CN107324976B - Method for preparing (E) - β -alkyl styrene compound - Google Patents
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Abstract
The invention discloses a method for preparing (E) - β -alkyl styrene compounds, which comprises the following steps of dissolving cinnamic acid compounds and aliphatic aldehyde compounds in chlorobenzene solvents, adding cuprous iodide and di-tert-butyl peroxide, reacting for 24 hours at 130 ℃, extracting and separating by column chromatography after the reaction is finished to obtain (E) - β -alkyl styrene compounds.
Description
Technical Field
The invention belongs to the field of organic synthesis chemistry, and relates to a method for synthesizing (E) - β -alkyl styrene compounds, in particular to a method for preparing (E) - β -alkyl styrene compounds by catalyzing a cinnamic acid compound and an aliphatic aldehyde compound by copper salt in the presence of an oxidant through decarboxylation and decarbonylation cross-coupling reaction.
Background
(E) β -alkylstyrene compound itself has obvious biological activity, and the double bond in the structure is easy to generate reactions such as conjugate addition and hydrogenation reduction, so (E) - β -alkylstyrene compound is an important synthetic intermediate in the field of organic synthesis, and it has wide application in other industrial fields, so its synthetic method is receiving attention, the traditional methods for preparing (E) - β -alkylstyrene compound through decarboxylation coupling reaction using cinnamic acid compound as reaction raw material are mainly (chem.1) 2012, maojinchening et al report that under the catalysis of copper salt and di-tert-butyl peroxide, the decarboxylation cross-coupling reaction of cinnamic acid compound and benzyl hydride compound under the catalysis of copper salt and the decarboxylation cross-coupling reaction of cinnamic acid compound to obtain (E) - β -benzylstyrene product (chem.commu.48, 7847, 2013-benzylbenzene carboxylic acid compound and benzyl hydrogen compound under the catalysis of di-tert-butyl persulfate, the reaction of cinnamic acid compound and benzyl hydrogen compound under the catalysis of di-tert-butyl persulfate, (2013) is under the catalysis of two kinds of alkyl benzene carboxylic acid compound, no limitation, the reaction, no limitation of reaction between aliphatic carboxylic acid compound and benzyl alcohol compound, No. 2, no more than two kinds of benzyl alcohol compound, No. 2, no limitation, No. 2, no mention that under the reaction of alkyl benzene carboxylic acid compound and No. 2, No. 2.
Therefore, there remains a need to develop and optimize new processes for the preparation of (E) - β -alkylstyrene compounds.
Disclosure of Invention
The invention mainly aims to provide a method for preparing (E) - β -alkylstyrene compounds aiming at the defects and shortcomings of the prior art, the method utilizes cinnamic acid compounds and aliphatic aldehyde compounds as raw materials, and generates (E) - β -alkylstyrene compounds by heating in chlorobenzene for decarboxylation and decarbonylation cross-coupling reaction.
The synthetic route principle of the invention is as follows:
wherein R is1Represented by H, or halogen atoms such as fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl and nitro, and the substituents can be substituted at ortho, meta, para and multi-positions of a benzene ring; r2Is represented by H or is C1～C5Straight chain alkyl radical, C2～C5Branched alkyl radical, C3～C6Cycloalkyl, phenyl, benzyl; r3Is represented by H or is C1～C5Straight chain alkyl radical, C2～C5Branched alkyl radical, C3～C6Cycloalkyl, phenyl, benzyl; r4Is represented by H or is C1～C5Straight chain alkyl radical, C2～C5Branched alkyl radical, C3～C6Cycloalkyl, phenyl, benzyl.
In order to achieve the purpose, the invention adopts the following technical scheme for synthesizing the compound:
sequentially adding a cinnamic acid compound 1, a fatty aldehyde compound 2, copper salt, an oxidant and an organic solvent into a pressure pipe, sealing the pressure pipe, placing the sealed pressure pipe in an oil bath for heating reaction, taking the pressure pipe out of the oil bath after the reaction is completed, cooling to room temperature, and performing rapid column chromatography separation to obtain the (E) - β -alkylstyrene compound 3.
