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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- 238000010189 synthetic method Methods 0.000 description 1
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- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
Images
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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
-
- 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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0046—Ruthenium compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2265—Carbenes or carbynes, i.e.(image)
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
- B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
- C08G61/04—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms
- C08G61/06—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds
- C08G61/08—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aliphatic carbon atoms prepared by ring-opening of carbocyclic compounds of carbocyclic compounds containing one or more carbon-to-carbon double bonds in the ring
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/50—Redistribution or isomerisation reactions of C-C, C=C or C-C triple bonds
- B01J2231/54—Metathesis reactions, e.g. olefin metathesis
- B01J2231/543—Metathesis reactions, e.g. olefin metathesis alkene metathesis
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/821—Ruthenium
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (8)
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| US80174206P | 2006-05-19 | 2006-05-19 | |
| US60/801,742 | 2006-05-19 | ||
| US85371706P | 2006-10-19 | 2006-10-19 | |
| US60/853,717 | 2006-10-19 | ||
| US85914806P | 2006-11-15 | 2006-11-15 | |
| US60/859,148 | 2006-11-15 |
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| KR1020147019358A Division KR20140097571A (ko) | 2005-12-16 | 2006-12-18 | 유기금속 루테늄 착물, 및 사치환 및 기타 입체장애된 올레핀의 제조를 위한 관련 방법 |
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| KR1020087017250A Ceased KR20080103961A (ko) | 2005-12-16 | 2006-12-18 | 유기금속 루테늄 착물, 및 사치환 및 기타 입체장애된올레핀의 제조를 위한 관련 방법 |
| KR1020147019358A Ceased KR20140097571A (ko) | 2005-12-16 | 2006-12-18 | 유기금속 루테늄 착물, 및 사치환 및 기타 입체장애된 올레핀의 제조를 위한 관련 방법 |
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| KR1020147019358A Ceased KR20140097571A (ko) | 2005-12-16 | 2006-12-18 | 유기금속 루테늄 착물, 및 사치환 및 기타 입체장애된 올레핀의 제조를 위한 관련 방법 |
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| Country | Link |
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| US (2) | US8008224B2 (https=) |
| EP (1) | EP1971616A1 (https=) |
| JP (1) | JP5522941B2 (https=) |
| KR (2) | KR20080103961A (https=) |
| CN (1) | CN101460513B (https=) |
| SG (1) | SG169326A1 (https=) |
| WO (1) | WO2007075427A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014027040A1 (en) | 2012-08-16 | 2014-02-20 | Uniwersytet Warszawski | Novel metal complexes, especially the ruthenium complexes, and use thereof |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US8877936B2 (en) * | 2008-04-09 | 2014-11-04 | California Institute Of Technology | Ruthenium olefin metathesis catalysts bearing N-heterocyclic carbene ligands with substituted backbone |
| FR2939331B1 (fr) | 2008-12-10 | 2012-08-10 | Inst Francais Du Petrole | Composition catalytique et procede de metathese de corps gras insature |
| AP2011006003A0 (en) | 2009-05-05 | 2011-12-31 | Stepan Co | Sulfonated internal olefin surfactant for enhancedoil recovery. |
| WO2011135029A1 (en) | 2010-04-28 | 2011-11-03 | Dsm Ip Assets B.V. | Metathesis crosslinkable coating compositions |
| JP5674059B2 (ja) * | 2011-01-24 | 2015-02-25 | 国立大学法人名古屋大学 | ルテニウム錯体を含む水素移動反応用触媒及び水素移動反応物の製造方法 |
| CN102145304B (zh) * | 2011-02-24 | 2012-08-08 | 华东师范大学 | 一种负载型格拉布斯催化剂的制备及其应用 |
| FR2983475B1 (fr) | 2011-12-02 | 2014-01-17 | IFP Energies Nouvelles | Procede de metathese d'olefines lineaires alpha utilisant un complexe du ruthenium comportant un carbene n-heterocyclique dissymetrique |
| JP6092379B2 (ja) | 2012-06-29 | 2017-03-08 | アペイロン シンセシス エス アー | 金属錯体、その適用、及びメタセシス反応の実施方法 |
| WO2017012379A1 (zh) * | 2015-07-20 | 2017-01-26 | 中国科学院上海有机化学研究所 | 草酸酰胺类配体及其在铜催化芳基卤代物偶联反应中的用途 |
| EP3376859B1 (en) | 2015-11-18 | 2021-01-06 | Provivi, Inc. | Microorganisms for the production of insect pheromones and related compounds |
