JPH0329050B2 - - Google Patents
Info
- Publication number
- JPH0329050B2 JPH0329050B2 JP57177726A JP17772682A JPH0329050B2 JP H0329050 B2 JPH0329050 B2 JP H0329050B2 JP 57177726 A JP57177726 A JP 57177726A JP 17772682 A JP17772682 A JP 17772682A JP H0329050 B2 JPH0329050 B2 JP H0329050B2
- Authority
- JP
- Japan
- Prior art keywords
- trans
- ethyl
- alkylcyclohexyl
- pentylcyclohexyl
- weight
- 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
- 150000001875 compounds Chemical class 0.000 claims description 55
- 239000000203 mixture Substances 0.000 claims description 55
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 47
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 20
- 239000004973 liquid crystal related substance Substances 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 235000010290 biphenyl Nutrition 0.000 claims description 12
- LFGDFCLIVISJSO-WGSAOQKQSA-N C1C[C@@H](CCCCC)CC[C@@H]1CCC1=CC=C(OCC)C=C1 Chemical compound C1C[C@@H](CCCCC)CC[C@@H]1CCC1=CC=C(OCC)C=C1 LFGDFCLIVISJSO-WGSAOQKQSA-N 0.000 claims description 10
- 239000004305 biphenyl Substances 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 9
- AITQOXOBSMXBRV-UHFFFAOYSA-N 4-[4-(4-pentylphenyl)phenyl]benzonitrile Chemical group C1=CC(CCCCC)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C#N)C=C1 AITQOXOBSMXBRV-UHFFFAOYSA-N 0.000 claims description 8
- APBBCFNZHALDSW-QAQDUYKDSA-N C1C[C@@H](CCC)CC[C@@H]1CCC1=CC=C(OCC)C=C1 Chemical compound C1C[C@@H](CCC)CC[C@@H]1CCC1=CC=C(OCC)C=C1 APBBCFNZHALDSW-QAQDUYKDSA-N 0.000 claims description 8
- HHPCNRKYVYWYAU-UHFFFAOYSA-N 4-cyano-4'-pentylbiphenyl Chemical group C1=CC(CCCCC)=CC=C1C1=CC=C(C#N)C=C1 HHPCNRKYVYWYAU-UHFFFAOYSA-N 0.000 claims description 7
- QKEBUASRTJNJJS-XUTJKUGGSA-N C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(C=2C=CC(=CC=2)C#N)C=C1 Chemical group C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(C=2C=CC(=CC=2)C#N)C=C1 QKEBUASRTJNJJS-XUTJKUGGSA-N 0.000 claims description 7
- PAOGJHSCNSVUMN-AFMUELSESA-N CCCCC[C@H]1CC[C@@H](CC1)c1ccc(CC[C@H]2CC[C@H](CCCC)CC2)cc1 Chemical compound CCCCC[C@H]1CC[C@@H](CC1)c1ccc(CC[C@H]2CC[C@H](CCCC)CC2)cc1 PAOGJHSCNSVUMN-AFMUELSESA-N 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- XFMPTZWVMVMELB-UHFFFAOYSA-N 4-(4-propylphenyl)benzonitrile Chemical group C1=CC(CCC)=CC=C1C1=CC=C(C#N)C=C1 XFMPTZWVMVMELB-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- CNOSQBDQVXWGOJ-KZIAUGABSA-N C1C[C@@H](CCCCC)CC[C@@H]1C(C=C1)=CC=C1CCC(C=C1)=CC=C1CC[C@@H]1CC[C@@H](CCCC)CC1 Chemical compound C1C[C@@H](CCCCC)CC[C@@H]1C(C=C1)=CC=C1CCC(C=C1)=CC=C1CC[C@@H]1CC[C@@H](CCCC)CC1 CNOSQBDQVXWGOJ-KZIAUGABSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000005037 alkyl phenyl group Chemical group 0.000 claims 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 238000002844 melting Methods 0.000 description 15
- 230000008018 melting Effects 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- -1 4-(trans-4-heptylcyclohexyl) -4-[2-(p-(trans-4-propylcyclohexyl)phenyl)ethyl]biphenyl Chemical group 0.000 description 8
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- 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 8
- 239000007788 liquid Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 238000006277 sulfonation reaction Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- DDFUULSUNIZKTC-IXFIMZJLSA-N C(CCCC)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C1=CC=C(C=C1)CC[C@@H]1CC[C@H](CC1)CCCCC Chemical group C(CCCC)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C1=CC=C(C=C1)CC[C@@H]1CC[C@H](CC1)CCCCC DDFUULSUNIZKTC-IXFIMZJLSA-N 0.000 description 5
- ZXWKTUCBAYGXJD-JFQKCFOJSA-N C(CCCC)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)C1=CC=C(C=C1)CC[C@@H]1CC[C@H](CC1)CCCCC Chemical group C(CCCC)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)C1=CC=C(C=C1)CC[C@@H]1CC[C@H](CC1)CCCCC ZXWKTUCBAYGXJD-JFQKCFOJSA-N 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- HMUGRILXVBKBID-UHFFFAOYSA-N 1-(bromomethyl)-4-[4-(bromomethyl)phenyl]benzene Chemical group C1=CC(CBr)=CC=C1C1=CC=C(CBr)C=C1 HMUGRILXVBKBID-UHFFFAOYSA-N 0.000 description 4
