CN105622378B - A method of preparing chalcone compounds - Google Patents

A method of preparing chalcone compounds Download PDF

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CN105622378B
CN105622378B CN201410618145.8A CN201410618145A CN105622378B CN 105622378 B CN105622378 B CN 105622378B CN 201410618145 A CN201410618145 A CN 201410618145A CN 105622378 B CN105622378 B CN 105622378B
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derivatives
nitro
acetophenone
itrile group
alkyl
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CN105622378A (en
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王峰
张志鑫
徐杰
王业红
王敏
张超锋
张健
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Dalian Institute of Chemical Physics of CAS
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Abstract

The present invention relates to a kind of methods for preparing chalcone compounds.This method, as reaction substrate, using metal oxide as catalyst, prepares chalcone compounds through oxidative condensation using the organic solution of acetophenone or derivatives thereof and benzyl alcohol or derivatives thereof.Its preparation process is as follows: in organic solvent, acetophenone or derivatives thereof, benzyl alcohol or derivatives thereof being mixed with metal oxide, is put into closed in pressure vessel, at 40~150 DEG C, stirring 0.5h~for 24 hours, separation can obtain chalcone compounds.It is easy that this method product is separated with catalyst, and catalyst can be recycled, and reaction process is simple controllable easy to operate, and wherein the yield of chalcone reaches as high as 66%.

Description

A method of preparing chalcone compounds
Technical field
The present invention relates to a kind of methods for preparing chalcone compounds, and in particular to arrives metal oxide oxidation catalyst acetophenone Or derivatives thereof reacted with benzyl alcohol or derivatives thereof and prepare chalcone compounds.
Background technique
Chalcone compounds, are a kind of α, and alpha, beta-unsaturated ketone is important one kind of natural products flavone compound. Wherein, C=C double bond and C=O double bond exist in the form being conjugated, this makes chalcone compounds chemical property active, can send out A variety of chemical reactions such as raw substitution, addition, condensation, oxidation, reduction, therefore chalcone compounds are a kind of important organic conjunctions At intermediate.In addition, due to chalcone compounds molecular structure have biggish flexibility, can in conjunction with many receptors, Therefore, with antitumor, anti-oxidant and scavenging activated oxygen, anti-gastric-ulcer, antibacterial, inhibition phosphodiesterase, anti-alopecia, rush Into hair regeneration and a variety of pharmacological activity such as antiviral.
There are many chemically synthesized approaches and methods of chalcone compounds, and classical chemical synthesis process is that acetophenone spreads out Biology realizes that reaction is usually under basic or acidic conditions with benzaldehyde derivative by Claisen-Schmidt condensation reaction It carries out.But since aldehyde compound is more active, benzaldehyde used in this method and its derivative use in air When be easy to happen oxidation etc. side reactions, reaction efficiency can be reduced, to cause unnecessary pollution and waste.In order to overcome this Unfavorable factor causes people using benzyl alcohol derivative and acetophenone derivs as the method for Material synthesis chalcone compounds Extensive concern.The noble metal catalysts such as palladium, gold (such as Pd/AlO (OH), Au/AlO (OH) etc.) are reported in document in oxygen gas In atmosphere, a large amount of alkali (such as K3PO4Deng) it is existing under the conditions of, catalytic phenylmethanol derivative and acetophenone derivs synthesizing chalcone class Compound.Since there are a large amount of inorganic bases in reaction system, along with the use of noble metal catalyst, urged to limit such The industrial applications of change system.
Therefore, find it is a kind of prepare simple, clean and effective catalyst, have for synthesizing chalcone class compound important Meaning.
Summary of the invention
Meaning of the present invention is to provide a kind of method that metal oxide oxidation catalyst prepares chalcone compounds.
To achieve the goals above, method provided by the invention is, with benzyl alcohol or derivatives thereof and acetophenone or its spread out Biology is reactant, and metal oxide is catalyst, prepares chalcone compounds.
