CN104470935A - 氧杂环硅烷及其制备方法 - Google Patents
氧杂环硅烷及其制备方法 Download PDFInfo
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- CN104470935A CN104470935A CN201380037246.XA CN201380037246A CN104470935A CN 104470935 A CN104470935 A CN 104470935A CN 201380037246 A CN201380037246 A CN 201380037246A CN 104470935 A CN104470935 A CN 104470935A
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- carbon atoms
- general formula
- substituted
- oxetane
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- 238000000034 method Methods 0.000 title claims abstract description 7
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 5
- -1 methoxy, ethoxy Chemical group 0.000 claims description 33
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 16
- 239000003054 catalyst Substances 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 12
- 238000006459 hydrosilylation reaction Methods 0.000 claims description 12
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical compound C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 claims description 8
- 150000002921 oxetanes Chemical class 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 229930195733 hydrocarbon Natural products 0.000 claims description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims description 6
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 229910000077 silane Inorganic materials 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 150000004756 silanes Chemical class 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- KKAXNAVSOBXHTE-UHFFFAOYSA-N boranamine Chemical compound NB KKAXNAVSOBXHTE-UHFFFAOYSA-N 0.000 claims description 3
- BWJRMVLPCQPWGR-UHFFFAOYSA-N boron;phosphane Chemical compound [B].P BWJRMVLPCQPWGR-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 125000004122 cyclic group Chemical group 0.000 description 8
- 229910052697 platinum Inorganic materials 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- QVBWMXPWFDUXFC-UHFFFAOYSA-N bis(2-methylpent-4-en-2-yloxy)silane Chemical compound CC(C)(CC=C)O[SiH2]OC(C)(C)CC=C QVBWMXPWFDUXFC-UHFFFAOYSA-N 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- FBEIPJNQGITEBL-UHFFFAOYSA-J tetrachloroplatinum Chemical compound Cl[Pt](Cl)(Cl)Cl FBEIPJNQGITEBL-UHFFFAOYSA-J 0.000 description 5
