DE60218807T2 - Rutheniumkomplexe und deren Verwendung zur Herstellung von Alkoholen - Google Patents
Rutheniumkomplexe und deren Verwendung zur Herstellung von Alkoholen Download PDFInfo
- Publication number
- DE60218807T2 DE60218807T2 DE60218807T DE60218807T DE60218807T2 DE 60218807 T2 DE60218807 T2 DE 60218807T2 DE 60218807 T DE60218807 T DE 60218807T DE 60218807 T DE60218807 T DE 60218807T DE 60218807 T2 DE60218807 T2 DE 60218807T2
- Authority
- DE
- Germany
- Prior art keywords
- different
- bis
- group
- hydrogen atom
- carbon atoms
- 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
- 150000003303 ruthenium Chemical class 0.000 title description 19
- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000001298 alcohols Chemical class 0.000 title 1
- 238000006243 chemical reaction Methods 0.000 claims description 106
- -1 3,5-xylyl group Chemical group 0.000 claims description 93
- 125000004432 carbon atom Chemical group C* 0.000 claims description 84
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 84
- 239000012327 Ruthenium complex Substances 0.000 claims description 61
- 239000001257 hydrogen Substances 0.000 claims description 55
- 229910052739 hydrogen Inorganic materials 0.000 claims description 55
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 52
- 150000001875 compounds Chemical class 0.000 claims description 50
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 44
- 150000002430 hydrocarbons Chemical group 0.000 claims description 42
- 238000000034 method Methods 0.000 claims description 36
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
- 239000002585 base Substances 0.000 claims description 27
- 230000001476 alcoholic effect Effects 0.000 claims description 20
- 150000001450 anions Chemical group 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 14
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 12
- 150000002431 hydrogen Chemical class 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
- BQUNSIYVDVZZEA-UHFFFAOYSA-N 4-bis(3,5-dimethylphenyl)phosphanylpentan-2-yl-bis(3,5-dimethylphenyl)phosphane Chemical compound C=1C(C)=CC(C)=CC=1P(C=1C=C(C)C=C(C)C=1)C(C)CC(C)P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 BQUNSIYVDVZZEA-UHFFFAOYSA-N 0.000 claims description 7
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 7
- ATHCDBOOSFQXPT-UHFFFAOYSA-N [3-bis(3,5-dimethylphenyl)phosphanyl-1,3-diphenylpropyl]-bis(3,5-dimethylphenyl)phosphane Chemical compound CC1=CC(C)=CC(P(C(CC(P(C=2C=C(C)C=C(C)C=2)C=2C=C(C)C=C(C)C=2)C=2C=CC=CC=2)C=2C=CC=CC=2)C=2C=C(C)C=C(C)C=2)=C1 ATHCDBOOSFQXPT-UHFFFAOYSA-N 0.000 claims description 7
- UXHGOSLRMLRAKR-UHFFFAOYSA-N [3-bis(3,5-dimethylphenyl)phosphanyl-2-methyl-1,3-diphenylpropyl]-bis(3,5-dimethylphenyl)phosphane Chemical compound C=1C(C)=CC(C)=CC=1P(C=1C=C(C)C=C(C)C=1)C(C=1C=CC=CC=1)C(C)C(C=1C=CC=CC=1)P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 UXHGOSLRMLRAKR-UHFFFAOYSA-N 0.000 claims description 7
- GFGZHQCWZWATGF-UHFFFAOYSA-N [3-bis(4-methylphenyl)phosphanyl-1,3-diphenylpropyl]-bis(4-methylphenyl)phosphane Chemical compound C1=CC(C)=CC=C1P(C=1C=CC(C)=CC=1)C(C=1C=CC=CC=1)CC(C=1C=CC=CC=1)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 GFGZHQCWZWATGF-UHFFFAOYSA-N 0.000 claims description 7
- RVNVDLRZOHJDCB-UHFFFAOYSA-N [3-bis(4-methylphenyl)phosphanyl-2-methyl-1,3-diphenylpropyl]-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C=1C=CC=CC=1)C(C)C(C=1C=CC=CC=1)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 RVNVDLRZOHJDCB-UHFFFAOYSA-N 0.000 claims description 7
- YOHVTQHWOPUYGB-UHFFFAOYSA-N [4-bis(3,5-dimethylphenyl)phosphanyl-3-methylpentan-2-yl]-bis(3,5-dimethylphenyl)phosphane Chemical compound C=1C(C)=CC(C)=CC=1P(C=1C=C(C)C=C(C)C=1)C(C)C(C)C(C)P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 YOHVTQHWOPUYGB-UHFFFAOYSA-N 0.000 claims description 7
- WDYGPMAMBXJESZ-UHFFFAOYSA-N 1,1-bis(4-methoxyphenyl)-3-methylbutane-1,2-diamine Chemical group C1=CC(OC)=CC=C1C(N)(C(N)C(C)C)C1=CC=C(OC)C=C1 WDYGPMAMBXJESZ-UHFFFAOYSA-N 0.000 claims description 6
- ZHIOKCFUZLQANC-UHFFFAOYSA-N 4-bis(4-methylphenyl)phosphanylpentan-2-yl-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C)CC(C)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZHIOKCFUZLQANC-UHFFFAOYSA-N 0.000 claims description 6
- 229940126062 Compound A Drugs 0.000 claims description 6
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 6
- LVYGXVVRZGNPMS-UHFFFAOYSA-N [4-bis(4-methylphenyl)phosphanyl-3-methylpentan-2-yl]-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C)C(C)C(C)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 LVYGXVVRZGNPMS-UHFFFAOYSA-N 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 6
- 150000001340 alkali metals Chemical class 0.000 claims description 5
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 5
- PONXTPCRRASWKW-KBPBESRZSA-N diphenylethylenediamine Chemical group C1([C@H](N)[C@@H](N)C=2C=CC=CC=2)=CC=CC=C1 PONXTPCRRASWKW-KBPBESRZSA-N 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 description 134
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 102
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 88
- 239000003054 catalyst Substances 0.000 description 54
- VURFVHCLMJOLKN-UHFFFAOYSA-N diphosphane Chemical class PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 description 53
