5-Hydroxy-3-methylfuran-2(5H)-one derivatives, their preparation methods and applications

Abstract

This invention discloses 5-hydroxy-3-methylfuran-2(5H)-one derivatives, their preparation methods, and applications. This invention provides three strigolactone analogs 1a-1y, 2a-2i, and 3a-3t, which exhibit excellent activity in promoting the seed germination of *Broomrapechameleon* and *Striga asiatica*. Compared with existing synthetic strigolactone analogs, they possess advantages such as simple structure, high activity, and high stability. Furthermore, the synthesis method is simple and economical, making them a class of strigolactone analogs with significant research value. They can be used for the control of root-parasitic weeds *Broomrapechameleon* and *Striga asiatica*.

Description

Technical Field

[0001] This invention relates to plant hormone compounds and their uses, specifically to strigolactone analogs 5-hydroxy-3-methylfuran-2(5H)-one derivatives and their preparation methods and applications. Background Technology

[0002] Controlling root-parasitic weeds has always been a difficult problem in agricultural production, and there is still a lack of effective drugs to alleviate this predicament. Previous studies have shown that strigolactones (SLs) secreted by the roots of host crops can stimulate the germination of root-parasitic weed seeds, and if the germinating seeds cannot parasitize within a limited time, they will die. Natural strigolactones all contain an enol ether butenolate lactone structure (also known as an enol ether D ring). Systematic structure-activity relationship studies have shown that the enol ether butenolate lactone structure is an essential structural unit for maintaining the activity of this class of compounds. Based on this, a series of natural strigolactone analogs have been synthesized. Summary of the Invention

[0003] The purpose of this invention is to provide a 5-hydroxy-3-methylfuran-2(5H)-one derivative, its preparation method, and its application.

[0004] To achieve the objectives of this invention, in a first aspect, this invention provides a 5-hydroxy-3-methylfuran-2(5H)-one derivative, with a structure as shown in Formula I, Formula II, or Formula III:

[0005]

[0006] In Equation I, R is selected from 1a to 1y:

[0007]

[0008] In Equation II, R is selected from 2a to 2i:

[0009]

[0010] In Equation III, R is selected from 3a to 3t:

[0011]

[0012] Secondly, the present invention provides a method for preparing the 5-hydroxy-3-methylfuran-2(5H)-one derivative.

[0013] The preparation method of compound I includes: adding a phenolic derivative to a tetrahydrofuran solution of 5-chloro-3-methylfuran-2(5H)-one, cooling to 0-5℃, then adding a catalytic amount of potassium tert-butoxide, reacting at room temperature to obtain the target compound.

[0014] The phenolic derivative has the structure R-OH, where R is selected from 1a to 1y.

[0015] Furthermore, the preparation method of compound I includes the following steps:

[0016] Step 1: Add 118.6 mmol of methylmalonic acid and 118.6 mmol of glyoxal to a reaction flask containing water, add 10 drops of concentrated sulfuric acid, and heat under reflux at 110-115℃ for 10-12 h to obtain intermediate I, namely 5-hydroxy-3-methyl-2(5H)-furanone.

[0017] The molar ratio of methylmalonic acid to glyoxal is 1:1.

[0018] Step 2: Add intermediate I to the reaction flask containing DCM, slowly add SOCl2 and then add DMF, heat and reflux at 90-95℃ for 1-2 hours to obtain intermediate II, namely 5-chloro-3-methylfuran-2(5H)-one.

[0019] Step 3: Under N2 protection, add the phenolic derivative and potassium iodide to a reaction flask containing THF, cool to 0-5℃, add potassium tert-butoxide and stir for 10-15 min, then add intermediate II and react at room temperature for 3-4 h to obtain the target compound.

[0020] The preparation method of compound II includes: adding a thiophenol derivative to a tetrahydrofuran solution of 5-chloro-3-methylfuran-2(5H)-one, cooling to 0-5℃, then adding a catalytic amount of potassium tert-butoxide, reacting at room temperature to obtain the target compound.

[0021] The structure of the thiophenol derivative is R-SH, where R is selected from 2a to 2i.

[0022] Furthermore, the preparation method of compound II includes the following steps:

[0023] Step 1: Add 118.6 mmol of methylmalonic acid and 118.6 mmol of glyoxal to a reaction flask containing water, add 10 drops of concentrated sulfuric acid, and heat under reflux at 110-115℃ for 10-12 h to obtain intermediate I, namely 5-hydroxy-3-methyl-2(5H)-furanone.

[0024] The molar ratio of methylmalonic acid to glyoxal is 1:1.

[0025] Step 2: Add intermediate I to the reaction flask containing DCM, slowly add SOCl2 and then add DMF, heat and reflux at 90-95℃ for 1-2 hours to obtain intermediate II, namely 5-chloro-3-methylfuran-2(5H)-one.

