JPH0430382B2 - - Google Patents
Info
- Publication number
- JPH0430382B2 JPH0430382B2 JP4826784A JP4826784A JPH0430382B2 JP H0430382 B2 JPH0430382 B2 JP H0430382B2 JP 4826784 A JP4826784 A JP 4826784A JP 4826784 A JP4826784 A JP 4826784A JP H0430382 B2 JPH0430382 B2 JP H0430382B2
- Authority
- JP
- Japan
- Prior art keywords
- trans
- ring
- mixture
- cyclohexylene
- formula
- 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
Links
- 239000000203 mixture Substances 0.000 claims description 141
- 150000001875 compounds Chemical class 0.000 claims description 129
- -1 2,5-disubstituted pyrimidine ring Chemical group 0.000 claims description 45
- 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 claims description 43
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 28
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 23
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical group C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 claims description 21
- 239000004973 liquid crystal related substance Substances 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 239000011737 fluorine Substances 0.000 claims description 11
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000004955 1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])C([H])([*:1])C([H])([H])C([H])([H])C1([H])[*:2] 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 240
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 147
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 144
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 90
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 87
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 73
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 63
- 238000002844 melting Methods 0.000 description 57
- 230000008018 melting Effects 0.000 description 57
- 239000003208 petroleum Substances 0.000 description 52
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 50
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 46
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 45
- 235000019341 magnesium sulphate Nutrition 0.000 description 45
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 43
- 239000000741 silica gel Substances 0.000 description 43
- 229910002027 silica gel Inorganic materials 0.000 description 43
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
- 239000012074 organic phase Substances 0.000 description 41
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
- 238000006243 chemical reaction Methods 0.000 description 32
- 238000010992 reflux Methods 0.000 description 29
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 28
- 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 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 238000000034 method Methods 0.000 description 27
- 229910052786 argon Inorganic materials 0.000 description 25
- 230000005587 bubbling Effects 0.000 description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 239000007788 liquid Substances 0.000 description 24
- 239000000725 suspension Substances 0.000 description 24
- 238000004587 chromatography analysis Methods 0.000 description 23
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 23
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- 239000013078 crystal Substances 0.000 description 18
- 239000003921 oil Substances 0.000 description 17
- 239000000284 extract Substances 0.000 description 16
- 238000006277 sulfonation reaction Methods 0.000 description 16
- 229910052799 carbon Inorganic materials 0.000 description 15
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 14
- 239000008346 aqueous phase Substances 0.000 description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 12
- 239000007858 starting material Substances 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 11
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- 210000004027 cell Anatomy 0.000 description 10
- 229910052700 potassium Inorganic materials 0.000 description 10
- 239000011591 potassium Substances 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- 238000001953 recrystallisation Methods 0.000 description 10
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- 239000003480 eluent Substances 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- DGCFSMRCHVOUNV-BZZBOHJJSA-N C1C[C@@H](/C=C/CC)CC[C@@H]1c1ccc(C#N)cc1 Chemical compound C1C[C@@H](/C=C/CC)CC[C@@H]1c1ccc(C#N)cc1 DGCFSMRCHVOUNV-BZZBOHJJSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000012230 colorless oil Substances 0.000 description 6
- 230000032050 esterification Effects 0.000 description 6
- 238000005886 esterification reaction Methods 0.000 description 6
