CN117466717A - Fully substituted alkyl alkenyl ether, preparation method and application - Google Patents
Fully substituted alkyl alkenyl ether, preparation method and application Download PDFInfo
- Publication number
- CN117466717A CN117466717A CN202311244212.XA CN202311244212A CN117466717A CN 117466717 A CN117466717 A CN 117466717A CN 202311244212 A CN202311244212 A CN 202311244212A CN 117466717 A CN117466717 A CN 117466717A
- Authority
- CN
- China
- Prior art keywords
- tert
- pentyl
- substituted alkyl
- copper
- alkenyl ether
- 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.)
- Pending
Links
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 title claims abstract description 82
- 125000000547 substituted alkyl group Chemical group 0.000 title claims abstract description 46
- 238000002360 preparation method Methods 0.000 title abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 23
- 238000000034 method Methods 0.000 claims abstract description 16
- 239000000654 additive Substances 0.000 claims abstract description 15
- 150000004703 alkoxides Chemical class 0.000 claims abstract description 15
- 230000000996 additive effect Effects 0.000 claims abstract description 14
- 239000003054 catalyst Substances 0.000 claims abstract description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000002904 solvent Substances 0.000 claims abstract description 8
- 238000010438 heat treatment Methods 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims abstract description 5
- 150000001555 benzenes Chemical class 0.000 claims abstract description 4
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 claims abstract 14
- -1 n-amyl Chemical group 0.000 claims description 55
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 30
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 30
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
- 125000005504 styryl group Chemical group 0.000 claims description 27
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 24
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 24
- 229910052731 fluorine Inorganic materials 0.000 claims description 23
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 21
- 125000001153 fluoro group Chemical group F* 0.000 claims description 21
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 21
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 21
- 239000010949 copper Substances 0.000 claims description 14
- 229910052802 copper Inorganic materials 0.000 claims description 14
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 claims description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 7
- JMQRNHTTZWNLMH-UHFFFAOYSA-M 1,3-bis(2,4,6-trimethylphenyl)imidazole;chlorocopper Chemical compound CC1=CC(C)=CC(C)=C1N1C(=[Cu]Cl)N(C=2C(=CC(C)=CC=2C)C)C=C1 JMQRNHTTZWNLMH-UHFFFAOYSA-M 0.000 claims description 4
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 claims description 4
- GPCDGGKVBPVZCT-UHFFFAOYSA-N 1,1-difluorocyclopropane Chemical group FC1(F)CC1 GPCDGGKVBPVZCT-UHFFFAOYSA-N 0.000 claims description 3
- AXCOCGJDERQVDK-UHFFFAOYSA-N 1,2,4,5-tetrafluoro-3-methoxybenzene Chemical compound COC1=C(F)C(F)=CC(F)=C1F AXCOCGJDERQVDK-UHFFFAOYSA-N 0.000 claims description 3
- 229910021589 Copper(I) bromide Inorganic materials 0.000 claims description 3
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 3
- 229910021595 Copper(I) iodide Inorganic materials 0.000 claims description 3
- 229910021594 Copper(II) fluoride Inorganic materials 0.000 claims description 3
- RFKZUAOAYVHBOY-UHFFFAOYSA-M copper(1+);acetate Chemical compound [Cu+].CC([O-])=O RFKZUAOAYVHBOY-UHFFFAOYSA-M 0.000 claims description 3
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 3
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 claims description 3
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 claims description 3
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 claims description 3
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 claims description 3
- GWFAVIIMQDUCRA-UHFFFAOYSA-L copper(ii) fluoride Chemical compound [F-].[F-].[Cu+2] GWFAVIIMQDUCRA-UHFFFAOYSA-L 0.000 claims description 3
- SEKCXMNFUDONGJ-UHFFFAOYSA-L copper;2-ethylhexanoate Chemical compound [Cu+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O SEKCXMNFUDONGJ-UHFFFAOYSA-L 0.000 claims description 3
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 claims description 3
- 229940045803 cuprous chloride Drugs 0.000 claims description 3
- KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 claims description 3
- 229940112669 cuprous oxide Drugs 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
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 3
- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- ZXMGHDIOOHOAAE-UHFFFAOYSA-N 1,1,1-trifluoro-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F ZXMGHDIOOHOAAE-UHFFFAOYSA-N 0.000 claims description 2
- ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 claims description 2
- YOBCNSPOCAOTDR-UHFFFAOYSA-L copper acetonitrile trifluoromethanesulfonate Chemical compound [Cu++].CC#N.CC#N.CC#N.CC#N.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F YOBCNSPOCAOTDR-UHFFFAOYSA-L 0.000 claims description 2
- SBTSVTLGWRLWOD-UHFFFAOYSA-L copper(ii) triflate Chemical compound [Cu+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F SBTSVTLGWRLWOD-UHFFFAOYSA-L 0.000 claims description 2
- JPUFNIIPFXQOCB-UHFFFAOYSA-M 1,3-bis[2,6-di(propan-2-yl)phenyl]imidazole;chlorocopper Chemical compound CC(C)C1=CC=CC(C(C)C)=C1N1C(=[Cu]Cl)N(C=2C(=CC=CC=2C(C)C)C(C)C)C=C1 JPUFNIIPFXQOCB-UHFFFAOYSA-M 0.000 claims 1
- FDIRIOAEXPIEBL-UHFFFAOYSA-L copper;thiophene-2-carboxylate Chemical compound [Cu+2].[O-]C(=O)C1=CC=CS1.[O-]C(=O)C1=CC=CS1 FDIRIOAEXPIEBL-UHFFFAOYSA-L 0.000 claims 1
- 239000002994 raw material Substances 0.000 abstract description 6
- 239000003446 ligand Substances 0.000 abstract description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 18
- 238000001228 spectrum Methods 0.000 description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 150000001336 alkenes Chemical class 0.000 description 5
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- DLBYCBMQDZFUIJ-UHFFFAOYSA-N (2,2-difluorocyclopropyl)benzene Chemical compound FC1(F)CC1C1=CC=CC=C1 DLBYCBMQDZFUIJ-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000006555 catalytic reaction Methods 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 2
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 229910021590 Copper(II) bromide Inorganic materials 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229940041181 antineoplastic drug Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- MSFHCZUIBARZOS-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)azanide copper(1+) Chemical compound [Cu+].FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F MSFHCZUIBARZOS-UHFFFAOYSA-N 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- HWUPLUNLNUHIQZ-UHFFFAOYSA-N copper;trifluoromethanesulfonic acid Chemical compound [Cu].OS(=O)(=O)C(F)(F)F.OS(=O)(=O)C(F)(F)F HWUPLUNLNUHIQZ-UHFFFAOYSA-N 0.000 description 1
- 229960003280 cupric chloride Drugs 0.000 description 1
- 238000009509 drug development Methods 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000005003 food packaging material Substances 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000002700 tablet coating Substances 0.000 description 1
- 238000009492 tablet coating Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/14—Unsaturated ethers
- C07C43/164—Unsaturated ethers containing six-membered aromatic rings
- C07C43/166—Unsaturated ethers containing six-membered aromatic rings having unsaturation outside the aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a fully substituted alkyl alkenyl ether, a preparation method and application thereof, wherein the preparation method comprises the following steps: dissolving a catalyst, an additive, 1-alkyne or polyfluorinated benzene and gem-difluoro cyclopropane in a solvent, heating to a set temperature value, fully reacting, and purifying to obtain the required full substituted alkyl alkenyl ether; the additive is one of alkoxide, alcohol and mixture of alkoxide in any proportion. The fully substituted alkyl alkenyl ether with a definite configuration can be obtained by the one-step method, and the preparation method is simple; the raw materials such as the catalyst, the ligand, the additive, the solvent and the like used in the preparation method are all commercial or relatively easily available, and the reaction conditions are mild and simple and are easy to operate.
Description
Technical Field
The invention relates to the technical field of compound synthesis, in particular to a fully substituted alkyl alkenyl ether, a preparation method and application.
Background
Alkyl alkenyl ether is a common organic compound and has wide application prospect in basic chemistry research, industrial production and drug research and development. Wherein, some alkyl alkenyl ethers with biological activity can be used as drug molecules for pharmacological research and drug development, and some alkyl alkenyl ethers with antibacterial, anti-inflammatory, anti-tumor activities and the like are widely applied to the fields of antibiotics, anticancer drugs and the like; the alkyl alkenyl ether has lower viscosity and higher solubility, so that the stability of industrial chemicals can be improved, and the alkyl alkenyl ether is also often used as a raw material of a surfactant, a lubricant, an antioxidant and the like; it is often used in the manufacture of adhesives, varnishes, paints and food packaging materials, tablet coatings and fillers, and the like, because it is susceptible to polymerization to form polymers.