- 229910052786 argon Inorganic materials 0.000 description 51
- 230000003287 optical effect Effects 0.000 description 50
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 48
- 239000012295 chemical reaction liquid Substances 0.000 description 47
- 239000002904 solvent Substances 0.000 description 40
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 32
- 239000003446 ligand Substances 0.000 description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- 239000011521 glass Substances 0.000 description 26
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
- 239000000758 substrate Substances 0.000 description 23
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 22
- 238000003756 stirring Methods 0.000 description 22
- 238000009876 asymmetric hydrogenation reaction Methods 0.000 description 21
- 230000015572 biosynthetic process Effects 0.000 description 21
- 238000004817 gas chromatography Methods 0.000 description 21
- 238000005984 hydrogenation reaction Methods 0.000 description 21
- 238000003786 synthesis reaction Methods 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 17
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- DYUQAZSOFZSPHD-UHFFFAOYSA-N Phenylpropanol Chemical compound CCC(O)C1=CC=CC=C1 DYUQAZSOFZSPHD-UHFFFAOYSA-N 0.000 description 14
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 13
- 229910052799 carbon Inorganic materials 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 12
- DHCWLIOIJZJFJE-UHFFFAOYSA-L dichlororuthenium Chemical compound Cl[Ru]Cl DHCWLIOIJZJFJE-UHFFFAOYSA-L 0.000 description 12
- 229910052707 ruthenium Inorganic materials 0.000 description 11
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- WDYGPMAMBXJESZ-GOSISDBHSA-N (2r)-1,1-bis(4-methoxyphenyl)-3-methylbutane-1,2-diamine Chemical compound C1=CC(OC)=CC=C1C(N)([C@H](N)C(C)C)C1=CC=C(OC)C=C1 WDYGPMAMBXJESZ-GOSISDBHSA-N 0.000 description 9
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 8
- 241000894007 species Species 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- GNKZMNRKLCTJAY-UHFFFAOYSA-N 4'-Methylacetophenone Chemical compound CC(=O)C1=CC=C(C)C=C1 GNKZMNRKLCTJAY-UHFFFAOYSA-N 0.000 description 6
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical class [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 6
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 6
- DVWQNBIUTWDZMW-UHFFFAOYSA-N 1-naphthalen-1-ylnaphthalen-2-ol Chemical compound C1=CC=C2C(C3=C4C=CC=CC4=CC=C3O)=CC=CC2=C1 DVWQNBIUTWDZMW-UHFFFAOYSA-N 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 150000003304 ruthenium compounds Chemical class 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- VYXHVRARDIDEHS-QGTKBVGQSA-N (1z,5z)-cycloocta-1,5-diene Chemical compound C\1C\C=C/CC\C=C/1 VYXHVRARDIDEHS-QGTKBVGQSA-N 0.000 description 4
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 4
- DAVFJRVIVZOKKS-UHFFFAOYSA-N 2-(4-methylphenyl)ethanol Chemical compound CC1=CC=C(CCO)C=C1 DAVFJRVIVZOKKS-UHFFFAOYSA-N 0.000 description 4
- GDWRKZLROIFUML-UHFFFAOYSA-N 4-phenylbutan-2-ol Chemical compound CC(O)CCC1=CC=CC=C1 GDWRKZLROIFUML-UHFFFAOYSA-N 0.000 description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 4
- 125000004423 acyloxy group Chemical group 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
- 125000002524 organometallic group Chemical group 0.000 description 4
- HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 4
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 4
- 125000003884 phenylalkyl group Chemical group 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- PONXTPCRRASWKW-UHFFFAOYSA-N 1,2-diphenylethane-1,2-diamine Chemical compound C=1C=CC=CC=1C(N)C(N)C1=CC=CC=C1 PONXTPCRRASWKW-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- ULBXWWGWDPVHAO-UHFFFAOYSA-N Chlorbufam Chemical compound C#CC(C)OC(=O)NC1=CC=CC(Cl)=C1 ULBXWWGWDPVHAO-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- FWXAUDSWDBGCMN-ZEQRLZLVSA-N chiraphos Chemical compound C=1C=CC=CC=1P([C@@H](C)[C@H](C)P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 FWXAUDSWDBGCMN-ZEQRLZLVSA-N 0.000 description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- GYZZZILPVUYAFJ-UHFFFAOYSA-N phanephos Chemical compound C1CC(C(=C2)P(C=3C=CC=CC=3)C=3C=CC=CC=3)=CC=C2CCC2=CC=C1C=C2P(C=1C=CC=CC=1)C1=CC=CC=C1 GYZZZILPVUYAFJ-UHFFFAOYSA-N 0.000 description 3
- GTBPUYSGSDIIMM-UHFFFAOYSA-N phosphane;ruthenium Chemical compound P.[Ru] GTBPUYSGSDIIMM-UHFFFAOYSA-N 0.000 description 3
- 125000003367 polycyclic group Chemical group 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- VEAFKIYNHVBNIP-UHFFFAOYSA-N 1,3-Diphenylpropane Chemical class C=1C=CC=CC=1CCCC1=CC=CC=C1 VEAFKIYNHVBNIP-UHFFFAOYSA-N 0.000 description 2
- UABXUIWIFUZYQK-UHFFFAOYSA-N 1-(furan-2-yl)ethanol Chemical compound CC(O)C1=CC=CO1 UABXUIWIFUZYQK-UHFFFAOYSA-N 0.000 description 2
- JMSUNAQVHOHLMX-UHFFFAOYSA-N 1-cyclohexylethanol Chemical compound CC(O)C1CCCCC1 JMSUNAQVHOHLMX-UHFFFAOYSA-N 0.000 description 2
- PPHIIIRFJKDTLG-UHFFFAOYSA-N 1-pyridin-2-ylethanol Chemical compound CC(O)C1=CC=CC=N1 PPHIIIRFJKDTLG-UHFFFAOYSA-N 0.000 description 2
- WUNFIVTVJXZDDJ-UHFFFAOYSA-N 1-thiophen-2-ylethanol Chemical compound CC(O)C1=CC=CS1 WUNFIVTVJXZDDJ-UHFFFAOYSA-N 0.000 description 2
- WYJOVVXUZNRJQY-UHFFFAOYSA-N 2-Acetylthiophene Chemical compound CC(=O)C1=CC=CS1 WYJOVVXUZNRJQY-UHFFFAOYSA-N 0.000 description 2
