JP2011132165A - シラノール基含有オレフィン化合物の製造方法 - Google Patents
シラノール基含有オレフィン化合物の製造方法 Download PDFInfo
- Publication number
- JP2011132165A JP2011132165A JP2009292506A JP2009292506A JP2011132165A JP 2011132165 A JP2011132165 A JP 2011132165A JP 2009292506 A JP2009292506 A JP 2009292506A JP 2009292506 A JP2009292506 A JP 2009292506A JP 2011132165 A JP2011132165 A JP 2011132165A
- Authority
- JP
- Japan
- Prior art keywords
- group
- triflate
- olefin compound
- substituted
- compound represented
- 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.)
- Pending
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- -1 olefin compound Chemical class 0.000 title claims abstract description 44
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 title claims abstract description 27
- 125000005372 silanol group Chemical group 0.000 title claims abstract description 23
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 25
- 239000003054 catalyst Substances 0.000 claims abstract description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
- 150000003624 transition metals Chemical class 0.000 claims abstract description 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- 150000002367 halogens Chemical class 0.000 claims abstract description 9
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 9
- 125000001424 substituent group Chemical group 0.000 claims abstract description 7
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 4
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 claims abstract description 4
- 125000005843 halogen group Chemical group 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 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 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 239000003446 ligand Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 150000001336 alkenes Chemical class 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 239000011574 phosphorus Substances 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 150000002430 hydrocarbons Chemical group 0.000 abstract description 8
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 8
- 125000005504 styryl group Chemical group 0.000 description 8
- 238000001269 time-of-flight mass spectrometry Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 6
