CN114341114B - 包含芳杂环和咪唑环的1,3-偶极化合物 - Google Patents
包含芳杂环和咪唑环的1,3-偶极化合物 Download PDFInfo
- Publication number
- CN114341114B CN114341114B CN202080042210.0A CN202080042210A CN114341114B CN 114341114 B CN114341114 B CN 114341114B CN 202080042210 A CN202080042210 A CN 202080042210A CN 114341114 B CN114341114 B CN 114341114B
- Authority
- CN
- China
- Prior art keywords
- compound
- linear
- branched
- optionally substituted
- group
- 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.)
- Active
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 142
- 125000002883 imidazolyl group Chemical group 0.000 title claims abstract description 32
- 125000006615 aromatic heterocyclic group Chemical group 0.000 title description 2
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 68
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 57
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 51
- 125000003118 aryl group Chemical group 0.000 claims abstract description 46
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 39
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 18
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 16
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 16
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 13
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 7
- 150000002430 hydrocarbons Chemical class 0.000 claims description 40
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 28
- 238000003786 synthesis reaction Methods 0.000 claims description 18
- 230000015572 biosynthetic process Effects 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 7
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 239000011593 sulfur Substances 0.000 claims description 6
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 239000001301 oxygen Chemical group 0.000 claims description 4
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 229920000642 polymer Polymers 0.000 abstract description 20
- 125000001072 heteroaryl group Chemical group 0.000 abstract description 18
- 238000004519 manufacturing process Methods 0.000 abstract description 7
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 2
- 229920006395 saturated elastomer Polymers 0.000 description 53
- -1 thiophene-diyl Chemical group 0.000 description 48
- 239000000203 mixture Substances 0.000 description 21
- 238000005481 NMR spectroscopy Methods 0.000 description 16
- 229920001971 elastomer Polymers 0.000 description 16
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 125000004429 atom Chemical group 0.000 description 11
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 11
- 239000012429 reaction media Substances 0.000 description 11
- 238000003756 stirring Methods 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 229920003048 styrene butadiene rubber Polymers 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000000806 elastomer Substances 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000005060 rubber Substances 0.000 description 8
- 229930091371 Fructose Natural products 0.000 description 7
- 239000005715 Fructose Substances 0.000 description 7
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 7
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- CKRZKMFTZCFYGB-UHFFFAOYSA-N N-phenylhydroxylamine Chemical compound ONC1=CC=CC=C1 CKRZKMFTZCFYGB-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 229920003244 diene elastomer Polymers 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- 125000001634 furandiyl group Chemical group O1C(=C(C=C1)*)* 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 5
- 239000002174 Styrene-butadiene Substances 0.000 description 5
- 239000012190 activator Substances 0.000 description 5
- 229920001577 copolymer Polymers 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 239000000945 filler Substances 0.000 description 5