- SJFNDMHZXCUXSA-UHFFFAOYSA-M methoxymethyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(COC)C1=CC=CC=C1 SJFNDMHZXCUXSA-UHFFFAOYSA-M 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 6
- 235000019345 sodium thiosulphate Nutrition 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 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 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
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- FIQRFWBYVFIOPU-UHFFFAOYSA-N 4-(4-formylcyclohexyl)benzonitrile Chemical compound C1CC(C=O)CCC1C1=CC=C(C#N)C=C1 FIQRFWBYVFIOPU-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- WFVBLRKVRNUULX-AXEKWBSNSA-N C1C[C@@H](/C=C/C)CC[C@@H]1c1ccc(C#N)cc1 Chemical compound C1C[C@@H](/C=C/C)CC[C@@H]1c1ccc(C#N)cc1 WFVBLRKVRNUULX-AXEKWBSNSA-N 0.000 description 5
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- KVFDZFBHBWTVID-UHFFFAOYSA-N cyclohexanecarbaldehyde Chemical compound O=CC1CCCCC1 KVFDZFBHBWTVID-UHFFFAOYSA-N 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000012452 mother liquor Substances 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 229910001961 silver nitrate Inorganic materials 0.000 description 5
- IMZFWBUCFOWCSW-SNAWJCMRSA-N 2-[(e)-pent-1-enyl]propane-1,3-diol Chemical compound CCC\C=C\C(CO)CO IMZFWBUCFOWCSW-SNAWJCMRSA-N 0.000 description 4
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- FQRGQOHRJZSGDM-SNAWJCMRSA-N 4-[(e)-pent-1-enyl]cyclohexane-1-carboxylic acid Chemical compound CCC\C=C\C1CCC(C(O)=O)CC1 FQRGQOHRJZSGDM-SNAWJCMRSA-N 0.000 description 4
- QKEBUASRTJNJJS-UHFFFAOYSA-N 4-[4-(4-pentylcyclohexyl)phenyl]benzonitrile Chemical group C1CC(CCCCC)CCC1C1=CC=C(C=2C=CC(=CC=2)C#N)C=C1 QKEBUASRTJNJJS-UHFFFAOYSA-N 0.000 description 4
- ZDEDXJOHDIZOGV-SNAWJCMRSA-N 4-[4-[(e)-pent-1-enyl]cyclohexyl]benzonitrile Chemical compound C1CC(/C=C/CCC)CCC1C1=CC=C(C#N)C=C1 ZDEDXJOHDIZOGV-SNAWJCMRSA-N 0.000 description 4
- YTYSCBUQUHCGOL-UHFFFAOYSA-N 8-(methoxymethylidene)-1,4-dioxaspiro[4.5]decane Chemical compound C1CC(=COC)CCC21OCCO2 YTYSCBUQUHCGOL-UHFFFAOYSA-N 0.000 description 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- LGZVXDCVOZLFAW-UHFFFAOYSA-N 4-(5-butylpyrimidin-2-yl)benzonitrile Chemical compound N1=CC(CCCC)=CN=C1C1=CC=C(C#N)C=C1 LGZVXDCVOZLFAW-UHFFFAOYSA-N 0.000 description 3
- SFNKUFOBKQJUEB-UHFFFAOYSA-N 4-oxocyclohexane-1-carbaldehyde Chemical compound O=CC1CCC(=O)CC1 SFNKUFOBKQJUEB-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
- JJCORTSDZLEUKP-JCNLHEQBSA-N C(=CCCCC)/[C@H]1CO[C@@H](OC1)C1=CC=C(C#N)C=C1 Chemical compound C(=CCCCC)/[C@H]1CO[C@@H](OC1)C1=CC=C(C#N)C=C1 JJCORTSDZLEUKP-JCNLHEQBSA-N 0.000 description 3
- DYSKOTSDIOSUSH-UAPYVXQJSA-N C(=CCCCCC)[C@@H]1CC[C@H](CC1)C1=CC=C(C#N)C=C1 Chemical compound C(=CCCCCC)[C@@H]1CC[C@H](CC1)C1=CC=C(C#N)C=C1 DYSKOTSDIOSUSH-UAPYVXQJSA-N 0.000 description 3
- 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 3
- GLPRRPVEFLLWHE-CTYIDZIISA-N C1C[C@@H](CCC=O)CC[C@@H]1C1=CC=C(C#N)C=C1 Chemical compound C1C[C@@H](CCC=O)CC[C@@H]1C1=CC=C(C#N)C=C1 GLPRRPVEFLLWHE-CTYIDZIISA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000004423 acyloxy group Chemical group 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000003989 dielectric material Substances 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 150000003230 pyrimidines Chemical group 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 230000004044 response Effects 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000011343 solid material Substances 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 2
- VKRKCBWIVLSRBJ-UHFFFAOYSA-N 1,4-dioxaspiro[4.5]decan-8-one Chemical compound C1CC(=O)CCC21OCCO2 VKRKCBWIVLSRBJ-UHFFFAOYSA-N 0.000 description 2
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 2
- GHMLTEGBYOLTBG-UHFFFAOYSA-N 4-(2,2-dibromoethenyl)cyclohexan-1-one Chemical compound BrC(Br)=CC1CCC(=O)CC1 GHMLTEGBYOLTBG-UHFFFAOYSA-N 0.000 description 2
- JHXJAWXZLWDDED-UHFFFAOYSA-N 4-(4-ethenylcyclohexyl)benzonitrile Chemical compound C1CC(C=C)CCC1C1=CC=C(C#N)C=C1 JHXJAWXZLWDDED-UHFFFAOYSA-N 0.000 description 2
- ZQVKTHRQIXSMGY-UHFFFAOYSA-N 4-Ethylbenzoic acid Chemical compound CCC1=CC=C(C(O)=O)C=C1 ZQVKTHRQIXSMGY-UHFFFAOYSA-N 0.000 description 2
- YATVXQYRIRTCCM-UHFFFAOYSA-N 4-[2-(4-oxocyclohexyl)ethyl]benzonitrile Chemical compound C1CC(=O)CCC1CCC1=CC=C(C#N)C=C1 YATVXQYRIRTCCM-UHFFFAOYSA-N 0.000 description 2
- QYLGTCULRPATII-UHFFFAOYSA-N 4-[4-(methoxymethylidene)cyclohexyl]benzonitrile Chemical compound C1CC(=COC)CCC1C1=CC=C(C#N)C=C1 QYLGTCULRPATII-UHFFFAOYSA-N 0.000 description 2