Specific preparation process is as follows:
In organic solvent, acetophenone or derivatives thereof and benzyl alcohol or derivatives thereof is added, using metal oxide as Catalyst, it is closed to be put into pressure vessel, at 40~150 DEG C, is stirred to react 0.5h~for 24 hours, isolated chalcones chemical combination Object.
Described acetophenone or derivatives thereof, structural formula are as follows:
Wherein R1For-H, nitro, itrile group, isonitrile base, halogenic substituent, C1-C10Alkyl, C1-C10Alkoxy or C1-C10's Substituted hydrocarbon radical, substituent group are one or more of nitro, itrile group, isonitrile base, halogen；
Described benzyl alcohol or derivatives thereof, structural formula are as follows:
Wherein R2For-H, nitro, itrile group, isonitrile base, halogenic substituent, C1-C10Alkyl, C1-C10Alkoxy or C1-C10's Substituted hydrocarbon radical, substituent group is, one or more of nitro, itrile group, isonitrile base, halogen.
The chalcone compounds, structural formula are as follows:
Wherein, R1For-H, nitro, itrile group, isonitrile base, halogenic substituent, C1-C10Alkyl, C1-C10Alkoxy or C1-C10 Substituted hydrocarbon radical, substituent group be one or more of nitro, itrile group, isonitrile base, halogen；
R2For-H, nitro, itrile group, isonitrile base, halogenic substituent, C1-C10Alkyl, C1-C10Alkoxy or C1-C10Take For alkyl, substituent group is one or more of nitro, itrile group, isonitrile base, halogen.
The molar concentration of the acetophenone or derivatives thereof is 0.234mol/L~1.488mol/L；
The molar concentration of the acetophenone or derivatives thereof is preferably 0.234mol/L~0.744mol/L；
The molar concentration of the acetophenone or derivatives thereof most preferably 0.234mol/L~0.468mol/L；
The molar concentration of benzyl alcohol or derivatives thereof is 0.351mol/L~2.232mol/L；
The molar concentration of benzyl alcohol or derivatives thereof is preferably 0.351mol/L~1.116mol/L；
The molar concentration of benzyl alcohol or derivatives thereof most preferably 0.351mol/L~0.702mol/L.
It is preferred that chalcone compounds are as follows: R in (formula 3)1=R2=-H, R1Replace for nitro, itrile group, isonitrile base, halogen Base, C1-C5Alkyl, C1-C5Alkoxy or C1-C5Substituted hydrocarbon radical, substituent group be nitro, itrile group, isonitrile base, in halogen One or more, R2For nitro, itrile group, isonitrile base, halogenic substituent, C1-C5Alkyl, C1-C5Alkoxy or C1-C5's Substituted hydrocarbon radical, substituent group are one or more of nitro, itrile group, isonitrile base, halogen；
Best chalcone compounds are as follows: R in (formula 3)1=R2=-H, R1Replace for nitro, itrile group, isonitrile base, halogen Base, C1-C3Alkyl, C1-C3Alkoxy or C1-C3Substituted hydrocarbon radical, substituent group be nitro, itrile group, isonitrile base, in halogen One or more, R2For nitro, itrile group, isonitrile base, halogenic substituent, C1-C3Alkyl, C1-C3Alkoxy or C1-C3's Substituted hydrocarbon radical, substituent group are one or more of nitro, itrile group, isonitrile base, halogen.
The metal oxide is MgO, MnO2、Y2O3、Nb2O5、Al2O3、ZrO2、TiO2、V2O5Or CeO2One of or It is two or more；
It is preferred that metal oxide is MgO, MnO2、Y2O3、Al2O3Or CeO2One or more of；
Best metal oxide is MnO2、Y2O3Or CeO2One or more of.
The mass ratio of the metal oxide dosage and acetophenone or derivatives thereof is 1:12~5:6；
The preferred mass ratio of the metal oxide dosage and acetophenone or derivatives thereof is 1:4~5:6；
Mass ratio most preferably 1:2~5:6 of the metal oxide dosage and acetophenone or derivatives thereof.
