CN110746305A - Polysubstituted dibenzoylbenzene derivative and synthetic method thereof - Google Patents
Polysubstituted dibenzoylbenzene derivative and synthetic method thereof Download PDFInfo
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Abstract
The invention provides a polysubstituted dibenzoylbenzene derivative and a synthesis method thereof, under the heating condition, tetraalkyne reacts with 2, 4-diphenyloxazole in toluene to generate DA, and the reaction is stopped after natural cooling to room temperature; purifying and separating the product to obtain the polysubstituted dibenzoyl benzene derivative. Compared with the existing polysubstituted dibenzoylbenzene, the invention provides a series of novel synthetic methods of polysubstituted dibenzoylbenzene derivatives. Compared with common polysubstituted dibenzoyl benzene, the polysubstituted dibenzoyl benzene prepared by the method has more complex and diversified structures. The substance of the invention may have wide effect in the medical industry, and the preparation method provided by the invention is simple, convenient and efficient, and has short reaction time and high efficiency.
Description
Technical Field
The invention belongs to the field of organic compounds, and particularly relates to a polysubstituted dibenzoylbenzene derivative and a synthetic method thereof.
Background
Benzene is a hydrocarbon, the simplest aromatic hydrocarbon, and is a colorless transparent liquid which is sweet, flammable and carcinogenic toxic at normal temperature and has a strong aromatic odor. It is insoluble in water, soluble in organic solvents and can be used as an organic solvent. Benzene has a ring system called a benzene ring, and a structure in which one hydrogen atom is removed from the benzene ring is called a phenyl group, which is represented by Ph, so that the chemical formula of benzene can also be written as PhH. Benzene is a basic raw material of petrochemical industry, and the yield and the technical level of production of the benzene are one of the marks of the national development level of the petrochemical industry.
Benzene has been a common solvent used in industry in the 1920 s, and is mainly used for degreasing metals. Because benzene is toxic, the production process in which a person can directly contact a solvent does not use benzene as a solvent.
Benzene has knock reducing effect and can be used as gasoline additive. Before tetraethyl lead began to be used in the 1950 s, all antiknock agents were benzene. However, with the lead-containing gasoline fading, the benzene is reused. Because benzene has adverse effect on human body and pollutes underground water quality, the benzene content in the gasoline limited by Europe and America is not more than 1%.
The most important industrial application of benzene is as a chemical raw material. Benzene can synthesize a series of benzene derivatives:
a series of compounds generated by benzene through substitution reaction, addition reaction, oxidation reaction, etc. can be used as raw materials for preparing plastics, rubber, fibre, dye, detergent, insecticide, etc. About 10% of benzene is used as a basic raw material for producing benzene-based intermediates. Benzene and ethylene produce ethylbenzene, which can be used to produce styrene for plastics; benzene and propylene produce cumene, which can be used to produce acetone and phenol for resins and binders via the cumene process; preparing cyclohexane for nylon; synthesizing maleic anhydride; nitrobenzene used to make aniline; various chlorobenzenes which are commonly used as pesticides; various alkylbenzenes have been synthesized for the production of detergents and additives. Synthesizing chemical products such as hydroquinone, anthraquinone, etc.
Disclosure of Invention
The invention aims to provide a method for synthesizing polysubstituted dibenzoylbenzene derivatives, which is simple, convenient and efficient, and has short reaction time and high efficiency.
The invention also aims to provide a polysubstituted dibenzoylbenzene derivative which has a more complex structure and a wide application prospect.
The invention provides a polysubstituted dibenzoyl benzene derivative, which has a structural formula as follows:
wherein E is CO2R and R are straight-chain alkyl, branched-chain alkyl or unsaturated alkyl; r1Is hydrogen, halogen, straight chain alkyl, branched chain alkyl, ester group, alkoxy or corresponding derivatives thereof.
Preferably, the polysubstituted dibenzoyl benzene derivative has a structural formula:
the invention provides a method for synthesizing polysubstituted dibenzoylbenzene derivatives, which comprises the following steps:
under the heating condition, reacting tetraalkyne with 2, 4-diphenyl oxazole in toluene, naturally cooling to room temperature, and stopping reaction; purifying and separating the product to obtain the polysubstituted dibenzoyl benzene derivative.
Further, the heating condition is as follows: heating to 100-110 ℃. Reacting for at least 8h under the condition.
Further, the mole ratio of the tetraalkyne to the 2, 4-diphenyloxazole to the toluene is 1: 1: 28-66;
the tetrayne structural formula
Wherein R is a linear alkyl group, a branched alkyl group or an unsaturated alkyl group; r1Is hydrogen, halogen, straight chain alkyl, branched chain alkyl, ester group, alkoxy or corresponding derivatives thereof.