[0026] Step 3: Under N2 protection, add thiophenol derivatives and potassium iodide to a reaction flask containing THF, cool to 0-5℃, add potassium tert-butoxide and stir for 10 minutes, then add intermediate II and react at room temperature for 3-4 hours to obtain the target compound.

[0027] The preparation method of compound III (R is selected from 3a to 31) includes: adding a benzoyl chloride derivative to a dichloromethane solution of 5-hydroxy-3-methyl-2(5H)-furanone, then adding a catalytic amount of DMAP, reacting at room temperature to obtain the target compound;

[0028] The structure of the benzoyl chloride derivative is as follows: R is selected from 3a to 31.

[0029] Furthermore, the preparation method of compound III includes the following steps:

[0030] Step 1: Add 118.6 mmol of methylmalonic acid and 118.6 mmol of glyoxal to a reaction flask containing water, add 10 drops of concentrated sulfuric acid, and heat under reflux at 110-115℃ for 10-12 h to obtain intermediate I, namely 5-hydroxy-3-methyl-2(5H)-furanone.

[0031] The molar ratio of methylmalonic acid to glyoxal is 1:1.

[0032] Step 2: Add 1.75 mmol of intermediate I and 1.75 mmol of DMAP to a reaction flask containing DCM and cool down to 0°C. Then add 1.75 mmol of benzoyl chloride derivative dissolved in dichloromethane dropwise. After the addition is complete, react at room temperature for 3-4 hours to obtain the target compound.

[0033] The molar ratio of intermediate I to benzoyl chloride derivative is 1:1.

[0034] The preparation method of compound III (R is selected from 3m to 3t) includes: adding 3.5 mmol of benzoic acid derivative to a dichloromethane solution of 1.75 mmol of 5-hydroxy-3-methyl-2(5H)-furanone, then adding catalytic amounts of DMAP 3.5 mmol and EDCI 3.5 mmol, reacting at room temperature to obtain the target compound;

[0035] The structure of the benzoic acid derivative is as follows: R is selected from 3m to 3t.

[0036] Furthermore, the preparation method of compound III includes the following steps:

[0037] Step 1: Add 118.6 mmol of methylmalonic acid and 118.6 mmol of glyoxal to a reaction flask containing water, add 10 drops of concentrated sulfuric acid, and heat under reflux at 110-115℃ for 10-12 h to obtain intermediate I, namely 5-hydroxy-3-methyl-2(5H)-furanone.

[0038] The molar ratio of methylmalonic acid to glyoxal is 1:1.

[0039] Step 2: Add 1.75 mmol of intermediate I, 3.5 mmol of EDCI, and 3.5 mmol of DMAP to a reaction flask containing DCM, add a benzoic acid derivative dissolved in dichloromethane, and react at room temperature for 3-4 hours to obtain the target compound.

[0040] The molar ratio of intermediate I, benzoic acid derivatives, is 1:2.

[0041] Thirdly, the present invention provides any of the following applications of the 5-hydroxy-3-methylfuran-2(5H)-one derivative:

[0042] (1) Used to induce seed germination of strigophytes and broom plants;

[0043] (2) Used for the prevention and control of strigophytes and broomrape plants.

[0044] By employing the above technical solution, the present invention has at least the following advantages and beneficial effects:

[0045] This invention utilizes a molecular model of strigolactone binding to strigolactone receptor protein and a "natural product common pharmacophore" strategy to design and synthesize novel strigolactone derivatives. It utilizes the 5-hydroxy-3-methyl-2(5H)-furanone structure of the alcohol ether butenoic acid lactone of natural strigolactone, and obtains 5-chloro-3-methylfuran-2(5H)-one by chlorination. Since the chloride ion on 5-chloro-3-methylfuran-2(5H)-one is easy to leave, it is easy to undergo substitution reactions with phenol derivatives and thiophenol derivatives. Therefore, by structurally modifying the 5-position of 5-chloro-3-methylfuran-2(5H)-one, a series of strigolactone analogs were synthesized. Simultaneously, by utilizing the hydroxyl group on 5-hydroxy-3-methyl-2(5H)-furanone to conduct esterification reactions with various substituted benzoyl chlorides or substituted benzyl carboxylic acids, a series of strigolactone analogs were synthesized. The germination activity of these compounds against broomrape and strigolactone seeds was determined. It was found that these compounds have excellent seed germination promoting activity, are easily degradable, have low residues, and are environmentally friendly. Furthermore, the synthesis method is simple and economical, and they can be used as germination activators for root-borne weeds.

[0046] This invention provides three strigolactone analogs with excellent germination-promoting activity for broomrape and strigophyte. Compared with existing synthetic strigolactone analogs, they have the characteristics of simple structure, high activity, and high stability. Moreover, the synthesis method is simple and economical. They are a class of strigolactone analogs with great research value and can be used for the control of root-parasitic weeds broomrape and strigophyte. Detailed Implementation

[0047] This invention provides three methods for synthesizing strigolactone analogs and their applications.