The cupric salt in the method is one of cuprous chloride, cuprous bromide, cupric bromide, cuprous iodide, cupric iodide, cuprous oxide, cupric carbonate, cupric pentahydrate, cupric acetate dihydrate and cupric chloride dihydrate, wherein the cuprous iodide is preferably used as the reaction catalyst.
The oxidant in the method is one of di-tert-butyl peroxide, benzoyl peroxide, dicumyl peroxide and tert-butyl hydroperoxide, wherein the di-tert-butyl peroxide is preferably used as the reaction oxidant.
The organic solvent in the method is one of acetonitrile, dimethyl sulfoxide, N-dimethylformamide, chlorobenzene, water and dichloromethane, wherein chlorobenzene is preferably used as the reaction solvent.
The dosage of the copper salt catalyst in the method is 10 mol% of the reactant cinnamic acid compound 1.
The temperature of the heating reaction in the oil bath in the above method is preferably 130 degrees centigrade, and the reaction time is preferably 24 hours.
The ratio of the cinnamic acid compound 1, the fatty aldehyde compound 2, the copper salt and the oxidant in the method is 1:2:0.1: 2.
Compared with the route of the prior art, the invention has the following advantages:
(1) the method has the advantages of wide substrate application range, mild reaction conditions, simple post-treatment process and high product yield.
(3) Provides a simple and efficient method which is superior to the method for preparing the (E) - β -alkyl styrene compound by catalyzing the decarboxylation and the decarbonylation cross-coupling reaction of the cinnamic acid compound and the fatty aldehyde compound by the copper salt reported in the prior literature.
Detailed Description
The invention is described in further detail with reference to specific examples, but the scope of the invention as claimed is not limited thereto.
Example 1 was carried out: 0.089g (0.5mmol) of p-methoxycinnamic acid 1a, 0.12g (1.0mmol) of phenylacetaldehyde 2a, 0.005g (0.05mmol) of copper chloride, 0.146g (1.0mmol) of di-tert-butyl peroxide and 2mL of chlorobenzene are sequentially added into a 10mL thick-walled pressure-resistant tube, and the mixture is magnetically stirred and reacted for 24 hours in an oil bath at 130 ℃, and the reaction progress is monitored by TLC. After the reaction, column chromatography separation is carried out to obtain petroleum ether (60-90℃)]To obtain (E) - β -benzyl p-methoxystyrene 3aa as pale yellow liquid 79mg with a yield of 70%.1H NMR(500Hz,CDCl3)(δ,ppm)7.37-7.29(m,7H),6.88(d,J＝5.0Hz,2H),6.45(d,J＝15.0Hz,1H),6.30-6.25(m,1H),3.85(s,3H),3.58(d,J＝10.0Hz,2H)；13C NMR(125Hz,CDCl3)(δ,ppm)158.9,140.5,130.5,130.4,128.7,128.5,127.2,127.1,126.1,114.0,55.3,39.3；HRMS,ESI(m/z):calcd for C16H15O[M-H]-223.1123; 223.1127 the reaction principle for carrying out example 1 is as follows:
example 2. 0.089g (0.5mmol) of p-methoxycinnamic acid 1a, 0.12g (1.0mmol) of phenylacetaldehyde 2a, 0.006g (0.05mmol) of copper carbonate, 0.146g (1.0mmol) of di-tert-butyl peroxide and 2mL of chlorobenzene were sequentially added to a 10mL thick-walled pressure-resistant tube, and the mixture was reacted in an oil bath at 130 ℃ for 24 hours with magnetic stirring, and the progress of the reaction was monitored by TLC.after the completion of the reaction, column chromatography [ petroleum ether (60-90 ℃) ]wasperformed to obtain (E) - β -benzyl p-methoxystyrene 3, and aa liquid 74mg was pale yellow, and the yield was 66%. the reaction principle of example 2 was as follows:
example 3.0.089 g (0.5mmol) of p-methoxycinnamic acid 1a, 0.12g (1.0mmol) of phenylacetaldehyde 2a, 0.004g (0.05mmol) of copper oxide, 0.146g (1.0mmol) of di-tert-butyl peroxide and 2mL of chlorobenzene are sequentially added into a 10mL thick-walled pressure-resistant tube, and the mixture is magnetically stirred for 24 hours in an oil bath at 130 ℃ to be reacted, and the reaction progress is monitored by TLC (thin-layer chromatography) (petroleum ether (60-90 ℃) is separated by column chromatography after the reaction is finished to obtain (E) - β -benzyl p-methoxystyrene 3, wherein the aa liquid is 77mg, the yield is 69 percent, and the reaction principle of the example 3 is as follows:
example 4 0.089g (0.5mmol) of p-methoxycinnamic acid 1a, 0.12g (1.0mmol) of phenylacetaldehyde 2a, 0.009g (0.05mmol) of copper acetate, 0.146g (1.0mmol) of di-tert-butyl peroxide and 2mL of chlorobenzene were sequentially added into a 10mL thick-walled pressure-resistant tube, and the mixture was magnetically stirred for 24 hours in an oil bath at 130 ℃ to monitor the progress of the reaction by TLC, and after the completion of the reaction, column chromatography [ petroleum ether (60-90 ℃) ] was performed to obtain (E) - β -benzyl p-methoxystyrene 3, which was 68mg of an aa liquid and had a yield of 61%. the reaction principle of example 4 was as follows:
example 5 0.089g (0.5mmol) of p-methoxycinnamic acid 1a, 0.12g (1.0mmol) of phenylacetaldehyde 2a, 0.009g (0.05mmol) of cuprous iodide, 0.146g (1.0mmol) of di-tert-butyl peroxide and 2mL of chlorobenzene were sequentially added into a 10mL thick-walled pressure-resistant tube, and the mixture was magnetically stirred for 24 hours in an oil bath at 130 ℃ to monitor the progress of the reaction by TLC, and after the completion of the reaction, column chromatography [ petroleum ether (60-90 ℃) ], to obtain (E) - β -benzyl p-methoxystyrene 3, 91mg of aa liquid, and the yield was 81%. the reaction principle of example 5 was as follows:
example 6.0.089 g (0.5mmol) of p-methoxycinnamic acid 1a, 0.12g (1.0mmol) of phenylacetaldehyde 2a, 0.009g (0.05mmol) of cuprous iodide, 0.242g (1.0mmol) of benzoyl peroxide and 2mL of chlorobenzene were sequentially added into a 10mL thick-walled pressure-resistant tube, and the mixture was magnetically stirred for 24 hours in an oil bath at 130 ℃ to monitor the progress of the reaction, and after the reaction was completed, column chromatography was performed [ petroleum ether (60-90 ℃) ], to obtain (E) - β -benzyl p-methoxystyrene 3, which was a pale yellow liquid 39mg, with a yield of 35%. the reaction principle of example 6 was as follows:
example 7.0.089 g (0.5mmol) of p-methoxycinnamic acid 1a, 0.12g (1.0mmol) of phenylacetaldehyde 2a, 0.009g (0.05mmol) of cuprous iodide, 0.09g (1.0mmol) of tert-butyl hydroperoxide and 2mL of chlorobenzene were sequentially added to a 10mL thick-walled pressure-resistant tube, and the mixture was reacted in an oil bath at 130 ℃ for 24 hours with magnetic stirring, and the progress of the reaction was monitored by TLC.after the reaction was completed, column chromatography was performed [ petroleum ether (60-90 ℃ C.) ], to obtain (E) - β -benzyl p-methoxystyrene 3aa, light yellow liquid 63mg, and yield 56%. the reaction principle of example 7 was as follows:
example 8 0.089g (0.5mmol) of p-methoxycinnamic acid 1a, 0.12g (1.0mmol) of phenylacetaldehyde 2a, 0.009g (0.05mmol) of cuprous iodide, 0.146g (1.0mmol) of di-tert-butyl peroxide and 2mL of acetonitrile were sequentially added to a 10mL thick-walled pressure-resistant tube, and the mixture was magnetically stirred in an oil bath at 130 ℃ for 24 hours to monitor the progress of the reaction by TLC, after the completion of the reaction, column chromatography [ petroleum ether (60-90 ℃) ]) was performed to obtain (E) - β -benzyl p-methoxystyrene 3, which was a pale yellow liquid 39mg, in a yield of 35%. the reaction principle of example 8 was as follows:
example 9 0.089g (0.5mmol) of p-methoxycinnamic acid 1a, 0.12g (1.0mmol) of phenylacetaldehyde 2a, 0.009g (0.05mmol) of cuprous iodide, 0.146g (1.0mmol) of di-tert-butyl peroxide and 2mL of dimethyl sulfoxide were sequentially added into a 10mL thick-walled pressure-resistant tube, and the mixture was reacted in an oil bath at 130 ℃ for 24 hours with magnetic stirring, and the progress of the reaction was monitored by TLC.after the reaction was completed, column chromatography was performed [ petroleum ether (60-90 ℃) ], to obtain (E) - β -benzyl p-methoxystyrene 3aa, which was a pale yellow liquid 30mg, with a yield of 27%. the reaction principle of example 9 was as follows:
example 10.0.089 g (0.5mmol) of p-methoxycinnamic acid 1a, 0.12g (1.0mmol) of phenylacetaldehyde 2a, 0.009g (0.05mmol) of cuprous iodide, 0.146g (1.0mmol) of di-tert-butyl peroxide and 2mL of dichloromethane were sequentially added to a 10mL thick-walled pressure-resistant tube, and the mixture was magnetically stirred in an oil bath at 130 ℃ for 24 hours to monitor the progress of the reaction by TLC, after the completion of the reaction, column chromatography [ petroleum ether (60-90 ℃) ], to obtain (E) - β -benzyl p-methoxystyrene 3, 34mg of aa liquid, with a yield of 30%. the reaction principle of example 9 was as follows:
example 11 of implementation: 0.074g (0.5mmol) of cinnamic acid 1b, 0.12g (1.0mmol) of phenylacetaldehyde 2a, 0.009g (0.05mmol) of cuprous iodide, 0.146g (1.0mmol) of di-tert-butyl peroxide and 2mL of chlorobenzene were sequentially added to a 10mL thick-walled pressure-resistant tube, and the reaction was magnetically stirred for 24 hours in an oil bath at 130 ℃ and the progress of the reaction was monitored by TLC. After the reaction, column chromatography separation is carried out to obtain petroleum ether (60-90℃)]To give (E) - β -benzylstyrene 3ba as a pale yellow liquid 81mg with a yield of 83%.1H NMR(500Hz,CDCl3)(δ,ppm)7.43(d,J＝10.0Hz,2H),7.39-7.36(m,3H),7.31(t,J＝10.0Hz,3H),7.28(d,J＝10.0Hz,2H),6.53(d,J＝15.0Hz,1H),6.46-6.41(m,1H),3.62(d,J＝5.0Hz,2H)；13C NMR(125Hz,CDCl3)(δ,ppm)140.2,137.6,131.1,129.3,128.7,128.5,127.2,126.2,126.1,39.4；HRMS ESI(m/z):calcd for C15H13[M-H]-193.1017; found,193.0963 the reaction principle for carrying out example 11 is as follows:
example 12 of implementation: 0.083g (0.5mmol) of p-fluorocinnamic acid 1c, 0.12g (1.0mmol) of phenylacetaldehyde 2a, 0.009g (0.05mmol) of cuprous iodide, 0.146g (1.0mmol) of di-tert-butyl peroxide and 2mL of chlorobenzene are sequentially added into a 10mL thick-walled pressure-resistant tube, and the mixture is magnetically stirred for reaction for 24 hours in an oil bath at 130 ℃, and the progress of the reaction is monitored by TLC. After the reaction, column chromatography separation is carried out to obtain petroleum ether (60-90℃)]To give (E) - β -benzyl p-fluorostyrene 3ca as a pale yellow liquid (88 mg), yield 83%.1H NMR(500Hz,CDCl3)(δ,ppm)7.39-7.35(m,4H),7.31-7.28(m,3H),7.03(t,J＝10.0Hz,2H),6.46(d,J＝15.0Hz,1H),6.36-6.30(m,1H),3.59(d,J＝5.0Hz,2H)；13C NMR(125Hz,CDCl3)(δ,ppm)163.1,161.1,140.1,133.7,133.6,129.9,128.7,128.5,127.6,127.5,126.3,115.5,115.3,39.3；HRMS ESI(m/z):calcd for C15H12F[M-H]-211.0923; found,211.0919 implementation of the reaction principle of example 12The following formula:
example 13: 0.091g (0.5mmol) of m-chlorocinnamic acid 1d, 0.12g (1.0mmol) of phenylacetaldehyde 2a, 0.009g (0.05mmol) of cuprous iodide, 0.146g (1.0mmol) of di-tert-butyl peroxide and 2mL of chlorobenzene are sequentially added into a 10mL thick-wall pressure-resistant tube, and the mixture is magnetically stirred and reacted for 24h under the condition of 130 ℃ in an oil bath, and the reaction progress is monitored by TLC. After the reaction, column chromatography separation is carried out to obtain petroleum ether (60-90℃)]To give (E) - β -benzyl m-chlorostyrene 3da in 80% yield as a pale yellow liquid 91 mg.1H NMR(500Hz,CDCl3)(δ,ppm)7.57-7.55(m,1H),7.40-7.36(m,3H),7.32-7.28(m,3H),7.27-7.19(m,2H),6.92(d,J＝15.0Hz,1H),6.42-6.36(m,1H),3.65(d,J＝5.0Hz,2H)；13C NMR(125Hz,CDCl3)(δ,ppm)139.9,135.6,132.8,132.1,129.6,128.7,128.6,128.2,127.4,126.8,126.7,126.3,39.6；HRMS ESI(m/z):calcd for C16H12Cl[M-H]-227.0627; found,227.0624 the reaction principle for carrying out example 13 is as follows:
example 14 was carried out: 0.108g (0.5mmol) of o-trifluoromethyl cinnamic acid 1e, 0.12g (1.0mmol) of phenylacetaldehyde 2a, 0.009g (0.05mmol) of cuprous iodide, 0.146g (1.0mmol) of di-tert-butyl peroxide and 2mL of chlorobenzene are sequentially added into a 10mL thick-walled pressure-resistant tube, and the mixture is magnetically stirred for reaction for 24 hours in an oil bath at 130 ℃, and the reaction progress is monitored by TLC. After the reaction, column chromatography separation is carried out to obtain petroleum ether (60-90℃)]To obtain (E) - β -benzyl o-trifluoromethylstyrene 3ea as a pale yellow liquid (110 mg) with a yield of 84%.1H NMR(500Hz,CDCl3)(δ,ppm)7.69-7.65(m,2H),7.51(t,J＝5.0Hz,1H),7.40-7.35(m,3H),7.32-7.28(m,3H),6.93(d,J＝15.0Hz,1H),6.41-6.35(m,1H),3.65(d,J＝5.0Hz,2H)；13C NMR(125Hz,CDCl3)(δ,ppm)139.7,136.7,133.6,131.8,128.7,128.6,127.4,127.3,126.9,126.6,126.4,125.7,125.6,39.6；HRMS ESI(m/z):calcd forC16H13F3[M-H]-261.0891; found,261.0887 the reaction principle for carrying out example 14 is as follows:
example 15 of implementation: 0.089g (0.5mmol) of p-methoxycinnamic acid 1a, 0.072g (1.0mmol) of isobutyraldehyde 2b, 0.009g (0.05mmol) of cuprous iodide, 0.146g (1.0mmol) of di-tert-butyl peroxide and 2mL of chlorobenzene are sequentially added into a 10mL thick-wall pressure-resistant tube, and are magnetically stirred for reaction for 24 hours in an oil bath at 130 ℃, and the reaction progress is monitored by TLC. After the reaction, column chromatography separation is carried out to obtain petroleum ether (60-90℃)]To obtain (E) - β -isopropyl-p-methoxystyrene 3ab as a pale yellow liquid (62 mg) with a yield of 70%.1H NMR(500Hz,CDCl3)(δ,ppm)7.32(t,J＝5.0Hz,2H),6.88(d,J＝10.0Hz,2H),6.32(d,J＝15.0Hz,1H),6.12-6.08(m,1H),3.84(s,3H),2.51-2.47(m,1H),1.12(d,J＝5.0Hz,6H)；13C NMR(125Hz,CDCl3)(δ,ppm)158.6,136.0,130.8,127.0,126.2,113.9,55.3,31.5,22.6；HRMS ESI(m/z):calcd for C12H15O[M-H]-175.1123; found,175.1119 the reaction principle for carrying out example 15 is as follows:
example 16: 0.089g (0.5mmol) of p-methoxycinnamic acid 1a, 0.100g (1.0mmol) of n-hexanal 2c, 0.009g (0.05mmol) of cuprous iodide, 0.146g (1.0mmol) of di-tert-butyl peroxide and 2mL of chlorobenzene are sequentially added into a 10mL thick-wall pressure-resistant tube, and are magnetically stirred for reaction for 24 hours in an oil bath at 130 ℃, and the reaction progress is monitored by TLC. After the reaction, column chromatography separation is carried out to obtain petroleum ether (60-90℃)]To give (E) - β -n-pentyl p-methoxystyrene 3ac as a pale yellow liquid (56 mg) in 55% yield.1H NMR(500Hz,CDCl3)(δ,ppm)7.31(d,J＝2.0Hz,2H),6.88(d,J＝10.0Hz,2H),6.36(d,J＝15.0Hz,1H),6.16-6.11(m,1H),3.84(s,3H),2.23-2.18(m,2H),1.55-1.50(m,2H),0.99(t,J＝5.0Hz,3H)；13C NMR(125Hz,CDCl3)(δ,ppm)158.7,130.9,129.2,128.9,127.0,113.9,55.3,35.1,22.7,13.7；HRMS ESI(m/z):calcd for C16H15O[M-H]-175.1123; found,175.1122 the reaction principle for carrying out example 16 is as follows:
example 17: 0.089g (0.5mmol) of p-methoxycinnamic acid 1a, 0.086g (1.0mmol) of pivalaldehyde 2d, 0.009g (0.05mmol) of cuprous iodide, 0.146g (1.0mmol) of di-tert-butyl peroxide and 2mL of chlorobenzene are sequentially added into a 10mL thick-walled pressure-resistant tube, and the mixture is magnetically stirred for reaction for 24 hours in an oil bath at 130 ℃, and the reaction progress is monitored by TLC. After the reaction, column chromatography separation is carried out to obtain petroleum ether (60-90℃)]To give (E) - β -tert-butyl p-methoxystyrene 3ad as a pale yellow liquid (167 mg) in 88% yield.1H NMR(500Hz,CDCl3)(δ,ppm)7.29(d,J＝2.0Hz,2H),6.82(d,J＝7.5Hz,2H),6.25(d,J＝15.0Hz,1H),6.12(d,J＝15.0Hz,1H),3.78(s,3H),1.09(s,9H)；13C NMR(125Hz,CDCl3)(δ,ppm)158.7,139.8,130.8,127.0,123.8,113.9,55.3,33.2,29.7；HRMS ESI(m/z):calcd for C13H17O[M-H]-189.1279; found,189.1273 the reaction principle for carrying out example 17 is as follows:
Claims (7)
1. a method for preparing (E) - β -alkyl styrene compounds is characterized by comprising the following steps of dissolving cinnamic acid compounds 1 and aliphatic aldehyde compounds 2 in an organic solvent, adding a copper compound catalyst and an oxidant, heating for reaction for 24 hours, extracting after the reaction is finished, and separating by column chromatography to obtain decarboxylation and decarbonylation cross-coupling products (E) - β -alkyl styrene compounds 3, wherein the reaction formula is as follows:
wherein R is1Represented by H, or halogen atoms such as fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl and nitro, and the substituents can be substituted at ortho, meta, para and multi-positions of a benzene ring; r2Is represented by H or is C1～C5Straight chain alkyl radical, C2～C5Branched alkyl radical, C3～C6Cycloalkyl, phenyl, benzyl; r3Is represented by H or is C1～C5Straight chain alkyl radical, C2～C5Branched alkyl radical, C3～C6Cycloalkyl, phenyl, benzyl; r4Is represented by H or is C1～C5Straight chain alkyl radical, C2～C5Branched alkyl radical, C3～C6Cycloalkyl, phenyl, benzyl. The copper compound catalyst is cuprous chloride, or one of cuprous bromide, cupric carbonate, cupric acetate, cuprous oxide, cupric oxide and cuprous iodide. The oxidant is di-tert-butyl peroxide, or one of benzoyl peroxide, dicumyl peroxide and tert-butyl hydroperoxide.
2. The process for synthesizing (E) - β -alkylstyrene compound 3 according to claim 1, wherein cuprous iodide is preferably used as the reaction catalyst.
3. The process for synthesizing (E) - β -alkylstyrene compound 3 according to claim 1, wherein di-tert-butyl peroxide is preferred as the reaction oxidizing agent.
4. The method for synthesizing (E) - β -alkylstyrene compound 3 according to claim 1, wherein the organic solvent is one of acetonitrile, dimethylsulfoxide, chlorobenzene, and dichloromethane.
5. The method for synthesizing (E) - β -alkylstyrene compound 3 according to claim 1, wherein the amount of the copper compound catalyst is 10 mol% of the reactant cinnamic acid compound 1.
6. The method for synthesizing (E) - β -alkylstyrene compound 3 according to claim 1, wherein the heating reaction temperature is 130 ℃ and the reaction time is 24 hours.
7. The method for synthesizing (E) - β -alkylstyrene compound 3 according to claim 1, wherein the mass ratio of cinnamic acid compound 1, aliphatic aldehyde compound 2, copper compound and oxidant is 1:2:0.1: 2.
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| CN (1) | CN107324976B (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1194674C (en) * | 1999-05-18 | 2005-03-30 | 卡里克斯治疗公司 | Novel stilbene compounds |
| CN102614927A (en) * | 2012-03-15 | 2012-08-01 | 苏州大学 | Copper catalyst system for decarboxylation coupling reaction |
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2017
- 2017-07-28 CN CN201710627981.6A patent/CN107324976B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1194674C (en) * | 1999-05-18 | 2005-03-30 | 卡里克斯治疗公司 | Novel stilbene compounds |
| CN102614927A (en) * | 2012-03-15 | 2012-08-01 | 苏州大学 | Copper catalyst system for decarboxylation coupling reaction |
Non-Patent Citations (2)
| Title |
|---|
| Iron-catalyzed direct alkenylation of sp3(C–H) bonds via decarboxylation of cinnamic acids under ligand-free conditions;Hailong Yang等;《Green Chemistry》;20130205;第15卷(第4期);976-981 * |
| 过渡金属催化烷基羧酸的脱羧偶联反应研究进展;戴建军等;《有机化学》;20130829;第33卷(第12期);2460-2468 * |
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