Organic solvent is in benzene, toluene, ortho-xylene, meta-xylene, paraxylene, isopropanol, methanol, ethyl alcohol or acetonitrile One or more；
Organic solvent is preferably one or more of benzene, toluene, ortho-xylene, meta-xylene or paraxylene；
Organic solvent most preferably paraxylene.
Mass percent of the organic solvent in total system is 54%~92%.
Preferable reaction temperature is 80~150 DEG C, preferred reaction time are as follows: 1h~for 24 hours；
Optimal reaction temperature is 120~150 DEG C, optimum reacting time are as follows: 6h~12h.
The preparation principle of chalcone and derivative are as follows: described benzyl alcohol or derivatives thereof and acetophenone or derivatives thereof exist Under the catalytic action of metal oxide, benzyl alcohol or derivatives thereof through air oxidation in-situ preparation benzaldehyde or derivatives thereof, with This benzaldehyde generated simultaneously or derivatives thereof and acetophenone or derivatives thereof generate chalcone or derivatives thereof through condensation reaction.
The present invention has following several advantages compared with the reaction process of announcement:
1, this reaction is reacted using metal oxide oxidation catalyst, and material is easy to get, and preparation is simple, the simple controllable easily behaviour of reaction process Make, stability is high, i.e. reusable after simple process；
2, using solid metal oxide as catalyst, reactant is easily isolated with catalyst；
3, there is preferable universality, it can catalyzed conversion generation for benzyl alcohol analog derivative and acetophenones derivative Corresponding chalcone compounds, wherein the yield of chalcone reaches as high as 66%；
4, it does not need to add additional additive or alkali in reaction system, is conducive to the separating-purifying of product；
5, using metal oxide catalyst compared with expensive noble metal catalyst is used, more economically.
Detailed description of the invention
Fig. 1 is product gas phase-mass spectrometry analysis of spectra of embodiment 6, and wherein Fig. 1 (a) is chromatogram, and Fig. 1 (b) is to protect Stay the time in the product of 13.222min, i.e. chalcone and the mass spectrogram compareed with standard gallery.
Specific embodiment
In order to which the present invention will be described in further detail, several specific implementation cases are given below, but the present invention is unlimited In these embodiments.
Embodiment 1
In 15mL pressure bottle, 2mL paraxylene, 5mmol acetophenone and 7.5mmol benzyl alcohol is added, adds 0.1g CeO2, it is stirred to react at 130 DEG C for 24 hours, after reaction, centrifuge separation, chromatography detects product, and conversion ratio is shown in selectivity Table 1.
Embodiment 2
In 15mL pressure bottle, 2mL paraxylene, 5mmol acetophenone and 7.5mmol benzyl alcohol is added, adds 0.1g MgO is stirred to react for 24 hours at 130 DEG C, and after reaction, centrifuge separation, chromatography detects product, and conversion ratio is shown in selectivity Table 1.
Embodiment 3
In 15mL pressure bottle, 2mL paraxylene, 5mmol acetophenone and 7.5mmol benzyl alcohol is added, adds 0.1g MnO2, it is stirred to react at 130 DEG C for 24 hours, after reaction, centrifuge separation, chromatography detects product, and conversion ratio is shown in selectivity Table 1.
Embodiment 4
In 15mL pressure bottle, 2mL paraxylene, 5mmol acetophenone and 7.5mmol benzyl alcohol is added, adds 0.1g Y2O3, it is stirred to react at 130 DEG C for 24 hours, after reaction, centrifuge separation, chromatography detects product, and conversion ratio is shown in selectivity Table 1.
Embodiment 5
In 15mL pressure bottle, 2mL paraxylene, 5mmol acetophenone and 7.5mmol benzyl alcohol is added, adds 0.1g Al2O3, it is stirred to react at 130 DEG C for 24 hours, after reaction, centrifuge separation, chromatography detects product, and conversion ratio is shown in selectivity Table 1.