- VSNGFYYRBATOTN-UHFFFAOYSA-N 4-(5-heptylpyrimidin-2-yl)benzonitrile Chemical compound N1=CC(CCCCCCC)=CN=C1C1=CC=C(C#N)C=C1 VSNGFYYRBATOTN-UHFFFAOYSA-N 0.000 description 4
- RGONNDWSVOCREF-UHFFFAOYSA-N 4-(5-pentylpyrimidin-2-yl)benzonitrile Chemical compound N1=CC(CCCCC)=CN=C1C1=CC=C(C#N)C=C1 RGONNDWSVOCREF-UHFFFAOYSA-N 0.000 description 4
- HJIVFZUPTYADSP-WKILWMFISA-N C1C[C@@H](CCCCC)CC[C@@H]1C(=O)OC1=CC=C(OC)C=C1 Chemical compound C1C[C@@H](CCCCC)CC[C@@H]1C(=O)OC1=CC=C(OC)C=C1 HJIVFZUPTYADSP-WKILWMFISA-N 0.000 description 4
- OMXWVWDCNNMTTN-CQXGVVMCSA-N C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(C=2C=CC(CC[C@@H]3CC[C@@H](CCCC)CC3)=CC=2)C=C1 Chemical group C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(C=2C=CC(CC[C@@H]3CC[C@@H](CCCC)CC3)=CC=2)C=C1 OMXWVWDCNNMTTN-CQXGVVMCSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- 230000005587 bubbling Effects 0.000 description 4
- 230000003098 cholesteric effect Effects 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 230000008707 rearrangement Effects 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 238000010792 warming Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- VJEGSDUNBNEIGN-WRNSKWPRSA-N C(CCC)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)CCC1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCC Chemical compound C(CCC)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)CCC1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCC VJEGSDUNBNEIGN-WRNSKWPRSA-N 0.000 description 3
- ZAUPPIHFDVKVJM-IYARVYRRSA-N C1C[C@@H](CCCCC)CC[C@@H]1C(=O)OC1=CC=C(OCCC)C=C1 Chemical compound C1C[C@@H](CCCCC)CC[C@@H]1C(=O)OC1=CC=C(OCCC)C=C1 ZAUPPIHFDVKVJM-IYARVYRRSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 239000004990 Smectic liquid crystal Substances 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 230000005540 biological transmission Effects 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 239000003989 dielectric material Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 238000004781 supercooling Methods 0.000 description 3
- DLLIPJSMDJCZRF-UHFFFAOYSA-N 4-(4-ethylphenyl)benzonitrile Chemical group C1=CC(CC)=CC=C1C1=CC=C(C#N)C=C1 DLLIPJSMDJCZRF-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- NXFDNAWPSPHRTH-OHRWXDHWSA-N C(CCC)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)CCC1=CC=C(C=C1)C1=CC=C(C=C1)CCCCC Chemical compound C(CCC)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)CCC1=CC=C(C=C1)C1=CC=C(C=C1)CCCCC NXFDNAWPSPHRTH-OHRWXDHWSA-N 0.000 description 2
- PWRDNJXXPYGEGF-UNWRIRMBSA-N C(CCCC)C1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=C(C=C1)CC[C@@H]1CC[C@H](CC1)CCCC Chemical group C(CCCC)C1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=C(C=C1)CC[C@@H]1CC[C@H](CC1)CCCC PWRDNJXXPYGEGF-UNWRIRMBSA-N 0.000 description 2
- DXVFNAYVVASPIS-LAEBDHFPSA-N C(CCCC)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C1=CC=C(C=C1)CCC1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCCC Chemical group C(CCCC)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C1=CC=C(C=C1)CCC1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCCC DXVFNAYVVASPIS-LAEBDHFPSA-N 0.000 description 2
- PGAFQKGVZJTPIY-HZCBDIJESA-N C(CCCC)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)C1=CC=CC=C1 Chemical group C(CCCC)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)C1=CC=CC=C1 PGAFQKGVZJTPIY-HZCBDIJESA-N 0.000 description 2
- YAZXDRDFNUEKBH-KOMQPUFPSA-N C1C[C@@H](CC)CC[C@@H]1C1=CN=C(C=2C=CC(=CC=2)C#N)N=C1 Chemical compound C1C[C@@H](CC)CC[C@@H]1C1=CN=C(C=2C=CC(=CC=2)C#N)N=C1 YAZXDRDFNUEKBH-KOMQPUFPSA-N 0.000 description 2