| WO2017087710A2 (en) | 2015-11-18 | 2017-05-26 | Provivi, Inc. | Production of fatty olefin derivatives via olefin metathesis |
| KR20180116238A (ko) * | 2015-12-10 | 2018-10-24 | 우미코레 아게 운트 코 카게 | 올레핀 복분해 촉매 |
| WO2017214133A2 (en) | 2016-06-06 | 2017-12-14 | Provivi, Inc. | Semi-biosynthetic production of fatty alcohols and fatty aldehydes |
| HUE073559T2 (hu) | 2017-02-17 | 2026-01-28 | Provivi Inc | Feromonok és kapcsolódó anyagok szintézise olefin-metatézisen keresztül |
| MX382401B (es) | 2017-05-17 | 2025-03-13 | Provivi Inc | Microorganismos para la producción de feromonas de insectos y compuestos relacionados. |
| US10683388B2 (en) * | 2017-08-15 | 2020-06-16 | University Of Florida Research Foundation, Incorporated | High temperature metathesis chemistry |
| CN108299506A (zh) * | 2018-01-29 | 2018-07-20 | 中国科学院成都有机化学有限公司 | N-杂环卡宾钌络合物及其制备方法和用途 |
| CN109225334B (zh) * | 2018-07-20 | 2021-05-18 | 吉林化工学院 | 一种具有邻位空间位阻结构的钌烯烃复分解催化剂及其制备方法和应用 |
| CN109364998B (zh) * | 2018-10-15 | 2021-07-06 | 天津科技大学 | 一种用于烯烃复分解反应的催化剂及其制备和应用方法 |
| CN111250168B (zh) * | 2018-11-30 | 2021-06-01 | 中国科学院大连化学物理研究所 | 一种钌基催化剂及其制备方法、应用 |
| CN110041262B (zh) | 2019-01-02 | 2020-03-27 | 成都开美思商务信息咨询中心(有限合伙) | 氮杂环卡宾配体及其钌催化剂、制备方法和应用 |
| CN112547126B (zh) * | 2020-12-21 | 2023-03-21 | 上海中化科技有限公司 | 钌卡宾化合物、其组合物、制备方法及应用 |
| CN113000066B (zh) * | 2021-01-09 | 2022-04-12 | 河南大学 | 一种z-选择性钌卡宾烯烃复分解催化剂及其制备方法和应用 |
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| DE19815275B4 (de) | 1998-04-06 | 2009-06-25 | Evonik Degussa Gmbh | Alkylidenkomplexe des Rutheniums mit N-heterozyklischen Carbenliganden und deren Verwendung als hochaktive, selektive Katalysatoren für die Olefin-Metathese |
| EP1180108B1 (en) | 1999-05-24 | 2003-08-27 | California Institute Of Technology | Imidazolidine-based metal carbene metathesis catalysts |
| JP3943015B2 (ja) * | 2000-08-10 | 2007-07-11 | トラスティーズ オブ ボストン カレッジ | リサイクル可能メタセシス触媒 |
| WO2002020535A1 (en) * | 2000-09-05 | 2002-03-14 | California Institute Of Technology | Highly active metathesis catalysts generated in situ from inexpensive and air stable precursors |
| US6759537B2 (en) * | 2001-03-23 | 2004-07-06 | California Institute Of Technology | Hexacoordinated ruthenium or osmium metal carbene metathesis catalysts |
| CA2442368C (en) * | 2001-03-30 | 2015-10-13 | California Institute Of Technology | Cross-metathesis reaction of functionalized and substituted olefins using group 8 transition metal carbene complexes as metathesis catalysts |
| US7683180B2 (en) * | 2001-04-16 | 2010-03-23 | California Institute Of Technology | Group 8 transition metal carbene complexes as enantionselective olefin metathesis catalysts |
| US6818586B2 (en) * | 2001-08-01 | 2004-11-16 | Cymetech, Llp | Hexacoordinated ruthenium or osmium metal carbene metathesis catalysts |
| EP2251360B1 (en) * | 2001-08-29 | 2013-07-31 | California Institute of Technology | Ring-opening metathesis polymerization of bridged bicyclic and polycyclic olefins containing two or more heteroatoms |
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- 2006-12-18 WO PCT/US2006/047934 patent/WO2007075427A1/en not_active Ceased
- 2006-12-18 US US11/640,400 patent/US8008224B2/en active Active
- 2006-12-18 SG SG201100293-8A patent/SG169326A1/en unknown
- 2006-12-18 EP EP06845551A patent/EP1971616A1/en not_active Withdrawn
- 2006-12-18 CN CN200680051426.3A patent/CN101460513B/zh not_active Expired - Fee Related
- 2006-12-18 KR KR1020147019358A patent/KR20140097571A/ko not_active Ceased
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2011
- 2011-08-30 US US13/221,871 patent/US8361922B2/en active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014027040A1 (en) | 2012-08-16 | 2014-02-20 | Uniwersytet Warszawski | Novel metal complexes, especially the ruthenium complexes, and use thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| US20070282148A1 (en) | 2007-12-06 |
| US20120123133A1 (en) | 2012-05-17 |
| US8008224B2 (en) | 2011-08-30 |
| KR20140097571A (ko) | 2014-08-06 |
| CN101460513A (zh) | 2009-06-17 |
| CN101460513B (zh) | 2014-08-27 |
| JP2009519947A (ja) | 2009-05-21 |
| JP5522941B2 (ja) | 2014-06-18 |
| SG169326A1 (en) | 2011-03-30 |
| EP1971616A1 (en) | 2008-09-24 |
| WO2007075427A1 (en) | 2007-07-05 |
| US8361922B2 (en) | 2013-01-29 |
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