- KUTWIQCBCSPAKD-UHFFFAOYSA-N 4-formylcyclohexane-1-carbonitrile Chemical compound O=CC1CCC(C#N)CC1 KUTWIQCBCSPAKD-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- VCKGSFQIXDKQOL-XYPYZODXSA-N C(=CCCC)/[C@@H]1CC[C@H](CC1)O Chemical compound C(=CCCC)/[C@@H]1CC[C@H](CC1)O VCKGSFQIXDKQOL-XYPYZODXSA-N 0.000 description 2
- DFPZWXHDBVKILW-SAABIXHNSA-N C(=CCCCC)[C@@H]1CC[C@H](CC1)C1=CC=C(C#N)C=C1 Chemical compound C(=CCCCC)[C@@H]1CC[C@H](CC1)C1=CC=C(C#N)C=C1 DFPZWXHDBVKILW-SAABIXHNSA-N 0.000 description 2
- VQBDFJALOVKGGM-PDYYIGBGSA-N C1C[C@@H](/C=C/COC(=O)C)CC[C@@H]1C1=CC=C(C=O)C=C1 Chemical compound C1C[C@@H](/C=C/COC(=O)C)CC[C@@H]1C1=CC=C(C=O)C=C1 VQBDFJALOVKGGM-PDYYIGBGSA-N 0.000 description 2
- WLPNBWHAGKJNCE-PDYYIGBGSA-N C1C[C@@H](CC/C=C/C)CC[C@@H]1c1ccc(C#N)cc1 Chemical compound C1C[C@@H](CC/C=C/C)CC[C@@H]1c1ccc(C#N)cc1 WLPNBWHAGKJNCE-PDYYIGBGSA-N 0.000 description 2
- MCYPADFEUZOILO-MJYONLJCSA-N CCCC1OC1[C@@H]1CC[C@@H](C=2C=CC(=CC=2)C#N)CC1 Chemical compound CCCC1OC1[C@@H]1CC[C@@H](C=2C=CC(=CC=2)C#N)CC1 MCYPADFEUZOILO-MJYONLJCSA-N 0.000 description 2
- CWZCLUUUQKXILI-KOMQPUFPSA-N COC=CC[C@@H]1CC[C@H](CC1)C1=CC=C(C#N)C=C1 Chemical compound COC=CC[C@@H]1CC[C@H](CC1)C1=CC=C(C#N)C=C1 CWZCLUUUQKXILI-KOMQPUFPSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 150000001241 acetals Chemical class 0.000 description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 150000004791 alkyl magnesium halides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 150000004074 biphenyls Chemical class 0.000 description 2
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- SGJSQQLUMMGQOS-UHFFFAOYSA-N cyclohexanecarbonitrile Chemical compound N#C[C]1CCCCC1 SGJSQQLUMMGQOS-UHFFFAOYSA-N 0.000 description 2
- 125000004956 cyclohexylene group Chemical group 0.000 description 2
- SMBQBQBNOXIFSF-UHFFFAOYSA-N dilithium Chemical compound [Li][Li] SMBQBQBNOXIFSF-UHFFFAOYSA-N 0.000 description 2
- 125000000532 dioxanyl group Chemical group 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 230000005670 electromagnetic radiation Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- POXSDSRWVJZWCN-UHFFFAOYSA-N triphenylphosphanium;iodide Chemical compound I.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 POXSDSRWVJZWCN-UHFFFAOYSA-N 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- GXMFPJIKPZDNCS-UHFFFAOYSA-M (4-cyanophenyl)methyl-triphenylphosphanium;chloride Chemical compound [Cl-].C1=CC(C#N)=CC=C1C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 GXMFPJIKPZDNCS-UHFFFAOYSA-M 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- CXBDYQVECUFKRK-UHFFFAOYSA-N 1-methoxybutane Chemical compound CCCCOC CXBDYQVECUFKRK-UHFFFAOYSA-N 0.000 description 1
- 125000006023 1-pentenyl group Chemical group 0.000 description 1
- RRGUVJJVBAZCFI-UHFFFAOYSA-N 2,2-dibromoethenylcyclohexane Chemical compound BrC(Br)=CC1CCCCC1 RRGUVJJVBAZCFI-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- MHZPFSMZADJIER-UHFFFAOYSA-N 2-cyclohexylbenzonitrile Chemical compound N#CC1=CC=CC=C1C1CCCCC1 MHZPFSMZADJIER-UHFFFAOYSA-N 0.000 description 1
- HYYFAYFMSHAWFA-UHFFFAOYSA-N 2-cyclohexylethylbenzene Chemical class C1CCCCC1CCC1=CC=CC=C1 HYYFAYFMSHAWFA-UHFFFAOYSA-N 0.000 description 1
- IBLVSWYGUFGDMF-UHFFFAOYSA-N 2-cyclohexylethylcyclohexane Chemical class C1CCCCC1CCC1CCCCC1 IBLVSWYGUFGDMF-UHFFFAOYSA-N 0.000 description 1
- MVRPPTGLVPEMPI-UHFFFAOYSA-N 2-cyclohexylphenol Chemical compound OC1=CC=CC=C1C1CCCCC1 MVRPPTGLVPEMPI-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 125000003229 2-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- BPPPUFSZQDCMEE-UHFFFAOYSA-N 2-oxocyclohexane-1-carbaldehyde Chemical compound O=CC1CCCCC1=O BPPPUFSZQDCMEE-UHFFFAOYSA-N 0.000 description 1
- RHYUFGNCUXTFTC-UHFFFAOYSA-N 2-pentylpropane-1,3-diol Chemical compound CCCCCC(CO)CO RHYUFGNCUXTFTC-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
- OXPDQFOKSZYEMJ-UHFFFAOYSA-N 2-phenylpyrimidine Chemical class C1=CC=CC=C1C1=NC=CC=N1 OXPDQFOKSZYEMJ-UHFFFAOYSA-N 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 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
- XFRVACCGEKPJDI-UHFFFAOYSA-N 4-(4-oxocyclohexyl)benzonitrile Chemical compound C1CC(=O)CCC1C1=CC=C(C#N)C=C1 XFRVACCGEKPJDI-UHFFFAOYSA-N 0.000 description 1
- WLPNBWHAGKJNCE-UHFFFAOYSA-N 4-(4-pent-3-enylcyclohexyl)benzonitrile Chemical compound C1CC(CCC=CC)CCC1C1=CC=C(C#N)C=C1 WLPNBWHAGKJNCE-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 239000005218 4-Cyano-4''-pentyl-p-terphenyl Substances 0.000 description 1
- LKVFCSWBKOVHAH-UHFFFAOYSA-N 4-Ethoxyphenol Chemical compound CCOC1=CC=C(O)C=C1 LKVFCSWBKOVHAH-UHFFFAOYSA-N 0.000 description 1
