CN117107255A - Method for synthesizing p-substituted phenol derivative - Google Patents

Method for synthesizing p-substituted phenol derivative Download PDF

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CN117107255A
CN117107255A CN202310661651.4A CN202310661651A CN117107255A CN 117107255 A CN117107255 A CN 117107255A CN 202310661651 A CN202310661651 A CN 202310661651A CN 117107255 A CN117107255 A CN 117107255A
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derivatives
substituted phenol
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methylphenol
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王珊
何红英
陶炫佐
蒋春辉
陆鸿飞
郑绍军
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Jiangsu University of Science and Technology
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    • C25B3/00—Electrolytic production of organic compounds
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    • C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
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Abstract

The invention discloses a method for synthesizing para-substituted phenol derivatives, which takes p-methylphenol and derivatives thereof and beta-phenylketoacid and derivatives thereof as raw materials, and prepares the corresponding para-substituted phenol derivatives through one-step electrosynthesis reaction by stirring an easily obtained electrode under the conditions of room temperature, anhydrous sodium carbonate, mixed solvent of acetonitrile and deionized water and constant current under the mild condition of no metal catalyst and stoichiometric amount of redox reagent. The method has the advantages of low price, reaction at room temperature, mild reaction conditions, convenient way provided by oxidation of the p-methylphenol, and the obtained p-substituted phenol is a key structural motif of many natural products and pharmaceutical intermediates, simple and convenient synthesis operation, environmental friendliness, no need of special protection and wide industrial production prospect.

Description

Method for synthesizing p-substituted phenol derivative
Technical Field
The invention belongs to the field of synthesis of natural products and pharmaceutical intermediates, and particularly relates to a method for synthesizing p-substituted phenol derivatives.
Background
Phenol derivatives find wide application in the materials science, synthetic chemistry and pharmaceutical industry. In particular, para-substituted phenols are key structural motifs of many natural products. For example Pinocembrin chalcone (2 ',4',6' -Trihydroxychalcone), a pinocembrin chalcone, is widely available from the antibacterial compounds of helichrysum. Pinocembrin chalcone can be used for preventing gastric ulcers in rats, against T47D cytokines, and for treating immunosuppression and other immunodeficiency or autoimmune diseases. The Parthenocissina is originally isolated from a grape plant, namely, five-leaf climbing tiger (Parthenocissus quinquefolia), is a relatively common stilbene oligomer, is a natural polyphenol substance and has the strongest antitumor activity, and a large number of researches show that the stilbene oligomer has various biological activities, such as antitumor, antioxidant, anti-inflammatory, and treatment of some metabolic related diseases (such as glycolipid metabolic abnormality and the like), has a certain protection effect on ischemia reperfusion injury, neurodegenerative injury and cardiovascular and cerebrovascular diseases, and is also expected to be used for preventing diseases such as diabetes and coronary heart disease caused by excessive obesity. Therefore, the bottom-up assembly of para-substituted phenols has attracted considerable attention.
Oxidative cross-coupling of C-H/X-H (x=c, N, O, S, etc.) is considered an effective strategy because they do not require further substrate pre-functionalization. Para-methylphenol, in turn, is an ideal precursor for access to para-substituted phenol derivatives by oxidative cross-coupling. However, previous oxidative cross-coupling methods functionalize the C (sp 3 ) H depends to a large extent on the superstoichiometric amount of the oxidizing agent, such as copper salts or oxynones, which generates stoichiometric amounts of unwanted chemical waste, with the aim of saving resources, there is a great need to develop a green and environmentally friendly synthesis process which meets the production requirements.
Disclosure of Invention
In order to overcome the defects of superstoichiometric oxidant, complex operation, harsh reaction conditions and the like existing in the prior art for synthesizing para-substituted phenol derivatives, the invention provides a method for synthesizing the para-substituted phenol derivatives.
