CN114853568A - 一种4,4,5,5,5-五氟戊醇的制备方法 - Google Patents
一种4,4,5,5,5-五氟戊醇的制备方法 Download PDFInfo
- Publication number
- CN114853568A CN114853568A CN202210261067.5A CN202210261067A CN114853568A CN 114853568 A CN114853568 A CN 114853568A CN 202210261067 A CN202210261067 A CN 202210261067A CN 114853568 A CN114853568 A CN 114853568A
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- CN
- China
- Prior art keywords
- reaction
- penta
- fluoropentanol
- allyl alcohol
- catalyst
- 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.)
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- QROUUECTKRZFHF-UHFFFAOYSA-N 4,4,5,5,5-pentafluoropentan-1-ol Chemical compound OCCCC(F)(F)C(F)(F)F QROUUECTKRZFHF-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title abstract description 14
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims abstract description 38
- 238000006243 chemical reaction Methods 0.000 claims abstract description 35
- 239000003054 catalyst Substances 0.000 claims abstract description 19
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 13
- 239000011737 fluorine Substances 0.000 claims abstract description 13
- 239000000852 hydrogen donor Substances 0.000 claims abstract description 9
- 239000003446 ligand Substances 0.000 claims abstract description 9
- 239000003960 organic solvent Substances 0.000 claims abstract description 5
- 239000003513 alkali Substances 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 23
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
- UXPOJVLZTPGWFX-UHFFFAOYSA-N pentafluoroethyl iodide Chemical group FC(F)(F)C(F)(F)I UXPOJVLZTPGWFX-UHFFFAOYSA-N 0.000 claims description 14
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical group CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 claims description 12
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 6
- 239000002585 base Substances 0.000 claims description 6
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 230000035484 reaction time Effects 0.000 claims description 6
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 6
- USYVEDJTMCGMKN-UHFFFAOYSA-N 1-bromo-1,1,2,2,2-pentafluoroethane Chemical compound FC(F)(F)C(F)(F)Br USYVEDJTMCGMKN-UHFFFAOYSA-N 0.000 claims description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 5
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 4
- LZKLAOYSENRNKR-LNTINUHCSA-N iron;(z)-4-oxoniumylidenepent-2-en-2-olate Chemical compound [Fe].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O LZKLAOYSENRNKR-LNTINUHCSA-N 0.000 claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 3
- 229910000024 caesium carbonate Inorganic materials 0.000 claims description 3
- LZWQNOHZMQIFBX-UHFFFAOYSA-N lithium;2-methylpropan-2-olate Chemical compound [Li+].CC(C)(C)[O-] LZWQNOHZMQIFBX-UHFFFAOYSA-N 0.000 claims description 3
- QCIWZIYBBNEPKB-UHFFFAOYSA-N tert-butyl(dimethyl)silane Chemical compound C[SiH](C)C(C)(C)C QCIWZIYBBNEPKB-UHFFFAOYSA-N 0.000 claims description 3
- ZGYICYBLPGRURT-UHFFFAOYSA-N tri(propan-2-yl)silicon Chemical compound CC(C)[Si](C(C)C)C(C)C ZGYICYBLPGRURT-UHFFFAOYSA-N 0.000 claims description 3
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 claims description 3
- LFKXWKGYHQXRQA-FDGPNNRMSA-N (z)-4-hydroxypent-3-en-2-one;iron Chemical compound [Fe].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O LFKXWKGYHQXRQA-FDGPNNRMSA-N 0.000 claims description 2
- JFJNVIPVOCESGZ-UHFFFAOYSA-N 2,3-dipyridin-2-ylpyridine Chemical compound N1=CC=CC=C1C1=CC=CN=C1C1=CC=CC=N1 JFJNVIPVOCESGZ-UHFFFAOYSA-N 0.000 claims description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 claims description 2
- 229960001701 chloroform Drugs 0.000 claims 1
- VWUXBMIQPBEWFH-WCCTWKNTSA-N Fulvestrant Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3[C@H](CCCCCCCCCS(=O)CCCC(F)(F)C(F)(F)F)CC2=C1 VWUXBMIQPBEWFH-WCCTWKNTSA-N 0.000 abstract description 8
- 229960002258 fulvestrant Drugs 0.000 abstract description 8
- 239000002994 raw material Substances 0.000 abstract description 8
- 229910000510 noble metal Inorganic materials 0.000 abstract description 7
- 238000009776 industrial production Methods 0.000 abstract description 4
- 239000000463 material Substances 0.000 abstract description 4
- 229910052751 metal Inorganic materials 0.000 abstract description 3
- 239000002184 metal Substances 0.000 abstract description 3
- 239000004094 surface-active agent Substances 0.000 abstract description 3
- 231100000331 toxic Toxicity 0.000 abstract description 3
- 230000002588 toxic effect Effects 0.000 abstract description 3
- 230000007613 environmental effect Effects 0.000 abstract description 2
- 239000000178 monomer Substances 0.000 abstract description 2
- 238000000746 purification Methods 0.000 abstract description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 239000011261 inert gas Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 238000010791 quenching Methods 0.000 description 5
