阅读说明：本技术 一种多取代含硒环戊(己)烯骨架衍生物及其合成方法 (Polysubstituted selenium-containing cyclopentene (hexene) skeleton derivative and synthetic method thereof ) 是由 纪顺俊 蔡忠建 王典亮 于 2021-07-06 设计创作，主要内容包括：本发明涉及一种多取代含硒环戊(己)烯骨架衍生物及其合成方法,以芳基乙炔类化合物、不饱和硒醚试剂作为反应原料,在自由基引发剂的作用下,一锅法制备了多取代含硒环戊(己)烯骨架衍生物。本发明合成过程简单高效、无需金属催化剂、反应条件温和,具有良好的官能团耐受性和底物普适性。此外,不同取代基团的环戊(己)烯化合物广泛存在于药物活性分子中,且含硒化合物在抗肿瘤、抗氧化、抗炎、抗菌、抗病毒等方面也具有良好的生物活性,因此利用本发明的合成方法通过简便、高效和可持续的策略来构建C-Se键以实现由简单底物出发获得复杂的含硒环戊(己)烯骨架衍生物,具有广泛的应用前景。(The invention relates to a polysubstituted selenium-containing cyclopentyl (hexyl) ene framework derivative and a synthesis method thereof. The method has the advantages of simple and efficient synthetic process, no need of metal catalysts, mild reaction conditions, and good functional group tolerance and substrate universality. In addition, the cyclopentyl (hexylene) compounds with different substituent groups are widely present in active molecules of the medicine, and the selenium-containing compound also has good biological activity in the aspects of tumor resistance, oxidation resistance, inflammation resistance, bacteria resistance, virus resistance and the like, so that the C-Se bond is constructed by utilizing the synthetic method of the invention through a simple, efficient and sustainable strategy to obtain the complex selenium-containing cyclopentyl (hexylene) skeleton derivative from a simple substrate, and the synthetic method has wide application prospect.)

1. A polysubstituted selenium-containing cyclopent (hex) ene skeleton derivative is characterized by having the following structural general formula:

wherein X is selected from phenyl, naphthyl or heteroaryl;

R¹selected from hydrogen, C1-C4 alkyl, C1-C4 alkoxy, halogen, amino, cyano, trifluoromethyl or nitro;

y is one of formulas 1 to 6:

R²selected from the group consisting of a methyl formate, an ethyl formate or a cyano group;

R³selected from the group consisting of a methyl formate, an ethyl formate or a cyano group;

R⁴selected from phenyl, substituted phenyl or C1-C2 alkyl.

2. The method for synthesizing the polysubstituted selenium-containing cyclopent (hex) ene skeleton derivative of claim 1, comprising the steps of:

(1) under the protective atmosphere, adding an aryl acetylene compound, an unsaturated selenide reagent and a free radical initiator into an organic solvent, and stirring for reaction;

(2) after the reaction is finished, sequentially carrying out vacuum concentration and column chromatography separation on the reaction solution to obtain the polysubstituted selenium-containing cyclopent (hexylene) skeleton derivative;

has the following reaction formula:

wherein R is⁵Selected from propenyl, butenyl, 2-cyclohexenyl, 2-cyclopentenyl, 1-methyl-1-cyclohexenyl or 1-methyl-1-cyclopentenyl.

3. The method for synthesizing a polysubstituted seleno-cyclopenta (hex) ene skeleton derivative according to claim 2, wherein in step (1), the arylacetylene compound is selected from one of the structures (1) to (19):

4. the method for synthesizing polysubstituted selenocyclopenta (hex) ene skeleton derivatives as claimed in claim 2, wherein in step (1), the unsaturated selenide reagent is selected from one of structures (20) - (34):

5. the method of claim 2, wherein in step (1), the radical initiator is one of azobisisobutyronitrile, azobisisoheptonitrile, dimethyl azobisisobutyrate, N-iodo-succinimide, N-bromosuccinimide, benzoyl peroxide, and tert-butyl hydroperoxide.

6. The method for synthesizing the polysubstituted selenocyclopenta (hex) ene skeleton derivative as claimed in claim 2, wherein in the step (1), the molar ratio of the arylacetylene compound to the unsaturated selenide reagent is 1: 3-3: 1.

7. The method for synthesizing the polysubstituted seleno-cyclopent (hex) ene skeleton derivative according to claim 2, wherein in the step (1), the molar ratio of the arylacetylene compound to the radical initiator is 1: 0.1-2.