Presently, low substituted alkyl alkenyl ethers are available through a variety of synthetic methods, the most common of which are synthesized by alkylation and alkenylation reactions. In the alkylation reaction, common methods include alkyl halogenation, reaction of an alkyl metal reagent with a halogenated olefin, oxidation of an alkyl sulfide, and the like. These methods can effectively introduce alkyl groups into alkenyl ethers to form alkyl alkenyl ethers. In the alkenylation reaction, common methods include acid-catalyzed reaction of olefin with alcohol, acid-catalyzed reaction of olefin with ether, metal-catalyzed reaction of olefin with alcohol, and the like. These methods can introduce olefins into ether molecules to form alkyl alkenyl ethers.
The existing preparation method is generally complex and easy to introduce impurities; the preparation method is simplest and also needs two steps of reactions, in the first step, alkyne, alcohol and high-valence iodine reagent are used as raw materials to prepare the full substituted alkenyl ether with high-valence iodine substituent; in the second step, the transition metal catalyzed carbon-carbon coupling reaction replaces the hypervalent iodine substituent with a carbon atom to finally obtain the fully substituted alkyl alkenyl ether, as shown in figure 1. However, this method requires two purification processes, and its raw materials such as a high-valence iodine reagent are not commercialized, and require separate preparation; the second part requires the use of noble metal catalysts and special ligands, which is costly and not very versatile.
Disclosure of Invention
Aiming at the problems existing in the prior art, the invention provides a fully substituted alkyl alkenyl ether, a preparation method and application thereof, and the fully substituted alkyl alkenyl ether with definite configuration is prepared by a one-step method.
The technical scheme adopted by the invention is as follows:
a fully substituted alkyl alkenyl ether with one of the following structures:
R 1 is one of methyl, ethyl, n-hexyl, cyclohexyl, phenyl containing substituent, benzyl and styryl;
R 2 is one of methyl, ethyl, n-hexyl, cyclohexyl and benzyl;
R 3 is one of hydrogen atom, methyl, ethyl, propyl, cyclopropyl, n-amyl, tert-amyl, n-hexyl, cyclohexyl, adamantyl, phenyl, benzyl and styryl;
R 4 is one of hydrogen atom, fluorine atom, methyl, ethyl, propyl, cyclopropyl, n-pentyl, tert-pentyl, n-hexyl, cyclohexyl, adamantyl, phenyl, benzyl, styryl, methoxy, tert-butoxy and benzyloxy;
R 5 is one of hydrogen atom, fluorine atom, methyl, ethyl, propyl, cyclopropyl, n-pentyl, tert-pentyl, n-hexyl, cyclohexyl, adamantyl, phenyl, benzyl, styryl, methoxy, tert-butoxy and benzyloxy;
R 6 is one of hydrogen atom, fluorine atom, methyl, ethyl, propyl, cyclopropyl, n-pentyl, tert-pentyl, n-hexyl, cyclohexyl, adamantyl, phenyl, benzyl, styryl, methoxy, tert-butoxy and benzyloxy;
R 7 is one of hydrogen atom, fluorine atom, methyl, ethyl, propyl, cyclopropyl, n-pentyl, tert-pentyl, n-hexyl, cyclohexyl, adamantyl, phenyl, benzyl, styryl, methoxy, tert-butoxy and benzyloxy;
R 8 is one of hydrogen atom, fluorine atom, methyl, ethyl, propyl, cyclopropyl, n-pentyl, tert-pentyl, n-hexyl, cyclohexyl, adamantyl, phenyl, benzyl, styryl, methoxy, tert-butoxy and benzyloxy;
R 9 is one of hydrogen atom, fluorine atom, methyl, ethyl, propyl, cyclopropyl, n-pentyl, tert-pentyl, n-hexyl, cyclohexyl, adamantyl, phenyl, benzyl, styryl, methoxy, tert-butoxy and benzyloxy;
R 10 is one of hydrogen atom, fluorine atom, methyl, ethyl, propyl, cyclopropyl, n-pentyl, tert-pentyl, n-hexyl, cyclohexyl, adamantyl, phenyl, benzyl, styryl, methoxy, tert-butoxy and benzyloxy.
A method for preparing fully substituted alkyl alkenyl ether, comprising the following steps:
dissolving a catalyst, an additive, 1-alkyne or polyfluorinated benzene and gem-difluoro cyclopropane in a solvent, heating to a set temperature value, fully reacting, and purifying to obtain the required full substituted alkyl alkenyl ether;
the additive is one of alkoxide, alcohol and mixture of alkoxide in any proportion.
Further, the catalyst is a copper metal compound.
Further, the alkoxide is one of lithium tert-butoxide, sodium tert-butoxide, potassium tert-butoxide and sodium bis (trimethylsilyl) amide.
Further, the molar ratio of the catalyst to the gem-difluorocyclopropane is 0.00001-1:1; the molar ratio of geminal difluorocyclopropane to additive is 1:1 to 10; the molar ratio of gem-difluorocyclopropane to 1-alkyne or polyfluoropene is 1:1 to 10.