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 5
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 5
- BGGDZDRRHQTSPV-UHFFFAOYSA-N 4-ethenyl-n,n-diphenylaniline Chemical compound C1=CC(C=C)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 BGGDZDRRHQTSPV-UHFFFAOYSA-N 0.000 description 4
- NUQVOOIGWRPOMR-UHFFFAOYSA-N CC(C)[SiH](C1=CC=CC=C1O)C(C)C Chemical compound CC(C)[SiH](C1=CC=CC=C1O)C(C)C NUQVOOIGWRPOMR-UHFFFAOYSA-N 0.000 description 4
- 239000006087 Silane Coupling Agent Substances 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YVXCIBYFVZRYPB-UHFFFAOYSA-N C1CCC(C1)[SiH](C2CCCC2)C3=CC=CC(=C3O)OS(=O)(=O)C(F)(F)F Chemical compound C1CCC(C1)[SiH](C2CCCC2)C3=CC=CC(=C3O)OS(=O)(=O)C(F)(F)F YVXCIBYFVZRYPB-UHFFFAOYSA-N 0.000 description 3
- GUSRYLJQOGIXET-UHFFFAOYSA-N C1CCC(CC1)C[SiH2]C2=C(C=CC(=C2)O)OS(=O)(=O)C(F)(F)F Chemical compound C1CCC(CC1)C[SiH2]C2=C(C=CC(=C2)O)OS(=O)(=O)C(F)(F)F GUSRYLJQOGIXET-UHFFFAOYSA-N 0.000 description 3
- JTXLHFWCHDCWCJ-UHFFFAOYSA-N C1CCC(CC1)[SiH](C2CCCCC2)C3=CC=CC(=C3O)OS(=O)(=O)C(F)(F)F Chemical compound C1CCC(CC1)[SiH](C2CCCCC2)C3=CC=CC(=C3O)OS(=O)(=O)C(F)(F)F JTXLHFWCHDCWCJ-UHFFFAOYSA-N 0.000 description 3
- ALDATRUPMNKBHE-UHFFFAOYSA-N CC(C)(C)C1=C(C(=C(C=C1)OS(=O)(=O)C(F)(F)F)[SiH2]C)O Chemical compound CC(C)(C)C1=C(C(=C(C=C1)OS(=O)(=O)C(F)(F)F)[SiH2]C)O ALDATRUPMNKBHE-UHFFFAOYSA-N 0.000 description 3
- UZHUJPMDYHFVJS-UHFFFAOYSA-N CC(C)(C)C1=C(C=CC(=C1[SiH2]C)OS(=O)(=O)C(F)(F)F)O Chemical compound CC(C)(C)C1=C(C=CC(=C1[SiH2]C)OS(=O)(=O)C(F)(F)F)O UZHUJPMDYHFVJS-UHFFFAOYSA-N 0.000 description 3
- IDYYHCSCMQZQJJ-UHFFFAOYSA-N CC(C)[SiH](C1=C(C=CC(=C1)O)OS(=O)(=O)C(F)(F)F)C(C)C Chemical compound CC(C)[SiH](C1=C(C=CC(=C1)O)OS(=O)(=O)C(F)(F)F)C(C)C IDYYHCSCMQZQJJ-UHFFFAOYSA-N 0.000 description 3
- FBUZOCAMXKKDFQ-UHFFFAOYSA-N CC(C)[SiH](C1=C(C=CC=C1OS(=O)(=O)C(F)(F)F)O)C(C)C Chemical compound CC(C)[SiH](C1=C(C=CC=C1OS(=O)(=O)C(F)(F)F)O)C(C)C FBUZOCAMXKKDFQ-UHFFFAOYSA-N 0.000 description 3
- IAWOXSRUWLFKLI-UHFFFAOYSA-N CC(C)[SiH](C1=CC=CC(=C1O)OS(=O)(=O)C(F)(F)F)C(C)C Chemical compound CC(C)[SiH](C1=CC=CC(=C1O)OS(=O)(=O)C(F)(F)F)C(C)C IAWOXSRUWLFKLI-UHFFFAOYSA-N 0.000 description 3
