NO316172B1 - 5,6-dihydropyron-derivater og farmasöytisk blanding - Google Patents

Info

Publication number

NO316172B1

NO316172B1 NO19962017A NO962017A NO316172B1 NO 316172 B1 NO316172 B1 NO 316172B1 NO 19962017 A NO19962017 A NO 19962017A NO 962017 A NO962017 A NO 962017A NO 316172 B1 NO316172 B1 NO 316172B1

Authority

NO

Norway

Prior art keywords

mmol

hydroxy

dihydro

pyran

prepared

Prior art date

1993-11-19

Links

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• Global Dossier
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• QBDAFARLDLCWAT-UHFFFAOYSA-N 2,3-dihydropyran-6-one Chemical class O=C1OCCC=C1 QBDAFARLDLCWAT-UHFFFAOYSA-N 0.000 title abstract description 22
• 239000008194 pharmaceutical composition Substances 0.000 title 1
• 238000011282 treatment Methods 0.000 claims abstract description 21
• 201000010099 disease Diseases 0.000 claims abstract description 11
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 11
• 150000001875 compounds Chemical class 0.000 claims description 243
• 239000000203 mixture Substances 0.000 claims description 49
• -1 2-isopropylphenyl Chemical group 0.000 claims description 40
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
• 150000003839 salts Chemical class 0.000 claims description 17
• 208000015181 infectious disease Diseases 0.000 claims description 15
• 241001430294 unidentified retrovirus Species 0.000 claims description 13
• 241000700605 Viruses Species 0.000 claims description 8
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
• 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 2
• KJGFQJMJXRDFNI-UHFFFAOYSA-N 4-hydroxy-5-[(3-methoxyphenyl)methyl]-2-phenyl-2-(2-phenylethyl)-3h-pyran-6-one Chemical group COC1=CC=CC(CC=2C(OC(CCC=3C=CC=CC=3)(CC=2O)C=2C=CC=CC=2)=O)=C1 KJGFQJMJXRDFNI-UHFFFAOYSA-N 0.000 claims 1
• 229940125904 compound 1 Drugs 0.000 claims 1
• 238000000034 method Methods 0.000 abstract description 133
• 208000030507 AIDS Diseases 0.000 abstract description 11
• 108010017640 Aspartic Acid Proteases Proteins 0.000 abstract description 10
• 102000004580 Aspartic Acid Proteases Human genes 0.000 abstract description 10
• 230000015572 biosynthetic process Effects 0.000 abstract description 8
• 238000003786 synthesis reaction Methods 0.000 abstract description 7
• 238000011161 development Methods 0.000 abstract description 4
• 208000035143 Bacterial infection Diseases 0.000 abstract 1
• 208000036142 Viral infection Diseases 0.000 abstract 1
• 230000001580 bacterial effect Effects 0.000 abstract 1
• 208000022362 bacterial infectious disease Diseases 0.000 abstract 1
• 230000000903 blocking effect Effects 0.000 abstract 1
• 238000002560 therapeutic procedure Methods 0.000 abstract 1
• 230000009385 viral infection Effects 0.000 abstract 1
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 257
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 235
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 215
• 239000007787 solid Substances 0.000 description 128
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 122
• 238000005160 1H NMR spectroscopy Methods 0.000 description 121
• 238000006243 chemical reaction Methods 0.000 description 118
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 112
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 100
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 100
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 81
• MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 81
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 68
• 238000007429 general method Methods 0.000 description 62
• 239000000047 product Substances 0.000 description 58
• 238000005481 NMR spectroscopy Methods 0.000 description 57
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 54
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 54
• 239000000243 solution Substances 0.000 description 51
• 239000002904 solvent Substances 0.000 description 43