- MDXFTQJULQIQCK-UHFFFAOYSA-N 3-[1-bis(3,5-dimethylphenyl)phosphanylethyl]hexan-2-yl-bis(3,5-dimethylphenyl)phosphane Chemical compound C=1C(C)=CC(C)=CC=1P(C=1C=C(C)C=C(C)C=1)C(C)C(CCC)C(C)P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 MDXFTQJULQIQCK-UHFFFAOYSA-N 0.000 description 2
- GKZZWXWHUFNYRY-UHFFFAOYSA-N 3-[1-bis(4-methylphenyl)phosphanylethyl]hexan-2-yl-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C)C(CCC)C(C)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 GKZZWXWHUFNYRY-UHFFFAOYSA-N 0.000 description 2
- FWXAUDSWDBGCMN-UHFFFAOYSA-N 3-diphenylphosphanylbutan-2-yl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(C)C(C)P(C=1C=CC=CC=1)C1=CC=CC=C1 FWXAUDSWDBGCMN-UHFFFAOYSA-N 0.000 description 2
- CTYPJIUQROQJBG-UHFFFAOYSA-N 4-diphenylphosphanylpentan-2-yl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(C)CC(C)P(C=1C=CC=CC=1)C1=CC=CC=C1 CTYPJIUQROQJBG-UHFFFAOYSA-N 0.000 description 2
- SAOXPNBHKSWHGW-UHFFFAOYSA-N 4-methylpent-3-en-2-ol Chemical compound CC(O)C=C(C)C SAOXPNBHKSWHGW-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- OYJLCOSEYYZULE-UHFFFAOYSA-N [1-[2-(trifluoromethylsulfonyloxy)naphthalen-1-yl]naphthalen-2-yl] trifluoromethanesulfonate Chemical group C1=CC=C2C(C3=C4C=CC=CC4=CC=C3OS(=O)(=O)C(F)(F)F)=C(OS(=O)(=O)C(F)(F)F)C=CC2=C1 OYJLCOSEYYZULE-UHFFFAOYSA-N 0.000 description 2
- MXGXXBYVDMVJAO-UHFFFAOYSA-N [1-[2-bis(3,5-dimethylphenyl)phosphanylnaphthalen-1-yl]naphthalen-2-yl]-bis(3,5-dimethylphenyl)phosphane Chemical group CC1=CC(C)=CC(P(C=2C=C(C)C=C(C)C=2)C=2C(=C3C=CC=CC3=CC=2)C=2C3=CC=CC=C3C=CC=2P(C=2C=C(C)C=C(C)C=2)C=2C=C(C)C=C(C)C=2)=C1 MXGXXBYVDMVJAO-UHFFFAOYSA-N 0.000 description 2
- IOPQYDKQISFMJI-UHFFFAOYSA-N [1-[2-bis(4-methylphenyl)phosphanylnaphthalen-1-yl]naphthalen-2-yl]-bis(4-methylphenyl)phosphane Chemical group C1=CC(C)=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 IOPQYDKQISFMJI-UHFFFAOYSA-N 0.000 description 2
- AAMCOZWAABMDIZ-UHFFFAOYSA-N [2-[bis(3,5-dimethylphenyl)phosphanyl-phenylmethyl]-1-phenyl-2-propan-2-ylpentyl]-bis(3,5-dimethylphenyl)phosphane Chemical compound C=1C(C)=CC(C)=CC=1P(C=1C=C(C)C=C(C)C=1)C(C=1C=CC=CC=1)C(C(C)C)(CCC)C(C=1C=CC=CC=1)P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 AAMCOZWAABMDIZ-UHFFFAOYSA-N 0.000 description 2
- SBNVVWCRXYIJKH-UHFFFAOYSA-N [2-[bis(3,5-dimethylphenyl)phosphanyl-phenylmethyl]-1-phenyl-2-propylpentyl]-bis(3,5-dimethylphenyl)phosphane Chemical compound C=1C(C)=CC(C)=CC=1P(C=1C=C(C)C=C(C)C=1)C(C=1C=CC=CC=1)C(CCC)(CCC)C(C=1C=CC=CC=1)P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 SBNVVWCRXYIJKH-UHFFFAOYSA-N 0.000 description 2
- RHLYTTHEUBUZPM-UHFFFAOYSA-N [2-[bis(3,5-dimethylphenyl)phosphanyl-phenylmethyl]-1-phenylbutyl]-bis(3,5-dimethylphenyl)phosphane Chemical compound C=1C(C)=CC(C)=CC=1P(C=1C=C(C)C=C(C)C=1)C(C=1C=CC=CC=1)C(CC)C(C=1C=CC=CC=1)P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 RHLYTTHEUBUZPM-UHFFFAOYSA-N 0.000 description 2
- WSVLBKCYINLNGL-UHFFFAOYSA-N [2-[bis(3,5-dimethylphenyl)phosphanyl-phenylmethyl]-1-phenylpentyl]-bis(3,5-dimethylphenyl)phosphane Chemical compound C=1C(C)=CC(C)=CC=1P(C=1C=C(C)C=C(C)C=1)C(C=1C=CC=CC=1)C(CCC)C(C=1C=CC=CC=1)P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 WSVLBKCYINLNGL-UHFFFAOYSA-N 0.000 description 2
- ZLTBXQBKKDLUCV-UHFFFAOYSA-N [2-[bis(3,5-dimethylphenyl)phosphanyl-phenylmethyl]-2-ethyl-1-phenylbutyl]-bis(3,5-dimethylphenyl)phosphane Chemical compound C=1C(C)=CC(C)=CC=1P(C=1C=C(C)C=C(C)C=1)C(C=1C=CC=CC=1)C(CC)(CC)C(C=1C=CC=CC=1)P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 ZLTBXQBKKDLUCV-UHFFFAOYSA-N 0.000 description 2
- FFMKXWIQWMYSDN-UHFFFAOYSA-N [2-[bis(3,5-dimethylphenyl)phosphanyl-phenylmethyl]-2-ethyl-1-phenylpentyl]-bis(3,5-dimethylphenyl)phosphane Chemical compound C=1C(C)=CC(C)=CC=1P(C=1C=C(C)C=C(C)C=1)C(C=1C=CC=CC=1)C(CC)(CCC)C(C=1C=CC=CC=1)P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 FFMKXWIQWMYSDN-UHFFFAOYSA-N 0.000 description 2
- XTIHICRGHPVJMZ-UHFFFAOYSA-N [2-[bis(3,5-dimethylphenyl)phosphanyl-phenylmethyl]-2-methyl-1-phenylbutyl]-bis(3,5-dimethylphenyl)phosphane Chemical compound C=1C(C)=CC(C)=CC=1P(C=1C=C(C)C=C(C)C=1)C(C=1C=CC=CC=1)C(C)(CC)C(C=1C=CC=CC=1)P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 XTIHICRGHPVJMZ-UHFFFAOYSA-N 0.000 description 2
- FRAQLEPXOUZWBA-UHFFFAOYSA-N [2-[bis(3,5-dimethylphenyl)phosphanyl-phenylmethyl]-2-methyl-1-phenylpentyl]-bis(3,5-dimethylphenyl)phosphane Chemical compound C=1C(C)=CC(C)=CC=1P(C=1C=C(C)C=C(C)C=1)C(C=1C=CC=CC=1)C(C)(CCC)C(C=1C=CC=CC=1)P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 FRAQLEPXOUZWBA-UHFFFAOYSA-N 0.000 description 2
- QWRJMOIPLRUIRB-UHFFFAOYSA-N [2-[bis(3,5-dimethylphenyl)phosphanyl-phenylmethyl]-3-methyl-1-phenyl-2-propan-2-ylbutyl]-bis(3,5-dimethylphenyl)phosphane Chemical compound C=1C(C)=CC(C)=CC=1P(C=1C=C(C)C=C(C)C=1)C(C=1C=CC=CC=1)C(C(C)C)(C(C)C)C(C=1C=CC=CC=1)P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 QWRJMOIPLRUIRB-UHFFFAOYSA-N 0.000 description 2
- AQEQKEWHSPTUFX-UHFFFAOYSA-N [2-[bis(3,5-dimethylphenyl)phosphanyl-phenylmethyl]-3-methyl-1-phenylbutyl]-bis(3,5-dimethylphenyl)phosphane Chemical compound C=1C(C)=CC(C)=CC=1P(C=1C=C(C)C=C(C)C=1)C(C=1C=CC=CC=1)C(C(C)C)C(C=1C=CC=CC=1)P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 AQEQKEWHSPTUFX-UHFFFAOYSA-N 0.000 description 2
