CN104447396A - Benzoin oxime derivative and preparation method thereof - Google Patents

Benzoin oxime derivative and preparation method thereof Download PDF

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CN104447396A
CN104447396A CN201410728358.6A CN201410728358A CN104447396A CN 104447396 A CN104447396 A CN 104447396A CN 201410728358 A CN201410728358 A CN 201410728358A CN 104447396 A CN104447396 A CN 104447396A
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preparation
derivative
benzoinoxime
ethyl acetate
compound
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CN104447396B (en
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胡益民
潘相相
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Anhui Normal University
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Anhui Normal University
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Abstract

The invention relates to a benzoin oxime derivative and a preparation method thereof. A structural formula of the benzoin oxime derivative is shown in the specification. The preparation method comprises the following steps: reacting malonate with propargyl bromide in anhydrous acetonitrile under the catalysis of sodium hydride to obtain a white solid product; by taking triethylamine as alkali, reacting the white solid product with phenylethynyl bromine or substituted phenylethynyl bromine in anhydrous acetonitrile under the catalysis of Pd(PPh3)2Cl2/CuI to obtain a light brown solid product; reacting the light brown solid product with benzoin oxime in toluene at 95-105 DEG C to obtain the benzoin oxime derivative. A brand new synthetic method of polysubstituted benzoin oxime is provided, and a series of new benzoin oxime derivatives are generated. Compared with normal benzoin oxime derivatives, the benzoin oxime derivative prepared by virtue of the preparation method has relatively complex and diverse structures by virtue of multiple cycles, and presents relatively wide application prospects in chemical industry production and clinic medicines.

Description

A kind of α-benzoinoxime derivative and preparation method thereof
Technical field
The present invention relates to organic compound field, be specifically related to a kind of α-benzoinoxime derivative and preparation method thereof.
Background technology
St-yrax, α-benzoinoxime and derivative thereof are widely used in industrial production and scientific research, such as st-yrax, α-benzoinoxime and derivative thereof are the important intermediates of organic synthesis and fine chemistry industry, are widely used in the fields such as chemical industry, medicine, spices, sequestrant, coating.In view of the special significance of st-yrax, α-benzoinoxime and derivative thereof, how to go the synthesis path expanding α-benzoinoxime and derivative thereof to cause countless organic synthesis man and chemist actively thinks deeply, and draw some effectively methods.
Common st-yrax, α-benzoinoxime synthetic method have:
One, with sodium cyanide, potassium cyanide for catalyzer:
With sodium cyanide, potassium cyanide for catalyzer, the intermolecular generation condensation of phenyl aldehyde generates st-yrax, recycling st-yrax reacts obtained α-benzoinoxime under the effect of alkali Anhydrous potassium carbonate with oxammonium hydrochloride, but sodium cyanide, potassium cyanide are hypertoxic drug, there is grave danger to human body and environmental safety, use inconvenience.
Two, take VITMAIN B1 as catalyzer:
By 1.8g VITMAIN B1,6 L water, 15mL ethanol and 15mL phenyl aldehyde mixing, slowly drip 150g/L NaOH, regulate pH9-10, shake up, at 60-75 DEG C, backflow 75min.Reaction mixture is cooled to room temperature, separates out Light yellow crystals, in ice bath, cooling makes crystallization complete, obtains synthesizing benzoic optimum yields.Again st-yrax is reacted under the effect of alkali Anhydrous potassium carbonate obtained α-benzoinoxime with oxammonium hydrochloride.This method productive rate is higher, avoids the use of hypertoxic medicine potassium cyanide, sodium cyanide, environmental protection simultaneously.
Summary of the invention
For the deficiency that prior art exists, the invention provides a kind of α-benzoinoxime derivative and preparation method thereof.
The technical solution used in the present invention is:
A kind of α-benzoinoxime derivative, its structural formula is:
Wherein E 1=E 2=CO 2r, R are straight chained alkyl, branched-chain alkyl, unsaturated alkyl or aryl radical; R 1, R 2for hydrogen, straight chained alkyl, branched-chain alkyl, halogen or alkoxyl group and corresponding derivative thereof.
A preparation method for α-benzoinoxime derivative, comprises the following steps:
(1) take sodium hydride as catalyzer, malonic ester and propargyl bromide are joined ice-water bath in anhydrous acetonitrile, stirring reaction, after purifies and separates, obtain white solid product, be i.e. compound 1;
The amount of substance of described sodium hydride, malonic ester, propargyl bromide is than being 4-5:1:2.2-3.2;
The concentration of described malonic ester in anhydrous acetonitrile is 0.5-0.8mol/L;
Described malonic ester is selected from malonates, propanedioic acid unsaturated alkyl ester, propanedioic acid aryl radical ester;
Described purifies and separates, for product is added water washing, is extracted with ethyl acetate, and decompression is spin-dried for, and is the ethyl acetate of 1:100: sherwood oil column chromatography for separation by volume ratio;
The described reaction times is more than 5h;
(2) compound 1 and the phenylacetylene base bromine of phenylacetylene base bromine or replacement are blended in Pd (PPh 3) 2cl 2in the anhydrous and oxygen-free catalyst system of/CuI, making alkali with triethylamine, take anhydrous acetonitrile as solvent, and stirred at ambient temperature reacts, and obtains light tan solid product, i.e. precursor compound 2 after purifies and separates;
Phenylacetylene base bromine, the Pd (PPh of described compound 1, phenylacetylene base bromine or replacement 3) 2cl 2, triethylamine amount of substance be 1:2.2-3.2:0.0085-0.014:4-5;
The substituting group of the phenylacetylene base bromine of described replacement is straight chained alkyl, branched-chain alkyl, halogen or alkoxyl group and corresponding derivative thereof;
The concentration of described compound 1 in anhydrous acetonitrile is 0.32-0.6mol/L;
Described Pd (PPh 3) 2cl 2in the anhydrous and oxygen-free catalyst system of/CuI, Pd (PPh 3) 2cl 2compare for 3:1 with the amount of substance of CuI;
Described purifies and separates, for product is added water washing, is extracted with ethyl acetate, and decompression is spin-dried for, and is the ethyl acetate of 1:100: sherwood oil column chromatography for separation by volume ratio;
The described reaction times is more than 10h;
(3) under the condition of 95-105 DEG C, precursor compound 2 prepared by step (2) is reacted more than 10 hours with α-benzoinoxime in toluene, yellow solid compound 3 is obtained, i.e. target product α-benzoinoxime derivative after being separated by product purification;
Described precursor compound 2 is 1:1.1-1.5 with the amount of substance ratio of α-benzoinoxime;
The concentration of precursor compound 2 in toluene is 0.2-0.5mol/L;
Described purifies and separates is washed by products in water, and extraction into ethyl acetate, decompression is spin-dried for, and is the ethyl acetate of 1:30: sherwood oil column chromatography for separation by volume ratio.
Compared with prior art, the invention provides a kind of synthetic method of polysubstituted α-benzoinoxime completely newly, generate a series of new α-benzoinoxime derivative.Relative to common α-benzoinoxime derivative, α-benzoinoxime derivative prepared by the present invention has the existence of many rings, and its structure is more complicated various, in Chemical Manufacture, clinical medicine, also will show more wide purposes prospect.
Embodiment
Embodiment 1
A kind of α-benzoinoxime derivative, structural formula is:
A preparation method for α-benzoinoxime derivative, described preparation method comprises the following steps:
A, precursor synthesize;
B, target product synthesize;
C, purifying.
Wherein, a, precursor synthesize, and comprise the following steps:
(1) with 830mmol sodium hydride for catalyzer, 200mmol diethyl malonate and 440mmol propargyl bromide are joined ice-water bath in 250mL anhydrous acetonitrile, stirring reaction 8 hours, product adds water washing, be extracted with ethyl acetate, decompression is spin-dried for, and column chromatography (volume ratio ethyl acetate: sherwood oil=1:100) obtains white solid product, i.e. compound 1;
(2) 80mmol compound 1 and 200mmol phenylacetylene base bromine are blended in 1.3gPd (PPh 3) 2cl 2in the anhydrous and oxygen-free catalyst system of/CuI, Pd (PPh 3) 2cl 2compare for 3:1 with the amount of substance of CuI, alkali is made with 320mmol triethylamine, with 200ml anhydrous acetonitrile for solvent, stirred at ambient temperature reacts 12 hours, products in water washs, and be extracted with ethyl acetate, decompression is spin-dried for, column chromatography (volume ratio ethyl acetate: sherwood oil=1:100) obtains light tan solid product, i.e. precursor compound 2.
Wherein b, target product synthesis, comprises the following steps:
Under the condition of 100 DEG C, 0.44g precursor compound 2 and 0.34g α-benzoinoxime are reacted 12 hours in 3mL toluene, obtains compound 3, i.e. the crude product of α-benzoinoxime derivative.
Wherein, c, purifying, comprise the following steps:
The crude product with water washing of α-benzoinoxime derivative prepared by step b, extraction into ethyl acetate, decompression is spin-dried for, and column chromatography (volume ratio ethyl acetate: sherwood oil=1:30) is separated and obtains yellow solid product, i.e. α-benzoinoxime derivative, column chromatography productive rate is 65.2%.
Yellow solid product structure is passed through; 1h NMR; 13c NMR measures.
Yellow solid product:
1H NMR(300MHz,CDCl 3)δ7.96(s,1H),7.93(s,1H),7.81(s,1H)，7.78(s,1H)，7.54–7.25(m,16H),6.63(s,1H)，,4.29–4.22(m,4H)，3.73(s,2H)，3.66(s,2H),1.32-1.27(t，6H).
13C NMR(75MHz,CDCl 3)δ196.89,171.49,166.91,144.95，144.48,143.29,139.96,134.86,134.64,134.44,132.04,131.23,130.46,129.88,129.15,129.09,129.03,128.87,128.33,128.20,128.00,127.71,127.31,123.53 ,119.13,114.09,95.54,87.32,77.31,77.06,76.81,61.83,59.45,40.97,39.03,14.07。
Embodiment 2
A kind of α-benzoinoxime derivative, structural formula is:
A preparation method for α-benzoinoxime derivative, described preparation method comprises the following steps:
A, precursor synthesize;
B, target product synthesize;
C, purifying.
Wherein, a, precursor synthesize, and comprise the following steps:
(1) with 800mmol sodium hydride for catalyzer, 200mmol Diisopropyl malonate and 500mmol propargyl bromide are joined ice-water bath in 200ml anhydrous acetonitrile, stirring reaction 10 hours, product adds water washing, be extracted with ethyl acetate, decompression is spin-dried for, and column chromatography (volume ratio ethyl acetate: sherwood oil=1:100) obtains white solid product, i.e. compound 3;
(2) 80mmol compound 1 is blended in 2.17gPd (PPh with 200mmol to methylbenzene acetylenebromide 3) 2cl 2in the anhydrous and oxygen-free catalyst system of/CuI, Pd (PPh 3) 2cl 2pd (PPh in/CuI 3) 2cl 2compare for 3:1 with the amount of substance of CuI, alkali is made with 350mmol triethylamine, with 250ml anhydrous acetonitrile for solvent, stirred at ambient temperature reacts 10 hours, products in water washs, and be extracted with ethyl acetate, decompression is spin-dried for, column chromatography (volume ratio ethyl acetate: sherwood oil=1:100) obtains light tan solid product, i.e. precursor compound 3.
Wherein b, target product synthesis, comprises the following steps:
Under the condition of 100 DEG C, 0.47g precursor compound 3 and 0.32g α-benzoinoxime react 11 hours in 5mL toluene, obtain compound 4, i.e. the crude product of α-benzoinoxime derivative.
Wherein, c, purifying, comprise the following steps:
The crude product with water washing of α-benzoinoxime derivative prepared by step b, extraction into ethyl acetate, decompression is spin-dried for, and column chromatography (volume ratio ethyl acetate: sherwood oil=1:30) is separated and obtains yellow solid product, i.e. α-benzoinoxime derivative, column chromatography productive rate is 73.6%.
Yellow solid product structure is passed through; 1h NMR; 13c NMR measures.
Yellow solid product:
1H NMR(300MHz,CDCl 3)δ7.95(s,1H),7.92(s,1H),7.80(s,1H)，7.78(s,1H)，7.53–7.19(m,10H),7.14–7.06(m,4H),6.60(s,1H)，,5.12–5.04(m,2H)，3.68(s,2H)，3.61(s,2H),2.36(s,3H)，2.32(s,3H),1.30-1.25(t，12H).
13C NMR(75MHz,CDCl 3)δ197.10,171.12,166.54,144.90，144.51,142.96,138.05,137.15,136.89,134.88,134.37,133.04,131.88,131.05,129.91,129.11,129.01,128.97,128.83,128.41,128.30,127.70,120.66,118.93,114.15,95.63,86.86,77.29,77.04,76.78,69.24,59.47,40.98,38.99,21.58,21.47,21.41,21.21,21.17,21.14。

Claims (10)

1. a α-benzoinoxime derivative, its structural formula is:
Wherein E 1=E 2=CO 2r, R are straight chained alkyl, branched-chain alkyl, unsaturated alkyl or aryl radical; R 1, R 2for hydrogen, straight chained alkyl, branched-chain alkyl, halogen or alkoxyl group and corresponding derivative thereof.
2. a preparation method for α-benzoinoxime derivative, comprises the following steps:
(1) take sodium hydride as catalyzer, malonic ester and propargyl bromide are joined ice-water bath in anhydrous acetonitrile, more than stirring reaction 5h, after purifies and separates, obtain white solid product, be i.e. compound 1;
(2) compound 1 and the phenylacetylene base bromine of phenylacetylene base bromine or replacement are blended in Pd (PPh 3) 2cl 2in the anhydrous and oxygen-free catalyst system of/CuI, making alkali with triethylamine, take anhydrous acetonitrile as solvent, and stirred at ambient temperature reaction more than 10h, obtains light tan solid product, i.e. precursor compound 2 after purifies and separates;
(3) under the condition of 95-105 DEG C, precursor compound 2 prepared by step (2) is reacted more than 10 hours with α-benzoinoxime in toluene, yellow solid compound 3 is obtained, i.e. target product α-benzoinoxime derivative after being separated by product purification.
3. preparation method as claimed in claim 2, it is characterized in that: in described step (1), the amount of substance of sodium hydride, malonic ester, propargyl bromide is than being 4-5:1:2.2-3.2, and the concentration of malonic ester in anhydrous acetonitrile is 0.5-0.8mol/L.
4. preparation method as claimed in claim 2, is characterized in that: in described step (1), malonic ester is selected from malonates, propanedioic acid unsaturated alkyl ester, propanedioic acid aryl radical ester.
5. preparation method as claimed in claim 2, is characterized in that: in described step (1), purifies and separates is for add water washing by product, and be extracted with ethyl acetate, decompression is spin-dried for, and is the ethyl acetate of 1:100: sherwood oil column chromatography for separation by volume ratio.
6. preparation method as claimed in claim 2, is characterized in that: phenylacetylene base bromine, the Pd (PPh of compound 1 in described step (2), phenylacetylene base bromine or replacement 3) 2cl 2, triethylamine amount of substance be 1:2.2-3.2:0.0085-0.014:4-5, the concentration of described compound 1 in anhydrous acetonitrile is 0.32-0.6mol/L.
7. preparation method as claimed in claim 2, is characterized in that: the substituting group of the phenylacetylene base bromine replaced in described step (2) is straight chained alkyl, branched-chain alkyl, halogen or alkoxyl group and corresponding derivative thereof.
8. preparation method as claimed in claim 2, is characterized in that: Pd (PPh in described step (2) 3) 2cl 2in the anhydrous and oxygen-free catalyst system of/CuI, Pd (PPh 3) 2cl 2compare for 3:1 with the amount of substance of CuI; Described purifies and separates, for product is added water washing, is extracted with ethyl acetate, and decompression is spin-dried for, and is the ethyl acetate of 1:100: sherwood oil column chromatography for separation by volume ratio.
9. preparation method as claimed in claim 2, is characterized in that: in described step (3), precursor compound 2 and the amount of substance of α-benzoinoxime are than being 1:1.1-1.5, and the concentration of precursor compound 2 in toluene is 0.2-0.5mol/L.
10. preparation method as claimed in claim 2, is characterized in that: purifies and separates described in described step (3) is for washing products in water, and extraction into ethyl acetate, decompression is spin-dried for, and is the ethyl acetate of 1:30: sherwood oil column chromatography for separation by volume ratio.
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CN116217785A (en) * 2023-03-09 2023-06-06 核工业北京化工冶金研究院 Molybdenum separation resin and preparation method and application thereof

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