- BTDUFFIVVRZWLJ-SNAWJCMRSA-N 4-[(e)-pent-1-enyl]cyclohexan-1-one Chemical compound CCC\C=C\C1CCC(=O)CC1 BTDUFFIVVRZWLJ-SNAWJCMRSA-N 0.000 description 1
- WYSJAQKTQAQGAD-SNAWJCMRSA-N 4-[(e)-pent-1-enyl]cyclohexane-1-carbaldehyde Chemical compound CCC\C=C\C1CCC(C=O)CC1 WYSJAQKTQAQGAD-SNAWJCMRSA-N 0.000 description 1
- VAFYGTJKWPMLCP-UHFFFAOYSA-N 4-[2-(4-formylcyclohexyl)ethyl]benzonitrile Chemical compound C1CC(C=O)CCC1CCC1=CC=C(C#N)C=C1 VAFYGTJKWPMLCP-UHFFFAOYSA-N 0.000 description 1
- QSELUNJFRLFQHE-UHFFFAOYSA-N 4-[2-(4-oxocyclohexyl)ethenyl]benzonitrile Chemical compound C1CC(=O)CCC1C=CC1=CC=C(C#N)C=C1 QSELUNJFRLFQHE-UHFFFAOYSA-N 0.000 description 1
- PCPICPGMEBRTKB-UHFFFAOYSA-N 4-[4-(2-oxoethyl)cyclohexyl]benzonitrile Chemical compound C1CC(CC=O)CCC1C1=CC=C(C#N)C=C1 PCPICPGMEBRTKB-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- UZHCGRNENGYSAM-UHFFFAOYSA-N 4-[4-(hydroxymethyl)cyclohexyl]benzonitrile Chemical compound C1CC(CO)CCC1C1=CC=C(C#N)C=C1 UZHCGRNENGYSAM-UHFFFAOYSA-N 0.000 description 1
- VGKZBAMIYUHSMU-UHFFFAOYSA-N 4-[[2-chloroethyl(nitroso)carbamoyl]amino]cyclohexane-1-carboxylic acid Chemical compound OC(=O)C1CCC(NC(=O)N(CCCl)N=O)CC1 VGKZBAMIYUHSMU-UHFFFAOYSA-N 0.000 description 1
- XHWMNHADTZZHGI-UHFFFAOYSA-N 4-butoxybenzaldehyde Chemical compound CCCCOC1=CC=C(C=O)C=C1 XHWMNHADTZZHGI-UHFFFAOYSA-N 0.000 description 1
- BALGERHMIXFENA-UHFFFAOYSA-N 4-butylcyclohexane-1-carboxylic acid Chemical compound CCCCC1CCC(C(O)=O)CC1 BALGERHMIXFENA-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
- RVLAXPQGTRTHEV-UHFFFAOYSA-N 4-pentylcyclohexane-1-carboxylic acid Chemical compound CCCCCC1CCC(C(O)=O)CC1 RVLAXPQGTRTHEV-UHFFFAOYSA-N 0.000 description 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- PFMAHTFPRKOLNO-UHFFFAOYSA-N 8-pent-1-ynyl-1,4-dioxaspiro[4.5]decane Chemical compound C1CC(C#CCCC)CCC21OCCO2 PFMAHTFPRKOLNO-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 238000006220 Baeyer-Villiger oxidation reaction Methods 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- HPYFCOOMGUPURW-AKMOFFSESA-N C(#N)C1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CC[C@@H]1CC[C@H](CC1)CCCCC Chemical compound C(#N)C1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CC[C@@H]1CC[C@H](CC1)CCCCC HPYFCOOMGUPURW-AKMOFFSESA-N 0.000 description 1
- DGCFSMRCHVOUNV-AMJRUAGCSA-N C(=C/CC)/[C@@H]1CC[C@H](CC1)C1=CC=C(C#N)C=C1 Chemical compound C(=C/CC)/[C@@H]1CC[C@H](CC1)C1=CC=C(C#N)C=C1 DGCFSMRCHVOUNV-AMJRUAGCSA-N 0.000 description 1
- UYJXCSVIJBFVBM-WKILWMFISA-N C(=CC)/[C@@H]1CC[C@H](CC1)CCC1=CC=C(C#N)C=C1 Chemical compound C(=CC)/[C@@H]1CC[C@H](CC1)CCC1=CC=C(C#N)C=C1 UYJXCSVIJBFVBM-WKILWMFISA-N 0.000 description 1
- RGGWJQPWUAEJNP-MQMHXKEQSA-N C(=CC)/[C@H]1CO[C@@H](OC1)C1=CC=C(C#N)C=C1 Chemical compound C(=CC)/[C@H]1CO[C@@H](OC1)C1=CC=C(C#N)C=C1 RGGWJQPWUAEJNP-MQMHXKEQSA-N 0.000 description 1
- WFVBLRKVRNUULX-CTYIDZIISA-N C(=CC)[C@@H]1CC[C@H](CC1)C1=CC=C(C#N)C=C1 Chemical compound C(=CC)[C@@H]1CC[C@H](CC1)C1=CC=C(C#N)C=C1 WFVBLRKVRNUULX-CTYIDZIISA-N 0.000 description 1
- COPSFUZNAFQQQJ-CTYIDZIISA-N C(=CCC)/[C@H]1CO[C@@H](OC1)C1=CC=C(C#N)C=C1 Chemical compound C(=CCC)/[C@H]1CO[C@@H](OC1)C1=CC=C(C#N)C=C1 COPSFUZNAFQQQJ-CTYIDZIISA-N 0.000 description 1
- DGCFSMRCHVOUNV-KOMQPUFPSA-N C(=CCC)[C@@H]1CC[C@H](CC1)C1=CC=C(C#N)C=C1 Chemical compound C(=CCC)[C@@H]1CC[C@H](CC1)C1=CC=C(C#N)C=C1 DGCFSMRCHVOUNV-KOMQPUFPSA-N 0.000 description 1
- WROGCTMSPBDIJI-SAABIXHNSA-N C(=CCCC)/[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C(C)=O Chemical compound C(=CCCC)/[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C(C)=O WROGCTMSPBDIJI-SAABIXHNSA-N 0.000 description 1
- FAIXBKMOULGLAG-QAQDUYKDSA-N C(=CCCC)/[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C(CC)=O Chemical compound C(=CCCC)/[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)C(CC)=O FAIXBKMOULGLAG-QAQDUYKDSA-N 0.000 description 1
- DCMZUWLDEMUZSY-CHDDOINTSA-N C(=CCCC)/[C@@H]1CC[C@H](CC1)OC(=O)[C@@H]1CC[C@H](CC1)CCCCC Chemical compound C(=CCCC)/[C@@H]1CC[C@H](CC1)OC(=O)[C@@H]1CC[C@H](CC1)CCCCC DCMZUWLDEMUZSY-CHDDOINTSA-N 0.000 description 1
- MFCWTLDYRQJSHK-KOMQPUFPSA-N C(=CCCC)/[C@H]1CO[C@@H](OC1)C1=CC=C(C#N)C=C1 Chemical compound C(=CCCC)/[C@H]1CO[C@@H](OC1)C1=CC=C(C#N)C=C1 MFCWTLDYRQJSHK-KOMQPUFPSA-N 0.000 description 1
- VCFMABDLFNKPGK-WGSAOQKQSA-N C(=CCCCC)/[C@@H]1CC[C@H](CC1)CCC1=CC=C(C#N)C=C1 Chemical compound C(=CCCCC)/[C@@H]1CC[C@H](CC1)CCC1=CC=C(C#N)C=C1 VCFMABDLFNKPGK-WGSAOQKQSA-N 0.000 description 1
- DUWTVMLHEJLRGX-MXVIHJGJSA-N C(=CCCCCC)/[C@@H]1CC[C@H](CC1)CCC1=CC=C(C#N)C=C1 Chemical compound C(=CCCCCC)/[C@@H]1CC[C@H](CC1)CCC1=CC=C(C#N)C=C1 DUWTVMLHEJLRGX-MXVIHJGJSA-N 0.000 description 1
