CN105669441A - Preparation method of alpha-acyloxyketone compound - Google Patents
Preparation method of alpha-acyloxyketone compound Download PDFInfo
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- CN105669441A CN105669441A CN201610018687.0A CN201610018687A CN105669441A CN 105669441 A CN105669441 A CN 105669441A CN 201610018687 A CN201610018687 A CN 201610018687A CN 105669441 A CN105669441 A CN 105669441A
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Abstract
The invention discloses a preparation method of an alpha-acyloxyketone compound. The preparation method comprises 1, mixing an aromatic ketone shown in the formula (II), a copper salt and an organic solvent and preheating the mixture to obtain a mixed system, 2, mixing a carboxylic acid shown in the formula (III) and an alkali compound, adding the mixture into the mixed system and carrying out a contact reaction process to obtain the alpha-acyloxyketone compound shown in the formula (I), wherein in the formula (I), R1, R2, R3, R4, R5, R6 and R7 respectively represent H, halogen, alkyl, substituted alkyl, aryl, substituted aryl, a heterocyclic substituent group, alkenyl, alkylacyloxy, phenylacyloxy, alkyloxy, aryloxy, an alkylamino group, an arylamino group or a nitro group. The preparation method is convenient for operation, has excellent yield and efficiency, utilizes easily available raw materials and can be widely used.
Description
Technical field
The present invention relates to a kind of preparation method of alpha-acyloxy ketone compounds.
Background technology
Alpha-acyloxy ketone compounds is the ubiquitous organic compound of a class, in Synthetic Organic ChemistryIt is the more material of a kind of more common use. Alpha-acyloxy ketone compounds class is to have biologyImportant component part in the natural products of meaning and pharmacy. It is also that ubiquity has closing of extensive useBecome intermediate, particularly, that mandelic acid derivatives has shown is anti-oxidant, urine preservatives, anti-HIV, anti-swollenKnurl, antimycotic and anti thrombotic action.
The preparation method of alpha-acyloxy ketone compounds had: 1) Chiral Amine catalysis: as DavidM. in 2002Barnes group utilizes Chiral Amine catalyst to synthesize alpha-acyloxy ketone compounds; Again such as 2008KeijiMaruoka seminar reported utilize Chiral Amine as the synthetic α of catalyst aldehyde compound-Acyloxy aldehyde.
2) peroxide and halogenating agent catalysis: as there being report mention MasahitoOchiai for 2005Group utilizes metachloroperbenzoic acid (m-CPBA), BF3·Et2O is as the synthetic alpha-acyloxy ketone of catalystCompounds. Again such as 2011 have reported that KazuakiIshihara Research team utilizes different peroxidatingThing and iodination reagent catalyst have synthesized a large amount of alpha-acyloxy ketone compounds, and a class is intramolecular anti-Should, form lactone structure, also having a class is intermolecular esterification. Again such as 2014 have reportedArumugamSudalai problem utilizes alkene and carboxylic acid under alkali condition, through elemental iodine and tert-butyl group mistakeHydrogen oxide catalysis can be synthesized alpha-acyloxy ketone compounds. Further also have 2014 Nian You seminar reportsRoad utilizes alpha-carbonyl TBAI and TBHP to synthesize multiple compounds as catalyst.
Obtain alpha-acyloxy ketone compounds although said method can synthesize, still have obviously and lackPoint: or be complex operation step; That productive rate is higher, but length consuming time; That reaction is joinedPut and there is higher requirement; Be that reaction yield is high, but there is huge application limitation.
Summary of the invention
The object of this invention is to provide a kind of preparation method of alpha-acyloxy ketone compounds, this alpha-acyloxyPreparation method's simple operation of ketone compounds, there is excellent productive rate and efficiency, and raw material easily when it's convenientIn extensive use.