- IVYGOJOVQHSDFF-UHFFFAOYSA-N [2-[bis(4-methylphenyl)phosphanyl-phenylmethyl]-1-phenyl-2-propan-2-ylpentyl]-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C=1C=CC=CC=1)C(C(C)C)(CCC)C(C=1C=CC=CC=1)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 IVYGOJOVQHSDFF-UHFFFAOYSA-N 0.000 description 2
- KHTSRJWARDCEEX-UHFFFAOYSA-N [2-[bis(4-methylphenyl)phosphanyl-phenylmethyl]-1-phenylbutyl]-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C=1C=CC=CC=1)C(CC)C(C=1C=CC=CC=1)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 KHTSRJWARDCEEX-UHFFFAOYSA-N 0.000 description 2
- USLBUBNERCGKFL-UHFFFAOYSA-N [2-[bis(4-methylphenyl)phosphanyl-phenylmethyl]-1-phenylpentyl]-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C=1C=CC=CC=1)C(CCC)C(C=1C=CC=CC=1)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 USLBUBNERCGKFL-UHFFFAOYSA-N 0.000 description 2
- GKZUGNSPZBOVMI-UHFFFAOYSA-N [2-[bis(4-methylphenyl)phosphanyl-phenylmethyl]-2,3-dimethyl-1-phenylbutyl]-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C=1C=CC=CC=1)C(C)(C(C)C)C(C=1C=CC=CC=1)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 GKZUGNSPZBOVMI-UHFFFAOYSA-N 0.000 description 2
- KGZZWGXDEOFHSI-UHFFFAOYSA-N [2-[bis(4-methylphenyl)phosphanyl-phenylmethyl]-2-ethyl-1-phenylpentyl]-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C=1C=CC=CC=1)C(CC)(CCC)C(C=1C=CC=CC=1)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 KGZZWGXDEOFHSI-UHFFFAOYSA-N 0.000 description 2
- FVPOOBCSIKOWCN-UHFFFAOYSA-N [2-[bis(4-methylphenyl)phosphanyl-phenylmethyl]-2-ethyl-3-methyl-1-phenylbutyl]-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C=1C=CC=CC=1)C(C(C)C)(CC)C(C=1C=CC=CC=1)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 FVPOOBCSIKOWCN-UHFFFAOYSA-N 0.000 description 2
- VXUKVXKDYZWRSS-UHFFFAOYSA-N [2-[bis(4-methylphenyl)phosphanyl-phenylmethyl]-2-methyl-1-phenylbutyl]-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C=1C=CC=CC=1)C(C)(CC)C(C=1C=CC=CC=1)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 VXUKVXKDYZWRSS-UHFFFAOYSA-N 0.000 description 2
- IVOPXXVEFMBQNN-UHFFFAOYSA-N [2-[bis(4-methylphenyl)phosphanyl-phenylmethyl]-3-methyl-1-phenylbutyl]-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C=1C=CC=CC=1)C(C(C)C)C(C=1C=CC=CC=1)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 IVOPXXVEFMBQNN-UHFFFAOYSA-N 0.000 description 2
- ZSQRXNYKHKDZHC-UHFFFAOYSA-N [3-[1-bis(3,5-dimethylphenyl)phosphanylethyl]-3,4-dimethylpentan-2-yl]-bis(3,5-dimethylphenyl)phosphane Chemical compound C=1C(C)=CC(C)=CC=1P(C=1C=C(C)C=C(C)C=1)C(C)C(C)(C(C)C)C(C)P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 ZSQRXNYKHKDZHC-UHFFFAOYSA-N 0.000 description 2
- OEJBGICQXZPYKN-UHFFFAOYSA-N [3-[1-bis(3,5-dimethylphenyl)phosphanylethyl]-3-ethyl-4-methylpentan-2-yl]-bis(3,5-dimethylphenyl)phosphane Chemical compound C=1C(C)=CC(C)=CC=1P(C=1C=C(C)C=C(C)C=1)C(C)C(C(C)C)(CC)C(C)P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 OEJBGICQXZPYKN-UHFFFAOYSA-N 0.000 description 2
- BSWAPLLPHMTDJB-UHFFFAOYSA-N [3-[1-bis(3,5-dimethylphenyl)phosphanylethyl]-3-ethylhexan-2-yl]-bis(3,5-dimethylphenyl)phosphane Chemical compound C=1C(C)=CC(C)=CC=1P(C=1C=C(C)C=C(C)C=1)C(C)C(CC)(CCC)C(C)P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 BSWAPLLPHMTDJB-UHFFFAOYSA-N 0.000 description 2
- CESWIDSGELLUFE-UHFFFAOYSA-N [3-[1-bis(3,5-dimethylphenyl)phosphanylethyl]-3-methylhexan-2-yl]-bis(3,5-dimethylphenyl)phosphane Chemical compound C=1C(C)=CC(C)=CC=1P(C=1C=C(C)C=C(C)C=1)C(C)C(C)(CCC)C(C)P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 CESWIDSGELLUFE-UHFFFAOYSA-N 0.000 description 2
- NRLOMXOLORYOQR-UHFFFAOYSA-N [3-[1-bis(3,5-dimethylphenyl)phosphanylethyl]-3-propan-2-ylhexan-2-yl]-bis(3,5-dimethylphenyl)phosphane Chemical compound C=1C(C)=CC(C)=CC=1P(C=1C=C(C)C=C(C)C=1)C(C)C(C(C)C)(CCC)C(C)P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 NRLOMXOLORYOQR-UHFFFAOYSA-N 0.000 description 2
- AYYBBEGCURNPKQ-UHFFFAOYSA-N [3-[1-bis(3,5-dimethylphenyl)phosphanylethyl]-3-propylhexan-2-yl]-bis(3,5-dimethylphenyl)phosphane Chemical compound C=1C(C)=CC(C)=CC=1P(C=1C=C(C)C=C(C)C=1)C(C)C(CCC)(CCC)C(C)P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 AYYBBEGCURNPKQ-UHFFFAOYSA-N 0.000 description 2
- ULKOTZWMCCJINY-UHFFFAOYSA-N [3-[1-bis(3,5-dimethylphenyl)phosphanylethyl]-4-methyl-3-propan-2-ylpentan-2-yl]-bis(3,5-dimethylphenyl)phosphane Chemical compound C=1C(C)=CC(C)=CC=1P(C=1C=C(C)C=C(C)C=1)C(C)C(C(C)C)(C(C)C)C(C)P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 ULKOTZWMCCJINY-UHFFFAOYSA-N 0.000 description 2
- AMVMENJBVIKCEB-UHFFFAOYSA-N [3-[1-bis(3,5-dimethylphenyl)phosphanylethyl]-4-methylpentan-2-yl]-bis(3,5-dimethylphenyl)phosphane Chemical compound C=1C(C)=CC(C)=CC=1P(C=1C=C(C)C=C(C)C=1)C(C)C(C(C)C)C(C)P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 AMVMENJBVIKCEB-UHFFFAOYSA-N 0.000 description 2
- APDQHTLFPNELDJ-UHFFFAOYSA-N [3-[1-bis(4-methylphenyl)phosphanylethyl]-3,4-dimethylpentan-2-yl]-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C)C(C)(C(C)C)C(C)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 APDQHTLFPNELDJ-UHFFFAOYSA-N 0.000 description 2
- CVSHORNWWRJEPR-UHFFFAOYSA-N [3-[1-bis(4-methylphenyl)phosphanylethyl]-3-ethyl-4-methylpentan-2-yl]-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C)C(C(C)C)(CC)C(C)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 CVSHORNWWRJEPR-UHFFFAOYSA-N 0.000 description 2