[0048] The strigolactone analogue of the present invention has a significant effect on promoting seed germination of broomrape and strigophyte.

[0049] The present invention adopts the following technical solution:

[0050] The present invention provides three classes of strigolactone analogs.

[0051] The first type of structure is as follows (Equation I):

[0052]

[0053] The second type of structure is as follows (Equation II):

[0054]

[0055] The third type of structure is as follows (Equation III):

[0056]

[0057] The seed germination activity provided by this invention is for strigolactone seeds and broomrape seeds. The germination activities of compounds 1a-1y, 2a-2i, 3a-3t and the control drug strigolactone GR24 at a concentration of 10 ppm were determined by plate method on the two different plants.

[0058] This invention provides a method for synthesizing strigolactone analogs with high yield, simple method and low environmental pollution. The first and second types of structures can be completed in three simple reaction steps, and the third type of structure only requires two simple reaction steps.

[0059] The preparation methods of compounds 1a to 1y are as follows:

[0060] Step 1: Methylmalonic acid and 40% glyoxal were added to a flask containing water, and 10 drops of concentrated sulfuric acid were added. The mixture was heated under reflux at 110°C for 12 hours to obtain intermediate I: 5-hydroxy-3-methyl-2(5H)-furanone.

[0061]

[0062] Step 2: After adding intermediate I to a flask containing DCM, SOCl2 was slowly added dropwise, followed by DMF. The mixture was heated and refluxed at 90°C for 1 hour to obtain intermediate II: 5-chloro-3-methylfuran-2(5H)-one.

[0063]

[0064] Step 3: Under N2 protection, add various substituted phenols and potassium iodide to a three-necked flask containing THF, cool to 0°C, add potassium tert-butoxide and stir for 10 minutes, then add intermediate II, remove the ice bath and react at room temperature for 3 hours.

[0065]

[0066] The preparation methods of compounds 2a to 2i are as follows:

[0067] Step 1: Methylmalonic acid and 40% glyoxal were added to a round-bottomed flask containing water, and then 10 drops of concentrated sulfuric acid were added. The mixture was heated under reflux at 110°C for 12 hours to obtain intermediate I: 5-hydroxy-3-methyl-2(5H)-furanone.

[0068]

[0069] Step 2: After adding intermediate I to a flask containing DCM, SOCl2 was slowly added dropwise, followed by DMF. The mixture was heated under reflux at 90°C for 1 hour to obtain intermediate II: 5-chloro-3-methylfuran-2(5H)-one.

[0070]

[0071] Step 3: Under N2 protection, various substituted thiophenols and potassium iodide are added to a three-necked flask containing THF. The mixture is cooled to 0°C in an ice bath, potassium tert-butoxide is added and stirred for 10 minutes. Then intermediate II is added, the ice bath is removed, and the mixture is reacted at a constant temperature for 3 hours.

[0072]

[0073] The preparation methods of compounds 3a to 31 are as follows:

[0074] Step 1: Methylmalonic acid and 40% glyoxal were added to a round-bottomed flask containing water, and then 10 drops of concentrated sulfuric acid were added. The mixture was heated under reflux at 110°C for 12 hours to obtain intermediate I: 5-hydroxy-3-methyl-2(5H)-furanone.

[0075]

[0076] Step 2: (1) Add intermediate I 5-hydroxy-3-methyl-2(5H)-furanone and DMAP to a flask containing DCM, cool to 0°C in an ice bath, and add various substituted benzoyl chlorides dissolved in dichloromethane dropwise. After the addition is complete, remove the ice bath and allow the reaction to proceed at a constant temperature for 3 hours.

[0077]

[0078] The preparation methods for compounds 3m to 3t are as follows:

[0079] Step 1: Methylmalonic acid and 40% glyoxal were added to a round-bottomed flask containing water, and then 10 drops of concentrated sulfuric acid were added. The mixture was heated under reflux at 110°C for 12 hours to obtain intermediate I: 5-hydroxy-3-methyl-2(5H)-furanone.

[0080]

[0081] Step 2: Add intermediate I 5-hydroxy-3-methyl-2(5H)-furanone, EDCI, and DMAP to a flask containing DCM and add various substituted benzoic acids dissolved in dichloromethane. React at room temperature for 3 hours.

[0082]

[0083] The following examples are used to illustrate the present invention, but are not intended to limit the scope of the invention. Unless otherwise specified, the technical means used in the examples are conventional means well known to those skilled in the art, and the raw materials used are all commercially available products.