- XKISENABXYKUPN-SAABIXHNSA-N C(=CCCCCC)/[C@H]1CO[C@@H](OC1)C1=CC=C(C#N)C=C1 Chemical compound C(=CCCCCC)/[C@H]1CO[C@@H](OC1)C1=CC=C(C#N)C=C1 XKISENABXYKUPN-SAABIXHNSA-N 0.000 description 1
- IKYJALHCSTWVAA-PDYYIGBGSA-N C(C)(=O)OC/C=C/[C@@H]1CC[C@H](CC1)C1=CC=C(C#N)C=C1 Chemical compound C(C)(=O)OC/C=C/[C@@H]1CC[C@H](CC1)C1=CC=C(C#N)C=C1 IKYJALHCSTWVAA-PDYYIGBGSA-N 0.000 description 1
- VYSDDLVESYHPEX-MRIGUKBISA-N C(C)(=O)OC1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)C1C(CCC)O1 Chemical compound C(C)(=O)OC1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)C1C(CCC)O1 VYSDDLVESYHPEX-MRIGUKBISA-N 0.000 description 1
- OVPIJXMGIFMSFZ-UAPYVXQJSA-N C(C)C1=CC=C(C=C1)CC[C@@H]1CC[C@H](CC1)C=CC Chemical compound C(C)C1=CC=C(C=C1)CC[C@@H]1CC[C@H](CC1)C=CC OVPIJXMGIFMSFZ-UAPYVXQJSA-N 0.000 description 1
- GACIIJWQASTOSL-UAPYVXQJSA-N C(C)C1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)C=CCCC Chemical compound C(C)C1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)C=CCCC GACIIJWQASTOSL-UAPYVXQJSA-N 0.000 description 1
- AJODKVIGMDUCMH-QAQDUYKDSA-N C(C)OC1=CC=C(C=C1)OC(=O)[C@@H]1CC[C@H](CC1)C=CCCC Chemical compound C(C)OC1=CC=C(C=C1)OC(=O)[C@@H]1CC[C@H](CC1)C=CCCC AJODKVIGMDUCMH-QAQDUYKDSA-N 0.000 description 1
- QKBXKKLRJJNALM-MRIGUKBISA-N C(C)OC1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)C1C(CCC)O1 Chemical compound C(C)OC1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)C1C(CCC)O1 QKBXKKLRJJNALM-MRIGUKBISA-N 0.000 description 1
- PWNHKJSWOZOBIM-CZIWCDLHSA-N C(C)OC1=CC=C(C=C1)[C@@H]1OC[C@H](CO1)C=CCCC Chemical compound C(C)OC1=CC=C(C=C1)[C@@H]1OC[C@H](CO1)C=CCCC PWNHKJSWOZOBIM-CZIWCDLHSA-N 0.000 description 1
- VAWVMZDDALHJJE-RZDIXWSQSA-N C(C)OC1=CC=C(C=C1)[C@@H]1OC[C@H](CO1)C=CCCCC Chemical compound C(C)OC1=CC=C(C=C1)[C@@H]1OC[C@H](CO1)C=CCCCC VAWVMZDDALHJJE-RZDIXWSQSA-N 0.000 description 1
- KAAXEXZMQKFPJB-KESTWPANSA-N C(CC)C1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)C=CCCC Chemical compound C(CC)C1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)C=CCCC KAAXEXZMQKFPJB-KESTWPANSA-N 0.000 description 1
- SZNAZUWGVGMMPI-SAABIXHNSA-N C(CC)C1=CC=C(C=C1)[C@@H]1OC[C@H](CO1)C=CCCC Chemical compound C(CC)C1=CC=C(C=C1)[C@@H]1OC[C@H](CO1)C=CCCC SZNAZUWGVGMMPI-SAABIXHNSA-N 0.000 description 1
- DEYRCIBYCNWQQO-OPMHRUBESA-N C(CC)[C@@H]1CC[C@H](CC1)[C@@H]1OC[C@H](CO1)C=CCCC Chemical compound C(CC)[C@@H]1CC[C@H](CC1)[C@@H]1OC[C@H](CO1)C=CCCC DEYRCIBYCNWQQO-OPMHRUBESA-N 0.000 description 1
- AHGCBYSIOMTIOX-HDRKRICHSA-N C(CC)[C@H]1CO[C@@H](OC1)[C@@H]1CC[C@H](CC1)C#N Chemical compound C(CC)[C@H]1CO[C@@H](OC1)[C@@H]1CC[C@H](CC1)C#N AHGCBYSIOMTIOX-HDRKRICHSA-N 0.000 description 1
- ANFZORPCFRUORL-CZIWCDLHSA-N C(CCC)OC1=CC=C(C=C1)[C@@H]1OC[C@H](CO1)C=CC Chemical compound C(CCC)OC1=CC=C(C=C1)[C@@H]1OC[C@H](CO1)C=CC ANFZORPCFRUORL-CZIWCDLHSA-N 0.000 description 1
- XGULFJBWCAJLIE-IRJFHVNHSA-N C(CCC)OC1=CC=C(C=C1)[C@@H]1OC[C@H](CO1)C=CCCCC Chemical compound C(CCC)OC1=CC=C(C=C1)[C@@H]1OC[C@H](CO1)C=CCCCC XGULFJBWCAJLIE-IRJFHVNHSA-N 0.000 description 1
- GVLQWFYOLYKACQ-GARHLSDISA-N C(CCC)[C@@H]1CC[C@H](CC1)[C@@H]1OC[C@H](CO1)C=CC Chemical compound C(CCC)[C@@H]1CC[C@H](CC1)[C@@H]1OC[C@H](CO1)C=CC GVLQWFYOLYKACQ-GARHLSDISA-N 0.000 description 1
- GIVBZAYEQUDELV-KTSLABGISA-N C(CCC)[C@H]1CO[C@@H](OC1)[C@@H]1CC[C@H](CC1)C#N Chemical compound C(CCC)[C@H]1CO[C@@H](OC1)[C@@H]1CC[C@H](CC1)C#N GIVBZAYEQUDELV-KTSLABGISA-N 0.000 description 1
- PPZAQODBLGYMRI-BIAGXBKMSA-N C(CCCC)[C@H]1CO[C@@H](OC1)[C@@H]1CC[C@H](CC1)C#N Chemical compound C(CCCC)[C@H]1CO[C@@H](OC1)[C@@H]1CC[C@H](CC1)C#N PPZAQODBLGYMRI-BIAGXBKMSA-N 0.000 description 1
- XIVBRVQPLLJXEP-GSOOHQETSA-N C1C[C@@H](/C=C/C(=O)OCC)CC[C@@H]1C1=CC=C(C#N)C=C1 Chemical compound C1C[C@@H](/C=C/C(=O)OCC)CC[C@@H]1C1=CC=C(C#N)C=C1 XIVBRVQPLLJXEP-GSOOHQETSA-N 0.000 description 1
- MVUCYBSJKHZUAT-GQEDJZSUSA-N C1C[C@@H](/C=C/CC)CC[C@@H]1CCC1=CC=C(C#N)C=C1 Chemical compound C1C[C@@H](/C=C/CC)CC[C@@H]1CCC1=CC=C(C#N)C=C1 MVUCYBSJKHZUAT-GQEDJZSUSA-N 0.000 description 1
- XFMYNNKIWBDMEJ-IXFYRXCXSA-N C1C[C@@H](/C=C/CCC)CC[C@@H]1CCC1=CC=C(C#N)C=C1 Chemical compound C1C[C@@H](/C=C/CCC)CC[C@@H]1CCC1=CC=C(C#N)C=C1 XFMYNNKIWBDMEJ-IXFYRXCXSA-N 0.000 description 1
- FYJJIOYIYFWBRF-WKILWMFISA-N C1C[C@@H](C=CCCC)CC[C@@H]1C1=CC=CC=C1C#N Chemical compound C1C[C@@H](C=CCCC)CC[C@@H]1C1=CC=CC=C1C#N FYJJIOYIYFWBRF-WKILWMFISA-N 0.000 description 1
- SBVVNFVXEQTYRJ-UAPYVXQJSA-N C1C[C@@H](CCC)CC[C@@H]1CCC1=CC=C(CC)C=C1 Chemical compound C1C[C@@H](CCC)CC[C@@H]1CCC1=CC=C(CC)C=C1 SBVVNFVXEQTYRJ-UAPYVXQJSA-N 0.000 description 1
- 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 description 1
- QCTHAGCDRXAJND-KOMQPUFPSA-N C1C[C@@H](CCC=C)CC[C@@H]1C1=CC=C(C#N)C=C1 Chemical compound C1C[C@@H](CCC=C)CC[C@@H]1C1=CC=C(C#N)C=C1 QCTHAGCDRXAJND-KOMQPUFPSA-N 0.000 description 1