8. The method for synthesizing the polysubstituted selenocyclopenta (hex) ene skeleton derivative according to claim 2, wherein in the step (1), the organic solvent is one or more of ethyl acetate, dimethyl sulfoxide, N-dimethylformamide, N-dimethylacetamide, 1, 4-dioxane and acetonitrile.

9. The method for synthesizing the polysubstituted seleno-cyclopenta (hex) ene skeleton derivative according to claim 2, wherein the reaction temperature in step (1) is 20-150 ℃.

10. The method for synthesizing the polysubstituted selenocyclopenta (hex) ene skeleton derivative according to claim 2, wherein the reaction time in step (1) is 2-12 h.

Technical Field

The invention relates to the technical field of organic synthesis, in particular to a polysubstituted selenium-containing cyclopentene (hexene) skeleton derivative and a synthesis method thereof.

Background

Cyclopent (hex) enes are a very important organic molecular backbone, wherein cyclopent (hex) ene compounds containing different substituent groups are widely present in natural products and pharmaceutically active molecules. For example, 1, 2-diaryl cyclopentene compounds SC-57666 and SC-58231 have been shown to be an excellent class of highly selective cyclooxygenase-2 (COX-2) inhibitors; the cyclopentenol Abacavir is an already commercialized anti-AIDS adjuvant drug; both the analgesic anesthetic morphine and vitamin A contain cyclohexene skeleton.

In addition, selenium-containing compounds are receiving increasing attention due to their potential biological, medical and material properties, and some selenium-containing compounds have been demonstrated to have good biological activity in anti-tumor, anti-oxidation, anti-inflammatory, antibacterial, antiviral, etc. For example, selenocysteine is currently considered as the 21 st standard amino acid, an indispensable element in organisms; ebselen is used as a novel anti-inflammatory drug and can be clinically used for treating diseases such as rheumatoid arthritis, osteoarthritis and the like; ethaselen showed significant antitumor activity.

Therefore, the development of a high-efficiency and convenient synthesis method of the polysubstituted selenium-containing cyclopent (hexylene) skeleton derivative has important significance.

Disclosure of Invention

The invention provides a polysubstituted selenium-containing cyclopent (hexene) ene skeleton derivative and a synthesis method thereof, the polysubstituted selenium-containing cyclopent (hexene) ene skeleton derivative is synthesized in one step under the action of a free radical initiator, the reaction conditions are mild, the operation is simple and safe, the atom economy is high, and the selenium-containing cyclopent (hexene) ene skeleton derivative has potential application value in the chemical/pharmaceutical industry.

In order to solve the technical problems, the invention provides the following technical scheme:

the invention provides a polysubstituted selenium-containing cyclopentene (hexene) skeleton derivative, which has the following structural general formula:

wherein X is selected from phenyl, naphthyl or heteroaryl;

R¹selected from hydrogen, C1-C4 alkyl, C1-C4 alkoxy, halogen, amino, cyano, trifluoromethyl or nitro;

y is one of formulas 1 to 6:

R²selected from the group consisting of a methyl formate, an ethyl formate or a cyano group;

R³selected from the group consisting of a methyl formate, an ethyl formate or a cyano group;

R⁴selected from phenyl, substituted phenyl or C1-C2 alkyl.

The second aspect of the present invention provides a method for synthesizing a polysubstituted selenium-containing cyclopent (hex) ene skeleton derivative, comprising the following steps:

(1) under the protective atmosphere, adding an aryl acetylene compound, an unsaturated selenide reagent and a free radical initiator into an organic solvent, and stirring for reaction;

(2) after the reaction is finished, sequentially carrying out vacuum concentration and column chromatography separation on the reaction solution to obtain the polysubstituted selenium-containing cyclopent (hexylene) skeleton derivative;

has the following reaction formula:

wherein R is⁵Selected from propenyl, butenyl, 2-cyclohexenyl, 2-cyclopentenyl, 1-methyl-1-cyclohexenyl or 1-methyl-1-cyclopentenyl.

Further, the protective atmosphere is argon, oxygen or air.

Further, the aryl acetylene compound is preferably phenylacetylene (1), 2-fluorophenylacetylene (2), 3-fluorophenylacetylene (3), 4-fluorophenylacetylene (4), 3-chlorophenylacetylene (5), 4-chlorophenylacetylene (6), 3-bromophenylacetylene (7), 4-bromophenylacetylene (8), 4-methylphenylacetylene (9), 4-methoxy phenylacetylene (10), 3-amino phenylacetylene (11), 4-nitro phenylacetylene (12), 4-nitrile phenylacetylene (13), 4-trifluoromethyl phenylacetylene (14), 3-pyridine acetylene (15), 2-pyridine acetylene (16), 3-thiophene acetylene (17), 2-thiophene acetylene (18) or naphthalene acetylene (19), wherein the specific structural formula corresponding to each number is as follows:

further, the unsaturated selenide reagent is preferably dimethyl 2-allyl-2- (phenylseleno) malonate (20), diethyl 2-allyl-2- (phenylseleno) malonate (21), ethyl 2-methyl-2- (phenylseleno) pent-4-enoate (22), 2-allyl-2- (phenylseleno) malononitrile (23), ethyl 2-cyano-2- (phenylseleno) pent-4-enoate (24), dimethyl 2-allyl-2- (methylseleno) malonate (25), dimethyl 2-allyl-2- (ethylseleno) malonate (26), dimethyl 2-allyl-2- (4-methoxyphenylseleno) malonate (27), Dimethyl 2-allyl-2- (2-methoxyphenylseleno) malonate (28), dimethyl 2-allyl-2- (4-carbomethoxyphenylseleno) malonate (29), dimethyl 2-alkenylbutyl-2- (phenylseleno) malonate (30), dimethyl 2- (cyclohex-2-en-1-yl) -2- (phenylseleno) malonate (31), dimethyl 2- (cyclopentyl-2-en-1-yl) -2- (phenylseleno) malonate (32), dimethyl 2- (cyclohex-1-en-1-ylmethyl) -2- (phenylseleno) malonate (33) or 2- (cyclopentyl-1-en-1-ylmethyl) -2- (phenylseleno) malonate Base) one of dimethyl malonate (34), the specific structural formula corresponding to each number is as follows:

further, the free radical initiator is one of azobisisobutyronitrile, azobisisoheptonitrile, azobisisobutyrate dimethyl ester, N-iodo-succinimide, N-bromo-succinimide, benzoyl peroxide and tert-butyl hydroperoxide.

Further, the radical initiator is preferably azobisisobutyronitrile.

Further, in the step (1), the molar ratio of the aryl acetylene compounds to the unsaturated selenide reagent is 1: 3-3: 1.

In the step (1), the molar ratio of the aryl acetylene compound to the radical initiator is 1: 0.1-2.

Further, in the step (1), the organic solvent is one or more of ethyl acetate, dimethyl sulfoxide, N-dimethyl formamide, N-dimethylacetamide, 1, 4-dioxane and acetonitrile.

Further, in the step (1), the reaction temperature is 20-150 ℃.

Further, in the step (1), the reaction time is 2-12 h.

Further, the column chromatography separation conditions are as follows: the stationary phase is 200-mesh silica gel powder with 300 meshes, the mobile phase is ethyl acetate (A) and petroleum ether (B), and the volume ratio of the ethyl acetate to the petroleum ether in the mobile phase change procedure is 1: 20.

Further, the structural formula of the reaction product is one of the following numbers (35) to (67):

the reaction principle of the invention is illustrated by taking phenylacetylene and dimethyl 2-allyl-2- (phenylseleno) malonate as an example to react under the action of Azobisisobutyronitrile (AIBN) to generate 3-phenyl-4- ((phenylseleno) methyl) cyclopent-2-ene-1, 1-diformate, and mainly comprises the following steps:

(1) under the heating condition of protective atmosphere, the isobutyronitrile free radical generated by nitrogen removal of AIBN attacks dimethyl 2-allyl-2- (phenylseleno) malonate to generate a free radical I and an intermediate II;

(2) the free radical I obtained in the process (1) attacks phenylacetylene to obtain a free radical intermediate III;

(3) the free radical intermediate III generates intramolecular addition cyclization to obtain a free radical intermediate IV;

(4) the final product 3-phenyl-4- ((phenylseleno) methyl) cyclopentyl-2-ene-1, 1-dimethyl diformate is obtained by the free radical intermediate IV through the free radical exchange with the intermediate II, and simultaneously, the isobutyronitrile free radical is regenerated to complete the cycle.

By the scheme, the invention at least has the following advantages:

1. according to the invention, through C-Se bond breakage/alkyne insertion, free cyclization of alkyne is applied to synthesis of selenium functionalized product, and limitation of traditional reaction type is broken through.

2. According to the invention, aryl acetylene compounds and unsaturated selenide reagents are used as reaction raw materials, and the polysubstituted selenium-containing cyclopentene skeleton derivatives are prepared by a one-pot method under the action of a free radical initiator, so that the preparation method is simple and easy to operate, does not need metal catalysts, and is mild in reaction conditions and high in atom economy.

3. According to the synthesis method of the polysubstituted selenium-containing cyclopent (hexene) ene skeleton molecule, four groups connected with the central carbon atom of a reaction substrate can be modularly replaced without affecting the reaction, and the synthesis method is fully proved to have good functional group tolerance and substrate universality.

4. The polysubstituted selenium-containing cyclopent (hexylene) skeleton derivative provided by the invention has potential application value in the chemical/pharmaceutical industry.

Drawings

FIG. 1 is a reaction flow chart of phenylacetylene and 2-allyl-2- (phenylseleno) malonic acid dimethyl ester for preparing 3-phenyl-4- ((phenylseleno) methyl) cyclopent-2-ene-1, 1-dicarboxylic acid dimethyl ester under the action of Azobisisobutyronitrile (AIBN).

Detailed Description

The present invention is further described below in conjunction with the following figures and specific examples so that those skilled in the art may better understand the present invention and practice it, but the examples are not intended to limit the present invention.

Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. The terminology used in the description of the invention herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. As used herein, the term "and/or" includes any and all combinations of one or more of the associated listed items.

The experimental methods used in the following examples are conventional methods unless otherwise specified, and materials, reagents and the like used therein are commercially available.

Example 1: synthesis of dimethyl 3-phenyl-4- ((phenylselenyl) methyl) cyclopent-2-ene-1, 1-dicarboxylate (35)

0.0204g of phenylacetylene, 0.1308g of dimethyl 2-allyl-2-phenylselenopropionate and 0.0097g of azobisisobutyronitrile were dissolved in 2.0mL of ethyl acetate under the protection of an inert gas, and the mixture was stirred at 80 ℃ for 10 hours. After the reaction is finished, the reaction solution is subjected to vacuum concentration and column chromatography separation (under column chromatography separation conditions, the stationary phase is 200-300 meshes of silica gel powder, the mobile phase is ethyl acetate (A) and petroleum ether (B), and the volume ratio of A to B in the mobile phase change process is 1:20) in sequence, so that 0.0682g of reaction product is obtained.

The above reaction product was characterized and the results were:¹h NMR (400MHz, deuterated chloroform) δ 7.51-7.48(m,2H),7.28-7.23(m,8H),6.11(d, J ═ 4.0Hz,1H),3.76(s,3H),3.72(s, 3H),3.57-3.51(m,1H),3.24-3.20(m,1H),2.91-2.85(m,1H),2.74-2.69(m,1H), 2.65-2.60(m,1H) ppm; according to the characterization data, the prepared reaction product is a pure product (the purity is more than 95%) of 3-phenyl-4- ((phenylseleno) methyl) cyclopentyl-2-ene-1, 1-dimethyl diformate; the product yield was calculated to be 79%.

Example 2: synthesis of dimethyl 3- (2-fluorophenyl) -4- ((phenylselenyl) methyl) cyclopent-2-ene-1, 1-dicarboxylate (36)

0.0240g of 2-fluoroacetylene, 0.1308g of dimethyl 2-allyl-2-phenylselenopropane, and 0.0097g of azobisisobutyronitrile were dissolved in 2.0mL of ethyl acetate under an inert gas atmosphere, and the mixture was stirred at 80 ℃ for 10 hours. After the reaction is finished, the reaction solution is subjected to vacuum concentration and column chromatography separation (under the column chromatography separation conditions, the stationary phase is 200-300 meshes of silica gel powder, the mobile phase is ethyl acetate (A) and petroleum ether (B), and the volume ratio of A to B in the mobile phase change process is 1:20) in sequence, so that 0.0800g of reaction product is obtained.

The above reaction product was characterized and the results were:¹h NMR (400MHz, deuterated chloroform) delta 7.48-7.45(m,2H),7.27-7.22(m,4H),7.17-7.13(m,1H),7.07-7.01(m,2H),6.22(s, 1H),3.78(s,3H),3.73(s,3H),3.68-3.62(m,1H),3.18-3.14(m,1H),2.92-2.86(m, 1H),2.74-2.68(m,1H),2.55-2.50(m,1H) ppm; according to the characterization data, the prepared reaction product is pure 3- (2-fluorophenyl) -4- ((phenylseleno) methyl) cyclopent-2-ene-1, 1-dimethyl dicarboxylate (purity is more than 95%); the product yield was calculated to be 89%.