The purification and separation specifically comprises the following steps: the obtained product is washed by water, extracted by ethyl acetate, and dried by spinning under reduced pressure, and the volume ratio of ethyl acetate to ethyl acetate is 1: 40: and (3) performing column chromatography separation on petroleum ether to obtain a white solid, namely the polysubstituted dibenzoylbenzene derivative. The column chromatography yield was about 77%.
Further, the preparation method of the tetraalkyne comprises the following steps:
1) adding malonate and propargyl bromide into anhydrous acetonitrile in an ice-water bath by using sodium hydride as a catalyst, reacting, and then purifying and separating to obtain a compound 1;
2) reacting the compound 1 prepared in the step 1) with phenylacetyleneBromine or substituted phenylethynyl bromine in Pd (PPh)3)2Cl2In the anhydrous and oxygen-free catalysis system of CuI, triethylamine is used as alkali, anhydrous acetonitrile is used as solvent, stirring reaction is carried out at room temperature, and after purification and separation, the product tetraalkyne is obtained.
Further, the molar ratio of the sodium hydride, the malonate, the propargyl bromide and the anhydrous acetonitrile in the step 1) is 4-5: 1: 2.2-3.2: 20-23;
preferably, the malonate in step 1) is selected from dimethyl malonate or diisopropyl malonate.
In the step 1), the reaction temperature is 0-5 ℃ under the condition of ice-water bath; the reaction time is more than 5 hours;
the purification and separation in the step 1) are specifically as follows: the product is washed by adding water, extracted by ethyl acetate and dried by spinning under reduced pressure to obtain a yellow brown solid product, namely the compound 1.
The compound 1 in the step 1) has a structural formula
R is straight-chain alkyl, branched-chain alkyl or unsaturated alkyl.
Step 2) reacting the compound 1 with phenylethynyl bromide or substituted phenylethynyl bromide, Pd (PPh)3)2Cl2The mass ratio of CuI, triethylamine and anhydrous acetonitrile is 1: 2.2-3.2: 0.03-0.04: 4-5: 30-45 parts of;
step 2), stirring for reaction, wherein the reaction time is more than 10 hours; the substituted phenylethynyl bromide has the substituent of halogen, straight-chain alkyl, branched-chain alkyl, ester group, alkoxy or corresponding derivatives thereof, and preferably, the substituted phenylethynyl bromide is selected from p-methylphenylethynyl bromide;
the purification and separation in the step 2) are specifically as follows: the product was washed with water, extracted with ethyl acetate, spin-dried under reduced pressure, and concentrated with ethyl acetate at a volume ratio of 1: 60: and (4) performing column chromatography separation on petroleum ether to obtain a light yellow solid product, namely the product tetraacetylene.
Pd (PPh) in step 2)3)2Cl2In the anhydrous oxygen-free catalytic system of/CuI, the mole ratio is Pd (PPh)3)2Cl2:CuI＝3:1。
Description of the invention: the tetraalkyne generates a benzyne intermediate when being heated to the temperature of 100-110 ℃, the benzyne intermediate and the 2, 4-diphenyloxazole firstly undergo DA reaction and then undergo oxidation with oxygen, and the required compound is obtained. Based on this, the reaction of the invention is that DA reaction firstly occurs and then oxidation by oxygen is carried out. The 2, 4-diphenyl oxazole of the invention is different from other types of oxazoles, especially dihydrooxazole, which does not have diene and is easy to generate nucleophilic reaction. Although the oxidation occurs in the reaction and oxygen is required to be present, it is not necessary to provide oxygen in particular, and it is only necessary to keep the reaction tube filled with the reaction reagent in the air at the time of starting the reaction.
Compared with the existing polysubstituted dibenzoylbenzene, the invention provides a series of novel synthetic methods of polysubstituted dibenzoylbenzene derivatives. Compared with common polysubstituted dibenzoyl benzene, the polysubstituted dibenzoyl benzene prepared by the method has more complex and diversified structures. The substance of the invention may have wide effect in the medical industry, and the preparation method provided by the invention is simple, convenient and efficient, and has short reaction time and high efficiency.
Drawings
FIG. 1 is a structural formula of a polysubstituted dibenzoylbenzene derivative according to the present invention;
FIG. 2 is a structural formula of a polysubstituted dibenzoylbenzene derivative prepared in example 1;
FIG. 3 is a structural formula of polysubstituted dibenzoylbenzene derivative prepared in example 2
FIG. 4 is a NMR spectrum of a polysubstituted dibenzoylbenzene derivative prepared in example 1;
FIG. 5 is a carbon NMR spectrum of a polysubstituted dibenzoylbenzene derivative prepared in example 1;
FIG. 6 is a NMR spectrum of a polysubstituted dibenzoylbenzene derivative prepared in example 2;
FIG. 7 is a NMR carbon spectrum of a polysubstituted dibenzoylbenzene derivative prepared in example 2;
FIG. 8 is a reaction equation of the preparation process of example 1;
FIG. 9 is the reaction mechanism of example 1;
FIG. 10 is a single crystal diagram of example 1 demonstrating the synthesis of the desired product of the present invention.