- 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 1
- 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 description 1
- FDOULMJAMZEPJE-KJASSIQRSA-N CC1OC1CC[C@@H]1CC[C@@H](C=2C=CC(=CC=2)C#N)CC1 Chemical compound CC1OC1CC[C@@H]1CC[C@@H](C=2C=CC(=CC=2)C#N)CC1 FDOULMJAMZEPJE-KJASSIQRSA-N 0.000 description 1
- 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 description 1
- ZVPJXLAUZCFNSJ-CTYIDZIISA-N COC=C[C@@H]1CC[C@H](CC1)C1=CC=C(C#N)C=C1 Chemical compound COC=C[C@@H]1CC[C@H](CC1)C1=CC=C(C#N)C=C1 ZVPJXLAUZCFNSJ-CTYIDZIISA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
- VSIAONCLXNMMBN-UHFFFAOYSA-N N#CC1=CC=C(C=CC(CCCC2)C2=O)C=C1 Chemical compound N#CC1=CC=C(C=CC(CCCC2)C2=O)C=C1 VSIAONCLXNMMBN-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- XBGPBJUZKAYGJB-NYZZOUQCSA-N O1C(C1CCC)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)O Chemical compound O1C(C1CCC)[C@@H]1CC[C@H](CC1)C1=CC=C(C=C1)O XBGPBJUZKAYGJB-NYZZOUQCSA-N 0.000 description 1
- BFKDZIAGYQYGNW-IWZNKUOBSA-N OC(CC)C1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)C=CCCC Chemical compound OC(CC)C1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)C=CCCC BFKDZIAGYQYGNW-IWZNKUOBSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 240000002380 Rosa carolina Species 0.000 description 1
- 239000004990 Smectic liquid crystal Substances 0.000 description 1
- RQPUZGKLFDPSJD-VMPITWQZSA-N [(e)-pent-1-enyl]cyclohexane Chemical compound CCC\C=C\C1CCCCC1 RQPUZGKLFDPSJD-VMPITWQZSA-N 0.000 description 1
- KQCKZTSJTGJTPL-UHFFFAOYSA-N [benzenesulfonyloxy-(4-methylphenyl)sulfonyloxy-methylsulfonyloxy-naphthalen-1-ylsulfonyloxy-lambda5-bromanyl] acetate Chemical compound C(C)(=O)OBr(OS(=O)(=O)C1=CC=CC2=CC=CC=C12)(OS(=O)(=O)C1=CC=C(C)C=C1)(OS(=O)(=O)C1=CC=CC=C1)OS(=O)(=O)C KQCKZTSJTGJTPL-UHFFFAOYSA-N 0.000 description 1
- 125000004036 acetal group Chemical group 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 1
- 235000019270 ammonium chloride Nutrition 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
- 239000012300 argon atmosphere Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 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
- 125000005605 benzo group Chemical group 0.000 description 1
- 230000008033 biological extinction Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-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
- IKWKJIWDLVYZIY-UHFFFAOYSA-M butyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCCC)C1=CC=CC=C1 IKWKJIWDLVYZIY-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000003098 cholesteric effect Effects 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 150000001851 cinnamic acid derivatives Chemical class 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000008094 contradictory effect Effects 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- JZCCFEFSEZPSOG-UHFFFAOYSA-L copper(II) sulfate pentahydrate Chemical compound O.O.O.O.O.[Cu+2].[O-]S([O-])(=O)=O JZCCFEFSEZPSOG-UHFFFAOYSA-L 0.000 description 1
- SZDVDUDLIIZMKX-UHFFFAOYSA-N copper;pyridine Chemical compound [Cu].C1=CC=NC=C1.C1=CC=NC=C1.C1=CC=NC=C1.C1=CC=NC=C1.C1=CC=NC=C1.C1=CC=NC=C1 SZDVDUDLIIZMKX-UHFFFAOYSA-N 0.000 description 1
- 210000002858 crystal cell Anatomy 0.000 description 1
- 125000004802 cyanophenyl group Chemical group 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- GCFAUZGWPDYAJN-UHFFFAOYSA-N cyclohexyl 3-phenylprop-2-enoate Chemical compound C=1C=CC=CC=1C=CC(=O)OC1CCCCC1 GCFAUZGWPDYAJN-UHFFFAOYSA-N 0.000 description 1
- VJCWGXGMXAVKJU-UHFFFAOYSA-N cyclohexyl cyclohexanecarboxylate Chemical class C1CCCCC1C(=O)OC1CCCCC1 VJCWGXGMXAVKJU-UHFFFAOYSA-N 0.000 description 1
- 125000003493 decenyl group Chemical group [H]C([*])=C([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])[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
- 239000012954 diazonium Substances 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 125000004310 dioxan-2-yl group Chemical group [H]C1([H])OC([H])([H])C([H])(*)OC1([H])[H] 0.000 description 1
- 150000002012 dioxanes Chemical class 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
- 230000007613 environmental effect Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- FPIQZBQZKBKLEI-UHFFFAOYSA-N ethyl 1-[[2-chloroethyl(nitroso)carbamoyl]amino]cyclohexane-1-carboxylate Chemical compound ClCCN(N=O)C(=O)NC1(C(=O)OCC)CCCCC1 FPIQZBQZKBKLEI-UHFFFAOYSA-N 0.000 description 1
- JHYNXXDQQHTCHJ-UHFFFAOYSA-M ethyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CC)C1=CC=CC=C1 JHYNXXDQQHTCHJ-UHFFFAOYSA-M 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 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