Embodiment 6
In 15mL pressure bottle, 2mL paraxylene, 5mmol acetophenone and 7.5mmol benzyl alcohol is added, adds 0.1g CeO2, 12h is stirred to react at 150 DEG C, after reaction, centrifuge separation, chromatography detects product, and conversion ratio is shown in selectivity Table 1.
Embodiment 7
In 15mL pressure bottle, 2mL isopropanol, 5mmol acetophenone and 7.5mmol benzyl alcohol is added, adds 0.1g CeO2, 12h is stirred to react at 150 DEG C, after reaction, centrifuge separation, chromatography detects product, and conversion ratio is shown in selectivity Table 1.
Embodiment 8
In 15mL pressure bottle, 2mL methanol, 5mmol acetophenone and 7.5mmol benzyl alcohol is added, adds 0.1g CeO2, 12h is stirred to react at 150 DEG C, after reaction, centrifuge separation, chromatography detects product, and conversion ratio is shown in selectivity Table 1.
Embodiment 9
In 15mL pressure bottle, 2mL acetonitrile, 5mmol acetophenone and 7.5mmol benzyl alcohol is added, adds 0.1g CeO2, 12h is stirred to react at 150 DEG C, after reaction, centrifuge separation, chromatography detects product, and conversion ratio is shown in selectivity Table 1.
Embodiment 10
In 15mL pressure bottle, 2mL paraxylene, 5mmol acetophenone and 7.5mmol benzyl alcohol is added, adds 0.1g CeO2, be filled with oxygen, 6h be stirred to react at 150 DEG C, after reaction, centrifuge separation, chromatography detect product, conversion ratio with Selectivity is shown in Table 1.
Embodiment 11
In 15mL pressure bottle, 2mL paraxylene, 5mmol acetophenone and 7.5mmol benzyl alcohol is added, adds 0.1g CeO2, be filled with argon gas, 6h be stirred to react at 150 DEG C, after reaction, centrifuge separation, chromatography detect product, conversion ratio with Selectivity is shown in Table 1.
Embodiment 12
In 15mL pressure bottle, 2mL paraxylene, 5mmol acetophenone and 7.5mmol is added to methylbenzyl alcohol, then plus Enter 0.1g CeO2, 12h is stirred to react at 150 DEG C, after reaction, centrifuge separation, chromatography detect product, conversion ratio with Selectivity is shown in Table 1.
Embodiment 13
In 15mL pressure bottle, 2mL paraxylene, 5mmol acetophenone and 7.5mmol P-methoxybenzyl alcohol is added, then 0.1g CeO is added2, 12h is stirred to react at 150 DEG C, after reaction, centrifuge separation, chromatography detects product, conversion ratio 1 is shown in Table with selectivity.
Embodiment 14
In 15mL pressure bottle, addition 2mL paraxylene, 5mmol acetophenone and 7.5mmol p nitrobenzyl alcohol, then plus Enter 0.1g CeO2, 12h is stirred to react at 150 DEG C, after reaction, centrifuge separation, chromatography detect product, conversion ratio with Selectivity is shown in Table 1.
Embodiment 15
In 15mL pressure bottle, 2mL paraxylene, 5mmol acetophenone and 7.5mmol is added to chlorobenzene methanol, adds 0.1g CeO2, 12h is stirred to react at 150 DEG C, after reaction, centrifuge separation, chromatography detects product, conversion ratio and choosing Selecting property is shown in Table 1.
Embodiment 16
In 15mL pressure bottle, addition 2mL paraxylene, 5mmol melilotal and 7.5mmol benzyl alcohol, then plus Enter 0.1g CeO2, 12h is stirred to react at 150 DEG C, after reaction, centrifuge separation, chromatography detect product, conversion ratio with Selectivity is shown in Table 1.
Embodiment 17
In 15mL pressure bottle, 2mL paraxylene, 5mmol acetanisole and 7.5mmol is added to chlorobenzene first Alcohol adds 0.1g CeO2, 12h is stirred to react at 150 DEG C, after reaction, centrifuge separation, chromatography detects product, turn Rate and selectivity are shown in Table 1.