- PCRZTLCKNOCRMZ-UHFFFAOYSA-N [3-[1-bis(4-methylphenyl)phosphanylethyl]-3-ethylhexan-2-yl]-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C)C(CC)(CCC)C(C)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 PCRZTLCKNOCRMZ-UHFFFAOYSA-N 0.000 description 2
- XDFASWDXPGKZNV-UHFFFAOYSA-N [3-[1-bis(4-methylphenyl)phosphanylethyl]-3-methylhexan-2-yl]-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C)C(C)(CCC)C(C)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 XDFASWDXPGKZNV-UHFFFAOYSA-N 0.000 description 2
- OBFIXLJMCPBDQE-UHFFFAOYSA-N [3-[1-bis(4-methylphenyl)phosphanylethyl]-3-propylhexan-2-yl]-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C)C(CCC)(CCC)C(C)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 OBFIXLJMCPBDQE-UHFFFAOYSA-N 0.000 description 2
- NOVMXOAQUKPIIW-UHFFFAOYSA-N [3-[1-bis(4-methylphenyl)phosphanylethyl]-4-methylpentan-2-yl]-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C)C(C(C)C)C(C)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 NOVMXOAQUKPIIW-UHFFFAOYSA-N 0.000 description 2
- VUDYQMOGQRVZHP-UHFFFAOYSA-N [3-bis(3,5-dimethylphenyl)phosphanyl-2,2-dimethyl-1,3-diphenylpropyl]-bis(3,5-dimethylphenyl)phosphane Chemical compound CC1=CC(C)=CC(P(C(C=2C=CC=CC=2)C(C)(C)C(P(C=2C=C(C)C=C(C)C=2)C=2C=C(C)C=C(C)C=2)C=2C=CC=CC=2)C=2C=C(C)C=C(C)C=2)=C1 VUDYQMOGQRVZHP-UHFFFAOYSA-N 0.000 description 2
- AVXOESWKKURTML-UHFFFAOYSA-N [4-bis(3,5-dimethylphenyl)phosphanyl-3,3-diethylpentan-2-yl]-bis(3,5-dimethylphenyl)phosphane Chemical compound C=1C(C)=CC(C)=CC=1P(C=1C=C(C)C=C(C)C=1)C(C)C(CC)(CC)C(C)P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 AVXOESWKKURTML-UHFFFAOYSA-N 0.000 description 2
- JVSIHODQUUVXLH-UHFFFAOYSA-N [4-bis(3,5-dimethylphenyl)phosphanyl-3,3-dimethylpentan-2-yl]-bis(3,5-dimethylphenyl)phosphane Chemical compound C=1C(C)=CC(C)=CC=1P(C=1C=C(C)C=C(C)C=1)C(C)C(C)(C)C(C)P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 JVSIHODQUUVXLH-UHFFFAOYSA-N 0.000 description 2
- ZZVWGSFRGNXCDV-UHFFFAOYSA-N [4-bis(3,5-dimethylphenyl)phosphanyl-3-ethyl-3-methylpentan-2-yl]-bis(3,5-dimethylphenyl)phosphane Chemical compound C=1C(C)=CC(C)=CC=1P(C=1C=C(C)C=C(C)C=1)C(C)C(C)(CC)C(C)P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 ZZVWGSFRGNXCDV-UHFFFAOYSA-N 0.000 description 2
- ZILHQDGTNMEODM-UHFFFAOYSA-N [4-bis(3,5-dimethylphenyl)phosphanyl-3-ethylpentan-2-yl]-bis(3,5-dimethylphenyl)phosphane Chemical compound C=1C(C)=CC(C)=CC=1P(C=1C=C(C)C=C(C)C=1)C(C)C(CC)C(C)P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 ZILHQDGTNMEODM-UHFFFAOYSA-N 0.000 description 2
- CRLCNFSEUMRFPB-UHFFFAOYSA-N [4-bis(4-methylphenyl)phosphanyl-3,3-diethylpentan-2-yl]-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C)C(CC)(CC)C(C)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 CRLCNFSEUMRFPB-UHFFFAOYSA-N 0.000 description 2
- KNVSHMGKPBFOIS-UHFFFAOYSA-N [4-bis(4-methylphenyl)phosphanyl-3,3-dimethylpentan-2-yl]-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C)C(C)(C)C(C)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 KNVSHMGKPBFOIS-UHFFFAOYSA-N 0.000 description 2
- NIMLQPWOYIZMGR-UHFFFAOYSA-N [4-bis(4-methylphenyl)phosphanyl-3-ethyl-3-methylpentan-2-yl]-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C)C(C)(CC)C(C)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 NIMLQPWOYIZMGR-UHFFFAOYSA-N 0.000 description 2
- OYMKXLXREBNETC-UHFFFAOYSA-N [4-bis(4-methylphenyl)phosphanyl-3-ethylpentan-2-yl]-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C)C(CC)C(C)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 OYMKXLXREBNETC-UHFFFAOYSA-N 0.000 description 2
- VCHDBLPQYJAQSQ-UHFFFAOYSA-N [5-(diphenylphosphanylmethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl-diphenylphosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CC1OC(C)(C)OC1CP(C=1C=CC=CC=1)C1=CC=CC=C1 VCHDBLPQYJAQSQ-UHFFFAOYSA-N 0.000 description 2
- UVNZNIGDKACWAA-UHFFFAOYSA-N [Ru].C1CC=CCCC=C1 Chemical compound [Ru].C1CC=CCCC=C1 UVNZNIGDKACWAA-UHFFFAOYSA-N 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- AKGGYBADQZYZPD-UHFFFAOYSA-N benzylacetone Chemical compound CC(=O)CCC1=CC=CC=C1 AKGGYBADQZYZPD-UHFFFAOYSA-N 0.000 description 2
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical group C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 2
- WIWBLJMBLGWSIN-UHFFFAOYSA-L dichlorotris(triphenylphosphine)ruthenium(ii) Chemical compound [Cl-].[Cl-].[Ru+2].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 WIWBLJMBLGWSIN-UHFFFAOYSA-L 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- YUWFEBAXEOLKSG-UHFFFAOYSA-N hexamethylbenzene Chemical compound CC1=C(C)C(C)=C(C)C(C)=C1C YUWFEBAXEOLKSG-UHFFFAOYSA-N 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000002198 insoluble material Substances 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 150000003003 phosphines Chemical class 0.000 description 2
- 238000001394 phosphorus-31 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- YAYGSLOSTXKUBW-UHFFFAOYSA-N ruthenium(2+) Chemical compound [Ru+2] YAYGSLOSTXKUBW-UHFFFAOYSA-N 0.000 description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 2
- PSQYTAPXSHCGMF-BQYQJAHWSA-N β-ionone Chemical compound CC(=O)\C=C\C1=C(C)CCCC1(C)C PSQYTAPXSHCGMF-BQYQJAHWSA-N 0.000 description 2