To achieve these goals, the invention provides a kind of alpha-acyloxy suc as formula structure shown in (I)The preparation method of ketone compounds, comprising:
1) will mix also pre-thermosetting with organic solvent suc as formula the aromatic ketone of structure shown in (II), mantoquita mixedFit system;
2) will mix suc as formula the carboxylic acid of structure shown in (III), alkali compounds, then be added to mixingIn system, carry out haptoreaction to make the alpha-acyloxy ketone compounds suc as formula structure shown in (I),
Wherein, in above formula, R1、R2、R3、R4、R5、R6、R7Be selected from independently of one another H, halogen,The aryl of the alkyl of C1-C15, the substituted alkyl of C1-C30, C6-C15, the substituted aryl of C6-C30,The alkenyl of heterocyclic substituent, C2-C15, the alkanoyloxy of C1-C15, C7-C15 benzoyloxy group,The aryl amine of the aryloxy group of C1-C15 alkoxyl, C6-C15, the alkylamino radical of C1-C15, C6-C15 orNitro.
By technique scheme, utilization of the present invention is suc as formula the aromatic ketone of structure shown in (II), suc as formula (III)Shown in the carboxylic acid of structure be reaction substrate, select the mantoquita cheap, toxicity is little (as CuBr2) beBrominated reagent. Aromatic ketone compounds forms alpha-substituted aromatic ketone under mantoquita effect, subsequently at alkaline barUnder part, generate alpha-acyloxy ketone compounds with the carboxylic acid reaction suc as formula structure shown in (III). The present invention is logicalCross the feeding sequence of reasonable arrangement, utilize ketone compounds and carboxylic acid reaction in the short period, finally utilizeRecrystallization can obtain alpha-acyloxy ketone compounds.
Other features and advantages of the present invention are described in detail the detailed description of the invention part subsequently.
Detailed description of the invention
Below the specific embodiment of the present invention is elaborated. Should be understood that, retouch in this placeThe detailed description of the invention of stating only, for description and interpretation the present invention, is not limited to the present invention.
The invention provides a kind of preparation side of the alpha-acyloxy ketone compounds suc as formula structure shown in (I)Method, comprising:
1) will mix also pre-thermosetting with organic solvent suc as formula the aromatic ketone of structure shown in (II), mantoquita mixedFit system;
2) will, suc as formula carboxylic acid, the alkali compounds of structure shown in (III), then be added to mixed systemIn carry out haptoreaction to make the alpha-acyloxy ketone compounds suc as formula structure shown in (I),
Wherein, in above formula, R1、R2、R3、R4、R5、R6、R7Be selected from independently of one another H, halogen,The aryl of the alkyl of C1-C15, the substituted alkyl of C1-C30, C6-C15, the substituted aryl of C6-C30,The alkenyl of heterocyclic substituent, C2-C15, the alkanoyloxy of C1-C15, C7-C15 benzoyloxy group,The aryl amine of the aryloxy group of C1-C15 alkoxyl, C6-C15, the alkylamino radical of C1-C15, C6-C15 orNitro.
In the present invention, aliphatic group, aryl, heterocyclic substituent and replacement aliphatic group and/or replacementSubstituted radical in aryl all can be selected in wide scope, but examines from reaction yield and efficiencyConsider, preferably, described alkyl is methyl, butyl; Described aryl is phenyl or naphthyl; Described heterocycle is gotDai Ji is selected from thienyl, furyl, pyrrole radicals or pyridine radicals; Described alkanoyloxy is acetoxyl group; InstituteStating alkoxyl is methoxyl group, phenoxy group; Substituted radical in described substituted alkyl and/or substituted aryl separatelyBe independently cycloalkyl, the C6-C15 of alkyl, the C3-C15 of H, halogen, C1-C15 aryl,The alkenyl of the substituted aryl of C7-C15, heterocyclic substituent, C2-C15, the alkanoyloxy of C1-C15,The aryl amine of the aryloxy group of C1-C15 alkoxyl, C6-C15, the alkylamino radical of C1-C15, C6-C15 orNitro. More preferably, described substituted alkyl is the tert-butyl group; Described substituted aryl is xenyl.