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 125000006038 hexenyl group Chemical group 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
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- WTDHULULXKLSOZ-UHFFFAOYSA-N hydroxylamine hydrochloride Substances Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 1
- WCYJQVALWQMJGE-UHFFFAOYSA-M hydroxylammonium chloride Chemical compound [Cl-].O[NH3+] WCYJQVALWQMJGE-UHFFFAOYSA-M 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 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
- 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
- 239000007791 liquid phase Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([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])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- FUKDIOJYNWYKQB-UHFFFAOYSA-N pent-1-ynylcyclohexane Chemical compound CCCC#CC1CCCCC1 FUKDIOJYNWYKQB-UHFFFAOYSA-N 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000004965 peroxy acids Chemical class 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
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000004892 pyridazines Chemical class 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 125000001174 sulfone group Chemical group 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 150000001911 terphenyls Chemical class 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- XMQSELBBYSAURN-UHFFFAOYSA-M triphenyl(propyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCC)C1=CC=CC=C1 XMQSELBBYSAURN-UHFFFAOYSA-M 0.000 description 1
- IIHPVYJPDKJYOU-UHFFFAOYSA-N triphenylcarbethoxymethylenephosphorane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OCC)C1=CC=CC=C1 IIHPVYJPDKJYOU-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([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])[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH143683 | 1983-03-16 | ||
| CH1539/83-1 | 1984-01-19 | ||
| CH226/84-4 | 1984-01-19 | ||
| CH1436/83-2 | 1984-01-19 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3339895A Division JPH0662603B2 (ja) | 1983-03-16 | 1991-11-28 | シクロヘキサンカルボニトリル誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59176221A JPS59176221A (ja) | 1984-10-05 |
| JPH0430382B2 true JPH0430382B2 (ru) | 1992-05-21 |
Family
ID=4210420
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4826784A Granted JPS59176221A (ja) | 1983-03-16 | 1984-03-15 | アルケニル化合物 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59176221A (ru) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1908814A1 (en) | 2006-10-05 | 2008-04-09 | Chisso Corporation | Liquid crystal compositon and liquid crystal display device |
| WO2009028367A1 (ja) | 2007-08-27 | 2009-03-05 | Chisso Corporation | 液晶組成物および液晶表示素子 |
| WO2010024142A1 (ja) | 2008-08-28 | 2010-03-04 | チッソ株式会社 | 液晶組成物および液晶表示素子 |
Families Citing this family (48)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6178753A (ja) * | 1984-09-27 | 1986-04-22 | Asahi Glass Co Ltd | トランス−エチレン誘導体化合物及びそれを含有する液晶組成物 |
| JPH0672125B2 (ja) * | 1984-12-20 | 1994-09-14 | 旭硝子株式会社 | トランス−エチレン誘導体化合物及びそれを含有する液晶組成物 |
| JPS61257935A (ja) * | 1985-01-11 | 1986-11-15 | Asahi Glass Co Ltd | トランス−エチレン誘導体化合物及びそれを含有する液晶組成物 |
| DE3787253D1 (de) * | 1986-11-20 | 1993-10-07 | Hoffmann La Roche | Ferroelektrische Flüssigkristalle. |
| JP2660702B2 (ja) * | 1987-12-14 | 1997-10-08 | チッソ株式会社 | 液晶組成物 |
| US5262084A (en) * | 1987-12-14 | 1993-11-16 | Chisso Corporation | Liquid crystal composition |
| JP2750436B2 (ja) * | 1988-09-19 | 1998-05-13 | チッソ株式会社 | アルケニルエーテル化合物及びそれを含む液晶組成物 |
| TW368516B (en) * | 1995-06-05 | 1999-09-01 | Chisso Corp | Alkenylcyclohexane derivatives and liquid crystal composition |
| US6017467A (en) * | 1996-06-28 | 2000-01-25 | Chisso Corporation | Propiolonitrile derivatives and liquid crystal compositions comprising the same |
| JP4366737B2 (ja) * | 1997-11-28 | 2009-11-18 | Ｄｉｃ株式会社 | フッ素置換４−（３−アルケニル）安息香酸とそのフェニルエステル誘導体及びそれを含有する液晶組成物 |
| DE602006005584D1 (de) * | 2005-11-16 | 2009-04-23 | Chisso Corp | Flüssigkristallzusammensetzung und Flüssigkristallanzeigevorrichtung |
| DE102008036808A1 (de) * | 2007-08-15 | 2009-02-19 | Merck Patent Gmbh | Flüssigkristallines Medium |
| WO2010032587A1 (ja) | 2008-09-17 | 2010-03-25 | チッソ株式会社 | 液晶組成物および液晶表示素子 |
| JP5545218B2 (ja) | 2008-10-27 | 2014-07-09 | Ｊｎｃ株式会社 | 液晶組成物および液晶表示素子 |
| CN104861989A (zh) | 2008-12-08 | 2015-08-26 | Jnc株式会社 | 液晶组成物以及液晶显示元件 |
| KR101702144B1 (ko) | 2008-12-10 | 2017-02-03 | 제이엔씨 주식회사 | 액정 조성물 및 액정 표시 소자 |
| EP3075816B1 (en) | 2009-01-22 | 2018-05-23 | JNC Corporation | Liquid crystal composition and liquid crystal display device |