Detailed Description
Example 1
A polysubstituted dibenzoylbenzene derivative has a structural formula as follows:
the synthesis method of the polysubstituted dibenzoylbenzene derivative comprises the following steps:
(1) adding 200mmol of dimethyl malonate and 440mmol of propargyl bromide into 210mL of anhydrous acetonitrile in an ice water bath by using 830mmol of sodium hydride as a catalyst, stirring for reacting for 8 hours, adding water into the product for washing, extracting by using ethyl acetate, and performing reduced pressure spin drying to obtain a brownish yellow solid product, namely a compound 1;
(2) 80mmol of Compound 1 and 200mmol of p-methylphenylethynyl bromide were mixed in Pd (PPh)3)2Cl2In the anhydrous oxygen-free catalytic system of CuI (2.56mmol/0.85mmol), the molar ratio is Pd (PPh)3)2Cl2CuI 3:1, using 336mmol triethylamine as base, using 150mL anhydrous acetonitrile as solvent, stirring reaction at room temperature for 12 hours, washing product with water, extracting with ethyl acetate, drying under reduced pressure, using ethyl acetate with volume ratio of 1: 60: and (4) performing column chromatography separation on petroleum ether to obtain a light yellow solid product, namely the product tetraacetylene.
(3) Reacting 1mmol of tetraalkyne prepared in the step (2) with 1mmol of 2, 4-diphenyloxazole in 5mL of toluene solvent at the temperature of 110 ℃ for 8 hours to obtain a compound 3, namely a crude product of the polysubstituted dibenzoylbenzene derivative; the crude product of the prepared polysubstituted dibenzoylbenzene derivative is washed with water, extracted with ethyl acetate, dried by spinning under reduced pressure, and purified by using ethyl acetate: the petroleum ether is separated by column chromatography with a ratio of 1:40 to obtain a white solid product, namely the polysubstituted dibenzoylbenzene derivative, and the yield of the column chromatography is about 77 percent.
The white solid product finally obtained in the step (3) is sinteredPassing through;1H NMR；13c NMR, the structure is as follows:
1H NMR(400MHz,CDCl3)δ7.82-6.95(m,18H),3.91(s,2H)3.78(s,6H),3.45(s,2H),2.36(s,3H),2.23(s,3H)。
13C NMR(125MHz,CDCl3)δ197.76,196.76,171.53,144.55,141.71,136.79,134.39,132.50,130.31,129.46,128.58,127.67,121.63,119.72,98.62,85.49,59.52,53.18,40.89,40.27,21.54,21.15。
example 2
A polysubstituted dibenzoylbenzene derivative has a structural formula as follows:
the synthesis method of the polysubstituted dibenzoylbenzene derivative comprises the following steps:
(1) adding 200mmol of diisopropyl malonate and 440mmol of propargyl bromide into 210mL of anhydrous acetonitrile in an ice water bath by using 830mmol of sodium hydride as a catalyst, stirring for reacting for 8 hours, adding water into the product for washing, extracting by using ethyl acetate, and performing reduced pressure spin drying to obtain a brownish yellow solid product, namely a compound 1;
(2) 80mmol of Compound 1 and 200mmol of phenylethynyl bromide were mixed in Pd (PPh)3)2Cl2In the anhydrous oxygen-free catalytic system of CuI (2.56mmol/0.85mmol), the molar ratio is Pd (PPh)3)2Cl2CuI 3:1, using 336mmol triethylamine as base, using 150mL anhydrous acetonitrile as solvent, stirring reaction at room temperature for 12 hours, washing product with water, extracting with ethyl acetate, drying under reduced pressure, using ethyl acetate with volume ratio of 1: 60: and (4) performing column chromatography separation on petroleum ether to obtain a light yellow solid product, namely the product tetraacetylene.
(3) Reacting 1mmol of tetraalkyne prepared in the step (2) with 1mmol of 2, 4-diphenyloxazole in 5mL of toluene solvent at the temperature of 110 ℃ for 8 hours to obtain a compound 3, namely a crude product of the polysubstituted dibenzoylbenzene derivative; the crude product of the prepared polysubstituted dibenzoylbenzene derivative is washed with water, extracted with ethyl acetate, dried by spinning under reduced pressure, and purified by using ethyl acetate: the petroleum ether is separated by column chromatography with the ratio of 1:40 to obtain a white solid product, namely the polysubstituted dibenzoylbenzene derivative, and the yield of the column chromatography is about 80 percent.