- SFEOKXHPFMOVRM-UHFFFAOYSA-N (+)-(S)-gamma-ionone Natural products CC(=O)C=CC1C(=C)CCCC1(C)C SFEOKXHPFMOVRM-UHFFFAOYSA-N 0.000 description 1
- PAORVUMOXXAMPL-VIFPVBQESA-N (2r)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoyl chloride Chemical compound CO[C@@](C(Cl)=O)(C(F)(F)F)C1=CC=CC=C1 PAORVUMOXXAMPL-VIFPVBQESA-N 0.000 description 1
- WDYGPMAMBXJESZ-SFHVURJKSA-N (2s)-1,1-bis(4-methoxyphenyl)-3-methylbutane-1,2-diamine Chemical compound C1=CC(OC)=CC=C1C(N)([C@@H](N)C(C)C)C1=CC=C(OC)C=C1 WDYGPMAMBXJESZ-SFHVURJKSA-N 0.000 description 1
- CXVHFAAZDBQQEE-UHFFFAOYSA-N 1,1-bis(4-methoxyphenyl)-3-phenylpropane-1,2-diamine Chemical compound C1=CC(OC)=CC=C1C(N)(C=1C=CC(OC)=CC=1)C(N)CC1=CC=CC=C1 CXVHFAAZDBQQEE-UHFFFAOYSA-N 0.000 description 1
- RYEKIQZUTHKUKD-UHFFFAOYSA-N 1,1-bis(4-methoxyphenyl)-4-methylpentane-1,2-diamine Chemical compound C1=CC(OC)=CC=C1C(N)(C(N)CC(C)C)C1=CC=C(OC)C=C1 RYEKIQZUTHKUKD-UHFFFAOYSA-N 0.000 description 1
- FUIAQGXJJSEAJH-UHFFFAOYSA-N 1,1-bis(4-methoxyphenyl)propane-1,2-diamine Chemical compound C1=CC(OC)=CC=C1C(N)(C(C)N)C1=CC=C(OC)C=C1 FUIAQGXJJSEAJH-UHFFFAOYSA-N 0.000 description 1
- CJLVEEKBJGYLAZ-UHFFFAOYSA-N 1,1-dinaphthalen-1-ylpropane-1,2-diamine Chemical compound C1=CC=C2C(C(N)(C=3C4=CC=CC=C4C=CC=3)C(N)C)=CC=CC2=C1 CJLVEEKBJGYLAZ-UHFFFAOYSA-N 0.000 description 1
- OWUQWDCZCOJEKU-UHFFFAOYSA-N 1,1-diphenylpropane-1,2-diamine Chemical compound C=1C=CC=CC=1C(N)(C(N)C)C1=CC=CC=C1 OWUQWDCZCOJEKU-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- RIFKADJTWUGDOV-UHFFFAOYSA-N 1-cyclohexylethanone Chemical compound CC(=O)C1CCCCC1 RIFKADJTWUGDOV-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- KZJRKRQSDZGHEC-UHFFFAOYSA-N 2,2,2-trifluoro-1-phenylethanone Chemical compound FC(F)(F)C(=O)C1=CC=CC=C1 KZJRKRQSDZGHEC-UHFFFAOYSA-N 0.000 description 1
- 229940087189 2,2,2-trifluoroacetophenone Drugs 0.000 description 1
- JITRCUREWFPMMJ-UHFFFAOYSA-N 2,3-dimethylbutane-1,1-diamine Chemical compound CC(C)C(C)C(N)N JITRCUREWFPMMJ-UHFFFAOYSA-N 0.000 description 1
- AJKVQEKCUACUMD-UHFFFAOYSA-N 2-Acetylpyridine Chemical compound CC(=O)C1=CC=CC=N1 AJKVQEKCUACUMD-UHFFFAOYSA-N 0.000 description 1
- BTHBTTSIBCWHHH-UHFFFAOYSA-N 2-[4-(2-methylpropyl)phenyl]prop-2-enoic acid Chemical compound CC(C)CC1=CC=C(C(=C)C(O)=O)C=C1 BTHBTTSIBCWHHH-UHFFFAOYSA-N 0.000 description 1
- XODAOBAZOQSFDS-UHFFFAOYSA-N 2-acetamido-3-phenylprop-2-enoic acid Chemical compound CC(=O)NC(C(O)=O)=CC1=CC=CC=C1 XODAOBAZOQSFDS-UHFFFAOYSA-N 0.000 description 1
- IEMMBWWQXVXBEU-UHFFFAOYSA-N 2-acetylfuran Chemical compound CC(=O)C1=CC=CO1 IEMMBWWQXVXBEU-UHFFFAOYSA-N 0.000 description 1
- JMMZCWZIJXAGKW-UHFFFAOYSA-N 2-methylpent-2-ene Chemical compound CCC=C(C)C JMMZCWZIJXAGKW-UHFFFAOYSA-N 0.000 description 1
- WMOCSBSDPNLVAZ-UHFFFAOYSA-N 3-methyl-1,1-dinaphthalen-1-ylbutane-1,2-diamine Chemical compound C1=CC=C2C(C(N)(C=3C4=CC=CC=C4C=CC=3)C(N)C(C)C)=CC=CC2=C1 WMOCSBSDPNLVAZ-UHFFFAOYSA-N 0.000 description 1
- UGYCWJKLMOREKO-UHFFFAOYSA-N 3-methyl-1,1-diphenylbutane-1,2-diamine Chemical compound C=1C=CC=CC=1C(N)(C(N)C(C)C)C1=CC=CC=C1 UGYCWJKLMOREKO-UHFFFAOYSA-N 0.000 description 1
- YEKVEZIQWSQYKZ-UHFFFAOYSA-N 3-methylpentyl-bis(4-methylphenyl)phosphane Chemical compound C1(=CC=C(C=C1)P(C1=CC=C(C=C1)C)CCC(CC)C)C YEKVEZIQWSQYKZ-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- OHMDCKMTIZTPKB-UHFFFAOYSA-N 4-methyl-1,1-dinaphthalen-1-ylpentane-1,2-diamine Chemical compound C1=CC=C2C(C(N)(C=3C4=CC=CC=C4C=CC=3)C(N)CC(C)C)=CC=CC2=C1 OHMDCKMTIZTPKB-UHFFFAOYSA-N 0.000 description 1
- PEXFGZJGEXXSBE-UHFFFAOYSA-N 4-methyl-1,1-diphenylpentane-1,2-diamine Chemical compound C=1C=CC=CC=1C(N)(C(N)CC(C)C)C1=CC=CC=C1 PEXFGZJGEXXSBE-UHFFFAOYSA-N 0.000 description 1
- 241001136792 Alle Species 0.000 description 1
- 241000234282 Allium Species 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229910021603 Ruthenium iodide Inorganic materials 0.000 description 1
- HIOCAISZRXEMPQ-UHFFFAOYSA-N [2-[bis(3,5-dimethylphenyl)phosphanyl-phenylmethyl]-2,3-dimethyl-1-phenylbutyl]-bis(3,5-dimethylphenyl)phosphane Chemical compound C=1C(C)=CC(C)=CC=1P(C=1C=C(C)C=C(C)C=1)C(C=1C=CC=CC=1)C(C)(C(C)C)C(C=1C=CC=CC=1)P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 HIOCAISZRXEMPQ-UHFFFAOYSA-N 0.000 description 1
- IKPDQIDCIKVOSY-UHFFFAOYSA-N [2-[bis(3,5-dimethylphenyl)phosphanyl-phenylmethyl]-2-ethyl-3-methyl-1-phenylbutyl]-bis(3,5-dimethylphenyl)phosphane Chemical compound C=1C(C)=CC(C)=CC=1P(C=1C=C(C)C=C(C)C=1)C(C=1C=CC=CC=1)C(C(C)C)(CC)C(C=1C=CC=CC=1)P(C=1C=C(C)C=C(C)C=1)C1=CC(C)=CC(C)=C1 IKPDQIDCIKVOSY-UHFFFAOYSA-N 0.000 description 1
- KXGRYZVGWIWQOC-UHFFFAOYSA-N [2-[bis(4-methylphenyl)phosphanyl-phenylmethyl]-2-ethyl-1-phenylbutyl]-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C=1C=CC=CC=1)C(CC)(CC)C(C=1C=CC=CC=1)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 KXGRYZVGWIWQOC-UHFFFAOYSA-N 0.000 description 1
- WBTDKJGJTWJAQP-UHFFFAOYSA-N [2-[bis(4-methylphenyl)phosphanyl-phenylmethyl]-2-methyl-1-phenylpentyl]-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C=1C=CC=CC=1)C(C)(CCC)C(C=1C=CC=CC=1)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 WBTDKJGJTWJAQP-UHFFFAOYSA-N 0.000 description 1
- NPXANIULGSLJDK-UHFFFAOYSA-N [2-[bis(4-methylphenyl)phosphanyl-phenylmethyl]-3-methyl-1-phenyl-2-propan-2-ylbutyl]-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C=1C=CC=CC=1)C(C(C)C)(C(C)C)C(C=1C=CC=CC=1)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 NPXANIULGSLJDK-UHFFFAOYSA-N 0.000 description 1
