CN113200850A - Preparation method of alpha-acyloxyketone compound - Google Patents
Preparation method of alpha-acyloxyketone compound Download PDFInfo
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- CN113200850A CN113200850A CN202110499986.1A CN202110499986A CN113200850A CN 113200850 A CN113200850 A CN 113200850A CN 202110499986 A CN202110499986 A CN 202110499986A CN 113200850 A CN113200850 A CN 113200850A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/035—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with saturated hydrocarbons
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- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B41/00—Formation or introduction of functional groups containing oxygen
- C07B41/12—Formation or introduction of functional groups containing oxygen of carboxylic acid ester groups
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Abstract
The invention discloses a preparation method of an alpha-acyloxyketone compound, which comprises the following steps: adding a 1, 3-dicarbonyl compound, carboxylate and a catalyst alkyl halide into an organic solvent, and stirring and reacting at the temperature of 20-30 ℃ for 0.5-1 h to obtain a reaction product which is a mixture; purifying the mixture to obtain alpha-acyloxy ketone; wherein the molar ratio of the 1, 3-dicarbonyl compound to the carboxylate to the alkyl halide is 1:1: 1. The method selects low-cost carboxylate as an acyloxylation reagent, has mild and green reaction conditions, uses a 1, 3-dicarbonyl compound as a raw material, and successfully realizes a novel method for efficiently and simply constructing a C-O bond through activation of a C-H bond at the alpha position of carbonyl and subsequent series reaction to obtain a series of alpha-acyloxyketone compounds.
Description
Technical Field
The invention belongs to the technical field of organic synthesis, and particularly relates to a preparation method of an alpha-acyloxyketone compound.
Background
Alpha-acyloxy ketone is a very important structural skeleton and widely exists in drug molecules and bioactive natural products, and in addition, the alpha-acyloxy ketone is an important drug molecule synthesis precursor and has wide application in organic synthesis.
The following methods are known for the synthesis of α -acyloxyketones: 1) the high-valence iodine reagent oxidizes compounds such as ketone, propargyl alcohol and terminal alkyne, 2) and nucleophilic substitution reaction of alpha-halogenated ketone and carboxylic acid; 3) intramolecular acyloxy group migration reaction of enamide, and the like; the three methods have the problems of harsh reaction conditions, complex operation, high price of an acyloxylation reagent and the like; therefore, the development of novel efficient methods for synthesizing alpha-acyloxyketone compounds is of great significance.
Disclosure of Invention
In order to solve the above problems in the prior art, the present invention provides a method for preparing an α -acyloxyketone compound.
The technical problem to be solved by the invention is realized by the following technical scheme:
a method for preparing an α -acyloxyketone compound, comprising: adding a 1, 3-dicarbonyl compound with a structure shown as (II), carboxylate with a structural formula shown as (III) and catalyst alkyl halide into an organic solvent, and stirring and reacting at the temperature of 20-30 ℃ for 0.5-1 h to obtain a reaction product which is a mixture; purifying the mixture to obtain alpha-acyloxy ketone with a structural formula shown in (I); wherein the molar ratio of the 1, 3-dicarbonyl compound to the carboxylate to the alkyl halide is 1:1: 1;
the reaction formula is as follows:
in the reaction formula, R1 and R2 are any of an alkyl group, an alkoxy group, and an aromatic group.
In the reaction formula, R3 is any one of an alkyl group and an aryl group.
Further, in the reaction formula, M is any one of sodium ion and potassium ion.
Further, the alkyl halide reagent is any one of N-bromosuccinimide, carbon tetrabromide, trichlorobromomethane, 1, 3-dibromo-5, 5-dimethylhydantoin, N-iodosuccinimide and N-chlorosuccinimide.
Further, the organic solvent is any one of dimethyl sulfoxide, N-dimethylformamide, N-dimethylacetamide and acetonitrile.
Further, the purification treatment comprises quenching, extracting, washing an organic phase, drying and column chromatography separation of the mixture in sequence.