- XIXOFKHADLKBQN-UAPYVXQJSA-N C1C[C@@H](CCCCC)CC[C@@H]1C1=CN=C(C=2C=CC(=CC=2)C#N)N=C1 Chemical compound C1C[C@@H](CCCCC)CC[C@@H]1C1=CN=C(C=2C=CC(=CC=2)C#N)N=C1 XIXOFKHADLKBQN-UAPYVXQJSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000007818 Grignard reagent Substances 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000004074 biphenyls Chemical class 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000004795 grignard reagents Chemical class 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- RVHSTXJKKZWWDQ-UHFFFAOYSA-N 1,1,1,2-tetrabromoethane Chemical compound BrCC(Br)(Br)Br RVHSTXJKKZWWDQ-UHFFFAOYSA-N 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- HXOWMHXGHNZDFT-UHFFFAOYSA-N 1-(bromomethyl)-4-pentylcyclohexane Chemical compound CCCCCC1CCC(CBr)CC1 HXOWMHXGHNZDFT-UHFFFAOYSA-N 0.000 description 1
- QPYKYLANDNYEIF-UHFFFAOYSA-N 1-hexyl-4-phenylcyclohexa-2,4-diene-1-carbonitrile Chemical group C1=CC(CCCCCC)(C#N)CC=C1C1=CC=CC=C1 QPYKYLANDNYEIF-UHFFFAOYSA-N 0.000 description 1
- WCJUJMPIFZMWOZ-UHFFFAOYSA-N 1-pentyl-4-phenylcyclohexa-2,4-diene-1-carbonitrile Chemical group C1=CC(CCCCC)(C#N)CC=C1C1=CC=CC=C1 WCJUJMPIFZMWOZ-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- HYYFAYFMSHAWFA-UHFFFAOYSA-N 2-cyclohexylethylbenzene Chemical class C1CCCCC1CCC1=CC=CC=C1 HYYFAYFMSHAWFA-UHFFFAOYSA-N 0.000 description 1
- WLNDDIWESXCXHM-UHFFFAOYSA-N 2-phenyl-1,4-dioxane Chemical class C1OCCOC1C1=CC=CC=C1 WLNDDIWESXCXHM-UHFFFAOYSA-N 0.000 description 1
- WLPATYNQCGVFFH-UHFFFAOYSA-N 2-phenylbenzonitrile Chemical group N#CC1=CC=CC=C1C1=CC=CC=C1 WLPATYNQCGVFFH-UHFFFAOYSA-N 0.000 description 1
- OXPDQFOKSZYEMJ-UHFFFAOYSA-N 2-phenylpyrimidine Chemical class C1=CC=CC=C1C1=NC=CC=N1 OXPDQFOKSZYEMJ-UHFFFAOYSA-N 0.000 description 1
- BWRMZQGIDWILAU-UHFFFAOYSA-N 4,6-diphenylpyrimidine Chemical class C1=CC=CC=C1C1=CC(C=2C=CC=CC=2)=NC=N1 BWRMZQGIDWILAU-UHFFFAOYSA-N 0.000 description 1
- VADSDVGLFDVIMG-UHFFFAOYSA-N 4-(4-hexylphenyl)benzonitrile Chemical group C1=CC(CCCCCC)=CC=C1C1=CC=C(C#N)C=C1 VADSDVGLFDVIMG-UHFFFAOYSA-N 0.000 description 1
- JFKUBRAOUZEZSL-UHFFFAOYSA-N 4-butylbenzoic acid Chemical compound CCCCC1=CC=C(C(O)=O)C=C1 JFKUBRAOUZEZSL-UHFFFAOYSA-N 0.000 description 1
- BOOGLODHTHQEQO-UHFFFAOYSA-N 4-cyclohexyl-2-phenylpyrimidine Chemical class C1CCCCC1C1=CC=NC(C=2C=CC=CC=2)=N1 BOOGLODHTHQEQO-UHFFFAOYSA-N 0.000 description 1
- QFFSAGSUDNLFFK-UHFFFAOYSA-N 4-pentylcyclohexane-1-carbaldehyde Chemical compound CCCCCC1CCC(C=O)CC1 QFFSAGSUDNLFFK-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- OESYGYCCZCPEGL-HZCBDIJESA-N BrCC1=CC=C(C=C1)C1=CC=C(C=C1)CC[C@@H]1CC[C@H](CC1)CCCCC Chemical group BrCC1=CC=C(C=C1)C1=CC=C(C=C1)CC[C@@H]1CC[C@H](CC1)CCCCC OESYGYCCZCPEGL-HZCBDIJESA-N 0.000 description 1
- XYGDUSLNOJYYAT-VYDRQYCRSA-N C(C)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C1=CC=C(C=C1)CCC1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCC Chemical group C(C)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C1=CC=C(C=C1)CCC1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCC XYGDUSLNOJYYAT-VYDRQYCRSA-N 0.000 description 1
- AFSDUUITWNSFMQ-XBZNQCHHSA-N C(C)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)C1=CC=C(C=C1)CC[C@@H]1CC[C@H](CC1)CCC Chemical group C(C)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)C1=CC=C(C=C1)CC[C@@H]1CC[C@H](CC1)CCC AFSDUUITWNSFMQ-XBZNQCHHSA-N 0.000 description 1
- IBIAWGSHXGZLOR-AGZHJDECSA-N C(CC)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C1=CC=C(C=C1)CCC1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCC Chemical group C(CC)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C1=CC=C(C=C1)CCC1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCC IBIAWGSHXGZLOR-AGZHJDECSA-N 0.000 description 1
- DPTZNSBWZDCAQO-WTZQBIJTSA-N C(CC)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C1=CC=C(C=C1)CC[C@@H]1CC[C@H](CC1)CCC Chemical group C(CC)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C1=CC=C(C=C1)CC[C@@H]1CC[C@H](CC1)CCC DPTZNSBWZDCAQO-WTZQBIJTSA-N 0.000 description 1
- ZMCRCIJHEIMCLT-ZVTZDLPXSA-N C(CC)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)CCC1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCC Chemical compound C(CC)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)CCC1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCC ZMCRCIJHEIMCLT-ZVTZDLPXSA-N 0.000 description 1