- OBYYNKWTNBZCET-UHFFFAOYSA-N CCC(C)[SiH](C(C)CC)C(C=C(C=C1)O)=C1OS(C(F)(F)F)(=O)=O Chemical compound CCC(C)[SiH](C(C)CC)C(C=C(C=C1)O)=C1OS(C(F)(F)F)(=O)=O OBYYNKWTNBZCET-UHFFFAOYSA-N 0.000 description 3
- YCJOBJKUCURENO-UHFFFAOYSA-N CCC(C)[SiH](C(C)CC)C=CC1=CC(O)=CC=C1 Chemical compound CCC(C)[SiH](C(C)CC)C=CC1=CC(O)=CC=C1 YCJOBJKUCURENO-UHFFFAOYSA-N 0.000 description 3
- NNZQKGKFSBDOOI-UHFFFAOYSA-N CCC(C)[SiH](C1=C(C=CC=C1OS(=O)(=O)C(F)(F)F)O)C(C)CC Chemical compound CCC(C)[SiH](C1=C(C=CC=C1OS(=O)(=O)C(F)(F)F)O)C(C)CC NNZQKGKFSBDOOI-UHFFFAOYSA-N 0.000 description 3
- MZFKRDDXWLSOHL-UHFFFAOYSA-N CCC(C)[SiH](C1=CC=CC(=C1O)OS(=O)(=O)C(F)(F)F)C(C)CC Chemical compound CCC(C)[SiH](C1=CC=CC(=C1O)OS(=O)(=O)C(F)(F)F)C(C)CC MZFKRDDXWLSOHL-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
- WKWKGCXQCFAJKJ-UHFFFAOYSA-N OC(C=C1)=CC([SiH](C2CCCC2)C2CCCC2)=C1OS(C(F)(F)F)(=O)=O Chemical compound OC(C=C1)=CC([SiH](C2CCCC2)C2CCCC2)=C1OS(C(F)(F)F)(=O)=O WKWKGCXQCFAJKJ-UHFFFAOYSA-N 0.000 description 3
- HWEVVPWNNQIABS-UHFFFAOYSA-N OC1=C(C=C([SiH2]C)C(C)(C)C)C=CC=C1 Chemical compound OC1=C(C=C([SiH2]C)C(C)(C)C)C=CC=C1 HWEVVPWNNQIABS-UHFFFAOYSA-N 0.000 description 3
- MAYYGIOMHKYHFX-UHFFFAOYSA-N OC1=C(C=C[SiH2]CC2CCCCC2)C=CC=C1 Chemical compound OC1=C(C=C[SiH2]CC2CCCCC2)C=CC=C1 MAYYGIOMHKYHFX-UHFFFAOYSA-N 0.000 description 3
- RYKNSHZDYDHPQZ-UHFFFAOYSA-N OC1=C(C=C[SiH](C(C)CC)C(C)CC)C=CC=C1 Chemical compound OC1=C(C=C[SiH](C(C)CC)C(C)CC)C=CC=C1 RYKNSHZDYDHPQZ-UHFFFAOYSA-N 0.000 description 3
- UKIFQHTWFSFTFT-UHFFFAOYSA-N OC1=C(C=C[SiH](C2CCCCC2)C2CCCCC2)C=CC=C1 Chemical compound OC1=C(C=C[SiH](C2CCCCC2)C2CCCCC2)C=CC=C1 UKIFQHTWFSFTFT-UHFFFAOYSA-N 0.000 description 3
- UZWAEHSKEAOEDN-UHFFFAOYSA-N OC1=CC=C(C=C([SiH2]C)C(C)(C)C)C=C1 Chemical compound OC1=CC=C(C=C([SiH2]C)C(C)(C)C)C=C1 UZWAEHSKEAOEDN-UHFFFAOYSA-N 0.000 description 3
- QXNNHLYMMFRIDW-UHFFFAOYSA-N OC1=CC=C(C=C[SiH](C(C)C)C(C)C)C=C1 Chemical compound OC1=CC=C(C=C[SiH](C(C)C)C(C)C)C=C1 QXNNHLYMMFRIDW-UHFFFAOYSA-N 0.000 description 3
- MLBCVEHWMALMOG-UHFFFAOYSA-N OC1=CC=C(C=C[SiH](C(C)CC)C(C)CC)C=C1 Chemical compound OC1=CC=C(C=C[SiH](C(C)CC)C(C)CC)C=C1 MLBCVEHWMALMOG-UHFFFAOYSA-N 0.000 description 3