Method for synthesizing p-substituted phenol derivative by using p-methylphenol and its derivativeWith beta-phenyl-keto acid and derivatives thereof>Adding inorganic base into the raw materials under the condition of no metal catalyst and stoichiometric amount of oxidant, taking a mixed solvent of acetonitrile and deionized water as a reaction solvent, performing one-step electrosynthesis on the corresponding p-benzyl substituted phenol derivative under the condition of room temperature, drying with anhydrous sodium sulfate after the reaction is finished, performing suction filtration, washing a filter cake with dichloromethane, distilling the filtrate under reduced pressure to remove the solvent, and finally separating and purifying by column chromatography to obtain a purified product; wherein R is 1 Is a substituent on the ortho position of methylphenol and derivatives thereof; r is R 2 Is a substituent on the ortho position of methylphenol and derivatives thereof; r is R 3 Is unsubstituted or mono-substituent or di-substituent on ortho-position, meta-position and para-position of benzene ring of beta-keto acid and its derivative.
The reaction formula is as follows:
as an improvement, the inorganic base is anhydrous sodium carbonate, the phenol and the derivative thereof are 1 equivalent, and the addition amount of the inorganic base is 0.5 equivalent; the volume ratio of acetonitrile to deionized water in the mixed solvent of acetonitrile and deionized water is 3:1.
as an improvement, the R 1 Is CH 3 、OMe、C(CH 3 ) 3 Or Br, R 2 Is CH 3 、OMe、C(CH 3 ) 3 Or Br, R 3 Is H, alkyl, halogen, alkoxy, or naphthalene ring.
As an improvement, the molar ratio of the p-methylphenol and the derivatives thereof to the beta-phenyl keto acid and the derivatives thereof is 1:1-3.
Further improved is that the molar ratio of the p-methylphenol and the derivatives thereof to the beta-phenyl keto acid and the derivatives thereof is 1:2.
As an improvement, the electrode device for one-step electrosynthesis is a platinum sheet electrode (15 mm. Times.15 mm. Times.0.1 mm) and a carbon rod electrode (15 mm. Times.15 mm. Times.0.2 mm).
As an improvement, the constant current of the one-step electrosynthesis is 3mA.
As an improvement, the stirring speed is 300r/min.
As an improvement, the room temperature is 25 ℃.
The beneficial effects are that:
compared with the prior art, the method for synthesizing the p-substituted phenol derivative has the following advantages:
1. aiming at the synthesis process with low safety in the prior art, the invention has the advantages that the reaction equipment is simple, the reaction can be carried out only by an electrocatalytic device, a carbon electrode, a platinum sheet electrode, a stirring magnet and a three-neck flask, the reaction time is short, and the process is easy to amplify;
2. the reaction condition is mild, the reaction can be carried out at room temperature and in an atmospheric environment, heating and inert gas protection are not needed, and the production cost is reduced;
3. acetonitrile and deionized water are selected as reaction solvents, no catalyst or oxidant is added, the method is environment-friendly, few byproducts are produced in the reaction process, and the reaction products are easy to purify, high in yield, green and economic;
4. the yield of the target compound is high and reaches 50-77%.
Drawings
FIG. 1 is a nuclear magnetic resonance spectrum of the target product of example 1;
FIG. 2 is a nuclear magnetic resonance spectrum of the target product of example 1;
FIG. 3 is a nuclear magnetic resonance spectrum of the target product of example 2;
FIG. 4 is a nuclear magnetic resonance spectrum of the target product of example 2;
FIG. 5 is a nuclear magnetic resonance spectrum of the target product of example 3;
FIG. 6 is a nuclear magnetic resonance spectrum of the target product of example 3;
FIG. 7 is a nuclear magnetic resonance spectrum of the target product of example 4;
FIG. 8 is a nuclear magnetic resonance spectrum of the target product of example 4;
FIG. 9 is a nuclear magnetic resonance spectrum of the target product of example 5;
FIG. 10 is a nuclear magnetic resonance spectrum of the target product of example 5;
FIG. 11 is a nuclear magnetic resonance spectrum of the target product of example 6;
FIG. 12 is a nuclear magnetic resonance spectrum of the target product of example 6;
FIG. 13 is a nuclear magnetic resonance spectrum of the target product of example 7;
FIG. 14 is a nuclear magnetic resonance spectrum of the target product of example 7;
FIG. 15 is a nuclear magnetic resonance spectrum of the target product of example 8;
FIG. 16 is a nuclear magnetic resonance spectrum of the target product of example 8.