- PFZOWZYHMHAVMJ-UHFFFAOYSA-N 2-methylpent-4-en-2-ylsilane Chemical compound CC(C)([SiH3])CC=C PFZOWZYHMHAVMJ-UHFFFAOYSA-N 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 238000007142 ring opening reaction Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- YZPNFYQRPJKWFJ-UHFFFAOYSA-N 2-methyl-1h-imidazol-1-ium;chloride Chemical compound Cl.CC1=NC=CN1 YZPNFYQRPJKWFJ-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N anhydrous n-heptane Natural products CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- HXVNBWAKAOHACI-UHFFFAOYSA-N 2,4-dimethyl-3-pentanone Chemical compound CC(C)C(=O)C(C)C HXVNBWAKAOHACI-UHFFFAOYSA-N 0.000 description 2
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 2
- UYOPRNGQFQWYER-UHFFFAOYSA-N 2-methylpent-4-en-2-ol Chemical compound CC(C)(O)CC=C UYOPRNGQFQWYER-UHFFFAOYSA-N 0.000 description 2
- NBDTZVVEDLDLSG-UHFFFAOYSA-N 4,6,6-trimethylheptan-2-yl acetate Chemical compound CC(C)(C)CC(C)CC(C)OC(C)=O NBDTZVVEDLDLSG-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- GWGGKTHSLIDRSP-UHFFFAOYSA-N chloro-methyl-(2-methylpent-4-en-2-yloxy)silane Chemical compound C[SiH](OC(C)(CC=C)C)Cl GWGGKTHSLIDRSP-UHFFFAOYSA-N 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- WDAXFOBOLVPGLV-UHFFFAOYSA-N ethyl isobutyrate Chemical compound CCOC(=O)C(C)C WDAXFOBOLVPGLV-UHFFFAOYSA-N 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].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.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 238000003797 solvolysis reaction Methods 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HNAGHMKIPMKKBB-UHFFFAOYSA-N 1-benzylpyrrolidine-3-carboxamide Chemical compound C1C(C(=O)N)CCN1CC1=CC=CC=C1 HNAGHMKIPMKKBB-UHFFFAOYSA-N 0.000 description 1
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- POMBIHTVGPLABX-UHFFFAOYSA-N 2,2,8,8-tetramethyl-1,7-dioxa-6-silaspiro[5.5]undecane Chemical compound CC1(C)CCC[Si]2(CCCC(C)(C)O2)O1 POMBIHTVGPLABX-UHFFFAOYSA-N 0.000 description 1
- UHOPWFKONJYLCF-UHFFFAOYSA-N 2-(2-sulfanylethyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCS)C(=O)C2=C1 UHOPWFKONJYLCF-UHFFFAOYSA-N 0.000 description 1
- 238000005133 29Si NMR spectroscopy Methods 0.000 description 1