- BXECUPNQMWUCAM-UHFFFAOYSA-N [2-[diphenylphosphanyl(phenyl)methyl]-1-phenyl-2-propylpentyl]-diphenylphosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(C=1C=CC=CC=1)C(CCC)(CCC)C(C=1C=CC=CC=1)P(C=1C=CC=CC=1)C1=CC=CC=C1 BXECUPNQMWUCAM-UHFFFAOYSA-N 0.000 description 1
- XCWYZIXPSHNMRA-UHFFFAOYSA-N [3-[1-bis(4-methylphenyl)phosphanylethyl]-3-propan-2-ylhexan-2-yl]-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C)C(C(C)C)(CCC)C(C)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 XCWYZIXPSHNMRA-UHFFFAOYSA-N 0.000 description 1
- ZXKFDTZODVDYED-UHFFFAOYSA-N [3-[1-bis(4-methylphenyl)phosphanylethyl]-4-methyl-3-propan-2-ylpentan-2-yl]-bis(4-methylphenyl)phosphane Chemical compound C=1C=C(C)C=CC=1P(C=1C=CC(C)=CC=1)C(C)C(C(C)C)(C(C)C)C(C)P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZXKFDTZODVDYED-UHFFFAOYSA-N 0.000 description 1
- QSKODNPGIWZAFX-UHFFFAOYSA-N [3-bis(4-methylphenyl)phosphanyl-2,2-dimethyl-1,3-diphenylpropyl]-bis(4-methylphenyl)phosphane Chemical compound C1=CC(C)=CC=C1P(C=1C=CC(C)=CC=1)C(C(C)(C)C(P(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 QSKODNPGIWZAFX-UHFFFAOYSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- QVYARBLCAHCSFJ-UHFFFAOYSA-N butane-1,1-diamine Chemical compound CCCC(N)N QVYARBLCAHCSFJ-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- JIXOCHSERUXVMW-UHFFFAOYSA-M chlororuthenium Chemical compound [Ru]Cl JIXOCHSERUXVMW-UHFFFAOYSA-M 0.000 description 1
- VHCQWQAYVBRQQC-UHFFFAOYSA-N cyclobutane-1,2-diamine Chemical compound NC1CCC1N VHCQWQAYVBRQQC-UHFFFAOYSA-N 0.000 description 1
- YMHQVDAATAEZLO-UHFFFAOYSA-N cyclohexane-1,1-diamine Chemical class NC1(N)CCCCC1 YMHQVDAATAEZLO-UHFFFAOYSA-N 0.000 description 1
- SSJXIUAHEKJCMH-UHFFFAOYSA-N cyclohexane-1,2-diamine Chemical compound NC1CCCCC1N SSJXIUAHEKJCMH-UHFFFAOYSA-N 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- ZWWQRMFIZFPUAA-UHFFFAOYSA-N dimethyl 2-methylidenebutanedioate Chemical compound COC(=O)CC(=C)C(=O)OC ZWWQRMFIZFPUAA-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- USKHBABPFFAKJD-UHFFFAOYSA-N methyl 2-acetamido-3-phenylprop-2-enoate Chemical compound COC(=O)C(NC(C)=O)=CC1=CC=CC=C1 USKHBABPFFAKJD-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- NOUUUQMKVOUUNR-UHFFFAOYSA-N n,n'-diphenylethane-1,2-diamine Chemical compound C=1C=CC=CC=1NCCNC1=CC=CC=C1 NOUUUQMKVOUUNR-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- GTCCGKPBSJZVRZ-UHFFFAOYSA-N pentane-2,4-diol Chemical compound CC(O)CC(C)O GTCCGKPBSJZVRZ-UHFFFAOYSA-N 0.000 description 1
- DCLNTMGZLBVLNZ-UHFFFAOYSA-N phosphane;ruthenium(2+) Chemical class P.P.[Ru+2] DCLNTMGZLBVLNZ-UHFFFAOYSA-N 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- GGHDAUPFEBTORZ-UHFFFAOYSA-N propane-1,1-diamine Chemical compound CCC(N)N GGHDAUPFEBTORZ-UHFFFAOYSA-N 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- WYRXRHOISWEUST-UHFFFAOYSA-K ruthenium(3+);tribromide Chemical compound [Br-].[Br-].[Br-].[Ru+3] WYRXRHOISWEUST-UHFFFAOYSA-K 0.000 description 1
- LJZVDOUZSMHXJH-UHFFFAOYSA-K ruthenium(3+);triiodide Chemical compound [Ru+3].[I-].[I-].[I-] LJZVDOUZSMHXJH-UHFFFAOYSA-K 0.000 description 1
- YBCAZPLXEGKKFM-UHFFFAOYSA-K ruthenium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Ru+3] YBCAZPLXEGKKFM-UHFFFAOYSA-K 0.000 description 1
- 150000003333 secondary alcohols Chemical group 0.000 description 1
- 238000011924 stereoselective hydrogenation Methods 0.000 description 1
- 238000011916 stereoselective reduction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 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
- C07F15/0053—Ruthenium compounds without a metal-carbon linkage
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Furan Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001401170 | 2001-12-28 | ||
| JP2001401170 | 2001-12-28 | ||
| JP2002248058 | 2002-08-28 | ||
| JP2002248058A JP3566955B2 (ja) | 2001-12-28 | 2002-08-28 | 新規ルテニウム錯体およびこれを触媒として用いるアルコール化合物の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60218807D1 DE60218807D1 (de) | 2007-04-26 |
| DE60218807T2 true DE60218807T2 (de) | 2007-12-06 |
Family
ID=26625402
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60218807T Expired - Lifetime DE60218807T2 (de) | 2001-12-28 | 2002-12-23 | Rutheniumkomplexe und deren Verwendung zur Herstellung von Alkoholen |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US6790973B2 (enExample) |
| EP (1) | EP1323724B1 (enExample) |
| JP (1) | JP3566955B2 (enExample) |
| CA (1) | CA2414265A1 (enExample) |
| DE (1) | DE60218807T2 (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004101580A1 (ja) | 2003-05-19 | 2004-11-25 | Takeda Pharmaceutical Company Limited | ホスフィン-ボラン錯体の製造法 |
| GB0316439D0 (en) | 2003-07-15 | 2003-08-20 | Johnson Matthey Plc | Catalysts |
| DE602004030129D1 (de) * | 2003-07-31 | 2010-12-30 | Basf Se | Insektenfalle sowie verfahren zum fangen und aufbewahren von schadinsekten |
| ATE509024T1 (de) | 2003-08-13 | 2011-05-15 | Takasago Perfumery Co Ltd | Neuer übergangsmetallkomplex und verfahren zur herstellung von optisch aktivem alkohol mit dem komplex |
| JP5078608B2 (ja) | 2005-03-30 | 2012-11-21 | 関東化学株式会社 | 光学活性キヌクリジノール類の製造方法 |
| MX2009000616A (es) * | 2006-07-27 | 2009-01-28 | Hoffmann La Roche | Hidrogenacion asimetrica de 1,1,1-trifluoroacetona. |