Example 3: synthesis of dimethyl 3- (3-bromophenyl) -4- ((phenylselenyl) methyl) cyclopent-2-ene-1, 1-dicarboxylate (41)

0.0361g of 3-bromophenylacetylene, 0.1308g of dimethyl 2-allyl-2-phenylselenopropane-malonate and 0.0097g of azobisisobutyronitrile were dissolved in 2.0mL of ethyl acetate under the protection of inert gas, and stirred at 80 ℃ for 10 hours. After the reaction, 0.0590g of reaction product was obtained by sequentially subjecting the reaction solution to vacuum concentration and column chromatography (under column chromatography conditions: silica gel powder with a stationary phase of 200-300 mesh, ethyl acetate (A) and petroleum ether (B) as mobile phases, and the volume ratio of A to B in the mobile phase change procedure was 1: 20).

The above reaction product was characterized and the results were:¹h NMR (400MHz, deuterated chloroform) delta 7.51-7.48(m,2H),7.40-7.37(m,2H),7.29-7.26(m,3H),7.15-7.13(m,2H),6.13, (m,1H),3.78(s,3H),3.73(s,3H),3.50-3.43(m,1H),3.19-3.15(m,1H),2.90-2.84 (m,1H),2.72-2.69(m,1H),2.67-2.61(m,1H) ppm; according to the characterization data, the prepared reaction product is pure 3- (3-bromophenyl) -4- ((phenylseleno) methyl) cyclopent-2-ene-1, 1-dimethyl dicarboxylate (purity is more than 95%); to the product yieldThe result was calculated to be 58%.

Example 4: synthesis of dimethyl 3- (3-aminophenyl) -4- ((phenylselenyl) methyl) cyclopent-2-ene-1, 1-dicarboxylate (45)

0.0234g of 3-aminophenylacetylene, 0.1308g of dimethyl 2-allyl-2-phenylselenopropane-rate and 0.0097g of azobisisobutyronitrile are dissolved in 2.0mL of ethyl acetate under the protection of inert gas, and stirred for 10 hours at 80 ℃. After the reaction, 0.0544g of reaction product was obtained by sequentially subjecting the reaction solution to vacuum concentration and column chromatography (under column chromatography conditions: silica gel powder with a stationary phase of 200-300 mesh, ethyl acetate (A) and petroleum ether (B) as mobile phases, and the volume ratio of A to B in the mobile phase change procedure was 1: 20).

The above reaction product was characterized and the results were:¹h NMR (400MHz, deuterated chloroform) delta 7.53-7.51(m,2H),7.27-7.25(m,3H),7.08-7.04(m,1H),6.67-6.64(m,1H), 6.59-6.57(m,1H),6.48-6.47(m,1H),6.06(s,1H),3.76(s,3H),3.71(s,3H), 3.51-3.44(m,1H),3.24-3.21(m,1H),2.89-2.84(m,1H),2.72-2.67(m,1H), 2.61-2.57(m,1H) ppm; according to the characterization data, the prepared reaction product is pure 3- (3-aminophenyl) -4- ((phenylseleno) methyl) cyclopent-2-ene-1, 1-dimethyl diformate (purity is more than 95%); the product yield was calculated to be 62%.

Example 5: synthesis of dimethyl 3-methyl-4- ((phenylselenyl) methyl) cyclopent-2-ene-1, 1-dicarboxylate (58)

0.0204g of phenylacetylene, 0.1060g of dimethyl 2-allyl-2- (methylseleno) malonate and 0.0097g of azobisisobutyronitrile were dissolved in 2.0mL of ethyl acetate under the protection of inert gas, and stirred at 80 ℃ for 10 hours. After the reaction, 0.0545g of reaction product was obtained by sequentially subjecting the reaction solution to vacuum concentration and column chromatography (under column chromatography conditions: silica gel powder with a stationary phase of 200-300 mesh, ethyl acetate (A) and petroleum ether (B) as mobile phases, and the volume ratio of A to B in the mobile phase change procedure was 1: 20).