Detailed Description
The following describes the technical scheme of the present invention in detail by combining examples, and is not meant to limit the present invention. All the following reagents were commercially available, and the required acetonitrile, 2,4, 6-trimethylphenol, 2, 6-dibromo-4-methylphenol, 2, 6-di-t-butyl-4-methylphenol, 2, 6-dimethoxy-4-methylphenol, tetrahydrofuran, substituted methyl ketone, dimethyl carbonate and the like were purchased from An Naiji, allatin, leyan, taitan technologies and the like.
Beta-phenylketoacids can be synthesized from dimethyl carbonate by the corresponding commercial reagents substituted methyl ketones (j.am. Chem. Soc.,2007,129,11583)
Example 1
The electrocatalytic reaction was carried out in an unseparated cell, with the anode being a carbon rod (15 mm. Times.15 mm. Times.0.2 mm) and the cathode being a platinum sheet (15 mm. Times.15 mm. Times.0.1 mm). 2,4, 6-trimethylphenol 1a (54.48 mg,0.4 mmol), 3-oxo-3-phenylpropionic acid 2a (131.33 mg,0.8 mmol), anhydrous sodium carbonate (21.2 mg,0.2 mmol) were placed in a 10mL three-necked flask and dissolved in acetonitrile/H 2 O (3 mL/1 mL). The electrolysis was continued at a constant current of 3.0mA for 4 hours at room temperature. The electrode was then washed with DCM, the combined solvents were dried over anhydrous sodium sulfate, the solvents were distilled off under reduced pressure, and column chromatography (petroleum ether: ethyl acetate=10:1) gave 3aa 71mg of the product
3aa of para-substituted phenol derivative, yellow oily liquid, yield 70%.
1 H NMR(400MHz,Chloroform-d)δ7.97(dd,J＝8.4,1.3Hz,2H),7.61–7.52(m,1H),7.46(t,J＝7.5Hz,2H),6.87(s,2H),4.62(s,1H),3.30–3.22(m,2H),2.98–2.90(m,2H),2.23(s,6H). 13 C NMR(101MHz,Chloroform-d)δ199.72,150.64,137.03,133.16,132.96,128.72,128.64,128.20,123.19,41.08,29.43,16.05.
Example 2
The electrocatalytic reaction was carried out in an unseparated cell, with the anode being a carbon rod (15 mm. Times.15 mm. Times.0.2 mm) and the cathode being a platinum sheet (15 mm. Times.15 mm. Times.0.1 mm). 2,4, 6-trimethylphenol 1a (54.48 mg,0.4 mmol), 3- (4-methoxyphenyl) -3-oxopropanoic acid 2a (131.33 mg,0.8 mmol), anhydrous sodium carbonate (21.2 mg,0.2 mmol) were placed in a 10mL three-necked flask and dissolved in acetonitrile/H 2 O (3 mL/1 mL). Electrolysis was continued at room temperature for 4 hours at a constant current of 3.0 mA. The electrode was then washed with DCM, the combined solvent was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and column chromatography (petroleum ether: ethyl acetate=10:1) was performed to give 3ab 85mg of the product
Para-substituted phenol derivative 3ab, yellow oily liquid with 75% yield.
1 H NMR(400MHz,Chloroform-d)δ7.95(d,J＝9.0Hz,H),6.93(d,J＝8.9Hz,2H),6.86(s,2H),4.62(s,1H),3.87(s,3H),3.24–3.16(m,2H),2.96–2.88(m,2H),2.23(s,6H).