Embodiment 18
In 15mL pressure bottle, 2mL paraxylene, 5mmol parachloroacetophenone and 7.5mmol is added to chlorobenzene methanol, then 0.1g CeO is added2, 12h is stirred to react at 150 DEG C, after reaction, centrifuge separation, chromatography detects product, conversion ratio 1 is shown in Table with selectivity.
Embodiment 19
In 15mL pressure bottle, 2mL paraxylene, 5mmol p-nitroacetophenone and 7.5mmol is added to chlorobenzene methanol, Add 0.1g CeO2, 12h is stirred to react at 150 DEG C, after reaction, centrifuge separation, chromatography detects product, conversion Rate and selectivity are shown in Table 1.
Comparative example 1
In 15mL pressure bottle, 2mL paraxylene, 5mmol acetophenone and 7.5mmol benzyl alcohol is added, adds 0.1g 1wt%Pd/CeO2, be stirred to react at 130 DEG C for 24 hours, after reaction, centrifuge separation, chromatography detect product, conversion ratio with Selectivity is shown in Table 1.
Comparative example 2
In 15mL pressure bottle, 2mL paraxylene, 5mmol acetophenone and 7.5mmol benzyl alcohol is added, adds 0.1g 1wt%PdO/CeO2, it is stirred to react at 130 DEG C for 24 hours, after reaction, centrifuge separation, chromatography detects product, conversion ratio 1 is shown in Table with selectivity.
Comparative example 3
In 15mL pressure bottle, 2mL paraxylene, 5mmol acetophenone and 7.5mmol benzyl alcohol is added, adds 0.1g 2wt%Pt/CeO2, be stirred to react at 130 DEG C for 24 hours, after reaction, centrifuge separation, chromatography detect product, conversion ratio with Selectivity is shown in Table 1.
Comparative example 4
In 15mL pressure bottle, 2mL paraxylene, 5mmol acetophenone and 7.5mmol benzyl alcohol is added, adds 0.1g 2wt%PtO2/CeO2, it is stirred to react at 130 DEG C for 24 hours, after reaction, centrifuge separation, chromatography detects product, conversion ratio 1 is shown in Table with selectivity.
Comparative example 5
In 15mL pressure bottle, 2mL paraxylene, 5mmol acetophenone and 7.5mmol benzyl alcohol is added, adds 0.1g 1wt%Rh/CeO2, be stirred to react at 130 DEG C for 24 hours, after reaction, centrifuge separation, chromatography detect product, conversion ratio with Selectivity is shown in Table 1.
1 metal oxide oxidation catalyst chalcone compounds synthetic reaction evaluation result of table
Embodiment Conversion ratio/% of ketone Selectivity/% of chalcones
Embodiment 1 64 86
Embodiment 2 36 90
Embodiment 3 21 100
Embodiment 4 18 45
Embodiment 5 2 100
Embodiment 6 74 89
Embodiment 7 49 8
Embodiment 8 11 67
Embodiment 9 10 64
Embodiment 10 51 89
Embodiment 11 64 45
Embodiment 12 68 81
Embodiment 13 57 79
Embodiment 14 11 100
Embodiment 15 64 64
Embodiment 16 55 87
Embodiment 17 55 88
Embodiment 18 69 77
Embodiment 19 27 58
Comparative example 1 54 76
Comparative example 2 72 93
Comparative example 3 39 94
Comparative example 4 78 90
Comparative example 5 68 85

Claims (10)

1. a kind of method for preparing chalcone compounds, it is characterised in that:
In organic solvent, acetophenone or derivatives thereof and benzyl alcohol or derivatives thereof is added, using metal oxide as catalysis Agent, it is closed to be put into pressure vessel, 40 ~ 150oUnder C, it is stirred to react the h of 0.5 h ~ 24, isolated chalcones chemical combination Object；
The metal oxide is MgO, MnO2、Y2O3、Al2O3Or CeO2One or more of.