- 239000008103 glucose Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 230000014509 gene expression Effects 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000005096 rolling process Methods 0.000 description 4
- 238000001542 size-exclusion chromatography Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 3
- NOEGNKMFWQHSLB-UHFFFAOYSA-N 5-hydroxymethylfurfural Chemical compound OCC1=CC=C(C=O)O1 NOEGNKMFWQHSLB-UHFFFAOYSA-N 0.000 description 3
- 239000002028 Biomass Substances 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 3
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 description 3
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- QNRMTGGDHLBXQZ-UHFFFAOYSA-N buta-1,2-diene Chemical group CC=C=C QNRMTGGDHLBXQZ-UHFFFAOYSA-N 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 3
- 229920002521 macromolecule Polymers 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- SATDLKYRVXFXRE-UHFFFAOYSA-N methyl 4-(chloromethyl)benzoate Chemical compound COC(=O)C1=CC=C(CCl)C=C1 SATDLKYRVXFXRE-UHFFFAOYSA-N 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- XOJVVFBFDXDTEG-UHFFFAOYSA-N pristane Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)C XOJVVFBFDXDTEG-UHFFFAOYSA-N 0.000 description 3
- 239000012763 reinforcing filler Substances 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- 239000003643 water by type Substances 0.000 description 3
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 description 2
- UDVZQBOKCFSBEU-UHFFFAOYSA-N 1-[4-[(2-methylimidazol-1-yl)methyl]phenyl]-N-phenylmethanimine oxide Chemical compound CC1=NC=CN1CC1=CC=C(C=[N+](C2=CC=CC=C2)[O-])C=C1 UDVZQBOKCFSBEU-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 2
- KAZRCBVXUOCTIO-UHFFFAOYSA-N 5-(chloromethyl)furan-2-carbaldehyde Chemical compound ClCC1=CC=C(C=O)O1 KAZRCBVXUOCTIO-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 101000801643 Homo sapiens Retinal-specific phospholipid-transporting ATPase ABCA4 Proteins 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- 102100033617 Retinal-specific phospholipid-transporting ATPase ABCA4 Human genes 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 230000004913 activation Effects 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- 230000000035 biogenic effect Effects 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000006352 cycloaddition reaction Methods 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 229940043279 diisopropylamine Drugs 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 150000007855 nitrilimines Chemical class 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 238000001208 nuclear magnetic resonance pulse sequence Methods 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000011002 quantification Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 125000006850 spacer group Chemical group 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 2
- 238000012584 2D NMR experiment Methods 0.000 description 1
- UYVCCHAKRASOGU-UHFFFAOYSA-N 5-[(2-methylimidazol-1-yl)methyl]furan-2-carbaldehyde Chemical compound Cc1nccn1Cc1ccc(C=O)o1 UYVCCHAKRASOGU-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 229910010082 LiAlH Inorganic materials 0.000 description 1
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 238000011000 absolute method Methods 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000011208 chromatographic data Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000011903 deuterated solvents Substances 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012039 electrophile Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 1
- 238000003919 heteronuclear multiple bond coherence Methods 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
- C07D233/61—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms not forming part of a nitro radical, attached to ring nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08C—TREATMENT OR CHEMICAL MODIFICATION OF RUBBERS
- C08C19/00—Chemical modification of rubber
- C08C19/22—Incorporating nitrogen atoms into the molecule