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 43
• 229910004298 SiO 2 Inorganic materials 0.000 description 41
• 238000004440 column chromatography Methods 0.000 description 41
• 238000000746 purification Methods 0.000 description 40
• 239000006185 dispersion Substances 0.000 description 38
• WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 37
• 239000012043 crude product Substances 0.000 description 34
• NPEQBQFWQFGATI-UHFFFAOYSA-N (4-methylphenyl)-oxo-phenylmethoxy-sulfanylidene-$l^{6}-sulfane Chemical compound C1=CC(C)=CC=C1S(=O)(=S)OCC1=CC=CC=C1 NPEQBQFWQFGATI-UHFFFAOYSA-N 0.000 description 31
• FDZPQUUHLRJKJL-UHFFFAOYSA-N (4-methylphenyl)-oxo-(2-phenylethoxy)-sulfanylidene-$l^{6}-sulfane Chemical compound C1=CC(C)=CC=C1S(=O)(=S)OCCC1=CC=CC=C1 FDZPQUUHLRJKJL-UHFFFAOYSA-N 0.000 description 29
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 26
• 229960000583 acetic acid Drugs 0.000 description 24
• 239000002253 acid Substances 0.000 description 23
• BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 23
• 239000012362 glacial acetic acid Substances 0.000 description 22
• MWFMGBPGAXYFAR-UHFFFAOYSA-N 2-hydroxy-2-methylpropanenitrile Chemical compound CC(C)(O)C#N MWFMGBPGAXYFAR-UHFFFAOYSA-N 0.000 description 21
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
• 239000003480 eluent Substances 0.000 description 19
• 239000000741 silica gel Substances 0.000 description 19
• 229910002027 silica gel Inorganic materials 0.000 description 19
• 125000004149 thio group Chemical group *S* 0.000 description 19
• 150000001299 aldehydes Chemical class 0.000 description 18
• OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 18
• 229910001868 water Inorganic materials 0.000 description 18
• WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 17
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 17
• 238000002360 preparation method Methods 0.000 description 17
• JYKPRQNMODBPRE-UHFFFAOYSA-N 4-hydroxy-2-phenyl-2-(2-phenylethyl)-3h-pyran-6-one Chemical compound C1C(O)=CC(=O)OC1(C=1C=CC=CC=1)CCC1=CC=CC=C1 JYKPRQNMODBPRE-UHFFFAOYSA-N 0.000 description 16
• 101150041968 CDC13 gene Proteins 0.000 description 16
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 16
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 16
• 238000003818 flash chromatography Methods 0.000 description 16
• KDDFNTSGICCJKF-UHFFFAOYSA-N 4-hydroxy-2,2-diphenyl-3h-pyran-6-one Chemical compound C1C(O)=CC(=O)OC1(C=1C=CC=CC=1)C1=CC=CC=C1 KDDFNTSGICCJKF-UHFFFAOYSA-N 0.000 description 15
• 241000725303 Human immunodeficiency virus Species 0.000 description 15
• PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 14
• 239000003112 inhibitor Substances 0.000 description 14
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 13
• 239000002585 base Substances 0.000 description 11
• 239000010410 layer Substances 0.000 description 11
• 239000011734 sodium Substances 0.000 description 11
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 10
• ROFVKEOGZVNSKN-UHFFFAOYSA-N 5-bromo-4-hydroxy-2,2-diphenyl-3h-pyran-6-one Chemical compound C1C(O)=C(Br)C(=O)OC1(C=1C=CC=CC=1)C1=CC=CC=C1 ROFVKEOGZVNSKN-UHFFFAOYSA-N 0.000 description 10
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
• 239000000543 intermediate Substances 0.000 description 10
• 150000002576 ketones Chemical class 0.000 description 10
• 239000011541 reaction mixture Substances 0.000 description 10
• VEXQIMLWUXENQF-UHFFFAOYSA-N 4-hydroxy-2-(3-methylbutyl)-2-phenyl-3h-pyran-6-one Chemical compound C=1C=CC=CC=1C1(CCC(C)C)CC(O)=CC(=O)O1 VEXQIMLWUXENQF-UHFFFAOYSA-N 0.000 description 9
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
• VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical compound SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 description 9
• 239000012044 organic layer Substances 0.000 description 9
• 239000000843 powder Substances 0.000 description 9
• RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 9
• SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 8
• 230000000840 anti-viral effect Effects 0.000 description 8
• 239000004305 biphenyl Substances 0.000 description 8
• 239000000872 buffer Substances 0.000 description 8
• 239000002775 capsule Substances 0.000 description 8
• 239000000284 extract Substances 0.000 description 8
• 238000010992 reflux Methods 0.000 description 8
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
• 102000035195 Peptidases Human genes 0.000 description 7
• 108091005804 Peptidases Proteins 0.000 description 7
• 239000004365 Protease Substances 0.000 description 7
• DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 7
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 7
• 239000012267 brine Substances 0.000 description 7
• 230000000694 effects Effects 0.000 description 7
• 230000005764 inhibitory process Effects 0.000 description 7
• 239000007788 liquid Substances 0.000 description 7
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
• 239000003826 tablet Substances 0.000 description 7
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical group C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
• 102000004190 Enzymes Human genes 0.000 description 6
• 108090000790 Enzymes Proteins 0.000 description 6
• 150000007513 acids Chemical class 0.000 description 6
• PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 6
• ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 6
• 229910052708 sodium Inorganic materials 0.000 description 6
• 239000000758 substrate Substances 0.000 description 6
• 229960000549 4-dimethylaminophenol Drugs 0.000 description 5
• RPKZKINTMCUJEV-UHFFFAOYSA-N 4-hydroxy-2-phenyl-2,3-dihydropyran-6-one Chemical compound C1C(O)=CC(=O)OC1C1=CC=CC=C1 RPKZKINTMCUJEV-UHFFFAOYSA-N 0.000 description 5
• PAUDLKMUQLCQQL-UHFFFAOYSA-N 4-hydroxy-2-phenyl-5-(2-phenylethyl)-2,3-dihydropyran-6-one Chemical compound O=C1OC(C=2C=CC=CC=2)CC(O)=C1CCC1=CC=CC=C1 PAUDLKMUQLCQQL-UHFFFAOYSA-N 0.000 description 5
• PQOFOXIQCWOYFL-UHFFFAOYSA-N 5-(4-hydroxy-6-oxo-2-phenyl-3h-pyran-2-yl)pentanoic acid Chemical compound C=1C=CC=CC=1C1(CCCCC(=O)O)CC(O)=CC(=O)O1 PQOFOXIQCWOYFL-UHFFFAOYSA-N 0.000 description 5
• ADSZRVGJNUXBQB-UHFFFAOYSA-N 5-bromo-4-hydroxy-2-phenyl-2-(2-phenylethyl)-3h-pyran-6-one Chemical compound C1C(O)=C(Br)C(=O)OC1(C=1C=CC=CC=1)CCC1=CC=CC=C1 ADSZRVGJNUXBQB-UHFFFAOYSA-N 0.000 description 5
• 150000001408 amides Chemical class 0.000 description 5
• 230000003197 catalytic effect Effects 0.000 description 5
• 239000003814 drug Substances 0.000 description 5
• 238000010828 elution Methods 0.000 description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
• 235000019341 magnesium sulphate Nutrition 0.000 description 5
• 238000012360 testing method Methods 0.000 description 5
• FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 4
• QEDRUXIMTJVXFL-UHFFFAOYSA-N 2-propan-2-ylbenzenethiol Chemical compound CC(C)C1=CC=CC=C1S QEDRUXIMTJVXFL-UHFFFAOYSA-N 0.000 description 4
• ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical class O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 description 4
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
• QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
• 108010010369 HIV Protease Proteins 0.000 description 4
• 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 4
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
• 239000003443 antiviral agent Substances 0.000 description 4
• WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
• 239000003153 chemical reaction reagent Substances 0.000 description 4
• 239000003795 chemical substances by application Substances 0.000 description 4
• 238000004587 chromatography analysis Methods 0.000 description 4
• 238000004519 manufacturing process Methods 0.000 description 4