Further, the reaction temperature is 55-65 ℃ and the reaction time is 0.5-72 hours.
Further, the copper metal compound is one of cuprous chloride, cuprous bromide, cuprous iodide, cuprous oxide, cuprous acetate, cuprous cyanide, thiophene-2-formate, copper tetra (acetonitrile) tetrafluoroborate, copper tetra (acetonitrile) trifluoromethanesulfonate, copper tetraethyl cyanide hexafluorophosphate, a combination of copper trifluoromethanesulfonate and benzene in a molar ratio of 2:1, chloro [1, 3-bis (2, 4, 6-trimethylphenyl) imidazole-2-subunit ] copper, chloro [1, 3-bis (2, 6-diisopropylphenyl) imidazole-2-subunit ] copper, copper difluoride, copper chloride, copper bromide, copper iodide, copper bis (2-ethylhexanoate), copper bis (trifluoromethanesulfonyl) imide.
Further, the 1-alkyne is octyne.
Further, the polyfluorophenyl is 2,3,5, 6-tetrafluoroanisole.
Use of a fully substituted alkyl alkenyl ether as an intermediate for incorporation into a biologically active molecule.
The beneficial effects of the invention are as follows:
(1) The fully substituted alkyl alkenyl ether with a definite configuration can be obtained by the one-step method, and the preparation method is simple;
(2) The raw materials such as the catalyst, the ligand, the additive, the solvent and the like used in the preparation method are all commercial or relatively easily available, and the reaction condition is mild and simple and is easy to operate;
(3) The invention can introduce fully substituted alkyl alkenyl ether structure with definite configuration into bioactive molecule.
Drawings
FIG. 1 is a reaction equation of a prior art scheme in the background art.
FIG. 2 shows the reaction equation of the present invention.
FIG. 3 is a nuclear magnetic resonance hydrogen spectrum of a fully substituted alkyl alkenyl ether obtained in example 1 of the present invention.
FIG. 4 shows the nuclear magnetic resonance spectrum of the fully substituted alkyl alkenyl ether obtained in example 1 of the present invention.
FIG. 5 shows the nuclear magnetic resonance hydrogen spectrum of the fully substituted alkyl alkenyl ether obtained in example 2 of the present invention.
FIG. 6 shows the nuclear magnetic resonance spectrum of the fully substituted alkyl alkenyl ether obtained in example 2 of the present invention.
FIG. 7 is a nuclear magnetic resonance hydrogen spectrum of a fully substituted alkyl alkenyl ether obtained in example 3 of the present invention.
FIG. 8 is a nuclear magnetic resonance spectrum of a fully substituted alkyl alkenyl ether obtained in example 3 of the present invention.
FIG. 9 shows nuclear magnetic resonance fluorine spectra of the fully substituted alkyl alkenyl ether obtained in example 3 of the present invention.
FIG. 10 shows the reaction equation of example 4 of the present invention.
Detailed Description
The invention will be further described with reference to the drawings and specific examples.
A fully substituted alkyl alkenyl ether with one of the following structures:
R 1 is one of methyl, ethyl, n-hexyl, cyclohexyl, phenyl containing substituent, benzyl and styryl;
R 2 is one of methyl, ethyl, n-hexyl, cyclohexyl and benzyl;
R 3 is one of hydrogen atom, methyl, ethyl, propyl, cyclopropyl, n-amyl, tert-amyl, n-hexyl, cyclohexyl, adamantyl, phenyl, benzyl and styryl;
R 4 is one of hydrogen atom, fluorine atom, methyl, ethyl, propyl, cyclopropyl, n-pentyl, tert-pentyl, n-hexyl, cyclohexyl, adamantyl, phenyl, benzyl, styryl, methoxy, tert-butoxy and benzyloxy;
R 5 is one of hydrogen atom, fluorine atom, methyl, ethyl, propyl, cyclopropyl, n-pentyl, tert-pentyl, n-hexyl, cyclohexyl, adamantyl, phenyl, benzyl, styryl, methoxy, tert-butoxy and benzyloxy;
R 6 is one of hydrogen atom, fluorine atom, methyl, ethyl, propyl, cyclopropyl, n-pentyl, tert-pentyl, n-hexyl, cyclohexyl, adamantyl, phenyl, benzyl, styryl, methoxy, tert-butoxy and benzyloxy;
R 7 is one of hydrogen atom, fluorine atom, methyl, ethyl, propyl, cyclopropyl, n-pentyl, tert-pentyl, n-hexyl, cyclohexyl, adamantyl, phenyl, benzyl, styryl, methoxy, tert-butoxy and benzyloxy;
R 8 is one of hydrogen atom, fluorine atom, methyl, ethyl, propyl, cyclopropyl, n-pentyl, tert-pentyl, n-hexyl, cyclohexyl, adamantyl, phenyl, benzyl, styryl, methoxy, tert-butoxy and benzyloxy;
R 9 is one of hydrogen atom, fluorine atom, methyl, ethyl, propyl, cyclopropyl, n-pentyl, tert-pentyl, n-hexyl, cyclohexyl, adamantyl, phenyl, benzyl, styryl, methoxy, tert-butoxy and benzyloxy;
R 10 is one of hydrogen atom, fluorine atom, methyl, ethyl, propyl, cyclopropyl, n-pentyl, tert-pentyl, n-hexyl, cyclohexyl, adamantyl, phenyl, benzyl, styryl, methoxy, tert-butoxy and benzyloxy.