13 C NMR(101MHz,Chloroform-d)δ198.33,163.54,150.61,133.12,130.47,130.13,128.63,123.18,113.83,55.60,40.76,29.64,16.06.
Example 3
The electrocatalytic reaction was carried out in an unseparated cell, with the anode being a carbon rod (15 mm. Times.15 mm. Times.0.2 mm) and the cathode being a platinum sheet (15 mm. Times.15 mm. Times.0.1 mm). P-methylphenol derivative 1a (54.48 mg,0.4 mmol), beta-phenylpropionic acid 2a (142.45 mg,0.8 mmol), anhydrous sodium carbonate (21.2 mg,0.2 mmol) was placed in a 10mL three-necked flask and dissolved in acetonitrile/H 2 O (3 mL/1 mL). Electrolysis was continued at room temperature for 4 hours at a constant current of 3.0 mA. The electrode was then washed with DCM, the combined solvents were dried over anhydrous sodium sulfate, the solvents were distilled off under reduced pressure, and column chromatography (petroleum ether: ethyl acetate=10:1) gave 3ac 75mg of product.
Para-substituted phenol derivative 3ac yellow oily liquid with 70% yield.
1 H NMR(400MHz,Chloroform-d)δ7.61(dd,J＝8.0,1.4Hz,1H),7.36(td,J＝7.5,1.4Hz,1H),7.24(d,J＝5.0Hz,2H),6.83(s,2H),4.55(s,1H),3.23–3.13(t,2H),2.94–2.86(t,2H),2.47(s,3H),2.22(s,6H).
13 C NMR(101MHz,Chloroform-d)δ203.98,150.61,138.18,138.09,132.81,132.06,131.33,128.62,128.53,125.77,123.16,43.87,29.64,21.37,16.04.
Example 4
The electrocatalytic reaction was carried out in an unseparated cell, with the anode being a carbon rod (15 mm. Times.15 mm. Times.0.2 mm) and the cathode being a platinum sheet (15 mm. Times.15 mm. Times.0.1 mm). 2,4, 6-trimethylphenol 1a (54.48 mg,0.4 mmol), 3-oxo-3- (p-tolyl) propionic acid 2a (142.45 mg,0.8 mmol), anhydrous sodium carbonate (21.2 mg,0.2 mmol) were placed in a 10mL three-necked flask and dissolved in acetonitrile/H 2 O (3 mL/1 mL). Electrolysis was continued at room temperature for 4 hours at a constant current of 3.0 mA. The electrode was then washed with DCM, the combined solvent was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and column chromatography (petroleum ether: ethyl acetate=10:1) was performed to give 3ad 75mg of the product
Para-substituted phenol derivative 3ad, yellow oily liquid, yield 70%.
1 H NMR(400MHz,Chloroform-d)δ7.88(d,J＝8.3Hz,2H),7.27(s,1H),7.25(s,1H),6.87(s,2H),4.75(s,1H),3.28–3.19(m,2H),2.97–2.89(m,2H),2.42(s,3H),2.24(s,6H).
13 C NMR(101MHz,Chloroform-d)δ199.47,150.63,143.92,134.50,132.99,129.38,128.60,128.31,123.22,40.96,29.51,21.74,16.06.
Example 5
The electrocatalytic reaction was carried out in an unseparated cell, with the anode being a carbon rod (15 mm. Times.15 mm. Times.0.2 mm) and the cathode being a platinum sheet (15 mm. Times.15 mm. Times.0.1 mm). 2,4, 6-trimethylphenol 1a (54.48 mg,0.4 mmol), 3-oxo-3-phenylpropionic acid 2a (171.25 mg,0.8 mmol), anhydrous sodium carbonate (21.2 mg,0.2 mmol) were placed in a 10mL three-necked flask and dissolved in acetonitrile/H 2 O (3 mL/1 mL). Electrolysis was continued at room temperature for 4 hours at a constant current of 3.0 mA. The electrode was then washed with DCM, the combined solvents were dried over anhydrous sodium sulfate, the solvents were distilled off under reduced pressure, and column chromatography (petroleum ether: ethyl acetate=10:1) was performed to give 3ae 73mg of the product.
Para-substituted phenol derivative 3aa yellow oily liquid with 60% yield.
1 H NMR(400MHz,Chloroform-d)δ8.47(s,1H),8.05(dd,J＝8.6,1.8Hz,1H),7.94(d,J＝8.2Hz,1H),7.91–7.85(m,2H),7.64–7.51(m,2H),6.91(s,2H),4.75(s,1H),3.44–3.35(m,2H),3.05–2.96(m,2H),2.25(s,6H).