2. according to the method for claim 1, it is characterised in that:
Described acetophenone or derivatives thereof, structural formula are as follows:
(formula 1)
Wherein R1For-H, nitro, itrile group, isonitrile base, halogenic substituent, C1-C10Alkyl, C1-C10Alkoxy or C1-C10Substitution Alkyl, substituent group are one or more of nitro, itrile group, isonitrile base, halogen；
Described benzyl alcohol or derivatives thereof, structural formula are as follows:
(formula 2)
Wherein R2For-H, nitro, itrile group, isonitrile base, halogenic substituent, C1-C10Alkyl, C1-C10Alkoxy or C1-C10Substitution Alkyl, substituent group is, one or more of nitro, itrile group, isonitrile base, halogen.
3. according to the method for claim 1, it is characterised in that:
The chalcone compounds, structural formula are as follows:
(formula 3)
Wherein, R1For-H, nitro, itrile group, isonitrile base, halogenic substituent, C1-C10Alkyl, C1-C10Alkoxy or C1-C10Substitution Alkyl, substituent group are one or more of nitro, itrile group, isonitrile base, halogen；
R2For-H, nitro, itrile group, isonitrile base, halogenic substituent, C1-C10Alkyl, C1-C10Alkoxy or C1-C10Substitution hydrocarbon Base, substituent group are one or more of nitro, itrile group, isonitrile base, halogen.
4. according to the method for claim 1, it is characterised in that:
The molar concentration of the acetophenone or derivatives thereof is the mol/L of 0.234 mol/L ~ 1.488；
The molar concentration of benzyl alcohol or derivatives thereof is the mol/L of 0.351 mol/L ~ 2.232.
5. according to method described in claim 1 or 3, it is characterised in that:
Chalcone compounds are as follows: R in (formula 3)1For-H, nitro, itrile group, isonitrile base, halogenic substituent, C1-C5Alkyl, C1- C5Alkoxy or C1-C5Substituted hydrocarbon radical, substituent group be one or more of nitro, itrile group, isonitrile base, halogen, R2 For-H, nitro, itrile group, isonitrile base, halogenic substituent, C1-C5Alkyl, C1-C5Alkoxy or C1-C5Substituted hydrocarbon radical, replace Group is one or more of nitro, itrile group, isonitrile base, halogen.
6. according to the method for claim 1, it is characterised in that:
Metal oxide is MnO2、Y2O3Or CeO2One or more of.
7. according to the method for claim 1, it is characterised in that:
The mass ratio of the metal oxide dosage and acetophenone or derivatives thereof is 1:12 ~ 5:6；
Organic solvent is one in benzene, toluene, ortho-xylene, meta-xylene, paraxylene, isopropanol, methanol, ethyl alcohol or acetonitrile Kind is two or more.
8. preparation method described in accordance with the claim 1, it is characterised in that: the molar concentration of described acetophenone or derivatives thereof is 0.234 mol/L ~ 0.744 mol/L；
The molar concentration of benzyl alcohol or derivatives thereof is the mol/L of 0.351 mol/L ~ 1.116；
The mass ratio of the metal oxide dosage and acetophenone or derivatives thereof is 1:4 ~ 5:6；
Organic solvent is one or more of benzene, toluene, ortho-xylene, meta-xylene or paraxylene.
9. preparation method described in accordance with the claim 1, it is characterised in that:
Mass percent of the organic solvent in total system is the % of 54 % ~ 92.
10. preparation method described in accordance with the claim 1, it is characterised in that:
Reaction temperature is 80 ~ 150oC, reaction time are as follows: the h of 1 h ~ 24.
CN201410618145.8A 2014-11-05 2014-11-05 A method of preparing chalcone compounds Expired - Fee Related CN105622378B (en)

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CN102786371A (en) * 2011-05-16 2012-11-21 陈道勇 New method for producing alpha,beta-unsaturated carbonyl compounds by using one-pot condensation reaction
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