CN109320496B - Selenocyanization reagent and preparation method and application thereof - Google Patents
Selenocyanization reagent and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses a selenocyanization reagent, which has a structural formula as follows:
Description
Technical Field
The invention relates to the field of organic chemistry, in particular to a selenocyanization reagent.
Background
Selenium is a scattered nonmetal element and is also an essential nutrient element for animals and plants. In nature, selenium occurs mainly in two forms: inorganic selenium and plant active selenium. In recent years, researches show that the intake of a proper amount of selenium element is beneficial to human health, and certain selenium-containing compounds have excellent antitumor activity and antioxidant activity (ebselen). For example, after an alkyl group with a selenocyano group at the terminal group is introduced into the carboxyl group of a classical antipyretic analgesic drug aspirin, the novel molecule has excellent antitumor activity. Therefore, the organic micromolecule compound containing the selenocyano has important application prospect in the fields of medicine, pesticide and material, and also has important application value in organic synthesis.
At present, in the preparation technology of selenocyano-containing compounds, inorganic selenocyanide reagent-potassium selenocyanate and alpha halogenated methyl ketone or aromatic methyl ketone are generally used for carrying out selenocyanization reaction under the promotion of oxidant and alkali to prepare the substances. The traditional method for introducing selenocyano solves the preparation problem of selenocyano-containing compounds to a certain extent, but still has great defects. First, selenocyanization using inorganic selenocyanizing agents requires the use of strong oxidants, which can have a very detrimental effect on the synthesis of certain oxidant-sensitive compounds. Secondly, the use of an inorganic selenocyanation reagent, potassium selenocyanate, which is poorly soluble in most organic solvents, inevitably further limits the scope of application of the selenocyanation reaction. Therefore, the search for an organic electrophilic selenocyanization reagent which has high selenocyanization reaction efficiency, mild reaction conditions and easy preparation is a technical problem which needs to be solved urgently at present.
Disclosure of Invention
An object of the present invention is to solve at least the above problems and to provide at least the advantages described later.
The invention also aims to provide a selenocyanization reagent which has very good organic electrophilicity, has mild reaction conditions and high selenocyanization reaction efficiency in the application of preparing the selenocyanide-containing compound, and can realize the industrial large-scale production of the selenocyanide-containing compound.
To achieve these objects and other advantages in accordance with the present invention, there is provided a selenocyanization reagent having the formula:
the invention also provides a preparation method of the selenocyanization reagent, which comprises the following steps:
s1, mixing the compound A and silver selenocyanate in an organic solvent, introducing protective gas, and after the reaction is finished, filtering under reduced pressure to obtain a concentrate;
s2, purifying and separating the concentrate in the S1 to obtain the selenocyanization reagent;
the structural formula of the compound A is as follows:
preferably, in the method for preparing the selenocyanization reagent, the reaction time in S1 is 12-72 hours, and more preferably 24 hours.
Preferably, in the preparation method of the selenocyanization reagent, the reaction temperature in S1 is 0-50 ℃, and more preferably 25-35 ℃.
Preferably, in the preparation method of the selenocyanization reagent, the reaction in the S1 is carried out under the condition of keeping out light.
Preferably, in the method for preparing the selenocyanization reagent, the organic solvent in S1 includes at least one of dichloromethane, 1, 2-dichloroethane, chloroform, acetonitrile, tetrahydrofuran, toluene, methanol, and ethanol.
In the method for preparing the selenocyanide reagent, the molar volume ratio of the compound A, the silver selenocyanate and the organic solvent in S1 is preferably 1mmol: 1-2 mmol: 1-10 mL, and more preferably 1mmol: 1.2-1.5 mmol: 2-5 mL.
Preferably, in the preparation method of the selenocyanization reagent, the protective gas in S1 at least includes one of nitrogen, helium, neon, argon, krypton, xenon, and radon.
Preferably, in the preparation method of the selenocyanization reagent, the purification and separation method in S2 is as follows: the concentrate was chromatographed on a neutral alumina column.
The selenocyanization reagent can also be applied to the preparation of selenocyano-containing compounds.
The invention at least comprises the following beneficial effects:
1. the selenocyanization reagent has very good practical effect in the application of preparing the selenocyano-containing compound. In general, the preparation of selenocyano-containing compounds requires the introduction of selenocyano by selenocyanization, which is essentially a nucleophilic substitution reaction and generally requires the completion of the reaction in an organic solvent; compared with the traditional inorganic selenocyanization reagent, the selenocyanization reagent has organic electrophilicity, so that the required reaction condition is mild when nucleophilic substitution reaction is carried out, and the preparation of the selenocyanide-containing compound can be completed without the promotion of strong oxidant, acidic environment or other conditions; moreover, the selenocyanide reagent is an organic electrophilic reagent, has a very good dissolving effect in various organic solvents, and widens the application range of the invention.