- 238000005070 sampling Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- CDVAIHNNWWJFJW-UHFFFAOYSA-N 3,5-diethoxycarbonyl-1,4-dihydrocollidine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C CDVAIHNNWWJFJW-UHFFFAOYSA-N 0.000 description 4
- 230000007547 defect Effects 0.000 description 4
- 206010006187 Breast cancer Diseases 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000000975 dye Substances 0.000 description 3
- 238000005286 illumination Methods 0.000 description 3
- -1 pentafluoroamyl ester Chemical class 0.000 description 3
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 2
- 208000026310 Breast neoplasm Diseases 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000005695 dehalogenation reaction Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000002905 metal composite material Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- WINZRPSJXIIXKQ-IWQZZHSRSA-N (z)-4,4,5,5,5-pentafluoro-2-iodopent-2-en-1-ol Chemical compound OC\C(I)=C\C(F)(F)C(F)(F)F WINZRPSJXIIXKQ-IWQZZHSRSA-N 0.000 description 1
- KBOAVUSWPXRQBC-UHFFFAOYSA-N 1,1,1,2,2-pentafluoropentane Chemical compound CCCC(F)(F)C(F)(F)F KBOAVUSWPXRQBC-UHFFFAOYSA-N 0.000 description 1
- PWHRYUWAMMUEPA-UHFFFAOYSA-N 2-bromo-4,4,5,5,5-pentafluoropentan-1-ol Chemical compound OCC(Br)CC(F)(F)C(F)(F)F PWHRYUWAMMUEPA-UHFFFAOYSA-N 0.000 description 1
- PRRSFMGODMUPJN-CABZTGNLSA-N 2-fluoro-4-[(2r,3s)-5,5,5-trifluoro-3-(3-fluoro-4-hydroxyphenyl)pentan-2-yl]phenol Chemical compound C1([C@@H](CC(F)(F)F)[C@@H](C)C=2C=C(F)C(O)=CC=2)=CC=C(O)C(F)=C1 PRRSFMGODMUPJN-CABZTGNLSA-N 0.000 description 1
- HIYFWRNMQLCCPO-UHFFFAOYSA-N 4,4,5,5,5-pentafluoro-2-iodopentan-1-ol Chemical compound OCC(I)CC(F)(F)C(F)(F)F HIYFWRNMQLCCPO-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229940046836 anti-estrogen Drugs 0.000 description 1
- 230000001833 anti-estrogenic effect Effects 0.000 description 1
- 239000003560 cancer drug Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 239000000328 estrogen antagonist Substances 0.000 description 1
- 102000015694 estrogen receptors Human genes 0.000 description 1
- 108010038795 estrogen receptors Proteins 0.000 description 1
- 229960002089 ferrous chloride Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 description 1
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
- GTLACDSXYULKMZ-UHFFFAOYSA-N pentafluoroethane Chemical compound FC(F)C(F)(F)F GTLACDSXYULKMZ-UHFFFAOYSA-N 0.000 description 1
- 229950009730 pentafluranol Drugs 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
Images
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/44—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by addition reactions, i.e. reactions involving at least one carbon-to-carbon double or triple bond
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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CN116162016A (zh) * | 2023-01-09 | 2023-05-26 | 山东重山光电材料股份有限公司 | 一种高纯五氟戊醇的制备方法 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2196449A1 (de) * | 2008-12-12 | 2010-06-16 | Saltigo GmbH | Verfahren zur Herstellung von Perfluoralkyl- oder Perfluoralkoxyalkanolen |
CN111004091A (zh) * | 2019-12-12 | 2020-04-14 | 西安近代化学研究所 | 一种制备4,4,5,5,5-五氟戊醇的方法 |
-
2022
- 2022-03-16 CN CN202210261067.5A patent/CN114853568B/zh active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP2196449A1 (de) * | 2008-12-12 | 2010-06-16 | Saltigo GmbH | Verfahren zur Herstellung von Perfluoralkyl- oder Perfluoralkoxyalkanolen |
CN111004091A (zh) * | 2019-12-12 | 2020-04-14 | 西安近代化学研究所 | 一种制备4,4,5,5,5-五氟戊醇的方法 |
Non-Patent Citations (3)
Title |
---|
HELL, SANDRINE M. ET AL.: "Hydrofluoromethylation of alkenes with fluoroiodomethane and beyond", 《CHEMICAL SCIENCE》, vol. 12, no. 36, pages 12149 - 12155 * |
LI, XUN ET AL.: "Laboratory scale preparation of 4, 4, 5, 5, 5-pentafluoropentane-1-thiol: an important chain of anti-breast cancer agents", 《TETRAHEDRON LETTERS》, vol. 35, no. 49, pages 9141 - 9144, XP002090321, DOI: 10.1016/0040-4039(94)88448-X * |
SHEN, YANGYONG ET AL.: "Csp-Csp3 Bond Formation via Iron(III)-Promoted Hydroalkynylation of Unactivated Alkenes", 《ORGANIC LETTERS》, vol. 19, no. 7, pages 1744 - 1747 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN116162016A (zh) * | 2023-01-09 | 2023-05-26 | 山东重山光电材料股份有限公司 | 一种高纯五氟戊醇的制备方法 |
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Address after: 124000 building 20, block a, West Industrial Park, GONGMAO Road, South Park Street, Shuangtaizi District, Panjin City, Liaoning Province Applicant after: Liaoning Fuyin Biotechnology Co.,Ltd. Address before: 124000 building 20, block a, West Industrial Park, GONGMAO Road, South Park Street, Shuangtaizi District, Panjin City, Liaoning Province Applicant before: Liaoning Dinuo Pharmaceutical Technology Co.,Ltd. |
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Denomination of invention: A preparation method of 4,4,5,5,5-pentafluoropentanol Granted publication date: 20230922 Pledgee: Panjin financing guarantee Group Co.,Ltd. Pledgor: Liaoning Fuyin Biotechnology Co.,Ltd. Registration number: Y2024980013146 |