[0084] Example 1: Synthesis of 5-hydroxy-3-methylfuran-2(5H)-one derivatives 1a-1y, 2a-2i, 3a-3t

[0085] Intermediate I (5-hydroxy-3-methyl-2(5H)-furanone): 7 g of methylmalonic acid and 9.3 mL of 40% glyoxal were added to a 100 mL round-bottom flask containing 60 mL of water. 10 drops of concentrated sulfuric acid were then added dropwise. The mixture was heated to reflux at 110 °C for 12 h, and the reaction was monitored by TLC until completion. Post-treatment: After cooling to room temperature, sodium chloride was added to saturation. The mixture was extracted with EA (100 mL / time, 3 times), and the organic phase was collected. The solution was dried over anhydrous Na₂SO₄ and purified by column chromatography (EA:PE = 1:5) to obtain a yellow solid product with a yield of 75%. mp 10⁵-10⁶ °C; 1 H NMR (600MHz, cdcl3) δ6.93-6.81 (m, 1H), 6.09 (s, 1H), 1.98-1.87 (m, 3H). 13C NMR (150MHz, cdcl3) 6170.78, 145.92, 131.87, 85.21, 10.38.HRMS [ESI - for C 11 H9ClO3[(MH) - ], m / z Calcd: 114.0317; Found: 114.0315.

[0086] Intermediate II (5-chloro-3-methylfuran-2(5H)-one): 4.17 g of 5-hydroxy-3-methyl-2(5H)-furanone was added to a 50 mL round-bottom flask containing 10 mL of DCM, followed by the slow addition of 1.5 mL of SOCl2 and then 200 μL of DMF. The mixture was heated to reflux at 90 °C for 1 h, and the reaction was monitored by TLC until completion. Post-treatment: After cooling to room temperature, the reaction was quenched with 10 mL of a DCM:PE (1:1) mixture and 20 mL of saturated sodium bicarbonate. Extraction was performed using DCM:PE (1:4) (20 mL / time, 3 times). The organic phase was collected, washed with saturated sodium chloride, dried over anhydrous Na2SO4, and purified by column chromatography (EA:PE = 1:10) to obtain a yellow oily product with a yield of 60%. mp 15-16 °C 1 H NMR (600MHz, cdcl3) δ7.07 (t, J=1.8Hz, 1H), 6.53 (t, J=1.7Hz, 1H), 2.00 (t, J=1.6Hz, 3H). 13 C NMR (150MHz, cdcl3) 6173.04, 144.86, 133.50, 97.07, 10.38.HRMS [ESI - for C 11 H9ClO3[(MH) - ], m / z Calcd: 131.9978; Found: 131.9977.

[0087] Compound 1a: Under N2 protection, 177 mg of phenol, 1 g of 4A molecular sieve, and 31 mg of potassium iodide were added to a 100 mL three-necked flask containing 20 mL of THF. The mixture was cooled to 0 °C in an ice bath. 212 mg of potassium tert-butoxide was added and stirred for 10 minutes. Then, 250 mg of 5-chloro-3-methylfuran-2(5H)-one was added. The ice bath was removed, and the reaction was carried out at a constant temperature for 3 hours. The reaction was monitored by TLC until completion. Post-treatment: 5 mL of water was added, and the mixture was extracted with ethyl acetate (25 mL / time, 3 times). The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA (20:1) to obtain a pale yellow solid product with a yield of 91%. mp 132-134 °C; 1H NMR (600MHz, dmso) δ7.39 (d, J=10.0Hz, 3H), 7.13 (t, J=7.6Hz, 3H), 6.71 (s, 1H), 1.91 (s, 3H). 13 C NMR (150MHz, DMSO) δ171.37, 156.01, 144.26, 132.80, 129.82, 123.24, 116.64, 98.64, 10.16.HRMS [ESI - for C 11 H 10 O3[(MH) - ], m / z Calcd: 109.0630; Found: 109.0633.

[0088] Compound 1b: Under N2 protection, 326 mg of 4-bromophenol, 1 g of 4A molecular sieve, and 31 mg of potassium iodide were added to a 100 mL three-necked flask containing 20 mL of THF. The mixture was cooled to 0 °C in an ice bath. 212 mg of potassium tert-butoxide was added and stirred for 10 minutes. Then, 250 mg of 5-chloro-3-methylfuran-2(5H)-one was added. The ice bath was removed, and the reaction was carried out at a constant temperature for 3 hours. The reaction was monitored by TLC until completion. Post-treatment: 5 mL of water was added, and the mixture was extracted with ethyl acetate (25 mL / time, 3 times). The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA (20:1) to obtain a white solid product with a yield of 95%. mp 147-148 °C; 1 H NMR (600MHz, dmso) δ7.63-7.45 (m, 2H), 7.38 (s, 1H), 7.14-7.00 (m, 2H), 6.68 (s, 1H), 1.91-1.85 (m, 3H). 13 C NMR (150MHz, DMSO) δ155.66, 144.42, 133.34, 132.94, 119.35, 115.35, 98.94, 10.55.HRMS [ESI-] for C 11 H9BrO3[(MH)-], m / z Calcd: 267.9735; Found: 267.726.