The invention has the beneficial effects that:
1. selecting low-cost carboxylate as an acyloxylation reagent, and obtaining the alpha-acyloxyketone compound with high yield by a one-pot method under mild and green reaction conditions;
2. 1, 3-dicarbonyl compounds are used as raw materials, a novel method for efficiently and simply constructing C-O bonds is successfully realized through activation of C-H bonds at alpha positions of carbonyl groups and subsequent series reaction, and a series of alpha-acyloxy ketone compounds are obtained;
3. the method has simple and easy process conditions, safety and reliability, and has good industrial application prospect.
Detailed Description
The present invention will be described in further detail with reference to specific examples, but the embodiments of the present invention are not limited thereto.
Example 1
The embodiment of the invention provides a preparation method of an alpha-acyloxyketone compound, and specifically the preparation method comprises the steps of taking a dry reaction tube, sequentially adding 0.4mmol of ethyl benzoylacetate, 0.4mmol of sodium benzoate, 2mL of dimethyl sulfoxide and 0.4mmol of carbon tetrabromide, and stirring at the temperature of 20-30 ℃ for reaction for 0.5h to obtain a mixture; then, 5mL of water was added to the mixture to quench and the mixture was extracted three times with 10mL of ethyl acetate, thereby separating the organic phase and the aqueous phase, and the extracts were combined, washed with saturated brine and dried over anhydrous sodium sulfate; and then removing the organic solvent by using a rotary evaporator to obtain a crude product of the alpha-acyloxyketone compound, performing column chromatography separation on the crude product by using 200-300-mesh silica gel, wherein the eluent is prepared from petroleum ether and ethyl acetate according to the volume ratio of 10:1, and the crude product is subjected to column chromatography separation to obtain a pure alpha-acyloxyketone compound with the yield of 90%. The reaction formula is shown as follows:
the reaction product obtained by the reaction formula is analyzed by a nuclear magnetic resonance analyzer:
by nuclear magnetic resonance hydrogen spectroscopy (1H NMR and nuclear magnetic resonance carbon Spectroscopy: (13C NMR) identified the product, and the characterization data were as follows:
1H NMR(400MHz,CDCl3)δ8.109-8.064(m,4H),7.638-7.565(m,2H),7.518-7.419(m,4H),6.534(s,1H),4.286(q,J＝7.2Hz,2H),1.235(t,J＝7.2Hz,3H)；
13C NMR(100MHz,CDCl3)δ189.68,165.16.165.03,134.22,134.14,133.74,130.07,129.20,128.73,128.46,74.90,62.41,13.86.
the above characterization data demonstrate that the product is a pure α -acyloxyketone compound.
Example 2
The embodiment of the invention provides a preparation method of an alpha-acyloxyketone compound, which comprises the following steps of taking a dry reaction tube, sequentially adding 0.4mmol of dibenzoylmethane, 0.4mmol of sodium benzoate, 2mL of dimethyl sulfoxide and 0.4mmol of N-bromosuccinimide, stirring and reacting at the temperature of 20-30 ℃ for 0.5h to obtain a mixture, adding 5mL of water into the mixture for quenching, extracting with 10mL of ethyl acetate for three times, separating an organic phase from a water phase, combining extract liquor, washing the organic phase with saturated saline solution, and drying with anhydrous sodium sulfate; and then removing the organic solvent by using a rotary evaporator to obtain a crude product of the alpha-acyloxyketone compound, performing column chromatography separation on the crude product by using 200-300-mesh silica gel, wherein the eluent is prepared from petroleum ether and ethyl acetate according to the volume ratio of 10:1, and the crude product is subjected to column chromatography separation to obtain a pure alpha-acyloxyketone compound with the yield of 88%. The reaction formula is shown as follows:
the reaction product obtained by the reaction formula is analyzed by a nuclear magnetic resonance analyzer:
by nuclear magnetic resonance hydrogen spectroscopy (1H NMR and nuclear magnetic resonance carbon Spectroscopy: (13C NMR) identified the product, and the characterization data were as follows:
1H NMR(400MHz,CDCl3)δ8.142-8.120(m,4H),8.088-8.085(m,2H),7.623-7.574(m,3H),7.506-7.423(m,6H)；
13C NMR(100MHz,CDCl3)δ191.02,164.88,134.25,133.78,130.08,129.54,128.77,128.54,128.50,80.70.
the above characterization data demonstrate that the product is a pure α -acyloxyketone compound.