In the present invention, the materials of each material can be selected in wide scope, but for when the scopeIn can obtain more excellent productive rate, preferably, with respect to the aromatic ketone of 1mmol, the use of mantoquitaAmount is 0.5-2.5mmol, and the consumption of carboxylic acid is 1-3mmol, and the consumption of alkali compounds is 1-4mmol,The consumption of organic solvent is 2-10ml.
In the present invention, the condition of preheating can be selected in wide scope, but in the scope timeIn can obtain more excellent productive rate, preferably, in step 1) in, preheating at least meets the following conditions:Reaction temperature is 30-120 DEG C, preferably 50-80 DEG C, and the reaction time is 0.5-6h.
In the present invention, catalytic condition can be selected in wide scope, but in scopeIn time, can obtain more excellent productive rate, preferably, in step 2) in, haptoreaction is at least satisfied:Reaction temperature is 50-80 DEG C, and the reaction time is 6-72h.
In the present invention, the kind of mantoquita can be selected in wide scope, but in the scope timeIn can obtain more excellent productive rate, preferably, mantoquita is selected from stannous chloride, cuprous bromide, iodate AsiaCopper, cuprous sulfide, cuprous cyanide, copper chloride, copper bromide, copper fluoride, copper trifluoromethanesulfcomposite, tetrafluoroOne or more in copper borate, cupric perchlorate, copper nitrate, copper sulphate, Schweinfurt green.
In the present invention, the kind of organic solvent can be selected in wide scope, but in scopeIn time, can obtain more excellent productive rate, preferably, organic solvent be selected from oxolane, dioxane,Benzene, toluene, water, benzotrifluoride, acetonitrile, carrene, chloroform, dichloroethanes, acetic acid secondEster, ether, methyl tert butyl ether, 2-butanone, n-hexane, cyclohexane, benzinum, methyl alcohol, ethanol,One or more in propyl alcohol, n-butanol, isobutanol, isoamyl alcohol.
In the present invention, the kind of alkali compounds can be selected in wide scope, but at modelEnclose in the time and can obtain more excellent productive rate, preferably, alkali compounds be selected from cesium carbonate, sodium carbonate,Potash, NaOH, potassium hydroxide, potassium phosphate, triethylamine, pyridine, 4-picoline, 2,3-Lutidines, N, one or more in N-diisopropyl ethyl amine, 4-methyl morpholine.
In the present invention, the mode of the post processing of reaction system can be selected in wide scope, as extraction,Crystallization and fractionation, but in order to improve the purity of the alpha-acyloxy ketone compounds making, preferably,Step 2) afterwards, this preparation method also comprises: reaction system is filtered, gone filtrate and remove solvent,Cross pillar and obtain product.
In the present invention, in order further to improve the productive rate of reaction, preferably, in step 1) before,This preparation method also comprises: organic solvent is carried out to anhydrous and oxygen-free processing.
Below will describe the present invention by embodiment.
Embodiment 1
The compound of structure shown in formula (I-1):
1), under the existence of oxygen, 1mmol propiophenone, 2mmol copper bromide are dissolved in to 2mL acetonitrileIn, and be placed in oil bath be warming up to 65 DEG C reaction 5h;
2) 3mmol potash, 1mmol benzoic acid are mixed and add reaction system, then add 4mLAcetonitrile, and at 65 DEG C, continue reaction 24h;
3) above-mentioned reaction system is filtered while hot, filtrate is removed after acetonitrile at Rotary Evaporators, then uses secondAcetoacetic ester extraction, after washed several times with water, uses anhydrous sodium sulfate drying organic phase, after being spin-dried for, crosses pillar, producesRate is 89%.