• QSRRZKPKHJHIRB-UHFFFAOYSA-N methyl 4-[(2,5-dichloro-4-methylthiophen-3-yl)sulfonylamino]-2-hydroxybenzoate Chemical compound C1=C(O)C(C(=O)OC)=CC=C1NS(=O)(=O)C1=C(Cl)SC(Cl)=C1C QSRRZKPKHJHIRB-UHFFFAOYSA-N 0.000 description 4
• XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 4
• 125000006239 protecting group Chemical group 0.000 description 4
• 230000009467 reduction Effects 0.000 description 4
• 239000012265 solid product Substances 0.000 description 4
• 238000003756 stirring Methods 0.000 description 4
• 125000001424 substituent group Chemical group 0.000 description 4
• 239000000725 suspension Substances 0.000 description 4
• 150000003573 thiols Chemical class 0.000 description 4
• BESYIRLKYLZBHL-UHFFFAOYSA-N 2-(3-chlorophenyl)-4-hydroxy-2,3-dihydropyran-6-one Chemical compound C1C(O)=CC(=O)OC1C1=CC=CC(Cl)=C1 BESYIRLKYLZBHL-UHFFFAOYSA-N 0.000 description 3
• BKJZKMOTBRSOJM-UHFFFAOYSA-N 2-(3-methylbutyl)-2-phenyl-3h-pyran-6-one Chemical compound C=1C=CC=CC=1C1(CCC(C)C)CC=CC(=O)O1 BKJZKMOTBRSOJM-UHFFFAOYSA-N 0.000 description 3
• MLEKQWLKSLEIEA-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-4-hydroxy-2,3-dihydropyran-6-one Chemical compound C1=CC(C(C)(C)C)=CC=C1C1OC(=O)C=C(O)C1 MLEKQWLKSLEIEA-UHFFFAOYSA-N 0.000 description 3
• PLGNLGVFOGRRRP-UHFFFAOYSA-N 2-[2-(1,3-benzodioxol-5-yl)ethyl]-4-hydroxy-2-phenyl-3h-pyran-6-one Chemical compound C1C(O)=CC(=O)OC1(C=1C=CC=CC=1)CCC1=CC=C(OCO2)C2=C1 PLGNLGVFOGRRRP-UHFFFAOYSA-N 0.000 description 3
• ATRIJCRJIFBNGD-UHFFFAOYSA-N 2-hexyl-4-hydroxy-2-phenyl-3h-pyran-6-one Chemical compound C=1C=CC=CC=1C1(CCCCCC)CC(O)=CC(=O)O1 ATRIJCRJIFBNGD-UHFFFAOYSA-N 0.000 description 3
• GPZXFICWCMCQPF-UHFFFAOYSA-N 2-methylbenzoyl chloride Chemical compound CC1=CC=CC=C1C(Cl)=O GPZXFICWCMCQPF-UHFFFAOYSA-N 0.000 description 3
• BATNPZRNMNBUQG-UHFFFAOYSA-N 2-pentyl-2-phenyl-3h-pyran-6-one Chemical compound C=1C=CC=CC=1C1(CCCCC)CC=CC(=O)O1 BATNPZRNMNBUQG-UHFFFAOYSA-N 0.000 description 3
• VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 3
• PZMSGKRRTOUKEI-UHFFFAOYSA-N 2-propan-2-ylbenzoyl chloride Chemical compound CC(C)C1=CC=CC=C1C(Cl)=O PZMSGKRRTOUKEI-UHFFFAOYSA-N 0.000 description 3
• MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 description 3
• YHOYYHYBFSYOSQ-UHFFFAOYSA-N 3-methylbenzoyl chloride Chemical compound CC1=CC=CC(C(Cl)=O)=C1 YHOYYHYBFSYOSQ-UHFFFAOYSA-N 0.000 description 3
• GINRGFSNHALPNV-UHFFFAOYSA-N 4-hydroxy-2-(4-methylpentyl)-2-phenyl-3h-pyran-6-one Chemical compound C=1C=CC=CC=1C1(CCCC(C)C)CC(O)=CC(=O)O1 GINRGFSNHALPNV-UHFFFAOYSA-N 0.000 description 3
• PPDDEMOYHPQLQW-UHFFFAOYSA-N 4-hydroxy-2-(4-methylphenyl)-2,3-dihydropyran-6-one Chemical compound C1=CC(C)=CC=C1C1OC(=O)C=C(O)C1 PPDDEMOYHPQLQW-UHFFFAOYSA-N 0.000 description 3
• GODAXOHAWOJXQP-UHFFFAOYSA-N 4-hydroxy-2-(4-methylsulfanylphenyl)-2,3-dihydropyran-6-one Chemical compound C1=CC(SC)=CC=C1C1OC(=O)C=C(O)C1 GODAXOHAWOJXQP-UHFFFAOYSA-N 0.000 description 3
• RRJCHYYXHYUPAM-UHFFFAOYSA-N 4-hydroxy-2-phenyl-2-propyl-3h-pyran-6-one Chemical compound C=1C=CC=CC=1C1(CCC)CC(O)=CC(=O)O1 RRJCHYYXHYUPAM-UHFFFAOYSA-N 0.000 description 3
• VNZOLPIHDIJPBZ-UHFFFAOYSA-N 4-hydroxypyran-2-one Chemical class OC=1C=COC(=O)C=1 VNZOLPIHDIJPBZ-UHFFFAOYSA-N 0.000 description 3
• CGIZQEXKNXCECU-UHFFFAOYSA-N 5-bromo-4-hydroxy-2-(3-methylbutyl)-2-phenyl-3h-pyran-6-one Chemical compound C=1C=CC=CC=1C1(CCC(C)C)CC(O)=C(Br)C(=O)O1 CGIZQEXKNXCECU-UHFFFAOYSA-N 0.000 description 3
• OKIJSNGRQAOIGZ-UHFFFAOYSA-N Butopyronoxyl Chemical compound CCCCOC(=O)C1=CC(=O)CC(C)(C)O1 OKIJSNGRQAOIGZ-UHFFFAOYSA-N 0.000 description 3
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
• 125000000217 alkyl group Chemical group 0.000 description 3
• 238000013459 approach Methods 0.000 description 3
• 239000003054 catalyst Substances 0.000 description 3
• WBKFWQBXFREOFH-UHFFFAOYSA-N dichloromethane;ethyl acetate Chemical compound ClCCl.CCOC(C)=O WBKFWQBXFREOFH-UHFFFAOYSA-N 0.000 description 3
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