Example 3
The embodiment of the invention provides a preparation method of an alpha-acyloxyketone compound, which comprises the following steps of taking a dry reaction tube, sequentially adding 0.4mmol of N-acetylacetone morpholine, 0.4mmol of sodium benzoate, 2mL of N, N-dimethylformamide and 0.4mmol of carbon tetrabromide, stirring at the temperature of 20-30 ℃ for reaction for 0.5h to obtain a mixture, adding 5mL of water into the mixture for quenching, extracting with 10mL of ethyl acetate for three times, separating an organic phase from a water phase, combining extract liquor, washing the organic phase with saturated salt water, and drying with anhydrous sodium sulfate; and then removing the organic solvent by using a rotary evaporator to obtain a crude product of the alpha-acyloxyketone compound, performing column chromatography separation on the crude product by using 200-300-mesh silica gel, wherein the eluent is prepared from petroleum ether and ethyl acetate according to the volume ratio of 10:1, and the crude product is subjected to column chromatography separation to obtain a pure alpha-acyloxyketone compound with the yield of 77%. The reaction formula is shown as follows:
the reaction product obtained by the reaction formula is analyzed by a nuclear magnetic resonance analyzer:
by nuclear magnetic resonance hydrogen spectroscopy (1H NMR and nuclear magnetic resonance carbon Spectroscopy: (13C NMR) identified the product, and the characterization data were as follows:
1H NMR(400MHz,CDCl3)δ8.142-8.120(m,4H),8.122-8.101(m,2H),7.646-7.608(m,1H),7.508-7.470(m,2H),5.963(s,1H),3.769-3.594(m,8H),2.414(s,3H)；
13C NMR(100MHz,CDCl3)δ200.56,164.90,162.66,133.80,129.83,128.54,128.34,77.14,66.50,66.42,46.41,42.86,26.84.
the above characterization data demonstrate that the product is a pure α -acyloxyketone compound.
Example 4
The embodiment of the invention provides a preparation method of an alpha-acyloxyketone compound, which comprises the following steps of taking a dry reaction tube, sequentially adding 0.4mmol of ethyl 3-oxo-3- (2-thienyl) propionate, 0.4mmol of sodium benzoate, 2mL of N, N-dimethylformamide and 0.4mmol of N-bromosuccinimide, stirring and reacting at the temperature of 20-30 ℃ for 0.5h to obtain a mixture, adding 5mL of water into the mixture for quenching, extracting with 10mL of ethyl acetate for three times, separating an organic phase from a water phase, combining extract liquor, washing the organic phase with saturated saline water, and drying with anhydrous sodium sulfate; and then removing the organic solvent by using a rotary evaporator to obtain a crude product of the alpha-acyloxyketone compound, performing column chromatography separation on the crude product by using 200-300-mesh silica gel, wherein the eluent is prepared from petroleum ether and ethyl acetate according to the volume ratio of 10:1, and the crude product is subjected to column chromatography separation to obtain a pure alpha-acyloxyketone compound with the yield of 93%. The reaction formula is shown as follows:
the reaction product obtained by the reaction formula is analyzed by a nuclear magnetic resonance analyzer:
by nuclear magnetic resonance hydrogen spectroscopy (1H NMR and nuclear magnetic resonance carbon Spectroscopy: (13C NMR) identified the product, and the characterization data were as follows:
1H NMR(400MHz,CDCl3)δ8.128(d,J＝7.6Hz,2H),8.021(d,J＝3.8Hz,1H),7.768(d,J＝4.8Hz,1H),7.603(t,J＝7.6Hz,1H),7.460(t,J＝7.6Hz,2H),7.185(t,J＝3.6Hz,1H),6.337(s,1H),4.296(q,J＝7.2Hz,2H),1.263(t,J＝7.2Hz,3H)；
13C NMR(100MHz,CDCl3)δ182.10,164.95,164.84,140.51,135.80,134.62,133.79,130.07,128.49,128.48,128.35,75.74,62.51,13.87.
the above characterization data demonstrate that the product is a pure α -acyloxyketone compound.