Passing the white solid product finally obtained in the step (3) through a structure;1H NMR；13c NMR, the structure is as follows:
1H NMR(400MHz,CDCl3)δ7.83-7.13(m,20H),5.13-5.04(q,2H),3.88(s,2H),3.45(s,2H),1.28-1.27(d,6H),1.23-1.22(d,6H)；
13C NMR(125 MHz,CDCl3)δ 197.65,196.84,170.66,145.06,141.71,136.95,132.55,129.88,128.28,127.46,122.78,121.24,98.23,85.97,69.58,59.56,40.72,40.12,21.52。
Claims (10)
1. a polysubstituted dibenzoylbenzene derivative is characterized in that the structural formula of the polysubstituted dibenzoylbenzene derivative is as follows:
wherein E is CO2R and R are straight-chain alkyl, branched-chain alkyl or unsaturated alkyl; r1Is hydrogen, halogen, straight chain alkyl, branched chain alkyl, ester group, alkoxy or corresponding derivatives thereof.
2. The polysubstituted dibenzoylbenzene derivative according to claim 1, having the formula:
3. a method for synthesizing polysubstituted dibenzoylbenzene derivatives according to claim 1 or 2, which comprises the steps of: under the heating condition, reacting tetraalkyne with 2, 4-diphenyl oxazole in toluene, naturally cooling to room temperature, and stopping reaction; purifying and separating the product to obtain the polysubstituted dibenzoyl benzene derivative.
4. The synthesis process according to claim 3, characterized in that the conditions under heating are: heating to 100-110 ℃.
5. The synthesis process according to claim 3 or 4, characterized in that the reaction is carried out under heating for at least 8 h.
6. The synthesis method according to claim 3 or 4, wherein the molar ratio of the tetraalkyne, the 2, 4-diphenyloxazole and the toluene is 1: 1: 28-66.
7. The synthetic method of claim 3 wherein said tetraalkyne structure is
Wherein R is a linear alkyl group, a branched alkyl group or an unsaturated alkyl group; r1Is hydrogen, halogen, straight chain alkyl, branched chain alkyl, ester group, alkoxy or corresponding derivatives thereof.
8. The synthesis process according to claim 3 or 7, characterized in that the preparation process of the tetraalkyne comprises the following steps:
1) adding malonate and propargyl bromide into anhydrous acetonitrile in an ice-water bath by using sodium hydride as a catalyst, reacting, and then purifying and separating to obtain a compound 1;
2) mixing the compound 1 prepared in the step 1) with phenylethynyl bromide or substituted phenylethynyl bromide in Pd (PPh)3)2Cl2In the anhydrous and oxygen-free catalysis system of CuI, triethylamine is used as alkali, anhydrous acetonitrile is used as solvent, stirring reaction is carried out at room temperature, and after purification and separation, the product tetraalkyne is obtained.
9. The synthesis method according to claim 8, wherein the molar ratio of the sodium hydride, the malonate, the propargyl bromide and the anhydrous acetonitrile in the step 1) is 4-5: 1: 2.2-3.2: 20-23.
10. The method of claim 8, wherein in step 2) compound 1 is reacted with phenylethynyl bromide or substituted phenylethynyl bromide, Pd (PPh)3)2Cl2The mass ratio of CuI, triethylamine and anhydrous acetonitrile is 1: 2.2-3.2: 0.03-0.04: 4-5: 30-45.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN109369508A (en) * | 2018-11-28 | 2019-02-22 | 安徽师范大学 | A kind of polysubstituted indole derivatives and preparation method thereof |
| CN114276380A (en) * | 2021-12-28 | 2022-04-05 | 安徽师范大学 | Polyalkynylbenzene conjugated compound and synthetic method thereof |
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| CN108727210A (en) * | 2018-06-20 | 2018-11-02 | 安徽师范大学 | A kind of substituted diphenylamine amine derivative and its synthetic method |
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| CN108727210A (en) * | 2018-06-20 | 2018-11-02 | 安徽师范大学 | A kind of substituted diphenylamine amine derivative and its synthetic method |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109369508A (en) * | 2018-11-28 | 2019-02-22 | 安徽师范大学 | A kind of polysubstituted indole derivatives and preparation method thereof |
| CN109369508B (en) * | 2018-11-28 | 2021-08-27 | 安徽师范大学 | Polysubstituted indole derivative and preparation method thereof |
| CN114276380A (en) * | 2021-12-28 | 2022-04-05 | 安徽师范大学 | Polyalkynylbenzene conjugated compound and synthetic method thereof |
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