2. The preparation method of the selenocyanide reagent has simple operation steps, and the selenocyanide reagent can be obtained by one-step displacement reaction of the compound A and silver selenocyanate in an organic solvent; meanwhile, the preparation method has high production efficiency, the preparation yield can reach 89%, and industrial large-scale production can be realized.
Additional advantages, objects, and features of the invention will be set forth in part in the description which follows and in part will become apparent to those having ordinary skill in the art upon examination of the following or may be learned from practice of the invention.
Detailed Description
The present invention is further described in detail below with reference to examples so that those skilled in the art can practice the invention with reference to the description. It is to be noted that the experimental methods described in the following embodiments are all conventional methods unless otherwise specified, and the reagents and materials are commercially available unless otherwise specified.
First, a preparation example of the selenocyanization reagent of the present invention.
Example 1
Step one, respectively adding 10mmol of compound A, 10mmol of silver selenocyanate (AgSeCN) and 100mL of dichloromethane into a round-bottom flask with an argon protection device, and stirring for reaction for 24 hours at the temperature of 25 ℃;
and step two, when the interior of the round-bottom flask is brown and a large amount of white solid is generated, carrying out reduced pressure filtration to obtain a filtrate, adding silica gel into the filtrate for concentration to obtain a concentrate, and carrying out column chromatography separation on the concentrate by using a neutral alumina column to obtain 8.2mmol of selenocyanization reagent with the chemical name of 1- (selenocyano) -1, 2-phenyliodoyl-3 (1H) -ketone.
The yield of 1- (selenocyano) -1, 2-phenyliodoyl-3 (1H) -one is 82%;
physical and chemical properties: a white solid;
the nuclear magnetic resonance hydrogen spectrum data are as follows:1H NMR(300MHz，CDCl3)8.32(d,J＝7.6Hz,1H),8.16(d,J＝7.4Hz,1H),8.02-8.07(m,1H),7.90-7.94(m,1H)；13C NMR(300MHz，CDCl3)165.3,136.8,132.0,131.7,130.6,128.1,117.3,87.9；HRMS(TOF-ES+)m/z:calcd for C8H4INNaO2Se[M+Na]+375.8350,found 375.8344。
example 2
The procedure is as in example 1, except that 11mmol of silver selenocyanate (AgSeCN) is used. This gave 8.4mmol of selenocyanization reagent in 84% yield.
Example 3
The procedure is as in example 1, except that 12mmol of silver selenocyanate (AgSeCN) is used. This gave 8.6mmol of selenocyanization reagent in 86% yield.
Example 4
The procedure is as in example 1, except that 13mmol of silver selenocyanate (AgSeCN) is used. This gave 8.7mmol of selenocyanization reagent in 87% yield.
Example 5
The procedure is as in example 1, except that 15mmol of silver selenocyanate (AgSeCN) is used. This gave 8.9mmol of selenocyanization reagent in 89% yield.
Example 6
The procedure is as in example 1, except that 16mmol of silver selenocyanate (AgSeCN) is used. This gave 8.8mmol of selenocyanization reagent in 88% yield.
Example 7
The procedure is as in example 1, except that 20mmol of silver selenocyanate (AgSeCN) is used. This gave 8.9mmol of selenocyanization reagent in 89% yield.
From the results of examples 1 to 6, it can be seen that when the molar ratio of the compound A and the silver selenocyanate is 1mmol: 1-2 mmol, the yield of the selenocyanation reagent is 82% -89%; with the increasing of the molar specific gravity of AgSeCN, when the molar ratio is increased from 1:1 to 1:1.2, the yield of the selenocyanization reagent is increased to 86 percent, the highest yield is reached to 89 percent when the molar ratio is increased to 1:1.5, and after the content of AgSeCN is increased continuously, the yield of the selenocyanization reagent is hardly increased any more, which indicates that the molar ratio of the compound A and the silver selenocyanate is a more preferable value for preparing the selenocyanization reagent within the range of 1mmol: 1.2-1.5 mmol.
Example 8
The procedure was as in example 1, except that 10mL of methylene chloride was used. This gave 7.5mmol of selenocyanization reagent in 75% yield.
Example 9
The procedure was as in example 1, except that 15mL of methylene chloride was used. This gave 7.6mmol of selenocyanization reagent in 76% yield.
Example 10
The procedure was as in example 1, except that 20mL of methylene chloride was used. This gave 8.1mmol of selenocyanization reagent in 81% yield.
Example 11
The procedure was as in example 1, except that 30mL of methylene chloride was used. This gave 8.3mmol of selenocyaniding reagent in 83% yield.
Example 12
The procedure was as in example 1, except that 50mL of methylene chloride was used. This gave 8.2mmol of selenocyanization reagent in 82% yield.
Example 13
The procedure was as in example 1, except that 80mL of methylene chloride was used. This gave 8.3mmol of selenocyaniding reagent in 83% yield.
The dichloromethane content in examples 8-13 and example 1 was sequentially increased from 10mL to 100mL, with a corresponding change in the yield of the selenocyanization reagent. When the content of the organic solvent dichloromethane is increased to 20mL, the yield of the preparation of the selenocyanization reagent is greatly improved to 81 percent; the dichloromethane is continuously increased to 50mL, and the yield of the selenocyanization reagent is continuously improved; however, when the amount of the selenocyanide exceeds 50mL, the amount of the dichloromethane is further increased, and the yield of the selenocyanide is hardly increased (the yield is maintained at about 82% to 83%), which means that the molar volume ratio of the compound A to the organic solvent dichloromethane is more preferably 1mmol:2 to 5 mL.
Example 14
The procedure was as in example 1, except that the reaction temperature was 0 ℃. This gave 7.1mmol of selenocyanization reagent in 71% yield.
Example 15
The procedure was as in example 1, except that the reaction temperature was 15 ℃. This gave 7.3mmol of selenocyanization reagent in 73% yield.
Example 16
The procedure was as in example 1, except that the reaction temperature was 35 ℃. This gave 8.4mmol of selenocyanization reagent in 84% yield.
Example 17
The procedure was as in example 1, except that the reaction temperature was 40 ℃. This gave 8.5mmol of selenocyanization reagent in 85% yield.
Example 18
The procedure was as in example 1, except that the reaction temperature was 50 ℃. This gave 8.6mmol of selenocyanization reagent in 86% yield.
From the results of example 1 and examples 14 to 18, it can be seen that the selenocyanization reagent can be prepared in high yield at reaction temperatures of 0 to 50 ℃. The yield of the selenocyanization reagent is continuously increased along with the increase of the reaction temperature, when the reaction temperature is increased to 25 ℃, the yield reaches 82%, and when the temperature exceeds 35 ℃, the yield is still increased, but is not particularly obvious, and the most suitable temperature for maintaining the yield of the selenocyanization reagent is 25-35 ℃ in consideration of the comprehensive reaction conditions and the cost.
Example 19
The procedure is as in example 1, except that the reaction time is 12 h. This gave 7mmol of selenocyanization reagent in 70% yield.
Example 20
The procedure is as in example 1, except that the reaction time is 72 h. This gave 8.7mmol of selenocyanization reagent in 87% yield.
From the results of example 1, example 19 and example 20, it can be seen that the yield of selenocyanide was increasing with increasing reaction time, reaching 84% at 24h, and that the effect on yield of selenocyanide was not particularly significant by continuing to increase reaction time, so that a reaction time of 24h was a further preference for maintaining the efficiency of preparation of selenocyanide.
Example 21
The procedure is as in example 1, except that the organic solvent is tetrahydrofuran. This gave 8mmol of selenocyaniding reagent in 80% yield.
The organic solvent is replaced by one of 1, 2-dichloroethane, chloroform, acetonitrile, toluene, methanol and ethanol, so that the preparation of the selenocyanization reagent is not greatly influenced, and the higher yield can be maintained.
Example 22
The procedure is as in example 1, except that the protective gas is nitrogen. This gave 7.7mmol of selenocyanization reagent in 77% yield.
The protection gas is replaced by one of helium, neon, krypton, xenon and radon, so that the preparation of the selenocyanization reagent is not greatly influenced, and the higher yield can be maintained.
Example 23
The procedure was as in example 1, except that the reaction was carried out under exclusion of light. This gave 8.5mmol of selenocyanization reagent in 85% yield.
From the results of example 1 and example 23, it can be seen that the reaction was carried out under protection from light, giving higher yields of the selenocyanide reagent.
In summary, it can be seen from the results of examples 1 to 23 that the preparation method of the present invention has very good effect in preparing the selenocyanization reagent, and the yield is as high as 89%.
Second, application example of the selenocyanization reagent of the present invention to preparation of a selenocyano group-containing Compound
The preparation method of the selenocyano-containing compound comprises the following steps:
adding 0.2mmol of alpha hydrogen-containing ketone compound and 0.24mmol of selenocyanization reagent of the invention into 2mL of dichloromethane, stirring and reacting for two hours at 25 ℃, tracking by TLC until the reaction is finished, adding silica gel (200-300 meshes) for sample mixing, separating by flash column chromatography, and separating by petroleum ether: the corresponding selenocyanide product was obtained eluting with ethyl acetate 9: 1.
Example 24
Preparing alpha-selenocyanobenzoyl acetic acid ethyl ester according to a first preparation method of a selenocyanoyl-containing compound;
in the first method, the structural formula of the alpha hydrogen-containing ketone compound is as follows:
the structural formula of the alpha-selenocyanobenzoyl acetic acid ethyl ester is as follows:
the yield of the alpha-selenocyanobenzoyl acetic acid ethyl ester is as follows: 88 percent;
physical and chemical properties: a colorless oil;
the nuclear magnetic resonance hydrogen spectrum data are as follows:1H NMR(300MHz，CDCl3)7.87-7.43(m,5H),5.54(s,1H),3.35(q,J＝7.6Hz,2H),2.25(t,J＝7.6Hz,3H)；13C NMR(75MHz，CDCl3)202.1,196.3,133.4,121.8,119.6,104.6,46.7,33.5；HRMS(TOF-ES+)m/z:calcd for C12H11NNaO3Se[M+Na]+319.9802,found 319.9795。
example 25
Preparing alpha-selenocyanotetralone according to the first preparation method of the selenocyanoyl-containing compound;
in the first method, the structural formula of the alpha hydrogen-containing ketone compound is as follows:
the structural formula of the alpha-selenocyanotetralone is as follows:
the yield of the alpha-selenocyanotetralone is 81 percent;
physical and chemical properties: white solid, mp ═ 82-83 ℃;
the nuclear magnetic resonance hydrogen spectrum data are as follows:1H NMR(300MHz，CDCl3)8.01(d,J＝7.6Hz,1H),7.60-7.57(m,1H),7.39-7.13(m,2H),5.04-4.99(m,1H),3.22-3.15(m,2H),2.94-2.89(m,1H),2.60-2.53(m,1H)；13C NMR(75MHz，CDCl3)194.2,144.1,135.0,130.4,129.0,127.7,127.3,102.5,53.2,32.5,30.3；HRMS(TOF-ES+)m/z:calcd for C11H9NNaOSe[M+Na]+273.9747,found273.9721.
example 26
Preparing alpha-selenocyanotetralone ethyl ester according to a first preparation method of a selenocyanoyl-containing compound;
in the first method, the structural formula of the alpha hydrogen-containing ketone compound is as follows:
the structural formula of the alpha-selenocyano tetrahydronaphthaleneacetic acid ethyl ester is as follows:
yield of ethyl α -selenocyanotetralonoate: 89 percent;
physical and chemical properties: a colorless oil;
the nuclear magnetic resonance hydrogen spectrum data are as follows:1H NMR(300MHz，CDCl3)7.46-7.33(m,2H),7.27-7.18(m,2H),5.33-5.21(m,2H),3.36-3.27(m,2H),2.93-2.87(q,J＝7.6Hz,2H),2.32-2.28(t,J＝7.6Hz,3H)；13C NMR(75MHz，CDCl3)201.7,197.3,141.5,137.9,132.2,128.7,127.4,125.5,104.6,56.6,47.8,36.6,33.2,30.3；HRMS(TOF-ES+)m/z:calcd for C14H13NNaO3Se[M+Na]+345.9958,found 345.9941。
example 27
Preparing alpha-selenocyanotetralone methyl ester according to a first preparation method of a selenocyanoyl-containing compound;
in the first method, the structural formula of the alpha hydrogen-containing ketone compound is as follows:
the structural formula of the alpha-selenocyanotetralone methyl ester is as follows:
yield of methyl α -selenocyanotetralonoate: 86 percent;
physical and chemical properties: a colorless oil;
the nuclear magnetic resonance hydrogen spectrum data are as follows:1H NMR(300MHz，CDCl3)7.47-7.41(m,2H),7.22-7.14(m,2H),5.31-5.22(m,2H),3.37-3.25(m,2H),2.37(s,3H)；13C NMR(75MHz，CDCl3)201.1,195.5,139.6,138.8,135.1,129.4,126.6,121.9,103.3,48.7,44.4,32.4,31.1；HRMS(TOF-ES+)m/z:calcd for C13H11NNaO3Se[M+Na]+331.9802,found 331.9807。
example 28
Preparing alpha-selenocyano-1-indanone ethyl ester according to the first preparation method of the selenocyano-containing compound;
in the first method, the structural formula of the alpha hydrogen-containing ketone compound is as follows:
the structural formula of the alpha-selenocyano-1-indanone ethyl ester is as follows:
yield of ethyl α -selenocyano-1-indanoate: 75 percent;
physical and chemical properties: a colorless oil;
the nuclear magnetic resonance hydrogen spectrum data are as follows:1H NMR(300MHz，CDCl3)7.74-7.62(m,2H),7.37-7.31(m,2H),5.32-5.25(m,2H),3.23-3.15(q,J＝7.6Hz,2H),2.26-2.53(t,J＝7.6Hz,3H)；13H NMR(75MHz，CDCl3)196.8,194.4,138.7,137.7,136.8,128.5,125.8,120.0,104.9,49.4,41.8,32.2,30.8；HRMS(TOF-ES+)m/z:calcd for C13H11NNaO3Se[M+Na]+331.9802,found331.9789。
the preparation method of the selenocyano-containing compound comprises the following steps:
the alpha hydrogen-containing ketone compound (0.2mmol) and potassium tert-butoxide (0.3mmol) were added to 2mL of anhydrous tetrahydrofuran, and the reaction was stirred at 25 ℃ for 30 minutes. Then adding the selenocyanization reagent (0.24mmol) of the invention, continuing to react for 6 hours at 25 ℃, tracing by TLC until the reaction is finished, adding water (2mL) to quench the reaction, extracting for 3 times by ethyl acetate (2mL), washing by saturated saline solution, combining organic phases, drying by anhydrous sodium sulfate, adding silica gel (200-mesh and 300-mesh) to mix samples, separating by flash column chromatography, using petroleum ether: the corresponding selenocyanide product was obtained eluting with ethyl acetate 9: 1.
Example 29
Preparing alpha-selenocyanoacetophenone according to the second preparation method of the selenocyanoyl-containing compound;
in the second method, the structural formula of the alpha hydrogen-containing ketone compound is as follows:
the structural formula of the alpha-selenocyanoacetophenone is as follows:
the yield of the alpha-selenium cyanoacetophenone is 73 percent;
physical and chemical properties: white solid, mp is 48-49 ℃;
nuclear magnetic resonance hydrogen spectrum data of1H NMR(300MHz，CDCl3)7.92(d,J＝7.6Hz,2H),7.55(t,J＝7.6Hz,1H),7.48(t,J＝7.6Hz,2H),4.93(s,2H)；13C NMR(75MHz，CDCl3)194.8,133.3,129.5,127.5,102.5,33.1；HRMS(TOF-ES+)m/z:calcd for C9H7NNaOSe[M+Na]+247.9591,found 247.9585。
Preparation method three of the selenocyano-containing compound:
preparing a selenocyano-containing compound by using an inorganic selenocyanization reagent.
Comparative example 1
Preparing a selenocyano-containing compound alpha-selenocyano tetralone ethyl ester, wherein the structural formula is as follows:
in an ice-water bath, to ethyl tetralone (43.6mg, 0.2mmol) in ethanol (1.5.0mL) were added potassium selenocyanate (34.7mg, 0.24mmol, 1.2 equiv) and dilute hydrochloric acid (3mol/L,0.5mL), respectively. The reaction was stirred at 0 ℃ for 5 minutes, followed by the addition of sodium nitrite (27.6mg, 2 equivalents) in portions. After continuing the reaction for 30 minutes at the temperature, the organic solvent is dried by spinning, the residue is extracted by ethyl acetate (2mL) for 2 times, the saturated saline solution (3mL) is washed for 2 times, the organic phase is dried and concentrated, and the alpha-seleno-cyanoacetophenone product is obtained by using 200-mesh 300-mesh silica gel flash column chromatography, and petroleum ether/ethyl acetate 9:1 is eluted to obtain 33.9mg of the alpha-seleno-cyanoacetophenone product with the yield of 68 percent.