[0089] Compound 1c: Under N2 protection, 243 mg of 4-bromophenol, 1 g of 4A molecular sieve, and 31 mg of potassium iodide were added to a 100 mL three-necked flask containing 20 mL of THF. The mixture was cooled to 0 °C in an ice bath. 212 mg of potassium tert-butoxide was added and stirred for 10 minutes. Then, 250 mg of 5-chloro-3-methylfuran-2(5H)-one was added. The ice bath was removed, and the reaction was carried out at a constant temperature for 3 hours. The reaction was monitored by TLC until completion. Post-treatment: 5 mL of water was added, and the mixture was extracted with ethyl acetate (25 mL / time, 3 times). The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA (20:1) to obtain a pale yellow solid product with a yield of 89%. mp 122-123 °C; 1 H NMR (600MHz, dmso) δ7.50-7.39 (m, 2H), 7.39-7.34 (m, 1H), 7.17-7.12 (m, 2H), 6.74-6.63 (m, 1H), 1.91-1.86 (m, 3H). 13 C NMR (150MHz, dmso) δ195.08, 171.61, 155.19, 144.43, 133.34, 130.02, 127.53, 118.91, 99.02, 10.55.HRMS[O3[(MH)-], m / z Calcd: 224.0240; Found: 224.0236.

[0090] Compound 1d: Under N2 protection, 212 mg of 4-fluorophenol, 1 g of 4A molecular sieve, and 31 mg of potassium iodide were added to a 100 mL three-necked flask containing 20 mL of THF. The mixture was cooled to 0 °C in an ice bath. 212 mg of potassium tert-butoxide was added and stirred for 10 minutes. Then, 250 mg of 5-chloro-3-methylfuran-2(5H)-one was added. The ice bath was removed, and the reaction was carried out at a constant temperature for 3 hours. The reaction was monitored by TLC until completion. Post-treatment: 5 mL of water was added, and the mixture was extracted with ethyl acetate (25 mL / time, 3 times). The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA (20:1) to obtain a white solid product with a yield of 90%. mp 133-134 °C; 1 H NMR (600MHz, cdcl3) δ7.09 (ddd, J=9.1, 4.4, 2.0Hz, 2H), 7.04-6.99 (m, 2H), 6.98-6.94 (m, 1H), 6.23-6.19 (m, 1H), 2.00 (t, J=2.0Hz, 4H). 13C NMR (150MHz, DMSO) δ171.66, 159.32, 157.74, 152.59, 144.50, 133.30, 119.06, 116.71, 116.55, 99.61, 10.52.HRMS [ESI-] for C 11 H9FO3[(MH)-], m / z Calcd: 208.1884; Found: 208.1885.

[0091] Compound 1e: Under N2 protection, 287 mg of methylparaben, 1 g of 4A molecular sieve, and 31 mg of potassium iodide were added to a 100 mL three-necked flask containing 20 mL of THF. The mixture was cooled to 0 °C in an ice bath. 212 mg of potassium tert-butoxide was added and stirred for 10 minutes. Then, 250 mg of 5-chloro-3-methylfuran-2(5H)-one was added. The ice bath was removed, and the reaction was carried out at a constant temperature for 3 hours. The reaction was monitored by TLC until completion. Post-treatment: 5 mL of water was added, and the mixture was extracted with ethyl acetate (25 mL / time, 3 times). The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA (20:1) to obtain a white solid product with a yield of 89%. mp 112-113 °C; 1 H NMR (600MHz, dmso) δ7.99 (dd, J=8.7, 2.8Hz, 2H), 7.43 (s, 1H), 7.25 (d, J=8.7Hz, 2H), 6.84 (s, 1H), 3.84 (d, J=2.7Hz, 3H), 1.95-1.89 (m, 3H). 13 C NMR (150MHz, DMSO) δ171.56, 166.08, 160.02, 144.36, 133.39, 131.79, 124.79, 116.69, 98.30, 52.44, 10.56.HRMS [ESI-] for C 13 H 12 O5(MH)-], m / z Calcd: 248.0685; Found: 248.0684.

[0092] Compound 1f: Under N2 protection, 257 mg of 2-hydroxy-4-methylbenzaldehyde, 1 g of 4A molecular sieve, and 31 mg of potassium iodide were added to a 100 mL three-necked flask containing 20 mL of THF. The mixture was cooled to 0 °C in an ice bath. 212 mg of potassium tert-butoxide was added and stirred for 10 minutes. Then, 250 mg of 5-chloro-3-methylfuran-2(5H)-one was added. The ice bath was removed, and the reaction was carried out at a constant temperature for 3 hours. The reaction was monitored by TLC until completion. Post-treatment: 5 mL of water was added, and the mixture was extracted with ethyl acetate (25 mL / time, 3 times). The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA (20:1) to obtain a white solid product with a yield of 92%. mp 125-126 °C; 1 H NMR (600MHz, cdcl3) δ7.05-6.79 (m, 1H), 6.75 (d, J=3.8Hz, 3H), 6.26 (s, 1H), 2.30 (d, J=3.3Hz, 6H), 2.02-1.98 (m, 3H). 13 C NMR (150MHz, DMSO) δ171.79, 156.51, 144.71, 139.49, 133.07, 125.12, 114.66, 99.12, 21.38, 10.53.HRMS [ESI-] for C 13 H 14 O3(MH)-], m / z Calcd: 218.2520; Found: 218.2522.