Shown in formula (I-1), the testing result of the nucleus magnetic hydrogen spectrum of the compound of structure is:1HNMR (500MHz,CDCl3)δ8.09(d,J＝7.5Hz,2H),8.00(d,J＝7.5Hz,2H),7.56(dd,J＝7.5Hz,J＝1.0Hz,2H),7.48(dd,J＝7.5Hz,J＝7.5Hz,2H),7.44(dd,J＝7.5Hz,J＝7.5Hz,2H),6.21(q,J＝7.0Hz,1H),1.67(d,J＝7.0Hz,3H)；13CNMR(125MHz,CDCl3)δ197.1,166.3,134.9,133.9,133.6,130.2,129.9,129.1,128.9,128.772.2,17.5.
Embodiment 2
Make the compound of structure shown in formula (I-2) according to the mode of embodiment 1, productive rate is 39%,Difference is the acetophenone that propiophenone is changed to equimolar amounts.
Shown in formula (I-2), the testing result of the nucleus magnetic hydrogen spectrum of the compound of structure is:1HNMR(500MHz,CDCl3)δ8.14(d,J＝7.5Hz,2H,),7.60～7.62(m,2H,),7.50～7.53(m,1H),7.97(d,J＝8.1Hz,2H,),7.44～7.53(m,2H,),7.55(m,1H,),5.58(s,2H)；13CNMR(125MHz,CDCl3)δ192.5,166.4,134.7,134.3,133.7,130.3,129.8,129.3,128.8,128.2,66.8.
Embodiment 3
Make the compound of structure shown in formula (I-1) according to the mode of embodiment 1, productive rate is trace,Difference is that copper bromide is changed to copper bromide and Schweinfurt green (mol ratio: 10:1).
Testing result and the embodiment 1 of nucleus magnetic hydrogen spectrum and nuclear-magnetism carbon spectrum are consistent.
Embodiment 4
Make the compound of structure shown in formula (I-1) according to the mode of embodiment 1, productive rate is 78%,Difference is that potash is changed to potassium phosphate.
Testing result and the embodiment 1 of nucleus magnetic hydrogen spectrum and nuclear-magnetism carbon spectrum are consistent.
Embodiment 5
Make the compound of structure shown in formula (I-1) according to the mode of embodiment 1, productive rate is 88%,Difference is that benzoic acid is changed to parachlorobenzoic-acid.
The testing result of nucleus magnetic hydrogen spectrum is: 1HNMR (500MHz, CDCl3) δ 8.02 (d, J=8.5Hz, 2H),7.99(d,J＝8.0Hz,2H),7.60(dd,J1＝7.5Hz,J2＝7.5Hz,1H),7.49(dd,J1＝7.5Hz,J2＝7.5Hz,2H),7.42(d,J＝8.0Hz,2H),6.19(q,J＝7.0Hz,1H),1.67(d,J＝7.0Hz,3H)；13CNMR(125MHz,CDCl3)δ196.9，165.5，140.2，134.7，134.1，131.6，129.2，129.1，128.9，128.3，72.5，17.6.
Embodiment 6
Make the compound of structure shown in formula (I-1) according to the mode of embodiment 1, productive rate is 51%,Difference is that acetonitrile is changed to ethanol
Testing result and the embodiment 1 of nucleus magnetic hydrogen spectrum and nuclear-magnetism carbon spectrum are consistent.
Embodiment 7
Make the compound of structure shown in formula (I-1) according to the mode of embodiment 1, productive rate is 35%,Difference is that the consumption of copper bromide is changed to 0.5mmol
Testing result and the embodiment 1 of nucleus magnetic hydrogen spectrum and nuclear-magnetism carbon spectrum are consistent.
Embodiment 8
Make the compound of structure shown in formula (I-1) according to the mode of embodiment 1, productive rate is 75%,Difference is that the consumption of copper bromide is changed to 2.5mmol.
Testing result and the embodiment 1 of nucleus magnetic hydrogen spectrum and nuclear-magnetism carbon spectrum are consistent.
Embodiment 9
Make the compound of structure shown in formula (I-1) according to the mode of embodiment 1, productive rate is 12%,Difference is that the consumption of potash is changed to 1mmol.
Testing result and the embodiment 1 of nucleus magnetic hydrogen spectrum and nuclear-magnetism carbon spectrum are consistent.