The above reaction product was characterized and the results were:¹h NMR (400MHz, deuterated chloroform) delta 7.41-7.39(m,2H),7.37-7.33(m,2H),7.31-7.27(m,1H),6.12(s,1H),3.78(s,3H), 3.73(s,3H),3.64-3.59(m, 1H)H) 2.94-2.85(m,2H),2.59-2.54(m,1H),2.47-2.42(m, 1H),1.97(s,3H) ppm; according to the characterization data, the prepared reaction product is a pure product (the purity is more than 95%) of 3-methyl-4- ((phenylseleno) methyl) cyclopentyl-2-ene-1, 1-dimethyl diformate; the product yield was calculated to be 69%.

Example 6: synthesis of diethyl 3-phenyl-4- ((2-methoxyphenyl seleno) methyl) cyclopent-2-ene-1, 1-dicarboxylate (61)

0.0204g of phenylacetylene, 0.1429g of dimethyl 2-allyl-2- (2-methoxyphenylseleno) malonate and 0.0097g of azobisisobutyronitrile are dissolved in 2.0mL of ethyl acetate under the protection of inert gas, and the mixture is stirred for 10 hours at the temperature of 80 ℃. After the reaction is finished, the reaction solution is sequentially subjected to vacuum concentration and column chromatography separation (under the column chromatography separation conditions, the stationary phase is 200-300 meshes of silica gel powder, the mobile phase is ethyl acetate (A) and petroleum ether (B), and the volume ratio of A to B in the mobile phase change process is 1:20), so that 0.0585g of a reaction product is obtained.

The above reaction product was characterized and the results were:¹h NMR (400MHz, deuterated chloroform) delta 7.42-7.21(m,7H),6.88-6.82(m,2H),6.12(s,1H),4.27-4.13(m,4H),3.84(s,3H), 3.56-3.50(m,1H),3.35-3.22(m,1H),2.90-2.84(m,1H),2.72-2.61(m,2H), 1.29-1.22(m,6H) ppm; according to the characterization data, the prepared reaction product is a pure product (the purity is more than 95%) of 3-phenyl-4- ((2-methoxyphenyl seleno) methyl) cyclopentyl-2-alkene-1, 1-diethyl phthalate; the product yield was calculated to be 60%.

Example 7: synthesis of dimethyl 3-phenyl-4- ((phenylseleno) methyl) cyclohex-2-ene-1, 1-dicarboxylate (63)

0.0204g of phenylacetylene, 0.1365g of dimethyl 2-alkenylbutyl-2- (phenylselenyl) malonate and 0.0097g of azobisisobutyronitrile are dissolved in 2.0mL of ethyl acetate under the protection of inert gas, and the mixture is stirred for 10 hours at the temperature of 80 ℃. After the reaction, 0.0584g of reaction product was obtained by sequentially subjecting the reaction solution to vacuum concentration and column chromatography (under column chromatography conditions: silica gel powder with a stationary phase of 200-300 mesh, ethyl acetate (A) and petroleum ether (B) as mobile phases, and the volume ratio of A to B in the mobile phase change procedure was 1: 20).

The above reaction product was characterized and the results were:¹h NMR (400MHz, deuterated chloroform) delta 7.38-7.36(m,2H),7.27-7.25(m,3H),7.22-7.21(m,3H),7.17-7.15(m,2H),6.11(s, 1H),3.78(s,3H),3.69(s,3H),2.96-2.92(m,1H),2.89-2.84(m,1H),2.64-2.59(m, 1H),2.32-2.27(m,1H),2.16-2.10(m,1H),2.05-1.97(m,2H) ppm; according to the characterization data, the prepared reaction product is a pure product (the purity is more than 95%) of 3-phenyl-4- ((phenylseleno) methyl) cyclohex-2-ene-1, 1-dimethyl dicarboxylate; the product yield was calculated to be 66%.

From the above examples, it can be seen that under the action of a radical initiator, a series of polysubstituted selenium-containing cyclopentene/cyclohexene compounds are constructed by the serial cyclization of radicals of unsaturated selenide and terminal alkyne. The synthetic method is simple to operate, mild in reaction conditions, and has good substrate universality, excellent chemical selectivity and good atom economy.

The above-mentioned embodiments are merely preferred embodiments for fully illustrating the present invention, and the scope of the present invention is not limited thereto. The equivalent substitution or change made by the technical personnel in the technical field on the basis of the invention is all within the protection scope of the invention. The protection scope of the invention is subject to the claims.