- DZRMYSWUCTVXKO-UHFFFAOYSA-N OC1=CC=C(C=C[SiH](C2CCCC2)C2CCCC2)C=C1 Chemical compound OC1=CC=C(C=C[SiH](C2CCCC2)C2CCCC2)C=C1 DZRMYSWUCTVXKO-UHFFFAOYSA-N 0.000 description 3
- KNRTVBAJJMXTFR-UHFFFAOYSA-N OC1=CC=CC(OS(C(F)(F)F)(=O)=O)=C1[SiH2]CC1CCCCC1 Chemical compound OC1=CC=CC(OS(C(F)(F)F)(=O)=O)=C1[SiH2]CC1CCCCC1 KNRTVBAJJMXTFR-UHFFFAOYSA-N 0.000 description 3
- KQIRUZPHXFUBJY-UHFFFAOYSA-N OC=1C=C(C=C[SiH2]CC2CCCCC2)C=CC1 Chemical compound OC=1C=C(C=C[SiH2]CC2CCCCC2)C=CC1 KQIRUZPHXFUBJY-UHFFFAOYSA-N 0.000 description 3
- JORWICKGPWTJFH-UHFFFAOYSA-N OC=1C=C(C=C[SiH](C(C)C)C(C)C)C=CC1 Chemical compound OC=1C=C(C=C[SiH](C(C)C)C(C)C)C=CC1 JORWICKGPWTJFH-UHFFFAOYSA-N 0.000 description 3
- LTRCATATIZEYIZ-UHFFFAOYSA-N OC=1C=C(C=C[SiH](C2CCCCC2)C2CCCCC2)C=CC1 Chemical compound OC=1C=C(C=C[SiH](C2CCCCC2)C2CCCCC2)C=CC1 LTRCATATIZEYIZ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 229910052707 ruthenium Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 2
- AHNYHYYIECFEQY-UHFFFAOYSA-N 2-phenylethenylsilicon Chemical compound [Si]C=CC1=CC=CC=C1 AHNYHYYIECFEQY-UHFFFAOYSA-N 0.000 description 2
- CMNOWTOZRJDHBB-UHFFFAOYSA-N C1CCC(C1)[SiH](C2CCCC2)C3=CC=CC=C3O Chemical compound C1CCC(C1)[SiH](C2CCCC2)C3=CC=CC=C3O CMNOWTOZRJDHBB-UHFFFAOYSA-N 0.000 description 2
- SWSVYYSEVIHBHF-UHFFFAOYSA-N C1CCC(CC1)[SiH](C2CCCCC2)C3=C(C=CC(=C3)O)OS(=O)(=O)C(F)(F)F Chemical compound C1CCC(CC1)[SiH](C2CCCCC2)C3=C(C=CC(=C3)O)OS(=O)(=O)C(F)(F)F SWSVYYSEVIHBHF-UHFFFAOYSA-N 0.000 description 2
- CYRKTJKMNILTDE-UHFFFAOYSA-N CC(C)(C)C1=C(C(=C(C=C1)OS(=O)(=O)C(F)(F)F)O)[SiH2]C Chemical compound CC(C)(C)C1=C(C(=C(C=C1)OS(=O)(=O)C(F)(F)F)O)[SiH2]C CYRKTJKMNILTDE-UHFFFAOYSA-N 0.000 description 2
- IRHARFLHWKSNBU-UHFFFAOYSA-N CCC(C)[SiH](C1=CC=CC=C1O)C(C)CC Chemical compound CCC(C)[SiH](C1=CC=CC=C1O)C(C)CC IRHARFLHWKSNBU-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- PWWSSEZENPGIMX-UHFFFAOYSA-N OC1=C(C=C[SiH](C(C)C)C(C)C)C=CC=C1 Chemical compound OC1=C(C=C[SiH](C(C)C)C(C)C)C=CC=C1 PWWSSEZENPGIMX-UHFFFAOYSA-N 0.000 description 2
- AFVZCAYHDYANOO-UHFFFAOYSA-N OC1=CC(=C(C=C1)Br)[SiH](C(C)C)C(C)C Chemical compound OC1=CC(=C(C=C1)Br)[SiH](C(C)C)C(C)C AFVZCAYHDYANOO-UHFFFAOYSA-N 0.000 description 2
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- LYURHTBFZVURIB-UHFFFAOYSA-N OC1=CC=CC(Br)=C1[SiH](C1CCCC1)C1CCCC1 Chemical compound OC1=CC=CC(Br)=C1[SiH](C1CCCC1)C1CCCC1 LYURHTBFZVURIB-UHFFFAOYSA-N 0.000 description 2
- FBLHHGKNOMKWRY-UHFFFAOYSA-N OC1=CC=CC(OS(C(F)(F)F)(=O)=O)=C1[SiH](C1CCCC1)C1CCCC1 Chemical compound OC1=CC=CC(OS(C(F)(F)F)(=O)=O)=C1[SiH](C1CCCC1)C1CCCC1 FBLHHGKNOMKWRY-UHFFFAOYSA-N 0.000 description 2
- UCIGSEBAACAJBP-UHFFFAOYSA-N OC1=CC=CC(OS(C(F)(F)F)(=O)=O)=C1[SiH](C1CCCCC1)C1CCCCC1 Chemical compound OC1=CC=CC(OS(C(F)(F)F)(=O)=O)=C1[SiH](C1CCCCC1)C1CCCCC1 UCIGSEBAACAJBP-UHFFFAOYSA-N 0.000 description 2
- FFYSRJBAAYDXFQ-UHFFFAOYSA-N OC=1C(=C(C=CC1)Br)[SiH](C(C)C)C(C)C Chemical compound OC=1C(=C(C=CC1)Br)[SiH](C(C)C)C(C)C FFYSRJBAAYDXFQ-UHFFFAOYSA-N 0.000 description 2
- FTTVFFOKEVFBHF-UHFFFAOYSA-N OC=1C(=C(C=CC1)Br)[SiH](C(C)CC)C(C)CC Chemical compound OC=1C(=C(C=CC1)Br)[SiH](C(C)CC)C(C)CC FTTVFFOKEVFBHF-UHFFFAOYSA-N 0.000 description 2
- CMFAKBMBMFOCFK-UHFFFAOYSA-N OC=1C=C(C=C([SiH2]C)C(C)(C)C)C=CC1 Chemical compound OC=1C=C(C=C([SiH2]C)C(C)(C)C)C=CC1 CMFAKBMBMFOCFK-UHFFFAOYSA-N 0.000 description 2
- NKNIBXILCKPSEU-UHFFFAOYSA-N OC=1C=C(C=C[SiH](C2CCCC2)C2CCCC2)C=CC1 Chemical compound OC=1C=C(C=C[SiH](C2CCCC2)C2CCCC2)C=CC1 NKNIBXILCKPSEU-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 239000011147 inorganic material Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 125000005369 trialkoxysilyl group Chemical group 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
Abstract
(Xは炭素数1〜60の置換又は非置換の一価炭化水素基であり、炭素原子の一部がヘテロ原子で置換されていてもよい。Halはハロゲン原子又はトリフレート基を表す。nは1〜10の整数で、Yは置換又は非置換の二価の共役性置換基を示す。R1、R2はそれぞれ独立に、炭素数1〜10の置換又は非置換の一価炭化水素基を示す。)
【効果】高収率で容易にシラノール基含有オレフィン化合物が得られる。
【選択図】なし
Description
そのため、シラノール基が縮合や置換等の副反応を起こすことなく、高収率で容易にシラノールが得られる方法の開発が望まれていた。
[1]下記一般式(i)で表されるオレフィン化合物と、下記一般式(ii)で表されるハロゲン含有化合物、又は下記一般式(iii)で表されるハロゲン含有化合物と、下記一般式(iv)で表されるオレフィン化合物を、遷移金属触媒存在下で反応させることを特徴とする下記一般式(1)で表されるシラノール基含有オレフィン化合物の製造方法。
(式中、Xは炭素数1〜60の置換又は非置換の一価炭化水素基であり、炭素原子の一部がヘテロ原子で置換されていてもよい。Halはハロゲン原子又はトリフレート基を表す。nは1〜10の整数で、Yは置換又は非置換の二価の共役性置換基を示す。R1、R2はそれぞれ独立に、炭素数1〜10の置換又は非置換の一価炭化水素基を示す。)
[II]Yがフェニレン基を表し、nが1である[I]に記載のシラノール基含有オレフィン化合物の製造方法。
[III]R1、R2がメチル基、イソプロピル基、sec−ブチル基、イソブチル基、シクロペンチル基、シクロヘキシル基、tert−ブチル基から選択される[I]又は[II]記載のシラノール基含有オレフィン化合物の製造方法。
上記式(2)、(3)において、A、Bは上記した通りであり、従って、式(2)は
又は
で表すことができ、式(3)は
又は