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1906181A FR3097222B1 (fr) | 2019-06-11 | 2019-06-11 | Nouveaux composes 1,3-dipolaires comprenant un heterocycle aromatique et un cycle imidazole |
| FRFR1906181 | 2019-06-11 | ||
| PCT/EP2020/066112 WO2020249623A1 (fr) | 2019-06-11 | 2020-06-10 | Nouveaux composes 1,3-dipolaires comprenant un heterocycle aromatique et un cycle imidazole |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN114341114A CN114341114A (zh) | 2022-04-12 |
| CN114341114B true CN114341114B (zh) | 2023-11-10 |
Family
ID=67441499
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202080042210.0A Active CN114341114B (zh) | 2019-06-11 | 2020-06-10 | 包含芳杂环和咪唑环的1,3-偶极化合物 |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP3983390A1 (de) |
| CN (1) | CN114341114B (de) |
| FR (1) | FR3097222B1 (de) |
| WO (1) | WO2020249623A1 (de) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR3130801A1 (fr) | 2021-12-21 | 2023-06-23 | Compagnie Generale Des Etablissements Michelin | Procédé de synthèse du 5-((2-méthyl-1H-imidazol-1-yl)méthyl)furan-2-carbaldéhyde et de nitrones à partir du 5-((2-méthyl-1H-imidazol-1-yl)méthyl)furan-2-carbaldéhyde |
Citations (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1129442A (zh) * | 1993-08-25 | 1996-08-21 | 山之内制药株式会社 | 苯并二氮杂䓬衍生物 |
| CN1177299A (zh) * | 1995-01-09 | 1998-03-25 | 史密丝克莱恩比彻姆公司 | 用作细胞因子的某些1,4,5－三取代咪唑化合物 |
| WO2000064905A2 (fr) * | 1999-04-23 | 2000-11-02 | Rhodia Chimie | Procede d'alpha-metallation d'un derive heterocyclique, monocyclique ou polycyclique et possedant au moins un heterocycle a 5 atomes, insature ou aromatique |
| CN1671701A (zh) * | 2002-07-25 | 2005-09-21 | 科学研究和应用咨询公司 | 新芳基咪唑衍生物、其制备及其治疗用途 |
| CA2558034A1 (en) * | 2004-03-09 | 2005-09-22 | Elan Pharmaceuticals, Inc. | Substituted hydroxyethylamine aspartyl protease inhibitors |
| WO2006056489A2 (en) * | 2004-11-26 | 2006-06-01 | L'oreal | Particular dissymmetrical cationic polyazo compounds, compositions comprising them as direct dye, process for dyeing keratin fibres and device therefor |
| WO2010100606A1 (en) * | 2009-03-03 | 2010-09-10 | Pfizer Inc. | Novel phenyl imidazoles and phenyl triazoles as gamma-secretase modulators |
| WO2011154457A1 (en) * | 2010-06-09 | 2011-12-15 | L'oreal | 2-pyrrolidone derivatives functionalized with an ester, acid or amide radical, cosmetic composition comprising them and use thereof for conditioning keratin materials |
| CN102985445A (zh) * | 2010-07-13 | 2013-03-20 | 米其林集团总公司 | 接枝结合氮分子的接枝聚合物 |
| CN105683165A (zh) * | 2013-10-25 | 2016-06-15 | 米其林集团总公司 | 带有咪唑官能团的1,3-偶极化合物 |
| WO2017064296A1 (fr) * | 2015-10-14 | 2017-04-20 | Arkema France | Procede de synthese de nitrones aromatiques |
| WO2019002756A1 (fr) * | 2017-06-28 | 2019-01-03 | Compagnie Generale Des Etablissements Michelin | Elastomère diénique portant des groupes imidazole |
-
2019
- 2019-06-11 FR FR1906181A patent/FR3097222B1/fr active Active
-
2020
- 2020-06-10 CN CN202080042210.0A patent/CN114341114B/zh active Active
- 2020-06-10 EP EP20732824.6A patent/EP3983390A1/de active Pending
- 2020-06-10 WO PCT/EP2020/066112 patent/WO2020249623A1/fr unknown
Patent Citations (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1129442A (zh) * | 1993-08-25 | 1996-08-21 | 山之内制药株式会社 | 苯并二氮杂䓬衍生物 |
| CN1177299A (zh) * | 1995-01-09 | 1998-03-25 | 史密丝克莱恩比彻姆公司 | 用作细胞因子的某些1,4,5－三取代咪唑化合物 |
| WO2000064905A2 (fr) * | 1999-04-23 | 2000-11-02 | Rhodia Chimie | Procede d'alpha-metallation d'un derive heterocyclique, monocyclique ou polycyclique et possedant au moins un heterocycle a 5 atomes, insature ou aromatique |
| CN1671701A (zh) * | 2002-07-25 | 2005-09-21 | 科学研究和应用咨询公司 | 新芳基咪唑衍生物、其制备及其治疗用途 |
| CA2558034A1 (en) * | 2004-03-09 | 2005-09-22 | Elan Pharmaceuticals, Inc. | Substituted hydroxyethylamine aspartyl protease inhibitors |