| JP5172124B2 (ja) | 2006-09-29 | 2013-03-27 | 関東化学株式会社 | ２位に置換基を有する光学活性キヌクリジノール類の製造方法 |
| CN101541716B (zh) * | 2006-11-27 | 2012-10-03 | 弗门尼舍有限公司 | 通过钌/二齿配位体的络合物进行的酯的氢化 |
| CA2703671A1 (en) * | 2007-10-30 | 2009-05-07 | Kanata Chemical Technologies Inc. | Cationic transition metal catalysts |
| WO2009124897A1 (de) * | 2008-04-08 | 2009-10-15 | Basf Se | Komplexverbindung, enthaltend metallatom und phosphinderivat als ligand |
| JP5507931B2 (ja) * | 2009-09-01 | 2014-05-28 | 関東化学株式会社 | 芳香族複素環をもつ光学活性アルコールの製造方法 |
| DE102010002482B3 (de) | 2010-03-01 | 2012-01-05 | Technische Universität Braunschweig | Lumineszente Organometallverbindung |
| KR101808261B1 (ko) * | 2010-04-28 | 2017-12-12 | 다카사고 고료 고교 가부시키가이샤 | 루테늄 착체 및 광학적으로 활성인 알코올 화합물의 제조방법 |
| EP2578570A1 (en) * | 2011-10-07 | 2013-04-10 | Almirall, S.A. | Novel process for preparing 5-(2-{[6-(2,2-difluoro-2-phenylethoxy)hexyl]amino}-1(r)-hydroxyethyl)-8-hydroxyquinolin-2(1h)-one via novel intermediates of synthesis. |
| JP6173702B2 (ja) * | 2012-02-01 | 2017-08-02 | 国立大学法人北海道大学 | 光学活性アミン化合物の製造方法 |
| JP6437187B2 (ja) * | 2013-07-26 | 2018-12-12 | 関東化學株式会社 | 光学活性２級アルコールの製造方法 |
| CN111320591B (zh) * | 2020-03-30 | 2023-03-31 | 陕西师范大学 | 一种合成手性γ-氨基醇的方法 |
| EP4516776A4 (en) * | 2022-04-26 | 2025-08-20 | Shenzhen Catalyst Tech Co Ltd | PROCESS FOR THE UNPROTECTED ASYMMETRIC PREPARATION OF NICOTINE |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2693190B1 (fr) * | 1992-07-02 | 1994-09-23 | Elf Aquitaine | Procédé d'hydrogénation énantiosélectif de la double liaison C=O OXO. |
| JP2731377B2 (ja) | 1994-12-07 | 1998-03-25 | 科学技術振興事業団 | 光学活性アルコール類の製造方法 |
| CA2164685C (en) | 1994-12-07 | 2005-03-08 | Takeshi Ohkuma | Method for producing an alcohol |
| JP4004123B2 (ja) | 1997-12-26 | 2007-11-07 | 独立行政法人科学技術振興機構 | ルテニウム錯体を触媒とするアルコール化合物の製造方法 |
| WO2001074829A1 (en) | 2000-03-30 | 2001-10-11 | Chirotech Technology Limited | Ruthenium-diphosphine complexes and their use as catalysts |
-
2002
- 2002-08-28 JP JP2002248058A patent/JP3566955B2/ja not_active Expired - Lifetime
- 2002-12-16 CA CA002414265A patent/CA2414265A1/en not_active Abandoned
- 2002-12-23 DE DE60218807T patent/DE60218807T2/de not_active Expired - Lifetime
- 2002-12-23 EP EP02028791A patent/EP1323724B1/en not_active Expired - Lifetime
- 2002-12-27 US US10/330,501 patent/US6790973B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JP2003252884A (ja) | 2003-09-10 |
| EP1323724A3 (en) | 2003-09-24 |
| EP1323724B1 (en) | 2007-03-14 |
| CA2414265A1 (en) | 2003-06-28 |
| US6790973B2 (en) | 2004-09-14 |
| DE60218807D1 (de) | 2007-04-26 |
| US20030166978A1 (en) | 2003-09-04 |
| EP1323724A2 (en) | 2003-07-02 |
| JP3566955B2 (ja) | 2004-09-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE60218807T2 (de) | Rutheniumkomplexe und deren Verwendung zur Herstellung von Alkoholen | |
| EP0564406B1 (de) | Ferrocenyldiphosphine als Liganden für homogene Katalysatoren | |
| EP0646590B1 (de) | Mit Fluoralkyl substituierte Ferrocenyldiphosphine als Liganden für homogene Katalysatoren | |
| DE69220061T2 (de) | Herstellung von chiralen phospholanen aus chiralen zyklischen sulfaten von 1,4-diolen | |
| DE69114986T2 (de) | Eine Phosphino-Binapthyl-Verbindung und Übergangsmetall-Komplexe davon. | |
| DE69602586T2 (de) | Rutheniumkatalysatoren und deren verwendung zur asymmetrischen cyclopentenonhydrierung | |
| DE69512415T2 (de) | Heteroaromatische diphospine als chirale liganden | |
| EP0612758A1 (de) | Ferrocenyldiphosphine als Liganden für homogene Katalysatoren | |
| EP0582692B1 (de) | Diphosphinliganden | |
| DE3874627T2 (de) | Herstellungsverfahren eines optisch aktiven alkohols. | |
| DE3784222T2 (de) | Ruthenium-phosphin-komplex-katalysatoren. | |
| DE69919256T2 (de) | Rutheniumphosphinkomplex und Verfahren zur deren Herstellung | |
| DE69111358T2 (de) | Optisch aktiver Iridiumphosphinkomplex und dessen Verwendung zur katalytischen Herstellung von optisch aktiven Alkoholen. | |
| DE102007022389A1 (de) | Ruthenium-Komplexe mit (P-P)-koordinierten Ferrocenyl-diphosphinliganden, Verfahren zu ihrer Herstellung sowie ihre Anwendung in der homogenen Katalyse | |
| DE3000445C2 (de) | Rhodiumkomplexe und deren Verwendung | |
| EP2107065A1 (de) | Ruthenium-Komplexe mit (P-P)-koordinierten Di-Phosphor-Donorliganden sowie Verfahren zu ihrer Herstellung | |
| DE3153690C2 (enExample) | ||
| WO2001009147A1 (de) | Neue chirale phosphorliganden und ihre verwendung in der herstellung optisch aktiver produkte | |
| DE69610131T2 (de) | Optisch aktive asymmetrische Diphosphine und Verfahren zur Herstellung optisch aktiver Substanzen in ihrer Anwesenheit | |
| DE69318666T2 (de) | Verfahren zur Herstellung von optisch aktiven gamma-Hydroxyketonen | |
| DE60203360T2 (de) | Neuer asymmetrischer Phosphin-Ligand | |
| DE60318533T2 (de) | Phosphinverbindungen, Übergangsmetallkomlexe mit den Verbindungen, die als Liganden darin enthalten sind, und asymmetrische Synthesekatalysatoren mit diesen Komplexen | |
| EP1119574B1 (de) | Substituierte isophosphindoline und ihre verwendung | |
| DE4103759A1 (de) | Verfahren zur herstellung von (s)- und (r)-alpha-aminosaeurederivaten durch asymmetrische hydrierung | |
| EP1636243B1 (de) | Chirale liganden zur anwendung in asymmetrischen synthesen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition |