JP5015774B2 - ジフルオロ置換複素環化合物および液晶媒体における構成要素としてのその使用 - Google Patents
ジフルオロ置換複素環化合物および液晶媒体における構成要素としてのその使用 Download PDFInfo
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- JP5015774B2 JP5015774B2 JP2007522947A JP2007522947A JP5015774B2 JP 5015774 B2 JP5015774 B2 JP 5015774B2 JP 2007522947 A JP2007522947 A JP 2007522947A JP 2007522947 A JP2007522947 A JP 2007522947A JP 5015774 B2 JP5015774 B2 JP 5015774B2
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- carbon atoms
- group
- alkanyl
- compound
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- 239000004973 liquid crystal related substance Substances 0.000 title claims description 39
- 150000001875 compounds Chemical class 0.000 claims description 98
- 229910052731 fluorine Inorganic materials 0.000 claims description 75
- 229910052739 hydrogen Inorganic materials 0.000 claims description 54
- 125000004432 carbon atom Chemical group C* 0.000 claims description 52
- 125000003545 alkoxy group Chemical group 0.000 claims description 37
- 239000011737 fluorine Substances 0.000 claims description 31
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 25
- 239000000460 chlorine Substances 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 24
- 229910052801 chlorine Inorganic materials 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 229910005965 SO 2 Inorganic materials 0.000 claims description 8
- 150000002596 lactones Chemical class 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 8
- IKGLACJFEHSFNN-UHFFFAOYSA-N hydron;triethylazanium;trifluoride Chemical compound F.F.F.CCN(CC)CC IKGLACJFEHSFNN-UHFFFAOYSA-N 0.000 claims description 6
- 239000007800 oxidant agent Substances 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 239000003153 chemical reaction reagent Substances 0.000 claims description 5
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims description 4
- 125000000962 organic group Chemical group 0.000 claims description 4
- 239000007858 starting material Substances 0.000 claims description 4
- RIQIOKOQHGSKLN-UHFFFAOYSA-N 5,5-dibromo-1,3-dimethylimidazolidine-2,4-dione Chemical compound CN1C(=O)N(C)C(Br)(Br)C1=O RIQIOKOQHGSKLN-UHFFFAOYSA-N 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- GRJJQCWNZGRKAU-UHFFFAOYSA-N pyridin-1-ium;fluoride Chemical compound F.C1=CC=NC=C1 GRJJQCWNZGRKAU-UHFFFAOYSA-N 0.000 claims description 3
- LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 claims description 2
- WCZAXBXVDLKQGV-UHFFFAOYSA-N n,n-dimethyl-2-(7-oxobenzo[c]fluoren-5-yl)oxyethanamine oxide Chemical compound C12=CC=CC=C2C(OCC[N+](C)([O-])C)=CC2=C1C1=CC=CC=C1C2=O WCZAXBXVDLKQGV-UHFFFAOYSA-N 0.000 claims description 2
- MRXQMNWIADOAJY-UHFFFAOYSA-M tetrabutylazanium;fluoride;dihydrofluoride Chemical compound F.F.[F-].CCCC[N+](CCCC)(CCCC)CCCC MRXQMNWIADOAJY-UHFFFAOYSA-M 0.000 claims description 2
- FZZMTSNZRBFGGU-UHFFFAOYSA-N 2-chloro-7-fluoroquinazolin-4-amine Chemical compound FC1=CC=C2C(N)=NC(Cl)=NC2=C1 FZZMTSNZRBFGGU-UHFFFAOYSA-N 0.000 claims 1
- MENYRYNFSIBDQN-UHFFFAOYSA-N 5,5-dibromoimidazolidine-2,4-dione Chemical compound BrC1(Br)NC(=O)NC1=O MENYRYNFSIBDQN-UHFFFAOYSA-N 0.000 claims 1
- QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 claims 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 1
- 229910052782 aluminium Inorganic materials 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- -1 1,4-cyclohexadienyl Chemical group 0.000 description 121
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- 125000000217 alkyl group Chemical group 0.000 description 26
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 23
- 125000003342 alkenyl group Chemical group 0.000 description 22
- 239000000203 mixture Substances 0.000 description 21
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 21
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 239000000243 solution Substances 0.000 description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 15
- 125000004093 cyano group Chemical group *C#N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 11
- 239000012071 phase Substances 0.000 description 11
- 239000000741 silica gel Substances 0.000 description 11
- 229910002027 silica gel Inorganic materials 0.000 description 11
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- IXNVNKMGHGWCFY-UHFFFAOYSA-N 3,4-dihydro-2h-benzo[h]chromene Chemical class C1=CC2=CC=CC=C2C2=C1CCCO2 IXNVNKMGHGWCFY-UHFFFAOYSA-N 0.000 description 9
- VMUXSMXIQBNMGZ-UHFFFAOYSA-N 3,4-dihydrocoumarin Chemical compound C1=CC=C2OC(=O)CCC2=C1 VMUXSMXIQBNMGZ-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 9
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- VZWXIQHBIQLMPN-UHFFFAOYSA-N chromane Chemical compound C1=CC=C2CCCOC2=C1 VZWXIQHBIQLMPN-UHFFFAOYSA-N 0.000 description 8
- 239000012074 organic phase Substances 0.000 description 8
- 229910052938 sodium sulfate Inorganic materials 0.000 description 8
- 235000011152 sodium sulphate Nutrition 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 125000000304 alkynyl group Chemical group 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- 125000001309 chloro group Chemical group Cl* 0.000 description 7
- FFOFSKWJTAJOGU-UHFFFAOYSA-N 4-butoxy-3-fluoro-2-hydroxybenzaldehyde Chemical compound CCCCOC1=CC=C(C=O)C(O)=C1F FFOFSKWJTAJOGU-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 239000013078 crystal Substances 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 125000001153 fluoro group Chemical group F* 0.000 description 5
- 125000003709 fluoroalkyl group Chemical group 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 229910052717 sulfur Inorganic materials 0.000 description 5
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 4
- KWBBLQCKYCTUPV-UHFFFAOYSA-N 2,2-difluoro-3-heptyl-3,4-dihydrochromene Chemical compound C1=CC=C2OC(F)(F)C(CCCCCCC)CC2=C1 KWBBLQCKYCTUPV-UHFFFAOYSA-N 0.000 description 4
- VCDAWCBLCCVSKE-UHFFFAOYSA-N 2h-benzo[h]chromene Chemical class C1=CC2=CC=CC=C2C2=C1C=CCO2 VCDAWCBLCCVSKE-UHFFFAOYSA-N 0.000 description 4
- LIAFZLSKEUJOPR-UHFFFAOYSA-N 4-butoxy-3-fluoro-2-phenylmethoxybenzaldehyde Chemical compound CCCCOC1=CC=C(C=O)C(OCC=2C=CC=CC=2)=C1F LIAFZLSKEUJOPR-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 125000003302 alkenyloxy group Chemical group 0.000 description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 4
- 125000003710 aryl alkyl group Chemical group 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- 125000004428 fluoroalkoxy group Chemical group 0.000 description 4
- 125000000623 heterocyclic group Chemical group 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 125000004001 thioalkyl group Chemical group 0.000 description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
- XXDIJWSZFWZBRM-WSKGJZFTSA-N (3z,5e,9e,11z,17e,19e)-8,14,16-trihydroxy-24-methyl-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-2-one Chemical compound CC1CCC\C=C\C=C\C(O)CC(O)C\C=C/C=C/C(O)C\C=C\C=C/C(=O)O1 XXDIJWSZFWZBRM-WSKGJZFTSA-N 0.000 description 3
- ABYXMXRYLPGYOZ-UHFFFAOYSA-N 3-heptyl-3,4-dihydrochromen-2-one Chemical compound C1=CC=C2OC(=O)C(CCCCCCC)CC2=C1 ABYXMXRYLPGYOZ-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000003990 capacitor Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- GCFAUZGWPDYAJN-UHFFFAOYSA-N cyclohexyl 3-phenylprop-2-enoate Chemical compound C=1C=CC=CC=1C=CC(=O)OC1CCCCC1 GCFAUZGWPDYAJN-UHFFFAOYSA-N 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- 230000005684 electric field Effects 0.000 description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- ZJLMKPKYJBQJNH-UHFFFAOYSA-N propane-1,3-dithiol Chemical compound SCCCS ZJLMKPKYJBQJNH-UHFFFAOYSA-N 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 125000006850 spacer group Chemical group 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- FEWLNYSYJNLUOO-UHFFFAOYSA-N 1-Piperidinecarboxaldehyde Chemical compound O=CN1CCCCC1 FEWLNYSYJNLUOO-UHFFFAOYSA-N 0.000 description 2
- PQYGFFABMUEQON-UHFFFAOYSA-N 1-bromo-4-butoxy-3-fluoro-2-(2-methoxyethoxymethoxy)benzene Chemical compound CCCCOC1=CC=C(Br)C(OCOCCOC)=C1F PQYGFFABMUEQON-UHFFFAOYSA-N 0.000 description 2
- ICCGDOXSRPJAQR-UHFFFAOYSA-N 2,2-difluoro-3,4-dihydrochromene Chemical compound C1=CC=C2OC(F)(F)CCC2=C1 ICCGDOXSRPJAQR-UHFFFAOYSA-N 0.000 description 2
- DXZSZRVCVYTOMJ-UHFFFAOYSA-N 2,2-difluoro-3h-1-benzofuran Chemical compound C1=CC=C2OC(F)(F)CC2=C1 DXZSZRVCVYTOMJ-UHFFFAOYSA-N 0.000 description 2
- 125000005714 2,5- (1,3-dioxanylene) group Chemical group [H]C1([H])OC([H])([*:1])OC([H])([H])C1([H])[*:2] 0.000 description 2
- NUSLQDOXLCYVTQ-UHFFFAOYSA-N 2-(2-methoxyphenyl)propanoic acid Chemical compound COC1=CC=CC=C1C(C)C(O)=O NUSLQDOXLCYVTQ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 2
- 229940125877 compound 31 Drugs 0.000 description 2
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical compound C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 238000006114 decarboxylation reaction Methods 0.000 description 2
- 125000004991 fluoroalkenyl group Chemical group 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000003566 oxetanyl group Chemical group 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 125000001148 pentyloxycarbonyl group Chemical group 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003413 spiro compounds Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000011593 sulfur Chemical group 0.000 description 2
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- IWIOHRVOBOYWQE-UHFFFAOYSA-N (1-cyclohexylcyclohexyl)benzene Chemical compound C1CCCCC1C1(C=2C=CC=CC=2)CCCCC1 IWIOHRVOBOYWQE-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- SJSRFXJWBKOROD-UHFFFAOYSA-N 1,1'-bi(cyclohexyl)-1-carboxylic acid Chemical compound C1CCCCC1C1(C(=O)O)CCCCC1 SJSRFXJWBKOROD-UHFFFAOYSA-N 0.000 description 1
- DHBXNPKRAUYBTH-UHFFFAOYSA-N 1,1-ethanedithiol Chemical compound CC(S)S DHBXNPKRAUYBTH-UHFFFAOYSA-N 0.000 description 1
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- 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
- 238000004896 high resolution mass spectrometry Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
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- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
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- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
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- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 238000006180 oxidative desulfurization-fluorination reaction Methods 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- BOTNYLSAWDQNEX-UHFFFAOYSA-N phenoxymethylbenzene Chemical compound C=1C=CC=CC=1COC1=CC=CC=C1 BOTNYLSAWDQNEX-UHFFFAOYSA-N 0.000 description 1
- OPYYWWIJPHKUDZ-UHFFFAOYSA-N phenyl cyclohexanecarboxylate Chemical compound C1CCCCC1C(=O)OC1=CC=CC=C1 OPYYWWIJPHKUDZ-UHFFFAOYSA-N 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 125000001174 sulfone group Chemical group 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
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 125000005407 trans-1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])[C@]([H])([*:2])C([H])([H])C([H])([H])[C@@]1([H])[*:1] 0.000 description 1
- PJANXHGTPQOBST-VAWYXSNFSA-N trans-stilbene Chemical group C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- NTJBWZHVSJNKAD-UHFFFAOYSA-N triethylazanium;fluoride Chemical compound [F-].CC[NH+](CC)CC NTJBWZHVSJNKAD-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/06—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2
- C07D311/08—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring
- C07D311/18—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 2 not hydrogenated in the hetero ring substituted otherwise than in position 3 or 7
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/32—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems
- C09K2019/327—Non-steroidal liquid crystal compounds containing condensed ring systems, i.e. fused, bridged or spiro ring systems containing a spiro ring system
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
- C09K19/3405—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a five-membered ring
- C09K2019/3408—Five-membered ring with oxygen(s) in fused, bridged or spiro ring systems
-
- C—CHEMISTRY; METALLURGY
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Description
a、b、c、d、およびeは、相互に独立して0または1であり;
R1およびR2は、相互に独立して、水素、−F、−Cl、−Br、−I、−CN、−SCN、−NCS、−SF5、炭素原子が最高15個のアルカニル、アルコキシ、アルケニル、またはアルキニルであり、これは、非置換、−CNもしくは−CF3による一置換、またはF、Cl、Br、および/もしくはIによる一置換もしくは多置換であり、この場合、これらの基では1個または複数のCH2基が各々の場合相互に独立して、ヘテロ原子(heteroatoms)が直接連結しないように−O−、−S−、−SO2−、−CO−、−(CO)O−、−O(CO)−、または−O(CO)O−により置換されていてもよく、または重合可能な基Pであり;
Y1、Y2、およびY3は、相互に独立して、水素、ハロゲン、炭素原子1から8個のハロゲン化アルキルまたはハロゲン化アルコキシであり;
A1、A2、A3、およびA4は、相互に独立して、非置換の、または、相互に独立して、−CN、−F、−Cl、−Br、−I、C 1 〜C 6 アルカニルあるいはC 1 〜C 6 アルコキシにより一置換から四置換されていてもよい1,4−フェニレン(ただしこのC 1 〜C 6 アルカニルは非置換、またはフッ素および/もしくは塩素により一置換または多置換されていてもよく、このC 1 〜C 6 アルコキシは非置換、またはフッ素および/もしくは塩素により一置換または多置換されていてもよい);1,4−シクロヘキシレン、1,4−シクロヘキシニレン、または1,4−シクロヘキサジエニレンであり、この中で、−CH2−は、相互に独立して、ヘテロ原子が直接連結しないように−O−または−S−により1回または2回置換されていてもよく、非置換、または−F、−Cl、−Br、および/もしくは−Iにより一置換、または多置換であってもよく;
Z1、Z2、Z3、およびZ4は、相互に独立して、単結合、−CF2O−、−OCF2−、−CH2CH2−、−CF2CF2−、−CF2CH2−、−CH2CF2−、−CHF−CHF−、−(CO)O−、−O(CO)−、−CH2O−、−OCH2−、−CF=CH−、−CH=CF−、−CF=CF−、−CH=CH−、または−C≡C−であり;
式Iの酸素複素環における
ここで、a、b、c、およびdが同時に0であり、eが1であり、R1が水素であり、Y1もY3も水素であり、
ただし本発明では特に、式I中、a+b+c+dが1または2であり、eが1であり、R1およびR2は相互に独立して、−F、炭素原子が最高15個のアルカニルまたはアルコキシであり、「アルキル」は「アルカニル」であり、A 1 、A 2 、A 3 、およびA 4 が、相互に独立して、請求項1に記載されるとおりの群から選択され、Z 1 、Z 2 、Z 3 、およびZ 4 は、単結合であり、酸素複素環における3位と4位との間の結合はC−C単結合である(C=C二重結合ではない)。以下、これ以外の場合について言及することもあるが、それは参考用である。
a、b、c、d、e、R1、R2、A1、A2、A3、A4、Y1、Y2、Y3、Z1、Z2、Z3、Z4、および
W1は、−SR3であり、
W2は、−SR4であり;
または
W1およびW2は、一緒に、=S、または−S−W3−S−であり、
(式中、
R3およびR4は、相互に独立して、炭素原子1から8個のアルキルであり;
W3は、炭素原子を少なくとも2個有する2価の有機基である)]
が、酸化剤の存在下でフッ素放出性の化合物と反応することを特徴とする。
R’−L−E−R” (1)
R’−L−COO−E−R” (2)
R’−L−OOC−E−R” (3)
R’−L−CH2CH2−E−R” (4)
R’−L−CF2O−E−R” (5)
式(1)、(2)、(3)、(4)、および(5)において、同一でも異なっていてもよいLおよびEは、各々の場合において相互に独立して、−Phe−、−Cyc−、−Phe−Phe−、−Phe−Cyc−、−Cyc−Cyc−、−Pyr−、−Dio−、−Thp−、−G−Phe−、および−G−Cyc−から形成される群からの2価の基、ならびにこれらの鏡像であり、Pheは、非置換またはフッ素により置換されている1,4−フェニレンであり、Cycは、トランス−1,4−シクロヘキシレンまたは1,4−シクロヘキセニレンであり、Pyrは、ピリミジン−2,5−ジイルまたはピリジン−2,5−ジイルであり、Dioは、1,3−ジオキサン−2,5−ジイルであり、Thpは、テトラヒドロピラン−2,5−ジイルであり、Gは、2−(トランス−1,4−シクロヘキシル)エチル、ピリミジン−2,5−ジイル、ピリジン−2,5−ジイル、1,3−ジオキサン−2,5−ジイル、またはテトラヒドロピラン−2,5−ジイルである。
グループA:0から90%、好ましくは20から90%、特に30から90%
グループB:0から80%、好ましくは10から80%、特に10から70%
グループC:0から80%、好ましくは5から80%、特に5から50%
である。
C:結晶相、N:ネマチック相、I:アイソトロピック相
温度は、別段の記載がなければ、℃である。
a)3−ヘプチル−3,4−ジヒドロクロメン−2−オン(6)の調製
調製は、Houben−Weyl、Methoden der Organischen Chemie、Georg Thieme Verlag、Stuttgart、New York、第4版、1993年に従って、以下の反応スキームに示す通りに行う。
δ=−74.0ppm(ddd,3JF,H=2.2Hz,3JF,H=3.8Hz,2JF,F=154Hz,1F,CF2O)、−79.1(ddd,3JF,H=3.0Hz,3JF,H=13.0Hz,2JF,F=154Hz,1F,CF2O)。
a)3−フルオロ−4−ブトキシ−2−ヒドロキシベンズアルデヒド(11)
m/e(%)=466[M+](100)、438[M+−CO](74)、382[M+−CO−Bu](84)。
δ=0.83〜1.59ppm(m,22H)、1.73〜1.94(m,5H)、2.45(tt,3J=3.0Hz,3J=11.5Hz,1H,Ar−CH(CH2)2,3.18(AB−dd,3J=6.5Hz,3J=16.0Hz,1H,Ar−CH2−CH)、3.30(AB−dd,3J=10.5Hz,3J=16.0Hz,1H,Ar−CH2−CH)、3.94(dd,3J=6.5Hz,3J=10.5Hz,1H,ArCHC(O)O−Ar)、4.03(t,3J=6.6Hz,2H,Ar−OCH2C3H7)、6.70(mc,1H,Ar−H)、6.83(mc,1H,Ar−H)、7.17(mc,4H,Ar−H)。
m/e(%)=556[M+](100)、460(87)。
19F−NMR(282MHz,CDCl3)
δ=−75.6ppm(ddd,3JF,H=2.2Hz,3JF,H=4.4Hz,2JF,F=153Hz,1F,CF2O)、−79.1(dd,3JF,H=18.8Hz,2JF,F=153Hz,1F,CF2O)。
m/e(%)=488[M+](100)、432[M+−Bu](52)。
a)3−フルオロ−2−ベンジルオキシ−4−ブトキシベンズアルデヒド(18)
m/e(%)=455[M+−OH](2)、275(70)、91[C7H7 +](100)。
δ=0.72〜1.90ppm(m,20H)、2.64(d,3J=6.2Hz,1H,OH)、2.82(dd,3J=4.1Hz,3J=8.2Hz,1H,CHCOOMe)、3.47(s,3H,OCH3)、4.10(q,3J=7.0Hz,−OCH2CH3)、4.99(dd,3J=6.2Hz,3J=8.2Hz,1H,Ar−CH(OH)−)、5.11(d,3J=10.9Hz,1H,PhCH2O−)、5.27(d,3J=11.4Hz,1H,PhCH2O−)、6.64(t,3J=8.2Hz,1H,Ar−H)、6.97(dd,3J=1.8Hz,3J=8.6Hz,1H,Ar−H)、7.42(mc,5H,Ar−H)。
m/e(%)=334[M+](84)、170(100)。
δ=0.78〜1.35(m,12H)、1.44(t,3J=7.1Hz,3H,CH3)、1.65〜1.85(m,5H)、2.54(mc,1H,CH)、2.87(AB−dd,3J=8.3Hz,2J=15.9Hz,1H,ArCH2)、2.95(AB−dd,3J=6.5Hz,2J=15.9Hz,1H,Ar−CH2−)、4.10(q,3J=7.0Hz,2H,CH3CH2O−)、6.66(dd,3J=7.27Hz,1H,Ar−H)、6.81(mc,1H,Ar−H)。
m/e(%)=424[M+](100)、256(70)。
MS(EI)
m/e(%)=356[M+](100)、328[M+−C2H5](45)。
δ=0.80〜1.37ppm(m,12H)、1.42(t,3J=7.0Hz,3H,CH3)、1.80(mc,5H)、2.40(mc,1H,Ar−CH2−)、2.84(mc,2H,Ar−CH2−および−CHCF2O)、4.09(q,3J=7.0Hz,2H,OCH2CH3)、6.61(dd,3J=6.4Hz,3J=8.5Hz,1H,Ar−H)、6.67(mc,1H,Ar−H)。
δ=−74.0ppm(dd,3JF,H=2.6Hz,2JF,F=152Hz,1F,CF2O)、−75.9(dd,3JF,H=19.2Hz,2JF,F=152Hz,1F,CF2O)、−157(dd,3JF,H=1.5Hz,3JF,H=7.2Hz,1F,Ar−F)。
a1)6−オキサ−1,4−ジチア[7,8]ベンゾスピロ[4.5]デカン(27)
δ=2.62ppm(t,3J=6.7Hz,2H,ArCH2CH2)、3.02(t,3J=6.7Hz,2H,ArCH2CH2)、3.53(mc,4H,−SCH2CH2S−)、6.87(mc,2H,Ar−H)、7.11(mc,2H,Ar−H)。
δ=2.07ppm(mc,1H,−SCH2CH2CH2S−)、2.25(mc,1H,−SCH2CH2CH2S−)、2.32(t,J=7.0Hz,2H,Ar−CH2CH2−)、2.71(dt,J=14.4Hz,J=3.4Hz,2H,−SCH2CH2CH2S−)、2.97(t,J=7.0Hz,2H,Ar−CH2−CH2)、3.64(mc,2H,−SCH2CH2CH2S−)、6.92(mc,2H,Ar−H)、7.08(d,J=7.6Hz,1H,Ar−H)、7.13(mc,その中に:t,J=7.6Hz,1H,Ar−H)。
1H−NMR(300MHz,CDCl3)
δ=2.32ppm(tt,3JF,H=8.9Hz,3JH,H=7.1Hz,2H,CH2)、2.96(t,3JH,H=7.1Hz,2H,CH2)、6.99(mc,2H,Ar−H)、7.18(mc,2H,Ar−H)。
δ=22.54(t,3JC,F=4.0Hz,CH2CH2CF2)、27.88(t,2JC,F=29.1Hz,CH2CH2CF2)、116.85(CH)、120.47(C)、123.03(CH)、123.16(t,1JC,F=255Hz,CF2O)、128.15(CH)、128.78(CH)、150.95(C)。
δ=−69.77ppm(t,3JF,H=8.9Hz,2F,CF2)。
m/e(%)=170(100)[M+]、150(7)[M+−HF]。
計算値:m/e=170.054716;実測値:m/e 170.054321。
δ=3.59ppm(t,3JF,H=14.0Hz,2H,CH2)、6.96(d,J=8.1Hz,1H,Ar−H)、7.04(dd,J=0.9Hz,J=7.5Hz,1H,Ar−H)、7.22(mc,2H,Ar−H)。
δ=−63.94ppm(t,3JF,H=14.0Hz,2F,CF2)
MS(EI)
m/e(%)=156(100)[M+]、136(6)[M+−HF]。
実施例番号338
実施例番号502
実施例番号1612
Claims (13)
- 一般式Iの化合物:
a、b、c、およびdは、相互に独立して0または1であり、ただし、a+b+c+dが1または2であり、eが1であり;
R1およびR2は、相互に独立して、−F、炭素原子が最高15個のアルカニルまたはアルコキシであり;
Y1、Y2、およびY3は、相互に独立して、水素、ハロゲン、炭素原子1から8個のハロゲン化アルカニルまたはハロゲン化アルコキシであり;
A 1 、A 2 、A 3 、およびA 4 が、相互に独立して、
Z1、Z2、Z3、およびZ4は、単結合であり;
式Iの酸素複素環における
- Y2およびY3が水素であることを特徴とする、請求項1に記載の化合物。
- Y1が水素、F、Cl、またはCF3であることを特徴とする、請求項1または2に記載の化合物。
- R1は、フッ素、炭素原子1から8個のアルカニルまたはアルコキシであり;
R2は、フッ素、炭素原子1から8個のアルカニルまたはアルコキシであることを特徴とする、請求項1〜3のいずれか一項に記載の化合物。 - a+bが0または1であり、c+dが0または1であることを特徴とする、請求項1〜4のいずれか一項に記載の化合物。
- aもdも0であり、
bは0または1であり、
cは1であり、
bが0である場合、R1はアルカニルまたはアルコキシであり、bが1である場合、R1はF、アルカニルまたはアルコキシであり;
R2はアルカニルまたはアルコキシであり;
bが1である場合、A2は
A3は
ことを特徴とする、請求項1から5のいずれか一項に記載の化合物。 - 請求項1〜6のいずれか一項に記載の一般式Iの化合物を調整するための出発材料として用いることができる一般式IIの化合物:
a、b、c、d、e、R1、R2、A1、A2、A3、A4、Y1、Y2、Y3、Z1、Z2、Z3、Z4、および
W1は、−SR3であり、
W2は、−SR4であり;または
W1およびW2は一緒に、=S、もしくは−S−W3−S−であり
ここで、
R3およびR4は、相互に独立して、炭素原子1から8個のアルカニルであり;
W3は、炭素原子が少なくとも2個の2価の有機基であり、
ただし前記W3は、橋に炭素原子を2、3、4、5、または6個有するアルキレン橋であるか(ただし、各々の場合におけるこれらの炭素原子の最高3個が、1または2個のさらなるC1〜C4アルカニル置換基を有することができ;このアルキレン橋の2個の隣接する炭素原子が
-
ただし前記W3は、橋に炭素原子を2、3、4、5、または6個有するアルキレン橋であるか(ただし、各々の場合におけるこれらの炭素原子の最高3個が、1または2個のさらなるC1〜C4アルカニル置換基を有することができ;このアルキレン橋の2個の隣接する炭素原子が
を特徴とする、請求項1から6のいずれか一項に記載した式Iの化合物を調製するためのプロセス。 - フッ素放出性の化合物が、HF、ピリジン−フッ化水素複合体、トリエチルアミン三フッ化水素酸塩(Et3N・3HF)、およびテトラブチルアンモニウムジヒドロゲントリフルオリドを含む群から選択され;酸化剤が、ジメチルジブロモヒダントイン(DBH)、N−クロロスクシンイミド(NCS)、N−ブロモスクシンイミド(NBS)、N−ヨードスクシンイミド(NIS)、塩素、臭素、SO2Cl2、SO2ClF、NOBF4、およびクロラミンTを含む群から選択されることを特徴とする、請求項8に記載のプロセス。
- W1およびW2は、−S−W3−S−であり、W3は、請求項8で定義した通りである式IIの化合物が、一般式III:
a、b、c、d、e、R1、R2、A1、A2、A3、A4、Z1、Z2、Z3、Z4、および
のラクトンが、2モル当量のトリアルカニルアルミニウムと、1モル当量のHS−W3−SHとの反応により得ることができる試薬と反応することにより調製されることを特徴とする、請求項8または9に記載のプロセス。 - 請求項1から6のいずれか一項に記載の式Iの化合物の、液晶媒体における使用。
- 請求項1から6のいずれか一項に記載の式Iの化合物の少なくとも1つを含むことを特徴とする、少なくとも2つの液晶化合物を有する液晶媒体。
- 請求項12に記載の液晶媒体を含む、電気光学ディスプレイ素子。
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- 2005-07-05 WO PCT/EP2005/007221 patent/WO2006012965A1/de active Application Filing
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DE102005031554B4 (de) | 2023-07-06 |
US7648742B2 (en) | 2010-01-19 |
WO2006012965A1 (de) | 2006-02-09 |
JP2008508200A (ja) | 2008-03-21 |
US20080071097A1 (en) | 2008-03-20 |
DE102005031554A1 (de) | 2006-03-23 |
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