Embodiment 10
Make the compound of structure shown in formula (I-1) according to the mode of embodiment 1, productive rate is 87%,Difference is that the consumption of potash is changed to 4mmol.
Testing result and the embodiment 1 of nucleus magnetic hydrogen spectrum and nuclear-magnetism carbon spectrum are consistent.
Embodiment 11
Make the compound of structure shown in formula (I-1) according to the mode of embodiment 1, productive rate is 91%,Difference is that benzoic consumption is changed to 3mmol, and the consumption of potash is changed to 3mmol.
Testing result and the embodiment 1 of nucleus magnetic hydrogen spectrum and nuclear-magnetism carbon spectrum are consistent.
Comparative example 1
Make the compound of structure shown in formula (I-1) according to the mode of embodiment 1, productive rate is 0%,Difference is not used copper bromide.
Testing result and the embodiment 1 of nucleus magnetic hydrogen spectrum and nuclear-magnetism carbon spectrum are consistent.
Comparative example 2
Make the compound of structure shown in formula (I-1) according to the mode of embodiment 1, productive rate is 0%,Difference is not used potash.
Testing result and the embodiment 1 of nucleus magnetic hydrogen spectrum and nuclear-magnetism carbon spectrum are consistent.
More than describe the preferred embodiment of the present invention in detail, still, the present invention is not limited to above-mentioned realityExecute the detail in mode, within the scope of technical conceive of the present invention, can be to technical side of the present inventionCase is carried out multiple simple variant, and these simple variant all belong to protection scope of the present invention.
It should be noted that in addition each the concrete technology spy described in above-mentioned detailed description of the inventionLevy, in reconcilable situation, can combine by any suitable mode, for fear of needn'tThe repetition of wanting, the present invention is to the explanation no longer separately of various possible combinations.
In addition, between various embodiment of the present invention, also can be combined, as long as itsWithout prejudice to thought of the present invention, it should be considered as content disclosed in this invention equally.
Claims (9)
1. suc as formula the preparation method of the alpha-acyloxy ketone compounds of structure shown in (I), its featureBe, comprise:
1) will mix also pre-thermosetting with organic solvent suc as formula the aromatic ketone of structure shown in (II), mantoquita mixedFit system;
2) will mix suc as formula the carboxylic acid of structure shown in (III), alkali compounds, described in being then added toIn mixed system, carry out haptoreaction to make the described alpha-acyloxy ketone suc as formula structure shown in (I)Compound,
Wherein, in above formula, R1、R2、R3、R4、R5、R6、R7Be selected from independently of one another H, halogen,The aryl of the alkyl of C1-C15, the substituted alkyl of C1-C30, C6-C15, the substituted aryl of C6-C30,The benzoyloxy group of the alkenyl of heterocyclic substituent, C2-C15, the alkanoyloxy of C1-C15, C7-C15,The alkylamino radical of the alkoxyl of C1-C15, the aryloxy group of C6-C15, C1-C15, the aryl amine of C6-C15Or nitro.
2. preparation method according to claim 1, is characterized in that, described alkyl be methyl,Butyl;
Described aryl is phenyl or naphthyl;
Described heterocyclic substituent is selected from thienyl, furyl, pyrrole radicals or pyridine radicals;
Described alkanoyloxy is acetoxyl group;
Described alkoxyl is methoxyl group, phenoxy group;
Substituted radical in described substituted alkyl and/or substituted aryl be independently of one another H, halogen,The aryl of the alkyl of C1-C15, the cycloalkyl of C3-C15, C6-C15, the substituted aryl of C7-C15,The alkenyl of heterocyclic substituent, C2-C15, the alkanoyloxy of C1-C15, C1-C15 alkoxyl, C6-C15Aryloxy group, the alkylamino radical of C1-C15, aryl amine or the nitro of C6-C15.
3. preparation method according to claim 2, is characterized in that, described substituted alkyl is uncleButyl; Described substituted aryl is xenyl.