- GZWWHMCARJYQTH-UHFFFAOYSA-N B.C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 Chemical compound B.C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 GZWWHMCARJYQTH-UHFFFAOYSA-N 0.000 description 1
- GBRYMKFYGMGUDD-UHFFFAOYSA-N B.C1CCCC1N(C1CCCC1)C1CCCC1 Chemical compound B.C1CCCC1N(C1CCCC1)C1CCCC1 GBRYMKFYGMGUDD-UHFFFAOYSA-N 0.000 description 1
- WXVNPYMBACBYSS-UHFFFAOYSA-N B.CN(C)CC1=CC=CC=C1 Chemical compound B.CN(C)CC1=CC=CC=C1 WXVNPYMBACBYSS-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000007848 Bronsted acid Substances 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 1
- 239000005046 Chlorosilane Substances 0.000 description 1
- XMSXQFUHVRWGNA-UHFFFAOYSA-N Decamethylcyclopentasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 XMSXQFUHVRWGNA-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229910003594 H2PtCl6.6H2O Inorganic materials 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910019029 PtCl4 Inorganic materials 0.000 description 1
- 229910008051 Si-OH Inorganic materials 0.000 description 1
- 229910006358 Si—OH Inorganic materials 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000005370 alkoxysilyl group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 229940045985 antineoplastic platinum compound Drugs 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- QSKKXNSTGHZSQB-UHFFFAOYSA-N azane;platinum(2+) Chemical class N.[Pt+2] QSKKXNSTGHZSQB-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- DSVRVHYFPPQFTI-UHFFFAOYSA-N bis(ethenyl)-methyl-trimethylsilyloxysilane;platinum Chemical class [Pt].C[Si](C)(C)O[Si](C)(C=C)C=C DSVRVHYFPPQFTI-UHFFFAOYSA-N 0.000 description 1
- CSGNXPFGEUCEIY-UHFFFAOYSA-N borane tributylphosphane Chemical compound B.CCCCP(CCCC)CCCC CSGNXPFGEUCEIY-UHFFFAOYSA-N 0.000 description 1
- WVMHLYQJPRXKLC-UHFFFAOYSA-N borane;n,n-dimethylmethanamine Chemical compound B.CN(C)C WVMHLYQJPRXKLC-UHFFFAOYSA-N 0.000 description 1
- VEWFZHAHZPVQES-UHFFFAOYSA-N boron;n,n-diethylethanamine Chemical compound [B].CCN(CC)CC VEWFZHAHZPVQES-UHFFFAOYSA-N 0.000 description 1
- UEWTUPCEHUAEOQ-UHFFFAOYSA-N boron;trimethylphosphane Chemical compound [B].CP(C)C UEWTUPCEHUAEOQ-UHFFFAOYSA-N 0.000 description 1
- QFLQJPFCNMSTJZ-UHFFFAOYSA-N boron;triphenylphosphane Chemical compound [B].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QFLQJPFCNMSTJZ-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 description 1
- 229950005499 carbon tetrachloride Drugs 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 229960001701 chloroform Drugs 0.000 description 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical class Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- UWGIJJRGSGDBFJ-UHFFFAOYSA-N dichloromethylsilane Chemical compound [SiH3]C(Cl)Cl UWGIJJRGSGDBFJ-UHFFFAOYSA-N 0.000 description 1
- QSELGNNRTDVSCR-UHFFFAOYSA-L dichloroplatinum;4-methylpyridine Chemical compound Cl[Pt]Cl.CC1=CC=NC=C1.CC1=CC=NC=C1 QSELGNNRTDVSCR-UHFFFAOYSA-L 0.000 description 1
- MROCJMGDEKINLD-UHFFFAOYSA-N dichlorosilane Chemical compound Cl[SiH2]Cl MROCJMGDEKINLD-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 150000003058 platinum compounds Chemical class 0.000 description 1
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- 125000005401 siloxanyl group Chemical group 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
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- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
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Abstract
本发明涉及通式(1)和(2)所示的氧杂环硅烷及其制备方法,其中,R1、R2、R1'、R2'、R3、R4、R3'、R4'、R5、R6、m、n以及n'如权利要求1中所定义的。
Description
技术领域
本发明涉及新型的氧杂环硅烷(硅氧杂环烷,Oxasilacyclen)以及其制备。
背景技术
DE102008000353A1描述了可交联的聚合物共混物以及其在无水硅烷交联中的应用,所述聚合物共混物中包含至少一种≡Si-O-C(R1)(R2)(R3)类型的烷氧基甲硅烷基基团。
Organic Letters 2010,12,4772-4775描述了一种通过分子内氢化硅烷化硅氧杂环己烷(Oxasilinane)和硅氧杂环庚烷(Oxasilepane)的合成。没有描述氧相邻的C原子四价取代的结构。
DE19628588A1描述了环硅烷酯及其溶剂分解产物,以及制备环硅烷酯和溶剂分解产物的方法。制备是经由氢硅烷而进行的,其经由有机氢硅烷酯阶段在氢化硅烷化反应中被转变为环状有机硅烷酯。
Tetrahedron Letters 1992,33,5037描述了使用Pt催化剂的分子内氢化硅烷化反应从而形成五元环。
DE102006048217和DE102010003108描述了环状烷氧基硅烷(cyclic alkoxysilanes)的制备。然而,在这种情况下,没有描述螺环硅烷(spirocyclic silanes)以及烷氧基取代的氧杂环硅烷(oxasilacycles)结构。也未提及通过分子内氢化硅烷化反应制备的具有氧相邻C原子四价取代的螺环氧杂环硅烷(spirocyclic oxasilacycles)以及烷氧基取代的氧杂环硅烷(oxasilacycles)
发明内容
通过本发明提供的是通式(1)和(2)的氧杂环硅烷
其中,
R1、R2、R1’,以及R2’是氢、卤素、氰基、OH、或未取代或者取代的烃氧基、酰氧基、烷氧基以及烃基,其在每种情况下具有1-50个碳原子,在其中每一种中不相邻的碳原子可由选自N、O、P以及S的杂原子取代,其中基团R1、R2、R1’、以及R2’中的两个或三个可以相互连接,
R3、R4、R3’以及R4’是未取代或者取代的在每种情况下含有1-50个碳原子的烃基,在其中每一种中不相邻的碳原子可由选自N、O、P以及S的杂原子,或高分子质量基团取代,
R5和R6为未取代或者取代的在每种情况下含有1-50个碳原子的烃基,在其中每一种中不相邻的碳原子可由选自N、O、P以及S的杂原子取代,
m为值0或1,以及