Comparative example 2
Preparing a selenocyano-containing compound alpha-selenocyanoacetophenone, which has a structural formula:
adding potassium selenocyanate (34.7mg, 0.24mmol, 1.2 times equivalent), iodine simple substance (25.4mg, 0.1mmol, 0.5 times equivalent) and tert-butyl hydroperoxide (30.8mg, 70% aqueous solution, 0.24mmol, 1.2 times equivalent) into acetophenone (24.0mg, 0.2mmol) in acetonitrile solvent (2.0mL), stirring and reacting for 12 hours at normal temperature, monitoring the reaction by a thin-layer chromatography dot plate, adding saturated aqueous solution of sodium thiosulfate (1mL), spin-drying the organic solvent, extracting the residue with ethyl acetate (2mL) for 2 times, washing with saturated saline (3mL) for 2 times, drying the organic phase, concentrating, performing 200-300-mesh silica gel fast column chromatography, and eluting with petroleum ether/ethyl acetate (9: 1) to obtain the alpha-selenium acetophenone product (34.9 mg, with a yield of 72%).
From the results of examples 24 to 29, it can be seen that the selenocyanide reagent of the present invention has very good application effect in the preparation of selenocyano-containing compounds, and not only the yield of the prepared selenocyano-containing compounds is very high, up to 89%, but also nucleophilic substitution reaction with most selenocyano-containing raw materials can be performed to prepare selenocyano-containing compounds, which shows that the selenocyano-containing compounds also make great breakthrough in the application range, and can realize industrial large-scale production value.
Comparative examples 1 and 2 are the preparation of selenocyano-containing compounds using an inorganic selenocyanizing agent of the prior art; of these, comparative example 1 and example 26 prepared the same selenocyano-containing compound, ethyl α -selenocyanotetralone ate, but comparative example 1 had more strict and complicated reaction requirements, and not only required conditions such as an ice water bath and diluted hydrochloric acid, but also had more complicated operation procedures, and the yield of ethyl α -selenocyanotetralone ate (68% in comparative example 1 and 89% in example 26) was lower.
Comparative example 2, another representative of the prior art, constitutes a control with example 29, and the product produced was α -seleno-cyanoacetophenone. Compared with the example 29, the yields of the alpha-selenocyanatophenone prepared by the two are approximately equivalent, but the reaction conditions required in the comparative example 2 are severer, and only when a strong oxidant such as tert-butyl hydroperoxide is added, a relatively good reaction effect can be maintained; example 29 is not limited by additional reaction conditions and requires only a single nucleophilic substitution reaction to produce a higher yield of product.
In conclusion, the selenocyanization reagent of the present invention has better application effect than the prior art.
While embodiments of the invention have been disclosed above, it is not limited to the applications listed in the description and the embodiments, which are fully applicable in all kinds of fields of application of the invention, and further modifications may readily be effected by those skilled in the art, so that the invention is not limited to the specific details without departing from the general concept defined by the claims and the scope of equivalents.
Claims (9)
1. A selenocyanization reagent, characterized in that it has the structural formula:
2. the method of preparing a selenocyanization reagent of claim 1, comprising the steps of:
s1, mixing the compound A and silver selenocyanate in an organic solvent, introducing protective gas, and after the reaction is finished, filtering under reduced pressure to obtain a concentrate; the reaction time is 12-72 hours, the temperature is 0-50 ℃, and the reaction is carried out under the condition of keeping out of the sun;
s2, purifying and separating the concentrate in the S1 to obtain the selenocyanization reagent;
the structural formula of the compound A is as follows:
3. the method of claim 2, wherein the organic solvent of S1 comprises at least one of dichloromethane, 1, 2-dichloroethane, chloroform, acetonitrile, tetrahydrofuran, toluene, methanol, and ethanol.
4. The method of claim 2, wherein the molar volume ratio of the compound a, the silver selenocyanate and the organic solvent in S1 is 1mmol: 1-2 mmol: 1-10 mL.
5. The method of claim 4, wherein the molar volume ratio of the compound A, the silver selenocyanate and the organic solvent in S1 is 1mmol: 1.2-1.5 mmol: 2-5 mL.
6. The method of claim 2, wherein the shielding gas in S1 comprises at least one of nitrogen, helium, neon, argon, krypton, xenon, and radon.
7. The method of claim 2, wherein the reaction time in S1 is 24 hours and the temperature is 25-35 ℃.
8. The method of claim 2, wherein the purification and separation in S2 is performed by: and (4) carrying out column chromatography separation on the concentrate by using a neutral alumina column.
9. Use of the selenocyanization reagent of claim 1 to prepare selenocyano-containing compounds.
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