4. according to the preparation method described in any one in claim 1-3, it is characterized in that, relativelyIn the described aromatic ketone of 1mmol, the consumption of described mantoquita is 0.5-2.5mmol, the consumption of described carboxylic acidFor 1-3mmol, the consumption of described alkali compounds is 1-4mmol, and the consumption of described acetonitrile is 2-10ml.
5. preparation method according to claim 4, is characterized in that, in step 1) in, described inReaction temperature at least meets the following conditions: reaction temperature is 30-120 DEG C, and preferably 50-80 DEG C, when reactionBetween be 0.5-6h.
6. preparation method according to claim 5, is characterized in that, in step 2) in, described inHaptoreaction is at least satisfied: reaction temperature is 50-80 DEG C, and the reaction time is 6-72h.
7. according to the preparation method described in claim 5 or 6, it is characterized in that, described mantoquita is selected fromStannous chloride, cuprous bromide, cuprous iodide, cuprous sulfide, cuprous cyanide, copper chloride, copper bromide,Copper fluoride, copper trifluoromethanesulfcomposite, tetrafluoro boric acid copper, cupric perchlorate, copper nitrate, copper sulphate, Schweinfurt greenIn one or more;
Preferably, described organic solvent is selected from oxolane, dioxane, benzene, toluene, water, trifluoroToluene, acetonitrile, carrene, chloroform, dichloroethanes, ethyl acetate, ether, the special fourth of methylBase ether, 2-butanone, n-hexane, cyclohexane, benzinum, methyl alcohol, ethanol, propyl alcohol, n-butanol, differentOne or more in butanols, isoamyl alcohol;
More preferably, described alkali compounds be selected from cesium carbonate, sodium carbonate, potash, NaOH,Potassium hydroxide, potassium phosphate, triethylamine, pyridine, 4-picoline, 2,3-lutidines, N, N-bis-One or more in isopropyl ethylamine, 4-methyl morpholine.
8. preparation method according to claim 7, is characterized in that, in step 2) afterwards, instituteStating preparation method also comprises: reaction system is filtered, gone filtrate and remove solvent, then by acetic acid secondEster extraction, then get organic phase and be dried and remove ethyl acetate, finally mistake chromatographic column obtains product.
9. preparation method according to claim 8, is characterized in that, in step 1) before, instituteStating preparation method also comprises: described organic solvent is carried out to anhydrous and oxygen-free processing.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106242934A (en) * | 2016-07-26 | 2016-12-21 | 云南民族大学 | A kind of β position C H key acetoxylation synthetic method of ketone |
| CN107829105A (en) * | 2017-11-16 | 2018-03-23 | 南阳师范学院 | A kind of method of electrochemistry formated α acyloxy ketone |
| CN111362794A (en) * | 2020-03-10 | 2020-07-03 | 河北科技大学 | Preparation method of α -acyloxyketone compound |
| CN111377814A (en) * | 2020-03-10 | 2020-07-07 | 河北科技大学 | Preparation method of α -acyloxyketone compound |
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| CN103987739A (en) * | 2011-12-16 | 2014-08-13 | 阿克伦大学 | Substituted phenacyl molecules and photoresponsive polymers |
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| CN103987739A (en) * | 2011-12-16 | 2014-08-13 | 阿克伦大学 | Substituted phenacyl molecules and photoresponsive polymers |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106242934A (en) * | 2016-07-26 | 2016-12-21 | 云南民族大学 | A kind of β position C H key acetoxylation synthetic method of ketone |
| CN107829105A (en) * | 2017-11-16 | 2018-03-23 | 南阳师范学院 | A kind of method of electrochemistry formated α acyloxy ketone |
| CN111362794A (en) * | 2020-03-10 | 2020-07-03 | 河北科技大学 | Preparation method of α -acyloxyketone compound |
| CN111377814A (en) * | 2020-03-10 | 2020-07-07 | 河北科技大学 | Preparation method of α -acyloxyketone compound |
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Application publication date: 20160615 |