[0093] Compound 1g: Under N2 protection, 231mg of 3,5-dimethylphenol, 1g of 4A molecular sieve, and 31mg of potassium iodide were added to a 100mL three-necked flask containing 20mL THF. The mixture was cooled to 0℃ in an ice bath, and 212mg of potassium tert-butoxide was added. After stirring for 10 minutes, 250mg of 5-chloro-3-methylfuran-2(5H)-one was added. The ice bath was removed, and the reaction was carried out at a constant temperature for 3 hours. The reaction was monitored by TLC until completion. Post-treatment: 5mL of water was added, and the mixture was extracted with ethyl acetate (25mL / time, 3 times). The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA (20:1) to obtain a white solid product with a yield of 94%. mp 125-126℃; 1 H NMR (600MHz, cdcl3) δ7.05-6.79 (m, 1H), 6.75 (d, J=3.8Hz, 3H), 6.26 (s, 1H), 2.30 (d, J=3.3Hz, 6H), 2.02-1.98 (m, 3H). 13C NMR (150MHz, DMSO) δ171.79, 156.51, 144.71, 139.49, 133.07, 125.12, 114.66, 99.12, 21.38, 10.53.HRMS [ESI - for C 13 H 14 O3(MH) - ], m / z Calcd: 218.2520; Found: 218.2522.

[0094] Compound 1h: Under N2 protection, 263 mg of 4-nitrophenol, 1 g of 4A molecular sieve, and 31 mg of potassium iodide were added to a 100 mL three-necked flask containing 20 mL of THF. The mixture was cooled to 0 °C in an ice bath. 212 mg of potassium tert-butoxide was added and stirred for 10 minutes. Then, 250 mg of 5-chloro-3-methylfuran-2(5H)-one was added. The ice bath was removed, and the reaction was carried out at a constant temperature for 3 hours. The reaction was monitored by TLC until completion. Post-treatment: 5 mL of water was added, and the mixture was extracted with ethyl acetate (25 mL / time, 3 times). The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA (20:1) to obtain a yellow solid with a yield of 85%. mp 115-116 °C; 1 H NMR (600MHz, dmso) δ8.29 (dd, J=9.1, 3.5Hz, 2H), 7.46 (s, 1H), 7.36 (dd, J=9.3, 3.4Hz, 2H), 6.91 (s, 1H), 1.96-1.89 (m, 3H). 13 C NMR (150MHz, DMSO) δ171.40, 161.22, 144.13, 143.16, 133.60, 126.40, 117.26, 98.19, 10.58.HRMS [ESI - for C 11 H9NO5[(MH) - ], m / z Calcd: 235.0481; Found: 235.0475.

[0095] Compound 1i: Under N2 protection, 231 mg of p-hydroxybenzaldehyde, 1 g of 4A molecular sieve, and 31 mg of potassium iodide were added to a 100 mL three-necked flask containing 20 mL of THF. The mixture was cooled to 0 °C in an ice bath. 212 mg of potassium tert-butoxide was added and stirred for 10 minutes. Then, 250 mg of 5-chloro-3-methylfuran-2(5H)-one was added. The ice bath was removed, and the reaction was carried out at a constant temperature for 3 hours. The reaction was monitored by TLC until completion. Post-treatment: 5 mL of water was added, and the mixture was extracted with ethyl acetate (25 mmol / time, 3 times). The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA (20:1) to obtain a yellow oily product with a yield of 90%. mp 12-14 °C; 1 H NMR (600MHz, dmso) δ9.92 (d, J=2.9Hz, 1H), 7.93 (dd, J=8.4, 2.9Hz, 2H), 7.43 (s, 1H), 7.31 (dd, J=8.5, 2.7Hz, 2H), 6.86 (s, 1H), 1.91 (s, 3H). 13 C NMR (150MHz, DMSO) δ191.98, 171.54, 160.92, 144.32, 133.46, 132.24, 132.02, 117.07, 98.18, 10.57.HRMS [ESI - for C 12 H 10 O4[(MH) - ], m / zCalcd: 218.0579; Found: 218.0573.