n和n’为至少1的整数值。
通式(1)和(2)的氧杂环硅烷因Si-O-C键的环状部分的存在是值得注意的,其中,C原子具有四价取代,并且在每种情况下正被讨论的化合物是具有至少一个另外的烃氧基的式(1)的螺环状化合物或式(2)的环状化合物。
未取代或者取代的烃氧基基团、酰氧基基团、烷氧基基团或者烃基基团,各自具有优选地1至12个碳原子,更特别地,1-6个碳原子。
烃基基团的实例是烷基基团,如甲基、乙基、正丙基、异丙基、1-正丁基、2-正丁基、异丁基、叔丁基、正戊基、异戊基、新戊基、叔戊基;己基基团,如正己基基团;庚基基团,如正庚基基团;辛基基团,如正辛基基团以及异辛基基团、如2,2,4-三甲基戊基基团;壬基基团,如正壬基基团;癸基基团,如正癸基基团;十二烷基基团,如正十二烷基基团;十六烷基基团,如正十六烷基基团;环烷基基团,如环戊基,环己基,环庚基基团以及甲基环己基基团;芳基基团,如苯基、萘基、蒽基以及菲基基团;烷芳基基团,如邻-、间-、对-甲苯基基团;二甲苯基基团和乙苯基基团;以及芳烷基基团,如苄基基团、α-以及β-苯乙基基团。
在烃基R3、R4、R3’、R4’、R5以及R6上的取代基可以是,例如,卤素(如氟、氯、或溴),或氰基基团。
基团R3、R4、R3’以及R4’具有优选地1至12,更特别地,1-6个碳原子。也优选的是其优选地具有(聚合)重复单元的高分子质量基团。
特别优选的基团R3,R4,R3’以及R4’是甲基、乙基、丙基、丁基、乙烯基、苯基、或者羧基基团(-C(O)OCH3)。
在通式(1)和(2)的氧杂环硅烷(oxasilacycles)中的环状部分是至少一个五元环(n,n’=1),优选地,六元环或七元环(n,n’=2,3)。
通式(1)和(2)的氧杂环硅烷具有两个环状部分(通式(1))或者一个环状部分(通式(2))。
通式(2)的氧杂环硅烷优选地具有至少一个OR5基团,其中,R5优选地是烷基或芳基。R6优选地是烷基、羰基或芳基基团,如甲基、乙基、丙基、苯基、甲氧基、乙氧基、乙酰氧基,例如。
优选的结构的实例如下:
a)n=2;R1、R2=H;R3、R4=CH3
b)n=3;R1、R2=H;R3、R4=CH3
c)n’=2;R1’、R2’=H;R3’、R4’=CH3;m=1;R5=CH3、R6=CH3
d)n’=2;R1’、R2’=H;R3’、R4’=CH3;m=1;R5=C2H5、R6=CH3
e)n’=2;R1’、R2’=H;R3’、R4’=CH3;m=1;R5=C2H5、R6=C2H5
f)n’=2;R1’、R2’=H;R3’、R4’=CH3;m=1;R5=i-C3H7、R6=CH3
g)n’=2;R1’、R2’=H;R3’、R4’=CH3;m=0;R5=CH3
h)n’=2;R1’、R2’=H;R3’、R4’=CH3;m=0;R5=C2H5
通过本发明另外提供的是一种由通式(3)的化合物制备通式(1)的氧杂环硅烷,以及由通式(4)的化合物制备通式(2)的氧杂环硅烷的方法,
其中,在氢化硅烷化催化剂存在的情况下,使通式(3)或(4)的硅烷反应。
通式(3)或(4)的硅烷可以通过使用技术人员熟悉的常规方法制备。例如,氯代硅烷可以与包含末端双键的相应醇反应,随后通过分子内氢化硅烷化实现环闭合。
通式(1)或(2)的氧杂环硅烷可以通过使用技术人员已知的氢化硅烷化催化剂的分子内氢化硅烷化而制备。给予优选的是使用铂金属或其化合物,或者三有机硼烷BR3或氨基硼烷复合物R3NBH3或膦-硼烷R3PBH3作为催化剂,其中,R是未取代的或由卤素原子取代的并且在每种情况下具有1至12个碳原子的烃基基团。
优选的铂金属及其化合物是铂和/或其化合物。使用所有迄今用来将与Si原子直接键合的氢原子加成到脂族不饱和化合物上的催化剂在此处是可能的。此类催化剂的实例是金属铂和铂粉末(细分的铂,finely divided platinum),其可以容纳在载体上,如二氧化硅,氧化铝,或活性炭等;铂化合物或复合物,如铂的卤化物,例如,PtCl4、H2PtCl6.6H2O、Na2PtCl4.4H2O、铂-烯烃复合物、铂-醇复合物、铂-醇盐复合物、铂-醚复合物、铂-醛复合物、铂-酮复合物、包含H2PtCl6.6H2O与环己酮的反应产物、铂-乙烯基硅氧烷复合物,更特别地,带或不带可检测的无机键合的卤素的铂-二乙烯基四甲基二硅氧烷复合物,双(γ-甲基吡啶)二氯化铂、三亚甲基二吡啶二氯化铂、二环戊二烯二氯化铂、二甲基亚砜-乙烯基二氯化铂(II)、以及四氯化铂与烯烃的反应产物、四氯化铂与伯胺或者仲胺的反应产物、或者四氯化铂与伯胺和仲胺的反应产物,如在1-辛烯溶液中四氯化铂与仲丁胺的反应产物,或铵-铂复合物如按照EP-B 110370。
例如,钯和/或其化合物,如四(三苯基膦)钯(0),是同样适合的。
在每种情况下以元素铂计算的并且基于通式(3)或(4)硅烷的重量,优选地以按重量0.5至500ppm(按重量百万分之一),更优选地,按重量2-300ppm的量使用铂催化剂。
氨基硼烷复合物R3NBH3的实例是三甲基胺-硼烷、三乙基胺-硼烷、三环戊基胺-硼烷、三苯基胺-硼烷、或二甲基苯基胺-硼烷。
膦硼烷R3PBH3的实例是三甲基膦硼烷、三丁基膦硼烷或者三苯基膦硼烷。
三有机硼烷BR3的实例是B(C6F5)3。
R优选地是由氟或者氯取代的烃基基团,更特别地,全氟代烃基基团。尤其优选作为催化剂使用的是B(C6F5)3。