A method for preparing fully substituted alkyl alkenyl ether, comprising the following steps:
dissolving a catalyst, an additive, 1-alkyne or polyfluorinated benzene and gem-difluoro cyclopropane in a solvent, heating to a set temperature value, fully reacting, and purifying to obtain the required full substituted alkyl alkenyl ether; the reaction is carried out under the condition of heating and stirring; after the reaction, the mixture was purified by silica gel column chromatography.
The additive is one of alkoxide, alcohol and mixture of alkoxide in any proportion. The alkoxide is one of lithium tert-butoxide, sodium tert-butoxide, potassium tert-butoxide and sodium bis (trimethylsilyl) amide. The solvent is one of 1, 2-dichloroethane, tetrahydrofuran, 1, 4-dioxane, ethylene glycol dimethyl ether, fluorobenzene, chlorobenzene, toluene and benzotrifluoride.
The catalyst is copper metal compound, which is one of cuprous chloride, cuprous bromide, cuprous iodide, cuprous oxide, cuprous acetate, cuprous cyanide, thiophene-2-formic acid, copper tetra (acetonitrile) tetrafluoroborate, copper tetra (acetonitrile) trifluoromethanesulfonic acid, copper tetraethyl cyanide hexafluorophosphate, a combination of copper trifluoromethanesulfonic acid and benzene with the molar ratio of 2:1, chlorine [1, 3-bis (2, 4, 6-trimethylphenyl) imidazole-2-subunit ] copper, chlorine [1, 3-bis (2, 6-diisopropylphenyl) imidazole-2-subunit ] copper, copper difluoride, cupric chloride, cupric bromide, copper iodide, copper bis (2-ethylhexanoate) and copper bis (trifluoromethylsulfonyl) imide.
The mol ratio of the catalyst to the gem-difluoro cyclopropane is 0.00001-1:1, and the optimal mol ratio is 0.02:1; the molar ratio of geminal difluorocyclopropane to additive is 1: 1-10, the optimal molar ratio is 1:4; the molar ratio of gem-difluorocyclopropane to 1-alkyne or polyfluoropene is 1: 1-10, the optimal molar ratio is 1:2.
The reaction temperature is 55-65 ℃ and the reaction time is 0.5-72 hours; the concentration of each raw material in the solvent is 0.1-5.0 mol/L.
Example 1
A method for preparing fully substituted alkyl alkenyl ether, comprising the following steps:
to the reaction flask was added in the nitrogen-protected glove box, a magnetic stirrer, 0.3mmol phenyl difluorocyclopropane, 0.2mmol/L octyne, 0.004mmol/L chloro [1, 3-bis (2, 4, 6-trimethylphenyl) imidazol-2-ylidene ] copper (I), 0.8mmol/L sodium t-butoxide, and 0.4mL tetrahydrofuran in this order. The nuts were capped and removed from the glove box and placed on a magnetic stirrer and allowed to react for 1 hour with stirring at 55 ℃.
The resulting reaction solution was transferred to a silica gel column, and eluted with an organic solvent (PE/dcm=5/1) to give a colorless liquid (R f =0.30), the yield tested was 89% (53.0 mg). The structural formula of the obtained fully substituted alkyl alkenyl ether is as follows:
its nuclear magnetic resonance hydrogen spectrum 1 H NMR is shown in FIG. 3, from which it can be seen (400 MHz, CDCl 3 )δ7.48–7.41(m,2H)，7.32–7.26(m,2H)，7.23–7.18(m,1H)，2.17(t,J＝6.9Hz,2H)，2.07(s,3H)，1.44(s,9H)，1.43–1.33(m,2H)，1.32–1.12(m,6H)，0.87(t,J＝7.0Hz,3H)。
Its nuclear magnetic resonance carbon spectrum 13 C NMR is shown in FIG. 4, from which it can be seen that (101 MHz, CDCl 3 )δ141.2，131.3，131.0，128.5，127.6，126.5，92.9，79.0，78.8，31.3，29.0，28.5，28.0，22.5，19.3，18.1，14.1。
HRMS(ESI,m/z)：calcd for C 21 H 30 ONa + [M+Na] + 321.2189，found 321.2186。
Example 2
A method for preparing fully substituted alkyl alkenyl ether, comprising the following steps:
to the reaction flask was added in the nitrogen-protected glove box, a magnetic stirrer, 0.3mmol phenyl difluorocyclopropane, 0.2mmol/L octyne, 0.004mmol/L chloro [1, 3-bis (2, 4, 6-trimethylphenyl) imidazol-2-ylidene ] copper (I), 0.8mmol/L sodium t-butoxide, and 0.4mL ethanol in this order. The nuts were capped and removed from the glove box, and the reaction was stirred on a magnetic stirrer at 65℃for 1 hour.
The resulting reaction solution was transferred to a silica gel column, and eluted with an organic solvent (PE/dcm=5/1) to give a colorless liquid (R f =0.30), 85% (44.9 mg) of the yield tested. The structural formula of the obtained fully substituted alkyl alkenyl ether is as follows:
its nuclear magnetic resonance hydrogen spectrum 1 H NMR is shown in FIG. 5, from which it can be seen (400 MHz, CDCl 3 )δ7.57–7.52(m,2H)，7.37–7.31(m,2H)，7.26(m,6H)，4.14(q,J＝7.0Hz,2H)，2.17(s,3H)，1.36(t,J＝7.0Hz,3H)。
Its nuclear magnetic resonance carbon spectrum 13 C NMR is shown in FIG. 6, from which it can be seen that (101 MHz, CDCl 3 )δ140.9，134.1，131.1，128.5，128.2，128.2，127.7，127.3，126.8，122.9，93.3，84.1，64.9，17.0，15.3。
HRMS(ESI,m/z)：calcd for C 19 H 19 O + [M+H] + 263.1430,found 263.1433。
Example 3
A method for preparing fully substituted alkyl alkenyl ether, comprising the following steps:
to the reaction flask was added in the nitrogen-protected glove box, a magnetic stirrer, 0.3mmol of phenyl difluorocyclopropane, 0.2mmol/L of 2,3,5, 6-tetrafluoroanisole, 0.004mmol/L of chloro [1, 3-bis (2, 4, 6-trimethylphenyl) imidazol-2-ylidene ] copper (I), 0.8mmol/L of sodium t-butoxide, and 0.4mL of tetrahydrofuran in this order. The nuts were capped and removed from the glove box, and the reaction was stirred on a magnetic stirrer at 65℃for 1 hour.
The resulting reaction solution was transferred to a silica gel column, and eluted with an organic solvent (PE/dcm=5/1) to give a colorless liquid (R f =0.30), yield 83% (49.1 mg) tested. The structural formula of the obtained fully substituted alkyl alkenyl ether is as follows:
its nuclear magnetic resonance hydrogen spectrum 1 H NMR is shown in FIG. 7, from which it can be seen (400 MHz, CDCl 3 )δ7.16–7.10(m,3H)，7.00(dd,J＝7.8,1.8Hz,2H)，4.00(t,J＝1.5Hz,3H)，2.18(s,3H)，1.23(s,9H)。
Its nuclear magnetic resonance carbon spectrum 13 C NMR is shown in FIG. 8, from which it can be seen that (101 MHz, CDCl 3 )δ144.4(dm,J＝247.3Hz)，140.8,140.4(dm,J＝263.2Hz)，138.2–137.6(m)，133.9，132.8，127.9，127.9，126.8，113.0–112.4(m)，79.7，62.0(t,J＝3.8Hz)，28.8，19.3。
Its nuclear magnetic resonance fluorine spectrum 19 F NMR is shown in FIG. 9, from which it can be seen (376 MHz, CDCl 3 )δ-139.5–-139.7(m)，-158.5–-158.7(m)。
HRMS(ESI,m/z):calcd for C 20 H 20 F 4 NaO 2 + [M+Na] + 391.1292,found 391.1294。
Example 4
The fully substituted alkyl alkenyl ethers obtained according to the invention can be introduced as intermediates into biologically active molecules. As shown in fig. 10, the active molecule is an alcohol, and the structure of the alkenyl ether is directly introduced into the active molecule as a component reactant in the reaction of the fully substituted alkyl alkenyl ether.
In the invention, three reactants undergo three-component coupling reaction to directly generate the full substituted alkenyl ether. When alkoxide is used alone as an additive, alkoxide acts both as a reactant and as a base. When alcohol and alkoxide are simultaneously used as additives, alcohol is used as a reactant while alkoxide is used as a base. The preparation method is simple and efficient, and can prepare the fully substituted alkyl alkenyl ether with definite configuration with high selectivity.
Claims (10)
1. A fully substituted alkyl alkenyl ether, characterized by one of the following structures:
R 1 is one of methyl, ethyl, n-hexyl, cyclohexyl, phenyl containing substituent, benzyl and styryl;
R 2 is one of methyl, ethyl, n-hexyl, cyclohexyl and benzyl;
R 3 is one of hydrogen atom, methyl, ethyl, propyl, cyclopropyl, n-amyl, tert-amyl, n-hexyl, cyclohexyl, adamantyl, phenyl, benzyl and styryl;
R 4 is one of hydrogen atom, fluorine atom, methyl, ethyl, propyl, cyclopropyl, n-pentyl, tert-pentyl, n-hexyl, cyclohexyl, adamantyl, phenyl, benzyl, styryl, methoxy, tert-butoxy and benzyloxy;
R 5 is one of hydrogen atom, fluorine atom, methyl, ethyl, propyl, cyclopropyl, n-pentyl, tert-pentyl, n-hexyl, cyclohexyl, adamantyl, phenyl, benzyl, styryl, methoxy, tert-butoxy and benzyloxy;
R 6 is one of hydrogen atom, fluorine atom, methyl, ethyl, propyl, cyclopropyl, n-pentyl, tert-pentyl, n-hexyl, cyclohexyl, adamantyl, phenyl, benzyl, styryl, methoxy, tert-butoxy and benzyloxy;
R 7 is hydrogen atom, fluorine atom, methyl groupOne of the groups of group, ethyl, propyl, cyclopropyl, n-pentyl, tert-pentyl, n-hexyl, cyclohexyl, adamantyl, phenyl, benzyl, styryl, methoxy, tert-butoxy and benzyloxy;
R 8 is one of hydrogen atom, fluorine atom, methyl, ethyl, propyl, cyclopropyl, n-pentyl, tert-pentyl, n-hexyl, cyclohexyl, adamantyl, phenyl, benzyl, styryl, methoxy, tert-butoxy and benzyloxy;
R 9 is one of hydrogen atom, fluorine atom, methyl, ethyl, propyl, cyclopropyl, n-pentyl, tert-pentyl, n-hexyl, cyclohexyl, adamantyl, phenyl, benzyl, styryl, methoxy, tert-butoxy and benzyloxy;
R 10 is one of hydrogen atom, fluorine atom, methyl, ethyl, propyl, cyclopropyl, n-pentyl, tert-pentyl, n-hexyl, cyclohexyl, adamantyl, phenyl, benzyl, styryl, methoxy, tert-butoxy and benzyloxy.
2. The method for preparing the fully substituted alkyl alkenyl ether according to claim 1, comprising the following steps:
dissolving a catalyst, an additive, 1-alkyne or polyfluorinated benzene and gem-difluoro cyclopropane in a solvent, heating to a set temperature value, fully reacting, and purifying to obtain the required full substituted alkyl alkenyl ether;
the additive is one of alkoxide, alcohol and mixture of alkoxide in any proportion.
3. The method for producing a fully substituted alkyl alkenyl ether according to claim 2, wherein the catalyst is a copper metal compound.
4. The method for producing a fully substituted alkyl alkenyl ether according to claim 2, wherein the alkoxide is one of lithium tert-butoxide, sodium tert-butoxide, potassium tert-butoxide, and sodium bis (trimethylsilyl) amide.
5. The method for producing a fully substituted alkyl alkenyl ether according to claim 2, wherein the molar ratio of the catalyst to the gem-difluorocyclopropane is 0.00001 to 1:1; the molar ratio of geminal difluorocyclopropane to additive is 1:1 to 10; the molar ratio of gem-difluorocyclopropane to 1-alkyne or polyfluoropene is 1:1 to 10.
6. The method for producing a fully substituted alkyl alkenyl ether according to claim 2, wherein the reaction temperature is 55 ℃ to 65 ℃ and the reaction time is 0.5 to 72 hours.
7. The method for producing a fully substituted alkyl alkenyl ether according to claim 3, wherein the copper metal compound is one of cuprous chloride, cuprous bromide, cuprous iodide, cuprous oxide, cuprous acetate, cuprous cyanide, copper thiophene-2-carboxylate, copper tetra (acetonitrile) tetrafluoroborate, copper tetra (acetonitrile) trifluoromethanesulfonate, copper tetraethyl cyanide hexafluorophosphate, copper trifluoromethanesulfonate and benzene in a molar ratio of 2:1, chloro [1, 3-bis (2, 4, 6-trimethylphenyl) imidazol-2-ylidene ] copper, chloro [1, 3-bis (2, 6-diisopropylphenyl) imidazol-2-ylidene ] copper, copper difluoride, copper chloride, copper bromide, copper iodide, copper bis (2-ethylhexanoate) and copper bis (trifluoromethanesulfonyl) imide.
8. The method for preparing the full substituted alkyl alkenyl ether according to claim 2, wherein the 1-alkyne is octyne.
9. The method for producing a fully substituted alkyl alkenyl ether according to claim 2, wherein the polyfluorophenyl is 2,3,5, 6-tetrafluoroanisole.
10. Use of a fully substituted alkyl alkenyl ether obtained by the process according to any one of claims 2 to 9 as an intermediate for introducing it into a biologically active molecule.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202311244212.XA CN117466717A (en) | 2023-09-25 | 2023-09-25 | Fully substituted alkyl alkenyl ether, preparation method and application |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202311244212.XA CN117466717A (en) | 2023-09-25 | 2023-09-25 | Fully substituted alkyl alkenyl ether, preparation method and application |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN117466717A true CN117466717A (en) | 2024-01-30 |
Family
ID=89626570
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202311244212.XA Pending CN117466717A (en) | 2023-09-25 | 2023-09-25 | Fully substituted alkyl alkenyl ether, preparation method and application |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN117466717A (en) |
-
2023
- 2023-09-25 CN CN202311244212.XA patent/CN117466717A/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN107602320B (en) | Synthesis method for preparing tri-substituted olefin based on nickel catalysis | |
| CN111420709B (en) | Application of N-heterocyclic carbene-based mixed nickel (II) complex in synthesis of 2-linear alkyl benzothiazole compound | |
| CN111961087B (en) | Semi-sandwich ruthenium complex containing ortho-position carborane-based benzothiazole, and preparation and application thereof | |
| CN110041235B (en) | N-phenyl-N-p-toluenesulfonyl trifluoroacetamide and application thereof | |
| CN104910104A (en) | Method for synthesizing dihydrofuran derivatives under catalytic action of copper | |
| CN112375105B (en) | Application of N, N-coordinated divalent nickel complex containing meta-carborane ligand | |
| US11890602B2 (en) | Application of the ionic iron (III) complex as catalyst in preparation of benzylamine compound | |
| CN105013535B (en) | A kind of catalyst and its synthetic method for preparing asymmetric conjugation diine hydrocarbon compound | |
| CN117466717A (en) | Fully substituted alkyl alkenyl ether, preparation method and application | |
| CN112159422B (en) | Method for synthesizing phenylboronic acid ester derivative under catalysis of iridium catalyst | |
| CN103748065B (en) | The manufacture method of 2-alkenyl amine compound | |
| US6476250B1 (en) | Optically active fluorinated binaphthol derivative | |
| CN114085242A (en) | Synthesis method of iron-catalyzed alkyl internal alkyne compound | |
| CN109678673B (en) | Synthetic method of aryl-substituted homoallyl alcohol | |
| CN108864173B (en) | Process for converting substituted sodium arylsulfinates into aryltri-n-butyltin | |
| CN108383754B (en) | Preparation method and application of aryl oxime ester compound | |
| CN110003062B (en) | N-phenyl-N-p-toluenesulfonyl difluoroacetamide and application thereof | |
| CN109810056B (en) | S-alkyl-S-quinolyl-N-sulfonyl nitrogen sulfur ylide compound and preparation and application thereof | |
| CN114933516B (en) | Method for synthesizing deuterated compound in ionic liquid medium | |
| CN112390831B (en) | Triplecene ring metal palladium compound and application thereof | |
| CN112125843B (en) | Preparation method of 3-hydroxymethyl-4-phenyl-3, 4-dihydroquinolinone compound | |
| CN112876515B (en) | Triptycene carbene allyl palladium compound and application thereof | |
| CN113845550B (en) | Flexible large-steric-hindrance N-heterocyclic carbene palladium complex containing halogenated benzene ring, preparation method and application thereof | |
| RU2439046C1 (en) | Method of producing diaryl acetylenes | |
| CN108586512A (en) | A kind of preparation method of New Type of Ethylene base silicon base compound |
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 |