JP2017501123A5 - - Google Patents
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- Publication number
- JP2017501123A5 JP2017501123A5 JP2016530946A JP2016530946A JP2017501123A5 JP 2017501123 A5 JP2017501123 A5 JP 2017501123A5 JP 2016530946 A JP2016530946 A JP 2016530946A JP 2016530946 A JP2016530946 A JP 2016530946A JP 2017501123 A5 JP2017501123 A5 JP 2017501123A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- tetrahydrofuran
- methanol
- alkyl
- bis
- 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.)
- Granted
Links
- 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 2
- 238000000034 method Methods 0.000 claims 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 18
- 239000003341 Bronsted base Substances 0.000 claims 14
- DSLRVRBSNLHVBH-UHFFFAOYSA-N 2,5-furandimethanol Chemical compound OCC1=CC=C(CO)O1 DSLRVRBSNLHVBH-UHFFFAOYSA-N 0.000 claims 10
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 claims 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 150000001875 compounds Chemical class 0.000 claims 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- 239000003960 organic solvent Substances 0.000 claims 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 2
- -1 alkyl lithium Chemical compound 0.000 claims 2
- 150000008052 alkyl sulfonates Chemical class 0.000 claims 2
- 239000002585 base Substances 0.000 claims 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 claims 2
- 239000012038 nucleophile Substances 0.000 claims 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- 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 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- QTTQWWFHVDQVPM-UHFFFAOYSA-N 2,5-bis(dodecoxymethyl)furan Chemical compound CCCCCCCCCCCCOCC1=CC=C(COCCCCCCCCCCCC)O1 QTTQWWFHVDQVPM-UHFFFAOYSA-N 0.000 claims 1
- OUCUZRKXZKSWLD-UHFFFAOYSA-N 2,5-bis(hexoxymethyl)furan Chemical compound CCCCCCOCC1=CC=C(COCCCCCC)O1 OUCUZRKXZKSWLD-UHFFFAOYSA-N 0.000 claims 1
- HFLFOIQILRBILM-UHFFFAOYSA-N 2,5-bis(octadecoxymethyl)furan Chemical compound C(CCCCCCCCCCCCCCCCC)OCC=1OC(=CC1)COCCCCCCCCCCCCCCCCCC HFLFOIQILRBILM-UHFFFAOYSA-N 0.000 claims 1
- PXACTUVBBMDKRW-UHFFFAOYSA-M 4-bromobenzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=C(Br)C=C1 PXACTUVBBMDKRW-UHFFFAOYSA-M 0.000 claims 1
- 239000007818 Grignard reagent Substances 0.000 claims 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 1
- WEPZQMOMPHLUFJ-UHFFFAOYSA-N [5-(hexoxymethyl)furan-2-yl]methanol Chemical compound C(CCCCC)OCC1=CC=C(O1)CO WEPZQMOMPHLUFJ-UHFFFAOYSA-N 0.000 claims 1
- YCZZQSFWHFBKMU-UHFFFAOYSA-N [5-(hydroxymethyl)oxolan-2-yl]methanol Chemical compound OCC1CCC(CO)O1 YCZZQSFWHFBKMU-UHFFFAOYSA-N 0.000 claims 1
- QJIQQUHELIPPML-UHFFFAOYSA-N [5-(octadecoxymethyl)furan-2-yl]methanol Chemical compound C(CCCCCCCCCCCCCCCCC)OCC1=CC=C(O1)CO QJIQQUHELIPPML-UHFFFAOYSA-N 0.000 claims 1
- 150000001346 alkyl aryl ethers Chemical class 0.000 claims 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 150000001983 dialkylethers Chemical class 0.000 claims 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 claims 1
- 150000004795 grignard reagents Chemical class 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 claims 1
- 229910000103 lithium hydride Inorganic materials 0.000 claims 1
- 239000011777 magnesium Substances 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 229910052987 metal hydride Inorganic materials 0.000 claims 1
- 150000004681 metal hydrides Chemical class 0.000 claims 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims 1
- 125000002524 organometallic group Chemical group 0.000 claims 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 claims 1
- 229910000105 potassium hydride Inorganic materials 0.000 claims 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims 1
- 229910000104 sodium hydride Inorganic materials 0.000 claims 1
- 239000012312 sodium hydride Substances 0.000 claims 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims 1
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 true JP2017501123A5 (enExample) | 2017-10-26 |
| JP6396462B2 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 |
|---|---|---|---|---|
| WO2014134716A1 (en) | 2013-03-08 | 2014-09-12 | The University Of British Columbia | Substituted organofluoroborates as imaging agents |
| US20160304479A1 (en) * | 2013-12-19 | 2016-10-20 | Archer Daniels Midland Company | Sulfonates of furan-2,5-dimethanol and (tetrahydrofuran-2,5-diyl)dimethanol and derivatives thereof |
| CN114262312B (zh) | 2015-04-14 | 2024-08-20 | 杜邦公司 | 用于生产2,5-呋喃二甲酸及其衍生物以及由其制成的聚合物的方法 |
| DE102016009798A1 (de) * | 2016-08-12 | 2018-02-15 | Henkel Ag & Co. Kgaa | Neue anionische Tenside und Wasch- und Reinigungsmittel, welche diese enthalten |
| DE102016009800A1 (de) | 2016-08-12 | 2018-02-15 | Henkel Ag & Co. Kgaa | Wasch- und Reinigungsmittel mit anionischen Tensiden aus nachwachsenden Rohstoffen |
| DE102017008072A1 (de) * | 2017-08-28 | 2019-02-28 | 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 |
| WO2020124237A1 (en) | 2018-12-18 | 2020-06-25 | Provincial Health Services Authority | Dual mode 18f-labelled theranostic compounds and uses thereof |
| WO2020229158A1 (en) | 2019-05-10 | 2020-11-19 | Unilever Plc | Compound and detergent composition |
| AU2021306453B2 (en) | 2020-07-06 | 2023-12-21 | Unilever Global Ip Limited | 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 |
| CN103443090B (zh) * | 2010-12-16 | 2016-08-24 | 阿彻丹尼尔斯米德兰德公司 | 从碳水化合物制备氨甲基呋喃和烷氧基甲基呋喃衍生物 |
-
2014
- 2014-12-12 KR KR1020167018816A patent/KR102100539B1/ko active Active
- 2014-12-12 JP JP2016530946A patent/JP6396462B2/ja active Active
- 2014-12-12 MX MX2016007952A patent/MX2016007952A/es unknown
- 2014-12-12 EP EP14871772.1A patent/EP3083576A4/en not_active Withdrawn
- 2014-12-12 HK HK16114626.5A patent/HK1226391A1/zh unknown
- 2014-12-12 AU AU2014366334A patent/AU2014366334B2/en active Active
- 2014-12-12 CA CA2931554A patent/CA2931554C/en active Active
- 2014-12-12 CN CN201480067612.0A patent/CN105814030A/zh active Pending
- 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
-
2017
- 2017-04-28 US US15/581,613 patent/US20170233358A1/en not_active Abandoned
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