在每种情况下,基于通式(3)或(4)的硅烷,优选地以0.1至10mol%,更优选地以0.5至5mol%的量使用三有机硼烷BR3。
分子内氢化硅烷化反应的温度优选地是-80℃至120℃,更优选地-10℃至50℃,更特别地0℃至30℃。
在存在或者缺乏非质子溶剂时,可以实施分子内氢化硅烷化反应。如果使用非质子溶剂,优选的溶剂或溶剂混合物分别是在0.1MPa下具有高达120℃的沸点或者沸程的那些。这些溶剂的实例是醚,如二噁烷、四氢呋喃、二乙醚、二异丙醚、二乙二醇二甲醚;氯代烃,如二氯甲烷、三氯甲烷、四氯甲烷、1,2-二氯乙烷、三氯乙烯;烃类,如戊烷、正己烷、己烷异构体混合物、庚烷、辛烷、洗苯(wash benzene)、石油醚、苯、甲苯、二甲苯;硅氧烷,更具体地是具有三甲基甲硅烷基末端基团的线性二甲基聚硅氧烷,其优选地具有0至6个二甲基硅氧烷单元,或优选地具有4至7个二甲基硅氧烷单元的环状二甲基聚硅氧烷,实例是六甲基二硅氧烷、八甲基三硅氧烷、八甲基环四硅氧烷以及十甲基环五硅氧烷;酮,如丙酮、甲基乙基酮、二异丙酮、和甲基异丁基酮(MIBK)等;酯,如乙酸乙酯、乙酸丁酯、丙酸丙酯、丁酸乙酯,和异丁酸乙酯;二硫化碳和硝基苯,或这些溶剂的混合物。
发现氧杂环硅烷可应用于对硅氧烷和有机聚合物进行修饰和交联。环状结构,如,例如,2-异丙氧基-2,6,6-三甲基-1,2-硅氧杂环己烷(2-isopropoxy-2,6,6-trimethyl-1,2-oxasilinane)可以用于制备新的可聚合的和可交联的远螯结构。当不添加催化剂时,这些结构与羟基封端的聚二甲基硅氧烷反应以形成远螯结构(telechele)。
通式(1)和(2)的氧杂环硅烷是值得注意的,因为在有催化剂时,发生开环反应,形成硅烷醇基团≡Si-OH以及末端双键。这其中一个实例是通过2,2,8,8-四甲基-1,7-二氧杂-6-硅螺[5,5]十一烷开环形成的如下结构:
与DE102008000353A1相比,没有乙烯基官能化合物作为低分子质量的消去反应产物(elimination product)释放。开环后,乙烯基官能化合物仍然在Si原子上。
开环反应特别优选地发生在无(大气)湿气进入。
优选的催化剂(K)是路易斯酸(Lewis acid)以及布郎斯台德酸(acid)酸。
在上式中的所有上述符号具有它们的限定,在每种情况下互相独立。
除非另外指明,否则下文中实施例中所有质量和百分比数值都是按重量给出,所有压力是0.10 MPa(绝对值),并且所有温度是20℃。
具体实施方式:
实施例1:双((2-甲基戊-4-烯-2-基)氧基)硅烷(3)的合成
在带有回流冷凝器和滴液漏斗的烘干三颈Schlenk烧瓶中装入250 mL干燥二乙醚,随后在滴液漏斗中添加约25 mL混合物,该混合物由在50 mL二乙醚中的31.9 g(389 mmol)的1-甲基咪唑与38.9 g(389 mmol)的2-甲基戊-4-烯-2-醇组成。
随后冷却混合物至-78℃并在搅拌下慢慢混合19.63 g(194 mmol)的二氯硅烷,该二氯硅烷至Schlenk管前已经预先在-78℃下冷凝。
在这个过程期间,在滴液漏斗里缓慢滴加剩余的溶液,在这之后,加热反应混合物至室温。在已经搅拌混合物10小时后,在Schlenk釉料(frit)上滤出形成的甲基咪唑盐酸盐并在减压下去除溶剂。通过分级冷凝(0.3 mbar,油浴温度:60℃)实现纯化以供应35.7 g(156 mmol,81%)无色液体状的双((2-甲基戊-4-烯-2-基)氧基)硅烷。
1H NMR(300 MHz,CDCl3,300 K):δ[ppm]=5.97–5.76(m,2H,H-3),5.14–5.00(H,4H,H-4),4.67(s,2H,Si-H),2.29(d,3J=7.3 Hz,4H,H-2),1.3(s,12,H-5)。
13C NMR(75 MHz,CDCl3,300 K):δ[ppm]=134.8(s),117.7(s),75.5(s),49.0(s),29.1(s,2C)。
(MS)(EI),m/z(%):213.16(13)[(M-CH3)+],187.13(100),129.08(87)[(M-C6H11O)+]。
HRMS(C11H21O2 28Si=[(M–CH3)+]):计算:213.1311,测得:213.1305。
实施例2:2,2,8,8-四甲基-1,7-二氧-6-硅-螺[5,5]十一烷(1)的合成
在烘干Schlenk烧瓶中装入在400mL干燥的二氯甲烷中的23.8g(104mmol)双((2-甲基戊-4-烯-2-基)氧基)硅烷,并在室温下搅拌添加1.06g(2.07mmol,2mol%)的催化剂B(C6F5)3。随后在室温下搅拌反应混合物16小时并通过分级冷凝纯化。
1HNMR(300MHz,CDCl3,300K):1.91-1.64(m,4H),1.60-1.38(m,4H),1.29(s,6H),1.20(s,6H),0.68-0.42(m,4H)。
13C NMR(126MHz,CDCl3,300K):74.4(s,2C),40.9(s,2C),31.7(s,2C),30.2(s,2C),17.8(s,2C),12.1(s,2C)。
29Si NMR(99MHz,CDCl3,300K):14.41(s)。