[0096] Compound 1j: Under N2 protection, 306 mg of 4-trifluoromethylphenol, 1 g of 4A molecular sieve, and 31 mg of potassium iodide were added to a 100 mL three-necked flask containing 20 mL of THF. The mixture was cooled to 0 °C in an ice bath. 212 mg of potassium tert-butoxide was added and stirred for 10 minutes. Then, 250 mg of 5-chloro-3-methylfuran-2(5H)-one was added. The ice bath was removed, and the reaction was carried out at a constant temperature for 3 hours. The reaction was monitored by TLC until completion. Post-treatment: 5 mL of water was added, and the mixture was extracted with ethyl acetate (25 mL / time, 3 times). The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA (20:1) to obtain a white solid product with a yield of 92%. mp 142-143 °C; 1 H NMR (600MHz, dmso) δ9.92 (d, J=2.9Hz, 1H), 7.93 (dd, J=8.4, 2.9Hz, 2H), 7.43 (s, 1H), 7.31 (dd, J=8.5, 2.7Hz, 2H), 6.86 (s, 1H), 1.91 (s, 3H). 13C NMR (150MHz, DMSO) δ191.98, 171.54, 160.92, 144.32, 133.46, 132.24, 132.02, 117.07, 98.18, 10.57.HRMS [ESI - for C 12 H 10 O4[(MH) - ], m / z Calcd: 218.0579; Found: 218.0573.

[0097] Compound 1k: Under N2 protection, 325 mg of 4-methylsulfonylphenol, 1 g of 4A molecular sieve, and 31 mg of potassium iodide were added to a 100 mL three-necked flask containing 20 mL of THF. The mixture was cooled to 0 °C in an ice bath. 212 mg of potassium tert-butoxide was added and stirred for 10 minutes. Then, 250 mg of 5-chloro-3-methylfuran-2(5H)-one was added. The ice bath was removed, and the reaction was carried out at a constant temperature for 3 hours. The reaction was monitored by TLC until completion. Post-treatment: 5 mL of water was added, and the mixture was extracted with ethyl acetate (25 mL / time, 3 times). The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA (20:1) to obtain a yellow solid product with a yield of 91%. mp 135-136 °C; 1 H NMR (600MHz, dmso) δ8.00-7.85(m, 2H), 7.53-7.42(m, 1H), 7.41-7.34(m, 2H), 6.93-6.85(m, 1H). 13 C NMR (151MHz, DMSO) δ171.48, 159.95, 144.25, 135.69, 133.51, 129.83, 117.26, 98.28, 44.27, 10.57.HRMS [ESI-] for C 12 H 12 O5S[(MH)-], m / z Calcd: 268.2830; Found: 268.2825.

[0098] Compound 1l: Under N2 protection, 284 mg of 4-tert-butylphenol, 1 g of 4A molecular sieve, and 31 mg of potassium iodide were added to a 100 mL three-necked flask containing 20 mL of THF. The mixture was cooled to 0 °C in an ice bath. 212 mg of potassium tert-butoxide was added and stirred for 10 minutes. Then, 250 mg of 5-chloro-3-methylfuran-2(5H)-one was added. The ice bath was removed, and the reaction was carried out at a constant temperature for 3 hours. The reaction was monitored by TLC until completion. Post-treatment: 5 mL of water was added, and the mixture was extracted with ethyl acetate (25 mL / time, 3 times). The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA (20:1) to obtain a yellow solid product with a yield of 91%. mp 141-142 °C; 1 H NMR (600MHz, dmso) δ7.36 (dt, J=9.0, 2.6Hz, 3H), 7.03 (dt, J=9.3, 2.9Hz, 2H), 6.69-6.54 (m, 1H), 1.88 (s, 3H), 1.25 (d, J=3.4Hz, 9H). 13 C NMR (150MHz, DMSO) δ171.79, 154.23, 146.00, 144.73, 133.14, 126.79, 116.60, 99.32, 34.41, 31.71, 10.56.HRMS [ESI - for C 15 H 18 O3(MH) - ], m / zCalcd: 246.1256; Found: 246.1259.

[0099] Compound 1mm: Under N2 protection, 321 mg of 4-hydroxybiphenyl, 1 g of 4A molecular sieve, and 31 mg of potassium iodide were added to a 100 mL three-necked flask containing 20 mL of THF. The mixture was cooled to 0 °C in an ice bath. 212 mg of potassium tert-butoxide was added and stirred for 10 minutes. Then, 250 mg of 5-chloro-3-methylfuran-2(5H)-one was added. The ice bath was removed, and the reaction was carried out at a constant temperature for 3 hours. The reaction was monitored by TLC until completion. Post-treatment: 5 mL of water was added, and the mixture was extracted with ethyl acetate (25 mL / time, 3 times). The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA (20:1) to obtain a white solid product with a yield of 89%. mp 135-136 °C; 1H NMR (600MHz, dmso) δ7.69-7.65 (m, 2H), 7.62 (d, J=7.5Hz, 2H), 7.44 (d, J=8.6Hz, 2H), 7.42 -7.39 (ml, 1H), 7.32 (t, J=7.4Hz, 1H), 7.23-7.16 (m, 2H), 6.74 (s, 1H), 1.93-1.86 (m, 3H). 13 C NMR (150MHz, DMSO) δ171.74, 155.98, 144.60, 139.88, 135.67, 133.26, 129.35, 128.45, 127.59, 126.86, 117.48, 99.05, 10.57.HRMS [ESI - for C 17 H 14 O3[(MH) - ], m / z Calcd: 266.0943; Found: 266.0935.