| TWI461512B (zh) | 2009-05-11 | 2014-11-21 | Jnc Corp | 液晶顯示元件 |
| JP5353491B2 (ja) | 2009-07-02 | 2013-11-27 | Ｊｎｃ株式会社 | 液晶組成物および液晶表示素子 |
| TWI491712B (zh) | 2010-02-12 | 2015-07-11 | Jnc Corp | 液晶組成物以及液晶顯示元件 |
| DE102011118210A1 (de) * | 2010-11-27 | 2012-05-31 | Merck Patent Gmbh | Flüssigkristallines Medium |
| TWI526525B (zh) | 2010-12-14 | 2016-03-21 | 捷恩智股份有限公司 | 液晶組成物及其使用、以及液晶顯示元件 |
| TWI512094B (zh) | 2011-04-14 | 2015-12-11 | Jnc Corp | 液晶組成物、液晶顯示元件及其用途 |
| JP5887713B2 (ja) * | 2011-05-10 | 2016-03-16 | Jnc株式会社 | フルオロビニル誘導体、液晶組成物及び液晶表示素子 |
| JP5729149B2 (ja) | 2011-06-08 | 2015-06-03 | Jnc株式会社 | 液晶組成物および液晶表示素子 |
| WO2013039051A1 (ja) | 2011-09-14 | 2013-03-21 | Jnc株式会社 | 化合物、液晶組成物および液晶表示素子 |
| EP2811003B1 (en) | 2012-02-03 | 2016-08-10 | JNC Corporation | Liquid crystal compound, liquid crystal composition, and liquid crystal display device |
| JP6107806B2 (ja) | 2012-02-23 | 2017-04-05 | Jnc株式会社 | 液晶組成物および液晶表示素子 |
| TWI550072B (zh) | 2012-04-02 | 2016-09-21 | 捷恩智股份有限公司 | 液晶組成物與其用途、及液晶顯示元件 |
| US9150787B2 (en) | 2012-07-06 | 2015-10-06 | Jnc Corporation | Liquid crystal composition and liquid crystal display device |
| TWI565790B (zh) | 2012-08-08 | 2017-01-11 | 捷恩智股份有限公司 | 液晶組成物、液晶顯示元件及液晶組成物的使用 |
| TWI638035B (zh) | 2012-09-24 | 2018-10-11 | 捷恩智股份有限公司 | 液晶顯示元件、以及液晶組成物及其用途 |
| TWI544063B (zh) | 2012-12-04 | 2016-08-01 | 捷恩智股份有限公司 | 液晶組成物及其用途、液晶顯示元件 |
| TWI631207B (zh) | 2013-05-28 | 2018-08-01 | 日商捷恩智股份有限公司 | 液晶組成物與其用途及液晶顯示元件 |
| EP3015533B1 (en) | 2013-06-26 | 2018-10-10 | JNC Corporation | Liquid crystal composition, and liquid crystal display element |
| US20160122301A1 (en) | 2013-06-26 | 2016-05-05 | Jnc Corporation | Liquid crystal composition and liquid crystal display device |
| JP5725321B1 (ja) | 2013-07-03 | 2015-05-27 | Jnc株式会社 | 液晶組成物および液晶表示素子 |
| CN105358656A (zh) | 2013-07-05 | 2016-02-24 | 捷恩智株式会社 | 液晶组合物及液晶显示元件 |
| US10280368B2 (en) | 2013-07-11 | 2019-05-07 | Jnc Corporation | Liquid crystal composition and liquid crystal display device |
| JPWO2015056540A1 (ja) | 2013-10-17 | 2017-03-09 | Jnc株式会社 | 液晶組成物および液晶表示素子 |
| KR20160077049A (ko) | 2013-10-25 | 2016-07-01 | 제이엔씨 주식회사 | 액정 조성물 및 액정 표시 소자 |
| US9994768B2 (en) | 2013-11-13 | 2018-06-12 | Jnc Corporation | Liquid crystal composition and liquid crystal display device |
| JP6610260B2 (ja) | 2013-11-18 | 2019-11-27 | Ｊｎｃ株式会社 | 液晶組成物および液晶表示素子 |
| EP3088489B1 (en) | 2013-12-26 | 2018-06-27 | JNC Corporation | Liquid-crystal composition and liquid-crystal display device |
| EP3127990B1 (en) | 2014-03-31 | 2019-10-09 | JNC Corporation | Liquid crystal display device and liquid crystal composition |
| KR20180109930A (ko) | 2016-02-19 | 2018-10-08 | 제이엔씨 주식회사 | 액정 조성물 및 액정 표시 소자 |
| US20190040319A1 (en) | 2016-03-25 | 2019-02-07 | Jnc Corporation | Liquid crystal composition and liquid crystal display device |
| EP3663379A4 (en) | 2017-08-02 | 2020-12-23 | JNC Corporation | LIQUID CRYSTAL COMPOSITE AND LIQUID CRYSTAL LIGHT CONTROL ELEMENT |
-
1984
- 1984-03-15 JP JP4826784A patent/JPS59176221A/ja active Granted
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1908814A1 (en) | 2006-10-05 | 2008-04-09 | Chisso Corporation | Liquid crystal compositon and liquid crystal display device |
| WO2009028367A1 (ja) | 2007-08-27 | 2009-03-05 | Chisso Corporation | 液晶組成物および液晶表示素子 |
| WO2010024142A1 (ja) | 2008-08-28 | 2010-03-04 | チッソ株式会社 | 液晶組成物および液晶表示素子 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59176221A (ja) | 1984-10-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0430382B2 (ru) | ||
| US5013478A (en) | Liquid crystals | |
| US4565425A (en) | Liquid crystals | |
| US4846998A (en) | Cyclohexane derivatives | |
| US4386007A (en) | Liquid crystalline naphthalene derivatives | |
| US4528114A (en) | Acetylenes | |
| US4460770A (en) | Liquid crystal mixture | |
| KR100549898B1 (ko) | 비스알케닐비사이클로헥산 및 액정 매질 | |
| JPH072654B2 (ja) | 液晶混合物 | |
| JPS5976027A (ja) | 新規な環化合物 | |
| JPH072653B2 (ja) | アルケニル化合物 | |
| JPS61112070A (ja) | 複素環式化合物 | |
| US4980486A (en) | Liquid crystalline compounds and mixtures | |
| JPH0641446B2 (ja) | シクロヘキサンカルボニトリル類 | |
| US4630896A (en) | Benzonitriles | |
| JPH0463070B2 (ru) | ||
| US4880562A (en) | Liquid crystal compound | |
| EP0563982B1 (en) | Polycyclic diene derivatives | |
| JPH08176033A (ja) | ベンゼン誘導体 | |
| US5230829A (en) | Phenylcyclohexanes, and a liquid-crystalline medium | |
| JPH04330019A (ja) | （４ｅ−シクロヘキシル−３−ブテニル）アリール誘導体及びその使用 | |
| JP3002429B2 (ja) | 液晶表示素子 | |
| JPS63502505A (ja) | カイラル化合物 | |
| 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 | |
| JPH045021B2 (ru) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |