CN113563224A - Synthesis method of tri-substituted olefin containing gamma-cyano - Google Patents

Synthesis method of tri-substituted olefin containing gamma-cyano Download PDF

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CN113563224A
CN113563224A CN202011645662.6A CN202011645662A CN113563224A CN 113563224 A CN113563224 A CN 113563224A CN 202011645662 A CN202011645662 A CN 202011645662A CN 113563224 A CN113563224 A CN 113563224A
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cyano
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substituted olefin
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陆晓雨
洪美岚
王金玉
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Chuzhou University
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Abstract

The invention provides a method for synthesizing tri-substituted olefin containing gamma-cyano, which takes ring ketoxime ester and aryl-alkyl acetylene as raw materials, and reacts in a solvent according to the following reaction formula under the action of a nickel catalyst, a ligand, alkali and a silicon reagent to obtain the tri-substituted olefin compound containing gamma-cyano and having a single configuration. The invention realizes the synthesis method of the tri-substituted olefin containing the gamma-cyano for the first time. Meanwhile, the tri-substituted olefin containing gamma-cyano group synthesized by the method has high regioselectivity and stereoselectivity, can completely obtain the tri-substituted olefin with a single configuration, and avoids the separation problem of the mixed olefin product. Cyano is an important organic structural segment, and widely exists in natural active products and drug molecules. The invention provides an efficient and convenient synthesis method for tri-substituted olefin containing gamma cyano. The reaction system has simple feeding mode, does not need to use a metal reagent sensitive to moisture and air, and is convenient in practical use.

Description

Synthesis method of tri-substituted olefin containing gamma-cyano
Technical Field
The invention relates to the technical field of compound substance preparation, in particular to a preparation method of tri-substituted olefin containing gamma-cyano.
Background
Substituted olefins are important compounds in organic chemistry and widely exist in the industries of materials, petrochemical industry, medicines and the like. The synthesis method of substituted olefin is always the focus of attention, the traditional synthesis method generally has the defects of harsh reaction conditions, high reaction temperature, need of using stronger alkali in a reaction system and the like, and the most important point is that the reaction selectivity is not high for synthesizing the substituted olefin with cis/trans isomers, the product is difficult to separate and the like. In addition, trisubstituted olefins with a single configuration have higher requirements in organic synthesis and drug synthesis, and the trisubstituted olefins are widely present in various drug and natural product molecules.
On the other hand, cyano is an important functional group, widely exists in various drug molecules, natural products and various active molecules, and the synthesis of cyano compounds is always an important research content of organic synthesis. However, the preparation method of the single-configuration tri-substituted olefin containing the gamma-cyano group is not seen. The invention reports that the gamma-cyano trisubstituted olefin with single configuration is prepared by taking the cyclic ketoxime ester and the aryl-alkyl acetylene as raw materials, and provides a simple, efficient and convenient synthetic method for a compound containing the gamma-cyano trisubstituted olefin.
Disclosure of Invention
The invention provides a method for synthesizing gamma-cyano trisubstituted olefin, which takes ring ketoxime ester and aryl-alkyl acetylene as raw materials, and reacts in a solvent according to the following reaction formula under the action of a nickel catalyst, a ligand, alkali and a silicon reagent to obtain a compound containing the gamma-cyano trisubstituted olefin with a single configuration shown in a general formula (I):
Figure BSA0000230057820000011
wherein Ar is an aryl substituent, R1、R2An alkyl substituent;
the nickel catalyst is a nickel (II) bromide diethylene glycol dimethyl ether compound;
the ligand is 4, 4 '-di-tert-butyl-2, 2' -bipyridine;
the solvent is N, N-dimethylacetamide;
the silicon reagent is bis (dimethylsilyl) ether.
Preferably, the base is potassium phosphate.
Preferably, the amount of the substance of the base is 2.5 times the amount of the substance of the cyclic ketoxime ester.
Preferably, the amount of the substance of intramolecular alkyne is 2.5 times the amount of the substance of cyclic ketoxime ester.
Preferably, the amount of the substance of the ligand is 10% of the amount of the substance of the cyclic ketoxime ester.
Preferably, the amount of material of the silicon reagent is 3 times the amount of material of the cyclic ketoxime ester.
Preferably, the reaction temperature is 40 ℃ and the reaction time is 12 h.
The invention uses the ring ketoxime ester and aryl-alkyl acetylene as reaction substrates, realizes the synthesis method of the tri-substituted olefin containing the gamma-cyano for the first time, and solves the problem of difficult synthesis of the tri-substituted olefin containing the gamma-cyano. The invention provides a method for synthesizing gamma-cyano trisubstituted olefin, which can provide a high-efficiency and convenient synthesis method for various gamma-cyano trisubstituted olefin compounds. The tri-substituted olefin synthesized by the method has high regioselectivity and stereoselectivity, can completely obtain the tri-substituted olefin with a single configuration, and avoids the separation problem of mixed olefin products. Meanwhile, the reaction system has a simple feeding mode, does not need to use a metal reagent sensitive to moisture and air, and is more convenient in actual use. In addition, the reaction system has mild reaction conditions and can be well compatible with some groups sensitive to alkali.
Drawings
The attached figure shows the characters and nuclear magnetic data of various gamma-cyano-containing tri-substituted olefin compounds prepared by the method
FIG. 1 is a hydrogen spectrum of synthetic Compound 1;
FIG. 2 is a carbon spectrum of synthetic Compound 1;
FIG. 3 is a hydrogen spectrum of synthetic Compound 2;
FIG. 4 is a carbon spectrum of synthetic Compound 2;
FIG. 5 is a hydrogen spectrum of synthetic Compound 3;
FIG. 6 is a carbon spectrum of synthetic Compound 3;
FIG. 7 is a hydrogen spectrum of synthetic Compound 4;
FIG. 8 is a carbon spectrum of synthetic Compound 4;
FIG. 9 is a hydrogen spectrum of synthetic compound 30;
FIG. 10 is a carbon spectrum of synthetic compound 30;
FIG. 11 is a hydrogen spectrum of synthetic compound 31;
FIG. 12 is a carbon spectrum of synthetic compound 31;
FIG. 13 is a hydrogen spectrum of synthetic compound 32;
FIG. 14 is a carbon spectrum of synthetic compound 32;
FIG. 15 is a hydrogen spectrum of synthetic compound 33;
FIG. 16 is a carbon spectrum of synthetic compound 33
FIG. 17 is a hydrogen spectrum of synthetic compound 34;
FIG. 18 is a carbon spectrum of synthetic compound 34;
Detailed Description
A specific embodiment of the present invention is described in detail below, but it should be understood that the scope of the present invention is not limited by the specific embodiment.
Example 1, the reaction formula for this example is as follows:
Figure BSA0000230057820000031
(1) under air, nickel (II) bromide-diethylene glycol dimethyl ether complex (8 mol%), 4, 4 '-di-tert-butyl-2, 2' -bipyridine (10 mol%), cyclobutanone oxime ester (1eq), and potassium phosphate (2.5eq) were added to a sealed reaction tube with branch tubes and containing magnetons, and the reaction tube was purged with argon three times. 1mL of N, N-dimethylacetamide was added to a reaction tube under argon atmosphere, the mixture was stirred at room temperature for 5 minutes, and then phenylpropargyne (2.5eq), and (Me) were added in this order under argon atmosphere2SiH)2O (3.0eq) is added into the reaction solution, a piston is tightly plugged, and the mixture is placed in an oil bath kettle at the temperature of 40 ℃ to be stirred and reacted for 12 hours.
(2) Adding ethyl acetate into the material obtained in the step (1), fully mixing, filtering solid residues by using a short silica gel column, and keeping an organic phase.
(3) The solvent in the organic phase obtained in step (2) was spin-dried to obtain a crude product, which was then purified by a silica gel column. The eluent is petroleum ether, the separation yield is 80%, and the product purity is 100%.
Example 2
The reaction formula for this example is shown below:
Figure BSA0000230057820000041
(1) under the air, nickel (II) bromide-diethylene glycol dimethyl ether complex (8 mol%), 4, 4 '-di-tert-butyl-2, 2' -bipyridine (10 mol%), cyclobutanone oxime ester (1eq) and potassium phosphate (3eq) are added into a sealed reaction tube with branch tubes and containing magnetons, and the reaction tube is pumped and flushed with argon for three times. 1mL of N, N-dimethylacetamide was added to the reaction tube under argon atmosphere, the mixture was stirred at room temperature for 5 minutes, and then phenylbutyyne (2.5eq), and (Me) were added in this order under argon atmosphere2SiH)2O (3.0eq) is added into the reaction solution, a piston is tightly plugged, and the mixture is placed in an oil bath kettle at the temperature of 40 ℃ to be stirred and reacted for 12 hours.
(2) Adding ethyl acetate into the material obtained in the step (1), fully mixing, filtering solid residues by using a short silica gel column, and keeping an organic phase.
(3) The solvent in the organic phase obtained in step (2) was spin-dried to obtain a crude product, which was then purified by a silica gel column. The eluent is petroleum ether, the separation yield is 81 percent, and the product purity is 100 percent.
The invention provides a method for synthesizing tri-substituted olefin containing gamma-cyano, which takes ring ketoxime ester and aryl-alkyl acetylene as reaction substrates, realizes the method for synthesizing tri-substituted olefin containing gamma-cyano for the first time, and solves the problem of difficult synthesis of tri-substituted olefin containing gamma-cyano. Meanwhile, the tri-substituted olefin synthesized by the method has high regioselectivity and stereoselectivity, can completely obtain the gamma-cyano tri-substituted olefin with a single configuration, and avoids the separation problem of mixed olefin products. Meanwhile, the reaction system has a simple feeding mode, does not need to use a metal reagent sensitive to moisture and air, and is more convenient in actual use. In addition, the reaction system has mild reaction conditions, can be well compatible with some groups sensitive to alkali, and provides an efficient preparation method for the tri-substituted olefin containing gamma-cyano single configuration.
The structure of various gamma-cyano trisubstituted olefin compounds prepared by the method
Figure BSA0000230057820000061
The above disclosure is only for the specific embodiment of the present invention, but the embodiment of the present invention is not limited thereto, and any variations that can be made by those skilled in the art should fall within the scope of the present invention.

Claims (7)

1. A method for synthesizing tri-substituted olefin containing gamma-cyano is characterized in that cyclic ketoxime ester and aryl-alkyl acetylene are used as raw materials, and are reacted in a solvent according to the following reaction formula under the action of a nickel catalyst, a ligand, alkali and a silicon reagent to obtain a gamma-cyano tri-substituted olefin compound with a single configuration of a general formula (I):
Figure FSA0000230057810000011
wherein Ar is an aryl substituent, R1、R2An alkyl substituent;
the nickel catalyst is a nickel (II) bromide diethylene glycol dimethyl ether compound;
the ligand is 4, 4 '-di-tert-butyl-2, 2' -bipyridine;
the solvent is N, N-dimethylacetamide;
the silicon reagent is bis (dimethylsilyl) ether.
2. The method for synthesizing tri-substituted olefin containing γ -cyano group according to claim 1, wherein the base is potassium phosphate.
3. The method for synthesizing trisubstituted olefin having γ -cyano group according to claim 1, wherein the amount of said base is 2.5 times the amount of said cyclic ketoxime ester.
4. The method for synthesizing trisubstituted alkene containing γ -cyano group according to claim 1, wherein the amount of the substance of intramolecular alkyne is 2.5 times of the amount of the substance of cycloalkanone oxime ester.
5. The method for synthesizing trisubstituted olefin having γ -cyano group according to claim 1, wherein the amount of said ligand substance is 10% of the amount of said cyclic ketoxime ester substance.
6. The method for synthesizing trisubstituted olefin having γ -cyano group according to claim 1, wherein the amount of said silicon reagent is 3 times the amount of said cyclic ketoxime ester.
7. The method for synthesizing the trisubstituted olefin containing gamma-cyano group according to claim 1, wherein the reaction temperature is 40 ℃ and the reaction time is 12 hours.
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115490614A (en) * 2022-09-03 2022-12-20 滁州学院 Method for synthesizing cyano-substituted enamine

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CN107602320A (en) * 2017-10-18 2018-01-19 滁州学院 It is a kind of that the synthetic method for preparing three substituted olefines is catalyzed based on nickel
CN111484472A (en) * 2019-01-28 2020-08-04 中国科学院上海有机化学研究所 Process for producing alkyl nitrile compound

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CN107602320A (en) * 2017-10-18 2018-01-19 滁州学院 It is a kind of that the synthetic method for preparing three substituted olefines is catalyzed based on nickel
CN111484472A (en) * 2019-01-28 2020-08-04 中国科学院上海有机化学研究所 Process for producing alkyl nitrile compound

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115490614A (en) * 2022-09-03 2022-12-20 滁州学院 Method for synthesizing cyano-substituted enamine
CN115490614B (en) * 2022-09-03 2024-04-12 滁州学院 Synthesis method of cyano-containing substituted enamine

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