13 C NMR(101MHz,Chloroform-d)δ199.70,150.69,135.66,134.29,132.94,132.62,129.86,129.65,128.64,128.54,127.88,126.86,123.98,123.27,41.18,29.56,16.08.
Example 6
The electrocatalytic reaction was carried out in an unseparated cell, with the anode being a carbon rod (15 mm. Times.15 mm. Times.0.2 mm) and the cathode being a platinum sheet (15 mm. Times.15 mm. Times.0.1 mm). 2, 6-dimethoxy-4-methylphenol 1a (67.23 mg,0.4 mmol), 3-oxo-3-phenylpropionic acid 2a (131.33 mg,0.8 mmol), anhydrous sodium carbonate (21.2 mg,0.2 mmol) were dissolved in acetonitrile/H in a 10mL three-necked flask 2 O (3 mL/1 mL). Electrolysis was continued at room temperature for 4 hours at a constant current of 3.0 mA. The electrode was then washed with DCM, the combined solvents were dried over anhydrous sodium sulfate, the solvents were distilled off under reduced pressure, and column chromatography (petroleum ether: ethyl acetate=10:1) was performed to give 3af74 mg of the product.
Para-substituted phenol derivative 3af, yellow oily liquid, 65% yield.
1 H NMR(400MHz,Chloroform-d)δ7.95(dd,J＝8.5,1.4Hz,2H),7.58–7.53(m,1H),7.45(t,J＝7.6Hz,2H),6.46(s,2H),5.43(s,1H),3.86(s,6H),3.31–3.24(m,2H),3.00(d,J＝8.0Hz,2H). 13 C NMR(101MHz,Chloroform-d)δ199.56,147.08,136.97,133.21,133.08,132.50,128.72,128.13,105.10,56.35,40.95,30.54.
Example 7
The electrocatalytic reaction was carried out in an unseparated cell, with the anode being a carbon rod (15 mm. Times.15 mm. Times.0.2 mm) and the cathode beingPlatinum sheet (15 mm. Times.15 mm. Times.0.1 mm). 2-tert-butyl-4, 6-dimethylphenol 1a (71.26 mg,0.4 mmol), 3-oxo-3-phenylpropionic acid 2a (131.33 mg,0.8 mmol), anhydrous sodium carbonate (21.2 mg,0.2 mmol) were placed in a 10mL three-necked flask and dissolved in acetonitrile/H 2 O (3 mL/1 mL). Electrolysis was continued at room temperature for 4 hours at a constant current of 3.0 mA. The electrode was then washed with DCM, the combined solvent was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and column chromatography (petroleum ether: ethyl acetate=10:1) was performed to give 3ag 71mg of the product
Para-substituted phenol derivative 3ag, yellow oily liquid, 60% yield.
1 H NMR(400MHz,Chloroform-d)δ7.98(dd,J＝8.4,1.4Hz,2H),7.59–7.54(m,1H),7.47(tt,J＝6.7,1.4Hz,2H),7.02(d,J＝2.3Hz,1H),6.91(d,J＝2.1Hz,1H),4.79(s,1H),3.31–3.26(m,2H),3.01–2.96(m,2H),2.25(s,3H),1.42(s,9H).
13 C NMR (101 MHz, chloroform-d) delta 199.93,151.13,137.03,135.85,133.13,132.42,128.69,128.57-128.31 (m), 128.20,125.41-124.93 (m), 123.26,41.16,34.62,29.90,29.87,16.15. Example 8
The electrocatalytic reaction was carried out in an unseparated cell, with the anode being a carbon rod (15 mm. Times.15 mm. Times.0.2 mm) and the cathode being a platinum sheet (15 mm. Times.15 mm. Times.0.1 mm). 2,4, 6-trimethylphenol 1a (54.48 mg,0.4 mmol), 3- (3, 4-dimethoxyphenyl) -3-oxopropionic acid 2a (179.37 mg,0.8 mmol), anhydrous sodium carbonate (21.2 mg,0.2 mmol) were placed in a 10mL three-necked flask and dissolved in acetonitrile/H 2 O (3 mL/1 mL). Electrolysis was continued at room temperature for 4 hours at a constant current of 3.0 mA. The electrode was then washed with DCM, the combined solvent was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and column chromatography (petroleum ether: ethyl acetate=10:1) was performed to give 3ah of the product 3ah 90mg of para-substituted phenol derivative 3ah as a dark yellow oily liquid in 77% yield.
