CN116284100A - Preparation method of fluoro alkenyl silane - Google Patents
Preparation method of fluoro alkenyl silane Download PDFInfo
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- CN116284100A CN116284100A CN202310259527.5A CN202310259527A CN116284100A CN 116284100 A CN116284100 A CN 116284100A CN 202310259527 A CN202310259527 A CN 202310259527A CN 116284100 A CN116284100 A CN 116284100A
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- -1 fluoro alkenyl silane Chemical compound 0.000 title claims abstract description 20
- 229910000077 silane Inorganic materials 0.000 title claims abstract description 18
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 32
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000002994 raw material Substances 0.000 claims abstract description 9
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229940112669 cuprous oxide Drugs 0.000 claims abstract description 8
- KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000002904 solvent Substances 0.000 claims abstract description 8
- 239000003054 catalyst Substances 0.000 claims abstract description 6
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000003999 initiator Substances 0.000 claims abstract description 4
- TYCFGHUTYSLISP-UHFFFAOYSA-N 2-fluoroprop-2-enoic acid Chemical compound OC(=O)C(F)=C TYCFGHUTYSLISP-UHFFFAOYSA-N 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 239000011737 fluorine Substances 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 150000003457 sulfones Chemical class 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 150000003377 silicon compounds Chemical class 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 abstract description 10
- 230000015572 biosynthetic process Effects 0.000 abstract description 7
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 abstract description 4
- 239000003153 chemical reaction reagent Substances 0.000 abstract description 3
- 238000001308 synthesis method Methods 0.000 abstract description 3
- 229910052751 metal Inorganic materials 0.000 abstract description 2
- 239000002184 metal Substances 0.000 abstract description 2
- 150000002739 metals Chemical class 0.000 abstract description 2
- 239000007809 chemical reaction catalyst Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 21
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 20
- 229910052786 argon Inorganic materials 0.000 description 10
- 239000012043 crude product Substances 0.000 description 10
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 9
- 238000005481 NMR spectroscopy Methods 0.000 description 9
- 238000001228 spectrum Methods 0.000 description 9
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 8
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 150000004756 silanes Chemical class 0.000 description 4
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- 150000003961 organosilicon compounds Chemical class 0.000 description 2
- 241000894007 species Species 0.000 description 2
- QONCEXMULRJPPY-VURMDHGXSA-N (z)-2-fluoro-3-phenylprop-2-enoic acid Chemical compound OC(=O)C(\F)=C\C1=CC=CC=C1 QONCEXMULRJPPY-VURMDHGXSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 102000035195 Peptidases Human genes 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000006115 defluorination reaction Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000007876 drug discovery Methods 0.000 description 1
- QGBMSFLTRRZTGI-UHFFFAOYSA-N ethyl(dimethyl)silane Chemical compound CC[SiH](C)C QGBMSFLTRRZTGI-UHFFFAOYSA-N 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- LZWQNOHZMQIFBX-UHFFFAOYSA-N lithium;2-methylpropan-2-olate Chemical compound [Li+].CC(C)(C)[O-] LZWQNOHZMQIFBX-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000007040 multi-step synthesis reaction Methods 0.000 description 1
- 238000006772 olefination reaction Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 235000019833 protease Nutrition 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0825—Preparations of compounds not comprising Si-Si or Si-cyano linkages
- C07F7/0827—Syntheses with formation of a Si-C bond
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Abstract
The invention belongs to the field of organic synthesis, and relates to a preparation method of monofluoroolefin silane. Cuprous oxide is used as a catalyst, di-tert-butyl peroxide is used as an initiator, tert-butyl alcohol is used as a solvent, and the reaction is carried out for 20 hours at 100 ℃ according to the following reaction formula, so that E-configuration monofluoroolefin silane is obtained. The reaction catalyst has the advantages of low price of raw materials, stereoselectivity of reaction, simple reaction operation, short route, no need of preparing special reagents in advance by using expensive metals, and high synthesis application value. Provides a high-efficiency and convenient synthesis method for E-configuration monofluoro alkenyl silane compounds.
Description
Technical Field
The invention relates to preparation of a compound, and belongs to the field of organic synthesis. In particular to a synthesis method of fluorine alkenyl silane.
Background
Organosilicon compounds are an important class of organic compounds that can be used as an important class of synthetic intermediates in organic synthesis. And has wide application in pesticide chemistry, medicinal chemistry and material science due to the unique physicochemical properties. Among these organosilicon compounds, the alkenyl silicon compounds have great application value and can participate in various types of conversion. On the other hand, the introduction of fluorine atoms in organic chemistry can improve the physical and chemical properties of parent organic molecules, and has great application value in the medicine research and material science. Among them, alkenyl fluorine compounds are an important class of organic structural fragments. Is an important fluorine-containing organic synthon, and can be used as an isostere of an amide bond in drug discovery research, thereby increasing the stability of conformation and peptidase. Therefore, the synthesized preparation of the fluorine alkenyl silicon compound has outstanding application value. The fluoroalkenyl silicon compounds were synthesized by an olefination reaction in the earliest year 2000. However, this method requires severe low temperature conditions, using a strong butyl lithium base, and requires the preparation of specific difficult-to-synthesize fluorine and silicon reagents (formula 1, bull. Chem. Soc. Jpn.2000, 73, 1685-1690). And the method can obtain a mixture of two configurations of E/Z, has low selectivity and difficult classification of products.
In 2018, wang group achieved the synthesis of monofluoroolefin silanes by defluorination and siliconization of geminal difluoroolefins. However, this strategy requires the use of an expensive iridium catalyst to prepare the silaborane first, and the reaction requires multiple steps. Meanwhile, the reaction requires the use of 3 equivalents of strong alkali lithium t-butoxide, which limits its applicability in synthetic chemistry (formula 2, adv. Synth. Catalyst. 2018, 360, 1032-1037).
Therefore, based on the defects existing in the current synthesis of monofluoroolefin silane, development and use of cheap and easily available raw materials, metals and high-selectivity synthesis of monofluoroolefin silane compounds have very important synthesis application values.
Disclosure of Invention
Aiming at the defects that the existing synthesis of monofluoro alkenyl silane compound has harsh reaction conditions, needs to use excessive alkali, has poor reaction stereoselectivity, needs multi-step synthesis, needs to use expensive iridium to prepare reaction raw materials, and the like. The invention realizes the method for synthesizing the monofluoroalkenyl silane compound with high efficiency and high selectivity by taking the fluoroacrylic acid and the cheap and commercial silane compound as raw materials under the catalysis of copper.
In order to solve the technical problems, the invention adopts the following technical scheme: a preparation method of fluoroalkenyl silane is characterized by comprising the following steps: the method comprises the steps of reacting fluoroacrylic acid and silane compounds serving as raw materials, using oxone as a catalyst, using di-tert-butyl peroxide as an initiator (DTBP) and using tert-butyl alcohol as a solvent according to the following reaction formula to obtain E-configuration monofluoroalkenyl silane compounds with a general formula (I):
wherein R is 1 Hydrogen, fluorine, chlorine, ester groups, cyano groups, trifluoromethyl groups, trifluoromethoxy groups, sulfones, and the like; r is ethyl, methyl, isopropyl and tert-butyl.
Preferably, the amount of the oxone species is 10% of the amount of the fluoroacrylic acid species.
Preferably, the amount of the substance of the silane compound is 5 times the amount of the substance of fluoroacrylic acid.
Preferably, the amount of the substance of di-t-butyl peroxide as initiator is 3 times the amount of the substance of fluoroacrylic acid.
Preferably, the reaction temperature is 100 degrees celsius and the reaction time is 20 hours.
The method realizes that the monofluoroalkenyl silane compound is prepared by taking the fluoroacrylic acid and the silane compound as raw materials and taking the cheap ketone catalyst as raw materials with high efficiency and high selectivity. The method has the advantages of cheap and easily obtained reaction raw materials, simple reaction operation, simple route, no need of preparing special reagents in advance and high synthesis application value. Provides a high-efficiency and practical synthesis method for the monofluoro alkenyl silane compound.
Detailed Description
The technical scheme of the invention is further described by the following specific embodiments:
example 1, the reaction scheme for this example is shown below:
(1) Cuprous oxide (10 mol%) and 2-fluoro-3-phenylacrylic acid (0.2 mmol,1 equiv) were added under air to a sealed reaction tube with a branch tube containing magnetons, and argon was purged three times. Under argon, 1.5mL of t-butanol and triethylsilane (5 equiv) were added to the reaction tube and reacted at 100℃for 20 hours.
(2) Spin-drying the solvent in the organic phase obtained in step (2) to obtain a crude product, and purifying the crude product with a silica gel column, wherein the separation yield is 65%, E/Z is more than 30:1, and the purity of the product is 100%.
Example 2
The reaction formula of this example is shown below:
(1) Cuprous oxide (10 mol%) and 2-fluoro-3- (p-fluoro, m-bromophenyl) acrylic acid (0.2 mmol,1 equiv) were added under air to a sealed reaction tube with a branched tube containing magnetons, and argon was purged three times from the reaction tube. Under argon, 1.5mL of t-butanol and triethylsilane (5 equiv) were added to the reaction tube and reacted at 100℃for 20 hours.
(2) Spin-drying the solvent in the organic phase obtained in step (2) to obtain a crude product, and purifying the crude product with a silica gel column, wherein the separation yield is 52%, E/Z is more than 30:1, and the purity of the product is 100%.
Example 3
The reaction formula of this example is shown below:
(1) Cuprous oxide (10 mol%) and tert-butyl 2-fluoro-3-benzoate acrylic acid (0.2 mmol,1 equiv) were added under air to a sealed reaction tube with a branch tube containing magnetons, and argon was purged three times. Under argon, 1.5mL of t-butanol and triethylsilane (5 equiv) were added to the reaction tube and reacted at 100℃for 20 hours.
(2) Spin-drying the solvent in the organic phase obtained in step (2) to obtain a crude product, and purifying the crude product with a silica gel column, wherein the separation yield is 63%, E/Z is more than 30:1, and the purity of the product is 100%.
Example 4
The reaction formula of this example is shown below:
(1) Under air, cuprous oxide (10 mol%), vitamin E-derived fluoroacrylic acid (0.2 mmol,1 equiv) was added to a sealed reaction tube with a branched tube containing magnetons, and the reaction tube was purged with argon three times. Under argon, 1.5mL of t-butanol and triethylsilane (5 equiv) were added to the reaction tube and reacted at 100℃for 20 hours.
(2) Spin-drying the solvent in the organic phase obtained in step (2) to obtain a crude product, and purifying the crude product by a silica gel column, wherein the separation yield is 56%, E/Z is more than 30:1, and the purity of the product is 100%.
Example 5
The reaction formula of this example is shown below:
(1) Cuprous oxide (10 mol%) and tert-butyl 2-fluoro-3-benzoate acrylic acid (0.2 mmol,1 equiv) were added under air to a sealed reaction tube with a branch tube containing magnetons, and argon was purged three times. Under argon, 1.5mL of t-butanol and dimethylethyl silane (5 equiv) were added to the reaction tube and reacted at 100℃for 20 hours.
(2) Spin-drying the solvent in the organic phase obtained in step (2) to obtain a crude product, and purifying the crude product with a silica gel column, wherein the separation yield is 65%, E/Z is more than 30:1, and the purity of the product is 100%.
The foregoing detailed description of the invention will be presented only by way of example and should not be taken as limiting the scope of the invention, i.e., the invention is not limited to the details of construction and the modification set forth in the following claims.
Drawings
FIG. 1 is a nuclear magnetic resonance hydrogen spectrum of a product 3a prepared according to the present invention;
FIG. 2 is a nuclear magnetic resonance fluorine spectrum of the product 3a prepared according to the present invention;
FIG. 3 is a nuclear magnetic resonance spectrum of the product 3a prepared according to the present invention;
FIG. 4 is a nuclear magnetic resonance hydrogen spectrum of the product 3e prepared according to the present invention;
FIG. 5 is a nuclear magnetic resonance fluorine spectrum of the product 3e prepared according to the present invention;
FIG. 6 is a nuclear magnetic resonance spectrum of product 3e prepared according to the present invention;
FIG. 7 is a hydrogen nuclear magnetic resonance spectrum of 3g of the product prepared according to the invention;
FIG. 8 is a nuclear magnetic resonance fluorine spectrum of 3g of the product prepared according to the invention;
FIG. 9 is a chart showing the nuclear magnetic resonance spectrum of 3g of the product prepared according to the present invention;
FIG. 10 is a nuclear magnetic resonance hydrogen spectrum of product 3o prepared according to the present invention;
FIG. 11 is a nuclear magnetic resonance fluorine spectrum of product 3o prepared according to the present invention;
FIG. 12 is a nuclear magnetic resonance spectrum of product 3o prepared according to the present invention;
FIG. 13 is a nuclear magnetic resonance hydrogen spectrum of the product 5a prepared according to the present invention;
FIG. 14 is a nuclear magnetic resonance fluorine spectrum of the product 5a prepared according to the present invention;
FIG. 15 is a nuclear magnetic resonance spectrum of the product 5a prepared according to the present invention.
Claims (2)
1. A preparation method of fluoroalkenyl silane is characterized by comprising the following steps: the method comprises the steps of taking fluoroacrylic acid and silane compound as raw materials, taking cuprous oxide as a catalyst, taking di-tert-butyl peroxide as an initiator and tert-butyl alcohol as a solvent, and reacting for 20 hours at 100 ℃ according to the following reaction formula to obtain E-configuration monofluoroalkenyl silicon compounds:
wherein R is 1 Hydrogen, fluorine, chlorine, ester groups, cyano groups, trifluoromethyl groups, trifluoromethoxy groups, sulfones, and the like; r is ethyl, methyl, isopropyl and tert-butyl.
2. A preparation method of fluoroalkenyl silane is characterized by comprising the following steps: the amount of cuprous oxide material was 10% of the amount of fluoroacrylic acid material; the amount of the substance of di-t-butyl peroxide is 3 times the amount of the substance of fluoroacrylic acid; the amount of the substance of the silane compound is 5 times the amount of the substance of the fluoroacrylic acid.
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2023
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