で表すことができ、式(i)と式(ii)、式(iv)と式(iii)の化合物が反応に供される。
遷移金属触媒の使用量は、式(2)の化合物1モルに対し0.0001〜10モル、特に0.001〜1モルが好ましい。
窒素雰囲気下、4−(ジフェニルアミノ)スチレン271.0mg(1.00mmol)、m−ヒドロキシジイソプロピルシリルブロモベンゼン286.0mg(1.00mmol)、トリエチルアミン143.3mg(1.42mmol)、2,6−ジ−tert−ブチル−4−メチルフェノール28.9mg(0.13mmol)、トリ−o−トリルホスフィン58.3mg(0.19mmol)、酢酸パラジウム31.6mg(0.14mmol)をジメチルアセトアミド7mlに加え、145℃で10時間撹拌した。得られた溶液を減圧濃縮し、水とトルエンを加えた後、分液操作により有機層を抽出した。得られた溶液を硫酸マグネシウムにより乾燥し、ロータリーエバポレーターにて減圧濃縮した後、HPLCにより精製して黄色液体308.3mgを得た。この溶液のMALDI−TOFMSスペクトルを測定した結果、m−(4−(ジフェニルアミノ)スチリル)ヒドロキシジイソプロピルシリルベンゼンであることが確認された。
MALDI−TOFMS m/z:477.2 (M+)
窒素雰囲気下、4−(ジフェニルアミノ)スチレン275.3mg(1.01mmol)、p−ヒドロキシジイソプロピルシリルブロモベンゼン290.9mg(1.02mmol)、トリエチルアミン150.6mg(1.49mmol)、2,6−ジ−tert−ブチル−4−メチルフェノール24.9mg(0.11mmol)、トリ−o−トリルホスフィン50.2mg(0.17mmol)、酢酸パラジウム12.3mg(0.06mmol)をジメチルアセトアミド7mlに加え、150℃で9時間撹拌した。この溶液のMALDI−TOFMSスペクトルを測定した結果、p−(4−(ジフェニルアミノ)スチリル)ヒドロキシジイソプロピルシリルベンゼンであることが確認された。
MALDI−TOFMS m/z:477.3 (M+)
窒素雰囲気下、4−(ジフェニルアミノ)スチレン273.6mg(1.00mmol)、m−ヒドロキシジ−sec−ブチルシリルブロモベンゼン297.5mg(0.95mmol)、トリエチルアミン149.6mg(1.48mmol)、2,6−ジ−tert−ブチル−4−メチルフェノール25.6mg(0.12mmol)、トリ−o−トリルホスフィン50.2mg(0.17mmol)、酢酸パラジウム12.1mg(0.05mmol)をジメチルアセトアミド5mlに加え、150℃で20時間撹拌した。この溶液のMALDI−TOFMSスペクトルを測定した結果、m−(4−(ジフェニルアミノ)スチリル)ヒドロキシジ−sec−ブチルシリルベンゼンであることが確認された。
MALDI−TOFMS m/z:505.2 (M+)
窒素雰囲気下、4−(ジフェニルアミノ)スチレン162.7mg(0.60mmol)、m−ヒドロキシジシクロペンチルシリルブロモベンゼン202.8mg(0.60mmol)、トリエチルアミン141.5mg(1.40mmol)、2,6−ジ−tert−ブチル−4−メチルフェノール32.5mg(0.15mmol)、トリ−o−トリルホスフィン50.2mg(0.17mmol)、酢酸パラジウム12.1mg(0.05mmol)をジメチルアセトアミド8mlに加え、150℃で8時間撹拌した。この溶液のMALDI−TOFMSスペクトルを測定した結果、m−(4−(ジフェニルアミノ)スチリル)ヒドロキシジシクロペンチルシリルベンゼンであることが確認された。
MALDI−TOFMS m/z:529.3 (M+)
Claims (7)
- 下記一般式(i)で表されるオレフィン化合物と、下記一般式(ii)で表されるハロゲン含有化合物、又は下記一般式(iii)で表されるハロゲン含有化合物と、下記一般式(iv)で表されるオレフィン化合物を、遷移金属触媒存在下で反応させることを特徴とする下記一般式(1)で表されるシラノール基含有オレフィン化合物の製造方法。
(式中、Xは炭素数1〜60の置換又は非置換の一価炭化水素基であり、炭素原子の一部がヘテロ原子で置換されていてもよい。Halはハロゲン原子又はトリフレート基を表す。nは1〜10の整数で、Yは置換又は非置換の二価の共役性置換基を示す。R1、R2はそれぞれ独立に、炭素数1〜10の置換又は非置換の一価炭化水素基を示す。) - Yがフェニレン基を表し、nが1である請求項1又は2記載のシラノール基含有オレフィン化合物の製造方法。
- R1、R2がメチル基、イソプロピル基、sec−ブチル基、イソブチル基、シクロペンチル基、シクロヘキシル基、tert−ブチル基から選択される請求項1〜4のいずれか1項記載のシラノール基含有オレフィン化合物の製造方法。
- リン化合物を配位子として添加して反応を行う請求項1〜5のいずれか1項記載のシラノール基含有オレフィン化合物の製造方法。
- 塩基を添加して反応を行う請求項1〜6のいずれか1項記載のシラノール基含有オレフィン化合物の製造方法。
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