1 H NMR(400MHz,Chloroform-d)δ7.58(dd,J＝8.4,2.0Hz,1H),7.52(d,J＝2.0Hz,1H),6.87(s,1H),6.86(s,2H),4.57(s,1H),3.93(s,3H),3.92(s,3H),3.23–3.16(m,2H),2.95–2.87(m,2H),2.22(s,6H).
13 C NMR(101MHz,Chloroform-d)δ198.36,153.29,150.63,149.09,133.08,130.26,128.63,123.18,122.79,110.22(d,J＝5.6Hz),110.08,56.14,40.66,29.75,16.06.。
In the foregoing, the protection scope of the present invention is not limited to the preferred embodiments of the present invention, and any simple changes or equivalent substitutions of the technical solutions that can be obviously obtained by those skilled in the art within the technical scope of the present invention disclosed in the present invention fall within the protection scope of the present invention.

Claims (9)

1. A process for synthesizing p-substituted phenol derivative features that p-methylphenol and its derivativeWith beta-phenyl-keto acid and derivatives thereof>Adding inorganic base and a mixed solvent of acetonitrile and deionized water as a reaction solvent under the condition of no metal catalyst and stoichiometric amount of oxidant, performing one-step electrosynthesis on the corresponding p-benzyl substituted phenol derivative at room temperature, drying with anhydrous sodium sulfate after the reaction is finished, performing suction filtration, washing a filter cake with dichloromethane, distilling the filtrate under reduced pressure to remove the solvent, and finally performing column chromatography separation and purification to obtain a purified product; wherein R is 1 Is a substituent on the ortho position of methylphenol and derivatives thereof; r is R 2 Is a substituent on the ortho position of methylphenol and derivatives thereof; r is R 3 Is unsubstituted or mono-substituent or di-substituent on ortho-position, meta-position and para-position of benzene ring of beta-keto acid and its derivative.
2. The method for synthesizing p-substituted phenol derivatives according to claim 1, wherein the inorganic base is anhydrous sodium carbonate, and phenol and its derivatives are 1 equivalent, and the addition amount of the inorganic base is 0.5 equivalent; the volume ratio of acetonitrile to deionized water in the mixed solvent of acetonitrile and deionized water is 3:1.
3. a method for synthesizing p-substituted phenol derivatives according to claim 1, wherein R is 1 Is CH 3 、OMe、C(CH 3 ) 3 Or Br, R 2 Is CH 3 、OMe、C(CH 3 ) 3 Or Br, R 3 Is H, alkyl, halogen, alkoxy, or naphthalene ring.
4. The method of synthesizing para-substituted phenol derivatives according to claim 1, wherein the molar ratio of para-methylphenol and its derivatives to beta-phenylpropionic acid and its derivatives is 1:1-3.
5. The method of synthesizing para-substituted phenol derivatives according to claim 4, wherein the molar ratio of para-methylphenol and derivatives thereof to beta-phenylpropionic acid and derivatives thereof is 1:2.
6. The method for synthesizing p-substituted phenol derivatives according to claim 1, wherein the electrode means for one-step electrosynthesis are a platinum sheet electrode and a carbon rod electrode.
7. The method for synthesizing a p-substituted phenol derivative according to claim 1, wherein the constant current of the one-step electrosynthesis is 3mA.
8. The method for synthesizing a p-substituted phenol derivative according to claim 1, wherein the stirring speed is 300r/min.
9. A method of synthesizing a para-substituted phenol derivative according to claim 1 wherein said room temperature is 25 ℃.
CN202310661651.4A 2023-06-06 2023-06-06 Method for synthesizing p-substituted phenol derivative Pending CN117107255A (en)

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