Example 5
The embodiment of the invention provides a preparation method of an alpha-acyloxyketone compound, which comprises the following steps of taking a dry reaction tube, sequentially adding 0.4mmol of ethyl acetoacetate, 0.4mmol of sodium benzoate, 2mL of dimethyl sulfoxide and 0.4mmol of N-iodosuccinimide, stirring at the temperature of 20-30 ℃ for reacting for 1h to obtain a mixture, adding 5mL of water into the mixture for quenching, extracting with 10mL of ethyl acetate for three times, separating an organic phase from a water phase, combining extract liquor, washing the organic phase with saturated saline solution, and drying with anhydrous sodium sulfate; and then removing the organic solvent by using a rotary evaporator to obtain a crude product of the alpha-acyloxyketone compound, performing column chromatography separation on the crude product by using 200-300-mesh silica gel, wherein the eluent is prepared from petroleum ether and ethyl acetate according to the volume ratio of 10:1, and the crude product is subjected to column chromatography separation to obtain a pure alpha-acyloxyketone compound with the yield of 64%. The reaction formula is shown as follows:
the reaction product obtained by the reaction formula is analyzed by a nuclear magnetic resonance analyzer:
by nuclear magnetic resonance hydrogen spectroscopy (1H NMR and nuclear magnetic resonance carbon Spectroscopy: (13C NMR) identified the product, and the characterization data were as follows:
1H NMR(400MHz,CDCl3)δ8.143-8.122(m,2H),7.640-7.603(m,1H),7.503-7.464(m,2H),5.723(s,1H),4.317(q,J＝7.2Hz,2H),2.433(s,3H),1.327(t,J＝7.2Hz,3H)；
13C NMR(100MHz,CDCl3)δ197.63,165.03,164.49,133.81,130.02,129.96,128.53,128.42,78.12,62.47,27.23,13.95.
the above characterization data demonstrate that the product is a pure α -acyloxyketone compound.
Example 6
The embodiment of the invention provides a preparation method of an alpha-acyloxyketone compound, which comprises the following steps of taking a dry reaction tube, sequentially adding 0.4mmol of ethyl benzoylacetate, 0.4mmol of sodium acetate, 2mL of dimethyl sulfoxide and 0.4mmol of carbon tetrabromide, stirring and reacting at the temperature of 20-30 ℃ for 1 hour to obtain a mixture, adding 5mL of water into the mixture for quenching, extracting with 10mL of ethyl acetate for three times, separating an organic phase from a water phase, combining extract liquor, washing the organic phase with saturated saline solution, and drying with anhydrous sodium sulfate; and then removing the organic solvent by using a rotary evaporator to obtain a crude product of the alpha-acyloxyketone compound, performing column chromatography separation on the crude product by using 200-300-mesh silica gel, wherein the eluent is prepared from petroleum ether and ethyl acetate according to the volume ratio of 10:1, and the crude product is subjected to column chromatography separation to obtain a pure alpha-acyloxyketone compound with the yield of 89%. The reaction formula is shown as follows:
the reaction product obtained by the reaction formula is analyzed by a nuclear magnetic resonance analyzer:
by nuclear magnetic resonance hydrogen spectroscopy (1H NMR and nuclear magnetic resonance carbon Spectroscopy: (13C NMR) identified the product, and the characterization data were as follows:
1H NMR(400MHz,CDCl3)δ8.013-7.993(m,2H),7.649-7.609(m,1H),7.516-7.478(m,2H),6.330(s,1H),4.249(q,J＝7.2Hz,2H),2.229(s,3H),1.215(t,J＝7.2Hz,3H)；
13C NMR(100MHz,CDCl3)δ189.61,169.46,165.09,134.16,134.14,129.13,128.72,74.42,62.42,20.43,13.82.
the above characterization data demonstrate that the product is a pure α -acyloxyketone compound.