| WO2006056489A2 (en) * | 2004-11-26 | 2006-06-01 | L'oreal | Particular dissymmetrical cationic polyazo compounds, compositions comprising them as direct dye, process for dyeing keratin fibres and device therefor |
| WO2010100606A1 (en) * | 2009-03-03 | 2010-09-10 | Pfizer Inc. | Novel phenyl imidazoles and phenyl triazoles as gamma-secretase modulators |
| CA2751534A1 (en) * | 2009-03-03 | 2010-09-10 | Pfizer Inc. | Novel phenyl imidazoles and phenyl triazoles as gamma-secretase modulators |
| WO2011154457A1 (en) * | 2010-06-09 | 2011-12-15 | L'oreal | 2-pyrrolidone derivatives functionalized with an ester, acid or amide radical, cosmetic composition comprising them and use thereof for conditioning keratin materials |
| CN102985445A (zh) * | 2010-07-13 | 2013-03-20 | 米其林集团总公司 | 接枝结合氮分子的接枝聚合物 |
| CN105683165A (zh) * | 2013-10-25 | 2016-06-15 | 米其林集团总公司 | 带有咪唑官能团的1,3-偶极化合物 |
| WO2017064296A1 (fr) * | 2015-10-14 | 2017-04-20 | Arkema France | Procede de synthese de nitrones aromatiques |
| WO2019002756A1 (fr) * | 2017-06-28 | 2019-01-03 | Compagnie Generale Des Etablissements Michelin | Elastomère diénique portant des groupes imidazole |
Also Published As
| Publication number | Publication date |
|---|---|
| FR3097222B1 (fr) | 2021-05-28 |
| CN114341114A (zh) | 2022-04-12 |
| FR3097222A1 (fr) | 2020-12-18 |
| WO2020249623A1 (fr) | 2020-12-17 |
| EP3983390A1 (de) | 2022-04-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Keizer et al. | Scale-up of the synthesis of ureidopyrimidinone functionalized telechelic poly (ethylenebutylene) | |
| CN113950494B (zh) | 带有侧链咪唑官能团的接枝聚合物 | |
| TWI428373B (zh) | 含硫聚合物、其製備方法及其應用 | |
| CN114341114B (zh) | 包含芳杂环和咪唑环的1,3-偶极化合物 | |
| Yang et al. | Visible-light-promoted selective O-alkylation of 2-pyridones with α-aryldiazoacetates | |
| CN112794979A (zh) | 仿生启发的具有超韧、超拉伸及自修复高回弹性聚氨酯弹性体的制备方法 | |
| KR101631481B1 (ko) | 아지리딘을 이용한 고분자 및 이의 제조방법 | |
| JP2021517192A (ja) | エチレンとミルセンとのコポリマー | |
| JP6080138B2 (ja) | グリシジル−４位修飾−１，２，３−トリアゾール誘導体ポリマー及びその合成方法 | |
| Yan et al. | Synthesis of well-defined star, star-block, and miktoarm star biodegradable polymers based on PLLA and PCL by one-pot azide–alkyne click reaction | |
| WO2018109396A1 (fr) | Compose 1,3-dipolaire portant une double liaison carbone-carbone conjuguée | |
| Huang et al. | Self-crosslinkable polymers from furan-functionalized Meldrum's acid and maleimides as effective precursors of free-standing and flexible crosslinked polymer films showing low dielectric constants | |
| Kakuchi et al. | The Passerini three-component reaction of aldehyde end-functionalized polymers via RAFT polymerization using chain transfer agents featuring aldehyde | |
| Sayed et al. | 1, 3-Dipolar cycloaddition polymerization reactions of novel macromolecules containing sym-tetrazine rings | |
| Swoboda et al. | Synthesis and characterization of a conjugated polymer with stable radicals in the side groups | |
| EP2430027B1 (de) | Triazol-/tetrazolpolymere aus der cycloaddition von funktionalisierten monomeren aus dianhydrohexitol, zwischenverbindungen, verfahren zur herstellung und anwendung | |
| JP4873570B2 (ja) | ポリ［２］カテナン化合物およびその単量体、ならびにそれらの製造方法 | |
| Herrlé et al. | Sustainable mechanosynthesis of diamide tetraols monomers and their enzymatic polymerization | |
| Dong et al. | Retracted Article: Metal-free [2+ 2+ 1] cycloaddition polymerization of alkynes, nitriles, and oxygen atoms to functional polyoxazoles | |
| JP6991541B2 (ja) | 分子サイズ認識可能な新規ケミカルプローブおよびその製造方法 | |
| Sharma et al. | Synthetic platform for mono-functionalised tridentate macrocycles as key precursors of mechanically-linked macromolecular systems | |
| Xiao et al. | Synthesis and characterization of camphorsulfonyl acetate of cellulose | |
| CN111944145A (zh) | 热固性聚三唑酯树脂及其复合材料、制备方法 | |
| BR102013020211A2 (pt) | método de obtenção de polímeros e copolímeros a partir de adutos dieno-dienófilo bifuncionais | |
| US20230312765A1 (en) | Compound comprising an epoxide group |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |