JP6396462B2 - フラン−２，５−ジメタノールおよび（テトラヒドロフラン−２，５−ジイル）ジメタノールのモノおよびジアルキルエーテルならびにその両親媒性誘導体 - Google Patents
フラン−２，５−ジメタノールおよび（テトラヒドロフラン−２，５−ジイル）ジメタノールのモノおよびジアルキルエーテルならびにその両親媒性誘導体 Download PDFInfo
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- JP6396462B2 JP6396462B2 JP2016530946A JP2016530946A JP6396462B2 JP 6396462 B2 JP6396462 B2 JP 6396462B2 JP 2016530946 A JP2016530946 A JP 2016530946A JP 2016530946 A JP2016530946 A JP 2016530946A JP 6396462 B2 JP6396462 B2 JP 6396462B2
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- Prior art keywords
- methyl
- tetrahydrofuran
- methanol
- furan
- fdm
- Prior art date
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- DSLRVRBSNLHVBH-UHFFFAOYSA-N 2,5-furandimethanol Chemical compound OCC1=CC=C(CO)O1 DSLRVRBSNLHVBH-UHFFFAOYSA-N 0.000 title claims description 57
- YCZZQSFWHFBKMU-UHFFFAOYSA-N [5-(hydroxymethyl)oxolan-2-yl]methanol Chemical compound OCC1CCC(CO)O1 YCZZQSFWHFBKMU-UHFFFAOYSA-N 0.000 title claims description 5
- 150000001346 alkyl aryl ethers Chemical class 0.000 title claims description 4
- 150000001983 dialkylethers Chemical class 0.000 title claims description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 60
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 49
- 239000003341 Bronsted base Substances 0.000 claims description 46
- 238000000034 method Methods 0.000 claims description 45
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 40
- 150000001875 compounds Chemical class 0.000 claims description 28
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 25
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 21
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 19
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 19
- 150000008052 alkyl sulfonates Chemical class 0.000 claims description 11
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 claims description 11
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 claims description 8
- 239000002585 base Substances 0.000 claims description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- GCXLHYPYUXENAH-UHFFFAOYSA-N [5-(dodecoxymethyl)furan-2-yl]methanol Chemical compound C(CCCCCCCCCCC)OCC1=CC=C(O1)CO GCXLHYPYUXENAH-UHFFFAOYSA-N 0.000 claims description 5
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 5
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 5
- CFSVRRKPLZTRQM-RNPORBBMSA-N (2R,5S)-2,5-bis(dodecoxymethyl)oxolane Chemical compound C(CCCCCCCCCCC)OC[C@@H]1O[C@@H](CC1)COCCCCCCCCCCCC CFSVRRKPLZTRQM-RNPORBBMSA-N 0.000 claims description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
- WEPZQMOMPHLUFJ-UHFFFAOYSA-N [5-(hexoxymethyl)furan-2-yl]methanol Chemical compound C(CCCCC)OCC1=CC=C(O1)CO WEPZQMOMPHLUFJ-UHFFFAOYSA-N 0.000 claims description 4
- QJIQQUHELIPPML-UHFFFAOYSA-N [5-(octadecoxymethyl)furan-2-yl]methanol Chemical compound C(CCCCCCCCCCCCCCCCC)OCC1=CC=C(O1)CO QJIQQUHELIPPML-UHFFFAOYSA-N 0.000 claims description 4
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims 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 claims description 4
- GKGRPKVJALYQLW-ZRKBJOGQSA-N (2R,5S)-2,5-bis(octadecoxymethyl)oxolane Chemical compound C(CCCCCCCCCCCCCCCCC)OC[C@@H]1O[C@@H](CC1)COCCCCCCCCCCCCCCCCCC GKGRPKVJALYQLW-ZRKBJOGQSA-N 0.000 claims description 3
- WCNKULSYBFSDRF-HDICACEKSA-N (2S,5R)-2,5-bis(hexoxymethyl)oxolane Chemical compound C(CCCCC)OC[C@@H]1O[C@@H](CC1)COCCCCCC WCNKULSYBFSDRF-HDICACEKSA-N 0.000 claims description 3
- CFSVRRKPLZTRQM-KYJUHHDHSA-N (2S,5S)-2,5-bis(dodecoxymethyl)oxolane Chemical compound C(CCCCCCCCCCC)OC[C@H]1O[C@@H](CC1)COCCCCCCCCCCCC CFSVRRKPLZTRQM-KYJUHHDHSA-N 0.000 claims description 3
- WCNKULSYBFSDRF-ROUUACIJSA-N (2S,5S)-2,5-bis(hexoxymethyl)oxolane Chemical compound C(CCCCC)OC[C@H]1O[C@@H](CC1)COCCCCCC WCNKULSYBFSDRF-ROUUACIJSA-N 0.000 claims description 3
- GKGRPKVJALYQLW-COCZKOEFSA-N (2S,5S)-2,5-bis(octadecoxymethyl)oxolane Chemical compound C(CCCCCCCCCCCCCCCCC)OC[C@H]1O[C@@H](CC1)COCCCCCCCCCCCCCCCCCC GKGRPKVJALYQLW-COCZKOEFSA-N 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- QTTQWWFHVDQVPM-UHFFFAOYSA-N 2,5-bis(dodecoxymethyl)furan Chemical compound CCCCCCCCCCCCOCC1=CC=C(COCCCCCCCCCCCC)O1 QTTQWWFHVDQVPM-UHFFFAOYSA-N 0.000 claims description 3
- OUCUZRKXZKSWLD-UHFFFAOYSA-N 2,5-bis(hexoxymethyl)furan Chemical compound CCCCCCOCC1=CC=C(COCCCCCC)O1 OUCUZRKXZKSWLD-UHFFFAOYSA-N 0.000 claims description 3
- HFLFOIQILRBILM-UHFFFAOYSA-N 2,5-bis(octadecoxymethyl)furan Chemical compound C(CCCCCCCCCCCCCCCCC)OCC=1OC(=CC1)COCCCCCCCCCCCCCCCCCC HFLFOIQILRBILM-UHFFFAOYSA-N 0.000 claims description 3
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims description 3
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 3
- PXACTUVBBMDKRW-UHFFFAOYSA-M 4-bromobenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(Br)C=C1 PXACTUVBBMDKRW-UHFFFAOYSA-M 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000012038 nucleophile Substances 0.000 claims description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims 10
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 78
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 69
- 238000006243 chemical reaction Methods 0.000 description 63
- 238000003756 stirring Methods 0.000 description 60
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 56
- 239000000203 mixture Substances 0.000 description 55
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 30
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 28
- 239000000741 silica gel Substances 0.000 description 28
- 229910002027 silica gel Inorganic materials 0.000 description 28
- -1 2,5-disubstituted furan Chemical class 0.000 description 26
- 239000004810 polytetrafluoroethylene Substances 0.000 description 26
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 26
- 238000003786 synthesis reaction Methods 0.000 description 25
- 230000015572 biosynthetic process Effects 0.000 description 24
- 239000000047 product Substances 0.000 description 21
- 229910052684 Cerium Inorganic materials 0.000 description 20
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 20
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 description 20
- MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 description 20
- 238000005481 NMR spectroscopy Methods 0.000 description 19
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 19
- NOEGNKMFWQHSLB-UHFFFAOYSA-N 5-hydroxymethylfurfural Chemical compound OCC1=CC=C(C=O)O1 NOEGNKMFWQHSLB-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- 239000012267 brine Substances 0.000 description 18
- 238000002474 experimental method Methods 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 229920001971 elastomer Polymers 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- 229910052786 argon Inorganic materials 0.000 description 14
- 239000003153 chemical reaction reagent Substances 0.000 description 14
- NJLAGDPRCAPJIF-MHSJTTIKSA-N (8S)-1',3',9-trihydroxy-6'-methoxy-3-[(1E,3E)-penta-1,3-dienyl]spiro[6,7-dihydro-2H-cyclopenta[g]isoquinoline-8,2'-cyclopenta[b]naphthalene]-1,4',5',8',9'-pentone Chemical compound COc1cc(=O)c2c(c1=O)c(=O)c1=C(O)[C@]3(CCc4cc5cc(\C=C\C=C\C)[nH]c(=O)c5c(O)c34)C(O)=c1c2=O NJLAGDPRCAPJIF-MHSJTTIKSA-N 0.000 description 13
- 239000000463 material Substances 0.000 description 13
- 239000012300 argon atmosphere Substances 0.000 description 12
- 239000007789 gas Substances 0.000 description 12
- 238000010186 staining Methods 0.000 description 12
- 239000007787 solid Substances 0.000 description 11
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 10
- 239000010410 layer Substances 0.000 description 10
- 241000894007 species Species 0.000 description 10
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 150000001350 alkyl halides Chemical class 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 238000006467 substitution reaction Methods 0.000 description 8
- 238000003818 flash chromatography Methods 0.000 description 7
- OIRDBPQYVWXNSJ-UHFFFAOYSA-N methyl trifluoromethansulfonate Chemical compound COS(=O)(=O)C(F)(F)F OIRDBPQYVWXNSJ-UHFFFAOYSA-N 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- BXGYYDRIMBPOMN-UHFFFAOYSA-N 2-(hydroxymethoxy)ethoxymethanol Chemical compound OCOCCOCO BXGYYDRIMBPOMN-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 0 CCCCCCCCCCCCCCCCCCOC[C@]1O[C@@](C*)CC1 Chemical compound CCCCCCCCCCCCCCCCCCOC[C@]1O[C@@](C*)CC1 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- YCZZQSFWHFBKMU-OLQVQODUSA-N [(2r,5s)-5-(hydroxymethyl)oxolan-2-yl]methanol Chemical compound OC[C@H]1CC[C@@H](CO)O1 YCZZQSFWHFBKMU-OLQVQODUSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 6
- 238000006266 etherification reaction Methods 0.000 description 6
- 230000000269 nucleophilic effect Effects 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 239000003880 polar aprotic solvent Substances 0.000 description 6
- 239000002243 precursor Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 238000010898 silica gel chromatography Methods 0.000 description 6
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- PBLNBZIONSLZBU-UHFFFAOYSA-N 1-bromododecane Chemical compound CCCCCCCCCCCCBr PBLNBZIONSLZBU-UHFFFAOYSA-N 0.000 description 5
- 150000002334 glycols Chemical class 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 239000004014 plasticizer Substances 0.000 description 5
- 150000003141 primary amines Chemical class 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 239000002270 dispersing agent Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 4
- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 3
- WSULSMOGMLRGKU-UHFFFAOYSA-N 1-bromooctadecane Chemical compound CCCCCCCCCCCCCCCCCCBr WSULSMOGMLRGKU-UHFFFAOYSA-N 0.000 description 3
- CDJGKSIVJSGTON-VXKWHMMOSA-N 2-[2-[[(2S,5S)-5-(dodecoxymethyl)oxolan-2-yl]methylamino]ethoxy]ethanol Chemical compound C(CCCCCCCCCCC)OC[C@@H]1CC[C@H](O1)CNCCOCCO CDJGKSIVJSGTON-VXKWHMMOSA-N 0.000 description 3
- BAVYZALUXZFZLV-UHFFFAOYSA-O Methylammonium ion Chemical compound [NH3+]C BAVYZALUXZFZLV-UHFFFAOYSA-O 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- IKDSOKHPPWSHDD-UHFFFAOYSA-M [5-(hexoxymethyl)furan-2-yl]methyl-trimethylazanium iodide Chemical compound [I-].CCCCCCOCC1=CC=C(C[N+](C)(C)C)O1 IKDSOKHPPWSHDD-UHFFFAOYSA-M 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 150000005215 alkyl ethers Chemical class 0.000 description 3
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 3
- 238000006264 debenzylation reaction Methods 0.000 description 3
- 230000008030 elimination Effects 0.000 description 3
- 238000003379 elimination reaction Methods 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 230000001404 mediated effect Effects 0.000 description 3
- JZMJDSHXVKJFKW-UHFFFAOYSA-N methyl sulfate Chemical compound COS(O)(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-N 0.000 description 3
- LLWRXQXPJMPHLR-UHFFFAOYSA-N methylazanium;iodide Chemical compound [I-].[NH3+]C LLWRXQXPJMPHLR-UHFFFAOYSA-N 0.000 description 3
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 230000005588 protonation Effects 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000001308 synthesis method Methods 0.000 description 3
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- CDJGKSIVJSGTON-FCHUYYIVSA-N 2-[2-[[(2S,5R)-5-(dodecoxymethyl)oxolan-2-yl]methylamino]ethoxy]ethanol Chemical compound C(CCCCCCCCCCC)OC[C@H]1CC[C@H](O1)CNCCOCCO CDJGKSIVJSGTON-FCHUYYIVSA-N 0.000 description 2
- PAJXWJFQRRBGBC-UHFFFAOYSA-N 2-[2-[[5-(octadecoxymethyl)furan-2-yl]methylamino]ethylamino]ethanol Chemical compound C(CCCCCCCCCCCCCCCCC)OCC1=CC=C(O1)CNCCNCCO PAJXWJFQRRBGBC-UHFFFAOYSA-N 0.000 description 2
- WKJYBARSSHPINT-UHFFFAOYSA-N 2-amino-1-ethoxyethanol Chemical class CCOC(O)CN WKJYBARSSHPINT-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229930091371 Fructose Natural products 0.000 description 2
- 239000005715 Fructose Substances 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- RJXUMEPHEPSNNX-CONSDPRKSA-N N-benzyl-1-[(2S,5S)-5-(octadecoxymethyl)oxolan-2-yl]methanamine Chemical compound C(C1=CC=CC=C1)NC[C@H]1O[C@@H](CC1)COCCCCCCCCCCCCCCCCCC RJXUMEPHEPSNNX-CONSDPRKSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- WYTQKXGSLVRFSB-UHFFFAOYSA-N [5-(hexoxymethyl)furan-2-yl]methanamine Chemical compound CCCCCCOCC1=CC=C(CN)O1 WYTQKXGSLVRFSB-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- 229940077388 benzenesulfonate Drugs 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003093 cationic surfactant Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000005595 deprotonation Effects 0.000 description 2
- 238000010537 deprotonation reaction Methods 0.000 description 2
- 230000008034 disappearance Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- CHTHALBTIRVDBM-UHFFFAOYSA-N furan-2,5-dicarboxylic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)O1 CHTHALBTIRVDBM-UHFFFAOYSA-N 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000000622 liquid--liquid extraction Methods 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000002390 rotary evaporation Methods 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 238000000638 solvent extraction Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 150000008163 sugars Chemical class 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical class OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 1
- SDTMFDGELKWGFT-UHFFFAOYSA-N 2-methylpropan-2-olate Chemical compound CC(C)(C)[O-] SDTMFDGELKWGFT-UHFFFAOYSA-N 0.000 description 1
- WWQGVCABJDSUME-UHFFFAOYSA-N 3-(2-aminoethoxy)propan-1-ol Chemical compound NCCOCCCO WWQGVCABJDSUME-UHFFFAOYSA-N 0.000 description 1
- 239000002028 Biomass Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 239000007848 Bronsted acid Substances 0.000 description 1
- JOCRQJSWWZHMSG-UVKLAMSESA-N CCCCCCCCCCCCOC(C1)C11O[C@H](CNCCOCCO)CC1 Chemical compound CCCCCCCCCCCCOC(C1)C11O[C@H](CNCCOCCO)CC1 JOCRQJSWWZHMSG-UVKLAMSESA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- RJXUMEPHEPSNNX-IOWSJCHKSA-N N-benzyl-1-[(2S,5R)-5-(octadecoxymethyl)oxolan-2-yl]methanamine Chemical compound C(C1=CC=CC=C1)NC[C@H]1O[C@H](CC1)COCCCCCCCCCCCCCCCCCC RJXUMEPHEPSNNX-IOWSJCHKSA-N 0.000 description 1
- 241000047703 Nonion Species 0.000 description 1
- 229920005830 Polyurethane Foam Polymers 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- KMQLSMYRAWYNNR-UHFFFAOYSA-N [5-[(benzylamino)methyl]furan-2-yl]methanol Chemical compound O1C(CO)=CC=C1CNCC1=CC=CC=C1 KMQLSMYRAWYNNR-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000005228 aryl sulfonate group Chemical group 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000012707 chemical precursor Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
- OGQYPPBGSLZBEG-UHFFFAOYSA-N dimethyl(dioctadecyl)azanium Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC OGQYPPBGSLZBEG-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000002803 fossil fuel Substances 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000013461 intermediate chemical Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 208000013409 limited attention Diseases 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
- 238000003760 magnetic stirring Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000011496 polyurethane foam Substances 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003864 primary ammonium salts Chemical class 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 150000003839 salts Chemical group 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 125000004079 stearyl 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])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
- 239000000758 substrate Substances 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical group CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/14—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/12—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/42—Singly bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361918239P | 2013-12-19 | 2013-12-19 | |
| US61/918,239 | 2013-12-19 | ||
| PCT/US2014/070021 WO2015094970A1 (en) | 2013-12-19 | 2014-12-12 | Mono- and dialkyl ethers of furan-2,5-dimethanol and (tetra-hydrofuran-2,5-diyl)dimethanol and amphiphilic derivatives thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017501123A JP2017501123A (ja) | 2017-01-12 |
| JP2017501123A5 JP2017501123A5 (enExample) | 2017-10-26 |
| JP6396462B2 true JP6396462B2 (ja) | 2018-09-26 |
Family
ID=53403552
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016530946A Active JP6396462B2 (ja) | 2013-12-19 | 2014-12-12 | フラン−２，５−ジメタノールおよび（テトラヒドロフラン−２，５−ジイル）ジメタノールのモノおよびジアルキルエーテルならびにその両親媒性誘導体 |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US9670174B2 (enExample) |
| EP (1) | EP3083576A4 (enExample) |
| JP (1) | JP6396462B2 (enExample) |
| KR (1) | KR102100539B1 (enExample) |
| CN (1) | CN105814030A (enExample) |
| AU (1) | AU2014366334B2 (enExample) |
| CA (1) | CA2931554C (enExample) |
| HK (1) | HK1226391A1 (enExample) |
| MX (1) | MX2016007952A (enExample) |
| WO (1) | WO2015094970A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2964658B1 (en) | 2013-03-08 | 2024-08-07 | The University Of British Columbia | Positron-emitting substituted organofluoroborates as imaging agents |
| KR20160098290A (ko) * | 2013-12-19 | 2016-08-18 | 아처 다니엘 미드랜드 캄파니 | 푸란-2,5-디메탄올 및 (테트라하이드로푸란-2,5-디일)디메탄올의 설포네이트 및 그 유도체 |
| HUE065368T2 (hu) | 2015-04-14 | 2024-05-28 | Du Pont | Eljárás 2,5-furándikabonsav és származékai elõállítására |
| DE102016009800A1 (de) | 2016-08-12 | 2018-02-15 | Henkel Ag & Co. Kgaa | Wasch- und Reinigungsmittel mit anionischen Tensiden aus nachwachsenden Rohstoffen |
| DE102016009798A1 (de) * | 2016-08-12 | 2018-02-15 | Henkel Ag & Co. Kgaa | Neue anionische Tenside und Wasch- und Reinigungsmittel, welche diese enthalten |
| DE102017008071A1 (de) | 2017-08-28 | 2019-02-28 | Henkel Ag & Co. Kgaa | Neue anionische Tenside und Wasch- und Reinigungsmittel, welche diese enthalten |
| DE102017008073A1 (de) * | 2017-08-28 | 2019-02-28 | Henkel Ag & Co. Kgaa | Neue anionische Tenside und Wasch- und Reinigungsmittel, welche diese enthalten |
| DE102017008072A1 (de) * | 2017-08-28 | 2019-02-28 | Henkel Ag & Co. Kgaa | Neue anionische Tenside und Wasch- und Reinigungsmittel, welche diese enthalten |
| US12427209B2 (en) | 2018-12-18 | 2025-09-30 | Provincial Health Services Authority | Dual mode 18F-labelled theranostic compounds and uses thereof |
| CN113710785A (zh) * | 2019-05-10 | 2021-11-26 | 联合利华知识产权控股有限公司 | 化合物和洗涤剂组合物 |
| EP4176028A1 (en) | 2020-07-06 | 2023-05-10 | Unilever IP Holdings B.V. | Irritation mitigating surfactants |
| CN114163407B (zh) * | 2020-09-11 | 2023-10-24 | 中国科学院宁波材料技术与工程研究所 | 抑制或杀灭微生物的呋喃环类成分、含其的制品及其应用 |
| KR102665866B1 (ko) | 2021-11-08 | 2024-05-14 | 한국생산기술연구원 | 테트라히드로퓨란-2,5-디메탄올을 사용한 테트라히드로퓨란-2,5-디에스터의 제조 및 분리 정제 방법 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0178261A3 (en) * | 1984-10-10 | 1986-12-30 | Sandoz Ag | Substituted 2-furanyl or 5-oxo-2-furanyl-alkoxy phosphoryl alkyl cyclimmonium salts |
| US4619917A (en) * | 1985-07-18 | 1986-10-28 | Sandoz Pharm. Corp. | Substituted 2-furanyl- or 5-oxo-2-furanyl methoxy phosphoryl alkyl cyclimmonium salts |
| ES2010568A6 (es) * | 1988-08-04 | 1989-11-16 | Uriach & Cia Sa J | Procedimiento para la obtencion de derivados 2,5-disustituidos de tetrahidrofurano. |
| US5208352A (en) * | 1992-04-02 | 1993-05-04 | Sandoz Ltd. | Process for preparing the R- and S-isomers of 2-hydroxy-methyl-2-octadecyloxymethyl-tetrahydrofuran and their use in preparing stereoisomers of pharmacologically active compounds |
| JP4419761B2 (ja) * | 2004-09-06 | 2010-02-24 | ダイソー株式会社 | スピロ骨格を持つキラルな相間移動触媒およびその製造法、並びにそれを用いた不斉触媒反応。 |
| DE102005023588A1 (de) * | 2005-05-18 | 2006-11-23 | Grünenthal GmbH | Salze substituierter Allophansäureester und deren Verwendung in Arzneimitteln |
| JO3240B1 (ar) * | 2007-10-17 | 2018-03-08 | Janssen Pharmaceutica Nv | c-fms مثبطات كيناز |
| US8669383B2 (en) * | 2010-12-16 | 2014-03-11 | Archer Daniels Midland Company | Preparation of aminomethyl furans and alkoxymethyl furan derivatives from carbohydrates |
-
2014
- 2014-12-12 CN CN201480067612.0A patent/CN105814030A/zh active Pending
- 2014-12-12 KR KR1020167018816A patent/KR102100539B1/ko active Active
- 2014-12-12 CA CA2931554A patent/CA2931554C/en active Active
- 2014-12-12 MX MX2016007952A patent/MX2016007952A/es unknown
- 2014-12-12 WO PCT/US2014/070021 patent/WO2015094970A1/en not_active Ceased
- 2014-12-12 US US15/038,066 patent/US9670174B2/en active Active
- 2014-12-12 EP EP14871772.1A patent/EP3083576A4/en not_active Withdrawn
- 2014-12-12 JP JP2016530946A patent/JP6396462B2/ja active Active
- 2014-12-12 HK HK16114626.5A patent/HK1226391A1/zh unknown
- 2014-12-12 AU AU2014366334A patent/AU2014366334B2/en active Active
-
2017
- 2017-04-28 US US15/581,613 patent/US20170233358A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US20160297785A1 (en) | 2016-10-13 |
| AU2014366334A1 (en) | 2016-06-02 |
| AU2014366334B2 (en) | 2018-01-18 |
| KR102100539B1 (ko) | 2020-04-13 |
| HK1226391A1 (zh) | 2017-09-29 |
| US20170233358A1 (en) | 2017-08-17 |
| KR20160098382A (ko) | 2016-08-18 |
| CN105814030A (zh) | 2016-07-27 |
| CA2931554C (en) | 2020-10-13 |
| WO2015094970A1 (en) | 2015-06-25 |
| EP3083576A1 (en) | 2016-10-26 |
| MX2016007952A (es) | 2016-09-09 |
| US9670174B2 (en) | 2017-06-06 |
| JP2017501123A (ja) | 2017-01-12 |
| EP3083576A4 (en) | 2017-08-02 |
| CA2931554A1 (en) | 2015-06-25 |
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