Example 7
The embodiment of the invention provides a preparation method of an alpha-acyloxyketone compound, which comprises the following steps of taking a dry reaction tube, sequentially adding 0.4mmol of ethyl benzoylacetate, 0.4mmol of sodium propionate, 2mL of dimethyl sulfoxide and 0.4mmol of N-bromosuccinimide, stirring and reacting at the temperature of 20-30 ℃ for 0.5h to obtain a mixture, adding 5mL of water into the mixture for quenching, extracting with 10mL of ethyl acetate for three times, separating an organic phase from a water phase, combining extract liquor, washing the organic phase with saturated saline solution, and drying with anhydrous sodium sulfate; and then removing the organic solvent by using a rotary evaporator to obtain a crude product of the alpha-acyloxyketone compound, performing column chromatography separation on the crude product by using 200-300-mesh silica gel, preparing eluent from petroleum ether and ethyl acetate according to the volume ratio of 10:1, performing column chromatography separation on the crude product to obtain a pure alpha-acyloxyketone compound, and collecting the pure alpha-acyloxyketone compound by 85%. The reaction formula is shown as follows:
the reaction product obtained by the reaction formula is analyzed by a nuclear magnetic resonance analyzer:
by nuclear magnetic resonance hydrogen spectroscopy (1H NMR and nuclear magnetic resonance carbon Spectroscopy: (13C NMR) identified the product, and the characterization data were as follows:
1H NMR(400MHz,CDCl3)δ8.019-8.000(m,2H),7.657-7.614(m,1H),7.525-7.486(m,2H),6.336(s,1H),4.255(q,J＝7.2Hz,2H),2.538(q,J＝7.6Hz,2H),1.222(t,J＝7.2Hz,3H),1.189(t,J＝7.6Hz,3H)；
13C NMR(100MHz,CDCl3)δ189.83,173.08.165.24,134.21,134.11,129.19,128.74,74.29,62.46,27.11,13.88,8.85.
the above characterization data demonstrate that the product is a pure α -acyloxyketone compound.
Specifically, the reaction principle of the present invention is as follows:
adding a 1, 3-dicarbonyl compound with a structure shown as (II), a halogenating reagent (namely alkyl halide) and carboxylate with a structural formula shown as (III) into an organic solvent, and reacting at room temperature for 0.5-1 hour to obtain an alpha-acyloxy ketone compound with a structural formula shown as (I), wherein the specific reaction formula is as follows:
the 1, 3-dicarbonyl compound generates halogenation reaction of alpha-C-H bond under the action of halogenating reagent to generate alpha-haloketone, and the obtained alpha-haloketone compound and acyloxy anion generate SN2 nucleophilic substitution reaction to obtain the alpha-acyloxy ketone compound.
The foregoing is a more detailed description of the invention in connection with specific preferred embodiments and it is not intended that the invention be limited to these specific details. For those skilled in the art to which the invention pertains, several simple deductions or substitutions can be made without departing from the spirit of the invention, and all shall be considered as belonging to the protection scope of the invention.
Claims (7)
1. A method for producing an α -acyloxyketone compound, comprising: adding a 1, 3-dicarbonyl compound with a structure shown as (II), carboxylate with a structural formula shown as (III) and catalyst alkyl halide into an organic solvent, and stirring and reacting at the temperature of 20-30 ℃ for 0.5-1 h to obtain a reaction product which is a mixture; purifying the mixture to obtain alpha-acyloxy ketone with a structural formula shown in (I); wherein the molar ratio of the 1, 3-dicarbonyl compound to the carboxylate to the alkyl halide is 1:1: 1;
the reaction formula is as follows:
2. the method for producing an α -acyloxyketone compound according to claim 1, wherein in the reaction formula, R1 and R2 are each an alkyl group, an alkoxy group, or an aromatic group.
3. The method for producing an α -acyloxyketone compound according to claim 1, wherein R3 is any one of an alkyl group and an aromatic group in the reaction formula.
4. The method for producing an α -acyloxyketone compound according to claim 1, wherein M in the reaction formula is any one of sodium ion and potassium ion.
5. The method of preparing an α -acyloxyketone compound according to claim 1, wherein the alkyl halide reagent is any one of N-bromosuccinimide, carbon tetrabromide, trichlorobromomethane, 1, 3-dibromo-5, 5-dimethylhydantoin, N-iodosuccinimide, and N-chlorosuccinimide.
6. The method for producing an α -acyloxyketone compound according to claim 1, wherein the organic solvent is any one of dimethylsulfoxide, N-dimethylformamide, N-dimethylacetamide, and acetonitrile.
7. The method of claim 1, wherein the purification treatment comprises quenching, extracting, washing the organic phase, drying, and column chromatography separation of the mixture.
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