MS(EI),m/z(%):228(7)[M+],213(100),[(M-CH3)+],186(19),129(26),127(23)。
HRMS(C12H24O2 28Si):计算:228.1546,测得:228.1542。
实施例3:甲基氯代((2-甲基戊-4-烯-2-基)氧基)硅烷的合成
将在500ml干燥戊烷中的20.00g(174mmol)二氯甲基硅烷装入带有滴液漏斗(250ml)的烘干的1升Schlenk烧瓶。在滴液漏斗里,将10.97g(134mmol)的甲基咪唑与13.39g(134mmol)的2-甲基戊-4-烯-2-醇溶解于150ml干燥的戊烷中,并在0℃下在1小时的时间添加它们。在0℃下已经搅拌混合物30分钟后,在Schlenk釉料上分离出析出的甲基咪唑盐酸盐,并在减压去除溶剂。在减压下通过蒸馏实现纯化;在10mbar和38℃下获得产物。
产率:19.7g(110.2mmol,68.5%)
1H NMR(500MHz,CDCl3,300K):δ[ppm]=5.93-5.79(m,1H),5.33-5.31(m,1H),5.13-5.05(m,2H),2.33(d,2H),1.35(s,6H),0.52(s,3H)。
实施例4:2-异丙氧基氯代(2-甲基戊-4-烯-2-基)硅烷(4)的合成
将在500ml干燥的戊烷中的4.3g(24mmol)来自于实施例3的甲基氯代((2-甲基戊-4-烯-2-基)氧基)硅烷装入带有滴液漏斗(250ml)的烘干的1升Schlenk烧瓶中。在滴液漏斗中,将1.58g(19mmol)的甲基咪唑与1.45g(24mmol)的异丙醇溶解于150ml干燥的戊烷中,并在0℃下在1小时的时间添加它们。在0℃下已经搅拌混合物45min后,在Schlenk釉料上分离出析出的甲基咪唑盐酸盐,并在减压去除溶剂。通过分级冷凝(油浴60℃,接收器N2冷凝的,压力:0.7-0.2mbar)纯化粗产物。
1H NMR(500MHz,CDCl3,300K):δ[ppm]=5.94-5.80(m,1H),5.08-5.02(m,2H),4.73(d,1H),4.16(sept,1H),2.28(d,2H),1.29(s,6H),1.21(d,2H)。
实施例5:2-异丙氧基-2,6,6,-三甲基-1,2-硅氧杂环己烷(2)
在烘干的Schlenk烧瓶中,将1.17g(5.78mmol)来自于实施例4的2-异丙氧基氯代(2-甲基戊-4-烯-2-基)硅烷与在二氯甲烷溶液中的40mg(0.08mmol,1.4mol%)的B(C6F5)3混合,并在室温下搅拌这种混合物12小时。随后在减压(200mbar)下去除二氯甲烷,通过分级冷凝纯化粗产物。
1HNMR(300MHz,CDCl3)δ4.24-4.06(m,1H),1.88-1.68(m,2H),1.56-1.42(m,2H),1.29(s,3H),1.17(t,J=5.9Hz,6H),0.74-0.43(m,2H),0.11(s,3H)。
MS(EI),m/z(%):187.2(100)[(M-CH3)+],160.1(15),159.1(24),145.1(28),143.1(13)[(M-OCH(CH3)2)+],117.1(23)。
HRMS(C12H24O2 28Si):计算:202.1389,测得:202.1381。
Claims (7)
1.一种通式(1)或(2)的氧杂环硅烷,
其中,R1、R2、R1’以及R2’是氢、卤素、氰基、OH、或者未取代或取代的烃氧基、酰氧基、或烃基,在每种情况下具有1-50个碳原子,在其中每一种中不相邻的碳原子可由选自N、O、P以及S的杂原子取代,其中基团R1、R2、R1’、以及R2’中的两个或三个可以相互连接,
R3,R4,R3’以及R4’是未取代或取代的在每种情况下具有1-50个碳原子的烃基,在其中每一种中不相邻的碳原子可由选自N、O、P以及S的杂原子或高分子质量基团取代,
R5和R6为未取代或取代的在每种情况下具有1-50个碳原子的烃基,在其中每一种中不相邻的碳原子可由选自N、O、P以及S的杂原子取代,
m为值0或1,以及
n和n’为至少1的整数值。
2.根据权利要求1中所述的氧杂环硅烷,其中,所述基团R3和R4以及R3’和R4’选自甲基、乙基、丙基、丁基、乙烯基、苯基或羧基-C(O)OCH3。
3.根据权利要求1或2中所述的氧杂环硅烷,其中,n是值1、2、或3。
4.根据上述权利要求中任一项所述的氧杂环硅烷,其中,R6选自甲基、乙基、丙基、苯基、甲氧基、乙氧基以及乙酰氧基。
5.根据上述权利要求中任一项所述的氧杂环硅烷,其中,所述烃基R3、R4、R3’、R4’、R5以及R6上的取代基是卤素或氢或氰基。
6.一种由通式(3)的化合物制备通式(1)的氧杂环硅烷的方法以及一种由通式(4)的硅烷制备通式(2)的氧杂环硅烷的方法,
其中,在氢化硅烷化催化剂存在的情况下,使通式(3)或(4)的硅烷反应。
7.根据权利要求6中所述的方法,其中,所述氢化硅烷化催化剂选自铂金属及其化合物、三有机硼烷BR3、氨基硼烷复合物R3NBH3、以及膦-硼烷R3NBH3,其中,R是未取代或由卤素原子取代的并且在每种情况下具有1-12个碳原子的烃基。
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