- BDMUSSXVPASJCR-DANJKSSVSA-N C(CC)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)C1=CC=C(C=C1)CC[C@@H]1CC[C@H](CC1)CCC Chemical group C(CC)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)C1=CC=C(C=C1)CC[C@@H]1CC[C@H](CC1)CCC BDMUSSXVPASJCR-DANJKSSVSA-N 0.000 description 1
- ZZOKAIFIKJSLJJ-WGSAOQKQSA-N C(CC)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)OCCCC Chemical compound C(CC)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)OCCCC ZZOKAIFIKJSLJJ-WGSAOQKQSA-N 0.000 description 1
- DRKLRGNFQPKQFG-AKMOFFSESA-N C(CC)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCC Chemical compound C(CC)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCC DRKLRGNFQPKQFG-AKMOFFSESA-N 0.000 description 1
- KTIPMVUJQZTABW-WTZQBIJTSA-N C(CC)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCCCCCC Chemical compound C(CC)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCCCCCC KTIPMVUJQZTABW-WTZQBIJTSA-N 0.000 description 1
- RBOFQSCGFMAYKD-OPMHRUBESA-N C(CC)[C@@H]1CC[C@H](CC1)O[C@@H]1CC[C@H](CC1)CCC Chemical compound C(CC)[C@@H]1CC[C@H](CC1)O[C@@H]1CC[C@H](CC1)CCC RBOFQSCGFMAYKD-OPMHRUBESA-N 0.000 description 1
- RYNMANKIRHRENQ-WXUXXXNLSA-N C(CCC)C1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=C(C=C1)CC[C@@H]1CC[C@H](CC1)CCCCC Chemical group C(CCC)C1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=C(C=C1)CC[C@@H]1CC[C@H](CC1)CCCCC RYNMANKIRHRENQ-WXUXXXNLSA-N 0.000 description 1
- AAFQYEUMQGMKIS-LAEBDHFPSA-N C(CCC)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C1=CC=C(C=C1)CCC1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCCCC Chemical group C(CCC)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C1=CC=C(C=C1)CCC1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCCCC AAFQYEUMQGMKIS-LAEBDHFPSA-N 0.000 description 1
- MVJWXKFVBFCEPR-XBZNQCHHSA-N C(CCC)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)CC[C@@H]1CC[C@H](CC1)CCCCC Chemical compound C(CCC)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)CC[C@@H]1CC[C@H](CC1)CCCCC MVJWXKFVBFCEPR-XBZNQCHHSA-N 0.000 description 1
- MMVQWSKUUDQYDU-KWQFAZJVSA-N C(CCCC)C1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=C(C=C1)CC[C@@H]1CC[C@H](CC1)CCC Chemical group C(CCCC)C1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=C(C=C1)CC[C@@H]1CC[C@H](CC1)CCC MMVQWSKUUDQYDU-KWQFAZJVSA-N 0.000 description 1
- PUFHZTAHFAVWOH-QAQDUYKDSA-N C(CCCC)C1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)C(=O)O Chemical compound C(CCCC)C1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)C(=O)O PUFHZTAHFAVWOH-QAQDUYKDSA-N 0.000 description 1
- RQKSDWLLCZEXDZ-MOOVDDBPSA-N C(CCCC)[C@@H]1CC[C@H](CC1)C1(CC=C(C=C1)C1=CC=CC=C1)C#N Chemical group C(CCCC)[C@@H]1CC[C@H](CC1)C1(CC=C(C=C1)C1=CC=CC=C1)C#N RQKSDWLLCZEXDZ-MOOVDDBPSA-N 0.000 description 1
- GHYIAIJFCWKIDL-IXFIMZJLSA-N C(CCCC)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C1=CC=C(C=C1)C=C[C@@H]1CC[C@H](CC1)CCCCC Chemical group C(CCCC)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C1=CC=C(C=C1)C=C[C@@H]1CC[C@H](CC1)CCCCC GHYIAIJFCWKIDL-IXFIMZJLSA-N 0.000 description 1
- PXJYLNDQCJSKJO-XUTJKUGGSA-N C(CCCC)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C1=CC=C(C=C1)C=O Chemical compound C(CCCC)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C1=CC=C(C=C1)C=O PXJYLNDQCJSKJO-XUTJKUGGSA-N 0.000 description 1
- RYLSAUKWNBSYFM-YRWLMJQZSA-N C(CCCC)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C1=CC=C(C=C1)CCC1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCC Chemical group C(CCCC)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C1=CC=C(C=C1)CCC1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCC RYLSAUKWNBSYFM-YRWLMJQZSA-N 0.000 description 1
- UHCMHEJUCNFSSD-RFKOGVRWSA-N C(CCCC)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C1=CC=C(C=C1)CCC1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCCCC Chemical group C(CCCC)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C1=CC=C(C=C1)CCC1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCCCC UHCMHEJUCNFSSD-RFKOGVRWSA-N 0.000 description 1
- XJCDFPXBVHBNMG-FUKPSZBCSA-N C(CCCC)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C1=CC=C(C=C1)CC[C@@H]1CC[C@H](CC1)CCC Chemical group C(CCCC)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C1=CC=C(C=C1)CC[C@@H]1CC[C@H](CC1)CCC XJCDFPXBVHBNMG-FUKPSZBCSA-N 0.000 description 1
- BITDTKIPCQRBNA-XUTJKUGGSA-N C(CCCC)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C1=CC=C(C=C1)CO Chemical compound C(CCCC)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C1=CC=C(C=C1)CO BITDTKIPCQRBNA-XUTJKUGGSA-N 0.000 description 1
- CVYAXDDQRNSBLX-QOKNKDNHSA-N C(CCCC)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)CCC1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCC Chemical compound C(CCCC)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)CCC1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCC CVYAXDDQRNSBLX-QOKNKDNHSA-N 0.000 description 1
- OLNSSFOLAUDPBI-CAWAAAKHSA-N C(CCCC)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)CCC1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCCCC Chemical compound C(CCCC)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)CCC1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCCCC OLNSSFOLAUDPBI-CAWAAAKHSA-N 0.000 description 1
- VYTGGYYLQUILKH-TVLXLKRTSA-N C(CCCC)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)C1=CC=C(C=C1)CC[C@@H]1CC[C@H](CC1)CCC Chemical group C(CCCC)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)C1=CC=C(C=C1)CC[C@@H]1CC[C@H](CC1)CCC VYTGGYYLQUILKH-TVLXLKRTSA-N 0.000 description 1
- SSXGYVMNQSFSDW-PCYFZWJMSA-N C(CCCC)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)CC[C@@H]1CC[C@H](CC1)CCC Chemical compound C(CCCC)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)CC[C@@H]1CC[C@H](CC1)CCC SSXGYVMNQSFSDW-PCYFZWJMSA-N 0.000 description 1
- KOMIDLVRQSJIHF-DANJKSSVSA-N C(CCCC)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)CC[C@@H]1CC[C@H](CC1)CCCCC Chemical compound C(CCCC)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)CC[C@@H]1CC[C@H](CC1)CCCCC KOMIDLVRQSJIHF-DANJKSSVSA-N 0.000 description 1
- GCMUCHNTBNZNCZ-NJSSPPMUSA-N C(CCCC)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCC Chemical compound C(CCCC)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCC GCMUCHNTBNZNCZ-NJSSPPMUSA-N 0.000 description 1
- UHVIWPVCOJWQJA-AFMUELSESA-N C(CCCC)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCCC Chemical compound C(CCCC)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCCC UHVIWPVCOJWQJA-AFMUELSESA-N 0.000 description 1
- DSSZJRSCCMKVJP-OZIXAUCHSA-N C(CCCCCC)C1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=C(C=C1)CC[C@@H]1CC[C@H](CC1)CCC Chemical group C(CCCCCC)C1=CC=C(C=C1)C1=CC=C(C=C1)C1=CC=C(C=C1)CC[C@@H]1CC[C@H](CC1)CCC DSSZJRSCCMKVJP-OZIXAUCHSA-N 0.000 description 1
- SPRYHIIFIRLRMZ-IXFIMZJLSA-N C(CCCCCC)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C1=CC=C(C=C1)CC[C@@H]1CC[C@H](CC1)CCC Chemical group C(CCCCCC)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C1=CC=C(C=C1)CC[C@@H]1CC[C@H](CC1)CCC SPRYHIIFIRLRMZ-IXFIMZJLSA-N 0.000 description 1
- CSQXIKALLMMUSC-JFQKCFOJSA-N C(CCCCCC)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)C1=CC=C(C=C1)CC[C@@H]1CC[C@H](CC1)CCC Chemical group C(CCCCCC)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)C1=CC=C(C=C1)CC[C@@H]1CC[C@H](CC1)CCC CSQXIKALLMMUSC-JFQKCFOJSA-N 0.000 description 1
- WHSUHSIGVAJSQK-DANJKSSVSA-N C(CCCCCC)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)CC[C@@H]1CC[C@H](CC1)CCC Chemical compound C(CCCCCC)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)CC[C@@H]1CC[C@H](CC1)CCC WHSUHSIGVAJSQK-DANJKSSVSA-N 0.000 description 1
- NEKUQYNBNZLDSC-MEMLXQNLSA-N C(CCCCCC)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)OCC Chemical compound C(CCCCCC)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)OCC NEKUQYNBNZLDSC-MEMLXQNLSA-N 0.000 description 1
- BXRJUPMACUZOBJ-ZWGSZDQZSA-N C(C[C@@H]1CC[C@H](CC1)CCCCC)[C@@H]1CC[C@H](CC1)CCCCC Chemical compound C(C[C@@H]1CC[C@H](CC1)CCCCC)[C@@H]1CC[C@H](CC1)CCCCC BXRJUPMACUZOBJ-ZWGSZDQZSA-N 0.000 description 1
- LXVTVIQMKOLVSY-CTYIDZIISA-N C1C[C@@H](CCC)CC[C@@H]1C(=O)OC1=CC=C(C#N)C=C1 Chemical compound C1C[C@@H](CCC)CC[C@@H]1C(=O)OC1=CC=C(C#N)C=C1 LXVTVIQMKOLVSY-CTYIDZIISA-N 0.000 description 1
- JAYBMJPZPJBTQZ-WKILWMFISA-N C1C[C@@H](CCCC)CC[C@@H]1C(=O)OC1=CC=C(OCC)C=C1 Chemical compound C1C[C@@H](CCCC)CC[C@@H]1C(=O)OC1=CC=C(OCC)C=C1 JAYBMJPZPJBTQZ-WKILWMFISA-N 0.000 description 1
- JRNQQLWJXYJSRU-JCNLHEQBSA-N C1C[C@@H](CCCCC)CC[C@@H]1C(=O)OC1=CC=C(C#N)C=C1 Chemical compound C1C[C@@H](CCCCC)CC[C@@H]1C(=O)OC1=CC=C(C#N)C=C1 JRNQQLWJXYJSRU-JCNLHEQBSA-N 0.000 description 1
- RXBBPIPXHBOXOU-KESTWPANSA-N C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(CCC)C=C1 Chemical compound C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(CCC)C=C1 RXBBPIPXHBOXOU-KESTWPANSA-N 0.000 description 1
- LUHIDQBRTFQIPW-OZIXAUCHSA-N CCCCCC(C=C1)=CC=C1C1=CC=C(CCC2=CC=C(CC[C@H]3CC[C@H](CCC)CC3)C=C2)C=C1 Chemical compound CCCCCC(C=C1)=CC=C1C1=CC=C(CCC2=CC=C(CC[C@H]3CC[C@H](CCC)CC3)C=C2)C=C1 LUHIDQBRTFQIPW-OZIXAUCHSA-N 0.000 description 1
- IOPLBWNKFIQMQW-OZIPULPJSA-N CCCCCCC[C@H](CC1)CC[C@@H]1C1=CC=C(CCC2=CC=C(CC[C@H]3CC[C@H](CCC)CC3)C=C2)C=C1 Chemical compound CCCCCCC[C@H](CC1)CC[C@@H]1C1=CC=C(CCC2=CC=C(CC[C@H]3CC[C@H](CCC)CC3)C=C2)C=C1 IOPLBWNKFIQMQW-OZIPULPJSA-N 0.000 description 1
- OZXCWVMDCDZZMJ-BZEGYMRZSA-N CCCCC[C@H](CC1)CC[C@@H]1C1=CC=C(CCC2=CC=C(CC[C@H]3CC[C@H](CCC)CC3)C=C2)C=C1 Chemical compound CCCCC[C@H](CC1)CC[C@@H]1C1=CC=C(CCC2=CC=C(CC[C@H]3CC[C@H](CCC)CC3)C=C2)C=C1 OZXCWVMDCDZZMJ-BZEGYMRZSA-N 0.000 description 1
- XMINAJWOXLLYRA-VYDRQYCRSA-N CCCCC[C@H](CC1)CC[C@@H]1C1=CC=C(CCC2=CC=C([C@H]3CC[C@H](CCCC)CC3)C=C2)C=C1 Chemical compound CCCCC[C@H](CC1)CC[C@@H]1C1=CC=C(CCC2=CC=C([C@H]3CC[C@H](CCCC)CC3)C=C2)C=C1 XMINAJWOXLLYRA-VYDRQYCRSA-N 0.000 description 1
- PXVNNKYCIZPRCF-NJSSPPMUSA-N CCCCC[C@H]1CC[C@@H](CC1)c1ccc(CC[C@H]2CC[C@H](CCC)CC2)cc1 Chemical compound CCCCC[C@H]1CC[C@@H](CC1)c1ccc(CC[C@H]2CC[C@H](CCC)CC2)cc1 PXVNNKYCIZPRCF-NJSSPPMUSA-N 0.000 description 1
- CECDPADATRVQLC-OZIXAUCHSA-N CCCCC[C@H]1CC[C@H](CCC(C=C2)=CC=C2C(C=C2)=CC=C2C2=CC=C(CCCCC)C=C2)CC1 Chemical group CCCCC[C@H]1CC[C@H](CCC(C=C2)=CC=C2C(C=C2)=CC=C2C2=CC=C(CCCCC)C=C2)CC1 CECDPADATRVQLC-OZIXAUCHSA-N 0.000 description 1
- VGGWMKFMMOWEQV-UEOVJWFCSA-N CCCCC[C@H]1CC[C@H](CCC2=CC=C(CCC(C=C3)=CC=C3C3=CC=C(CCCC)C=C3)C=C2)CC1 Chemical compound CCCCC[C@H]1CC[C@H](CCC2=CC=C(CCC(C=C3)=CC=C3C3=CC=C(CCCC)C=C3)C=C2)CC1 VGGWMKFMMOWEQV-UEOVJWFCSA-N 0.000 description 1
- ORJCMFBPRROMGB-RHMHBARZSA-N CCCCC[C@H]1CC[C@H](CCC2=CC=C(CCC(C=C3)=CC=C3C3=CC=C(CCCCC)C=C3)C=C2)CC1 Chemical compound CCCCC[C@H]1CC[C@H](CCC2=CC=C(CCC(C=C3)=CC=C3C3=CC=C(CCCCC)C=C3)C=C2)CC1 ORJCMFBPRROMGB-RHMHBARZSA-N 0.000 description 1
- NUIWJPARGZSPMG-WTZQBIJTSA-N CCCCC[C@H]1CC[C@H](CCc2ccc(cc2)[C@H]2CC[C@H](CCCCC)CC2)CC1 Chemical compound CCCCC[C@H]1CC[C@H](CCc2ccc(cc2)[C@H]2CC[C@H](CCCCC)CC2)CC1 NUIWJPARGZSPMG-WTZQBIJTSA-N 0.000 description 1
- OFJDELISSIYBDL-LWZIEXQQSA-N CCC[C@H](CC1)CC[C@@H]1C1=CC=C(CCC2=CC=C([C@H]3CC[C@H](CC)CC3)C=C2)C=C1 Chemical compound CCC[C@H](CC1)CC[C@@H]1C1=CC=C(CCC2=CC=C([C@H]3CC[C@H](CC)CC3)C=C2)C=C1 OFJDELISSIYBDL-LWZIEXQQSA-N 0.000 description 1
- IFWXEEYFJPUALZ-QVYRIUEQSA-N CCC[C@H]1CC[C@H](CCC2=CC=C(CCC(C=C3)=CC=C3C3=CC=C(CC)C=C3)C=C2)CC1 Chemical compound CCC[C@H]1CC[C@H](CCC2=CC=C(CCC(C=C3)=CC=C3C3=CC=C(CC)C=C3)C=C2)CC1 IFWXEEYFJPUALZ-QVYRIUEQSA-N 0.000 description 1
- PVYRICGWDBNUFA-KWQFAZJVSA-N CCC[C@H]1CC[C@H](CCC2=CC=C(CCC(C=C3)=CC=C3C3=CC=C(CCC)C=C3)C=C2)CC1 Chemical compound CCC[C@H]1CC[C@H](CCC2=CC=C(CCC(C=C3)=CC=C3C3=CC=C(CCC)C=C3)C=C2)CC1 PVYRICGWDBNUFA-KWQFAZJVSA-N 0.000 description 1
- YFXUPSMQJXOATM-OLJJXAFESA-N CCC[C@H]1CC[C@H](CCC2=CC=C(CCC3=CC=C([C@H]4CC[C@H](CC)CC4)C=C3)C=C2)CC1 Chemical compound CCC[C@H]1CC[C@H](CCC2=CC=C(CCC3=CC=C([C@H]4CC[C@H](CC)CC4)C=C3)C=C2)CC1 YFXUPSMQJXOATM-OLJJXAFESA-N 0.000 description 1
- NUGINMSPSAUIHI-RWXFHALSSA-N CCC[C@H]1CC[C@H](CCC2=CC=C(CCC3=CC=C([C@H]4CC[C@H](CCC)CC4)C=C3)C=C2)CC1 Chemical compound CCC[C@H]1CC[C@H](CCC2=CC=C(CCC3=CC=C([C@H]4CC[C@H](CCC)CC4)C=C3)C=C2)CC1 NUGINMSPSAUIHI-RWXFHALSSA-N 0.000 description 1
- AKDMWIJCFAISBY-JENPDSIZSA-N CCC[C@H]1CC[C@H](CCc2ccc(cc2)[C@H]2CC[C@H](CC)CC2)CC1 Chemical compound CCC[C@H]1CC[C@H](CCc2ccc(cc2)[C@H]2CC[C@H](CC)CC2)CC1 AKDMWIJCFAISBY-JENPDSIZSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 238000006828 Rosenmund reduction reaction Methods 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- SFHGONLFTNHXDX-UHFFFAOYSA-N [4-[4-(hydroxymethyl)phenyl]phenyl]methanol Chemical group C1=CC(CO)=CC=C1C1=CC=C(CO)C=C1 SFHGONLFTNHXDX-UHFFFAOYSA-N 0.000 description 1
- KNJOQRFTJUYXTB-KBRNKZTISA-M [Br-].C(CCCC)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C1=CC=C(C=C1)C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound [Br-].C(CCCC)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C1=CC=C(C=C1)C[P+](C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1 KNJOQRFTJUYXTB-KBRNKZTISA-M 0.000 description 1
- VITCXWNGUMTQRJ-UHFFFAOYSA-L [Li+].[Li+].[Cl-].[Cl-].Cl.Cl Chemical compound [Li+].[Li+].[Cl-].[Cl-].Cl.Cl VITCXWNGUMTQRJ-UHFFFAOYSA-L 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 125000005337 azoxy group Chemical group [N+]([O-])(=N*)* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001851 cinnamic acid derivatives Chemical class 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 210000002858 crystal cell Anatomy 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- VJCWGXGMXAVKJU-UHFFFAOYSA-N cyclohexyl cyclohexanecarboxylate Chemical class C1CCCCC1C(=O)OC1CCCCC1 VJCWGXGMXAVKJU-UHFFFAOYSA-N 0.000 description 1
- IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical class C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000004817 gas chromatography Methods 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
- 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
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- BKRIRZXWWALTPU-UHFFFAOYSA-N methyl 4-(4-methoxycarbonylphenyl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC=C(C(=O)OC)C=C1 BKRIRZXWWALTPU-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000001564 phenyl benzoates Chemical class 0.000 description 1
- OPYYWWIJPHKUDZ-UHFFFAOYSA-N phenyl cyclohexanecarboxylate Chemical class C1CCCCC1C(=O)OC1=CC=CC=C1 OPYYWWIJPHKUDZ-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000001911 terphenyls Chemical class 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- CMSYDJVRTHCWFP-UHFFFAOYSA-N triphenylphosphane;hydrobromide Chemical compound Br.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 CMSYDJVRTHCWFP-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- 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
- C09K19/42—Mixtures of liquid crystal compounds covered by two or more of the preceding groups C09K19/06 - C09K19/40
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/32—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen
- C07C1/325—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen the hetero-atom being a metal atom
- C07C1/326—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen the hetero-atom being a metal atom the hetero-atom being a magnesium atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C1/00—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon
- C07C1/32—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen
- C07C1/34—Preparation of hydrocarbons from one or more compounds, none of them being a hydrocarbon starting from compounds containing hetero-atoms other than or in addition to oxygen or halogen reacting phosphines with aldehydes or ketones, e.g. Wittig reaction
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/44—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reduction and hydrolysis of nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C5/00—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms
- C07C5/02—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation
- C07C5/03—Preparation of hydrocarbons from hydrocarbons containing the same number of carbon atoms by hydrogenation of non-aromatic carbon-to-carbon double bonds
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/54—Quaternary phosphonium compounds
- C07F9/5456—Arylalkanephosphonium compounds
-
- 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
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
- C09K19/3028—Cyclohexane rings in which at least two rings are linked by a carbon chain containing carbon to carbon single bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH6572/81-0 | 1981-10-14 | ||
| CH6572/81A CH648539A5 (en) | 1981-10-14 | 1981-10-14 | Phenylethanes and use thereof in liquid-crystalline mixtures |
| CH1725/82-2 | 1982-03-19 | ||
| CH4172/82-2 | 1982-07-08 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5872528A JPS5872528A (ja) | 1983-04-30 |
| JPH0329050B2 true JPH0329050B2 (zh) | 1991-04-23 |
Family
ID=4311709
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57177726A Granted JPS5872528A (ja) | 1981-10-14 | 1982-10-12 | フエニルエタン類 |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS5872528A (zh) |
| CH (1) | CH648539A5 (zh) |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57144229A (en) * | 1981-01-30 | 1982-09-06 | Hoffmann La Roche | (trans-4-alkylcyclohexyl) ethanes |
| JPS57163324A (en) * | 1981-03-06 | 1982-10-07 | Dainippon Ink & Chem Inc | 1-cyclohexyl-2-cyclohexylphenylethane derivative |
| JPS588022A (ja) * | 1981-07-09 | 1983-01-18 | Dainippon Ink & Chem Inc | １−シクロヘキシル−２−シクロヘキシルビフエニルエタン誘導体 |
| JPS588023A (ja) * | 1981-07-09 | 1983-01-18 | Dainippon Ink & Chem Inc | １，２−ジ−（シクロヘキシルフエニル）エタン誘導体 |
| JPS5810529A (ja) * | 1981-07-09 | 1983-01-21 | Dainippon Ink & Chem Inc | １，４−ジ−（シクロヘキシルエチル）ビフエニル誘導体 |
-
1981
- 1981-10-14 CH CH6572/81A patent/CH648539A5/de not_active IP Right Cessation
-
1982
- 1982-10-12 JP JP57177726A patent/JPS5872528A/ja active Granted
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57144229A (en) * | 1981-01-30 | 1982-09-06 | Hoffmann La Roche | (trans-4-alkylcyclohexyl) ethanes |
| JPS57163324A (en) * | 1981-03-06 | 1982-10-07 | Dainippon Ink & Chem Inc | 1-cyclohexyl-2-cyclohexylphenylethane derivative |
| JPS588022A (ja) * | 1981-07-09 | 1983-01-18 | Dainippon Ink & Chem Inc | １−シクロヘキシル−２−シクロヘキシルビフエニルエタン誘導体 |
| JPS588023A (ja) * | 1981-07-09 | 1983-01-18 | Dainippon Ink & Chem Inc | １，２−ジ−（シクロヘキシルフエニル）エタン誘導体 |
| JPS5810529A (ja) * | 1981-07-09 | 1983-01-21 | Dainippon Ink & Chem Inc | １，４−ジ−（シクロヘキシルエチル）ビフエニル誘導体 |
Also Published As
| Publication number | Publication date |
|---|---|
| CH648539A5 (en) | 1985-03-29 |
| JPS5872528A (ja) | 1983-04-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4583826A (en) | Phenylethanes | |
| JP6797544B2 (ja) | フッ素化ジベンゾフランおよびジベンゾチオフェン誘導体 | |
| US4526704A (en) | Multiring liquid crystal esters | |
| EP0325796B1 (en) | A liquid crystal compound and a mixture containing the same | |
| US4349452A (en) | Cyclohexylcyclohexanoates | |
| KR20150108325A (ko) | 4,6-다이플루오로다이벤조퓨란 유도체 | |
| USRE34264E (en) | Tolan derivative and a liquid crystal mixture containing the same | |
| JP2003176251A (ja) | 液晶化合物 | |
| US4925278A (en) | Liquid crystalline esters | |
| JPH0662603B2 (ja) | シクロヘキサンカルボニトリル誘導体 | |
| EP1860089B1 (en) | Difluorobenzene derivative and nematic liquid crystal composition making use of the same | |
| JPH04501270A (ja) | フェニルシクロヘキサン化合物および液晶相 | |
| JP2786264B2 (ja) | アルコキシメチル―及びアルケニロキシメチルシクロヘキサン類 | |
| JPH02180840A (ja) | 大きな屈折率異方性を有する新規な液晶化合物 | |
| JPH045021B2 (zh) | ||
| JPS62234066A (ja) | フエニルピリジン誘導体 | |
| JP3134473B2 (ja) | シス−１，４−置換２−ブテン誘導体 | |
| US4816179A (en) | Dihalogeno-aromatic compound | |
| JP2007039642A (ja) | ジフルオロベンゼン誘導体及びこれを用いた液晶組成物 | |
| JP2927957B2 (ja) | フェニルシクロヘキサン類および液晶媒体 | |
| US5858275A (en) | Chlorobenzene derivative and liquid crystal composition containing the same | |
| JPS5818348A (ja) | 新規なトランス−４−〔２−（トランス−４−アルキルシクロヘキシル）エチル〕シクロヘキサンカルボニトリル | |
| JPH02279649A (ja) | 四環状のエステル化合物およびエーテル化合物 | |
| JPH0329050B2 (zh) | ||
| JPS61143350A (ja) | カルボニトリル化合物 |