[0100] Compound 1n: Under N2 protection, 234 mg of 3-methoxyphenol, 1 g of 4A molecular sieve, and 31 mg of potassium iodide were added to a 100 mL three-necked flask containing 20 mL of THF. The mixture was cooled to 0 °C in an ice bath. 212 mg of potassium tert-butoxide was added and stirred for 10 minutes. Then, 250 mg of 5-chloro-3-methylfuran-2(5H)-one was added. The ice bath was removed, and the reaction was carried out at a constant temperature for 3 hours. The reaction was monitored by TLC until completion. Post-treatment: 5 mL of water was added, and the mixture was extracted with ethyl acetate (25 mL / time, 3 times). The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA (20:1) to obtain a yellow oily product with a yield of 92%. mp 16-17 °C; 1 H NMR (600MHz, dmso) δ7.37 (s, 1H), 7.25 (t, J=7.9Hz, 1H), 6.68 (dd, J=15.2, 8.8Hz, 4H), 3.78-3.68 (m, 3H), 1.88 (s, 3H). 13 C NMR (150MHz, dmso) δ171.74, 160.94, 157.53, 144.58, 133.17, 130.72, 109.31, 108.97, 103.31, 98.94, 55.74, 10.54.HRMS [ESI - for C 12 H 12 O4[(MH) - ], m / z Calcd: 220.0736; Found: 220.0725.

[0101] Compound 1o: Under N2 protection, 272 mg of 2-naphthol, 1 g of 4A molecular sieve, and 31 mg of potassium iodide were added to a 100 mL three-necked flask containing 20 mL of THF. The mixture was cooled to 0 °C in an ice bath. 212 mg of potassium tert-butoxide was added and stirred for 10 minutes. Then, 250 mg of 5-chloro-3-methylfuran-2(5H)-one was added. The ice bath was removed, and the reaction was carried out at a constant temperature for 3 hours. The reaction was monitored by TLC until completion. Post-treatment: 5 mL of water was added, and the mixture was extracted with ethyl acetate (25 mL / time, 3 times). The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA (20:1) to obtain a white solid product with a yield of 95%. mp 119-120 °C; 1 H NMR (600MHz, dmso) δ7.38 (dt, J=3.8, 1.8Hz, 1H), 7.20 (dd, J=8.7, 2.3Hz, 2H), 7.08-6.97 (m, 2H), 6.65 (d, J=2.5Hz, 1H), 2.57 (q, J=7.6Hz, 2H), 1.92-1.83 (m, 3H), 1.16 (t, J=7.5Hz, 3H). 13 C NMR (150MHz, DMSO) δ171.75, 154.45, 144.64, 139.06, 133.11, 129.29, 117.04, 99.34, 27.75, 16.14, 10.50.HRMS [ESI - for C 15 H 12 O3[(MH) - ], m / z Calcd: 240.0786; Found: 240.0785.

[0102] Compound 1p: Under N2 protection, 180 mg of 4-hydroxypyridine, 1 g of 4A molecular sieve, and 31 mg of potassium iodide were added to a 100 mL three-necked flask containing 20 mL of THF. The mixture was cooled to 0 °C in an ice bath. 212 mg of potassium tert-butoxide was added and stirred for 10 minutes. Then, 250 mg of 5-chloro-3-methylfuran-2(5H)-one was added. The ice bath was removed, and the reaction was carried out at a constant temperature for 3 hours. The reaction was monitored by TLC until completion. Post-treatment: 5 mL of water was added, and the mixture was extracted with ethyl acetate (25 mL / time, 3 times). The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA (20:1) to obtain a white solid product with a yield of 90%. mp 126-127 °C; 1 H NMR (600MHz, dmso) δ7.69 (d, J=7.3Hz, 2H), 7.38 (s, 1H), 6.75 (s, 1H), 6.11 (d, J=7.1Hz, 2H), 1.97-1.84 (m, 3H).13 C NMR (150MHz, DMSO) δ171.46, 143.19, 139.16, 134.89, 118.35, 90.06, 10.88.HRMS [ESI - for C 10 H9NO3[(MH) - ], m / z Calcd: 191.0582; Found: 191.0574.

[0103] Compound 1q: Under N2 protection, 204 mg of 4-methylphenol, 1 g of 4A molecular sieve, and 31 mg of potassium iodide were added to a 100 mL three-necked flask containing 20 mL of THF. The mixture was cooled to 0 °C in an ice bath. 212 mg of potassium tert-butoxide was added and stirred for 10 minutes. Then, 250 mg of 5-chloro-3-methylfuran-2(5H)-one was added. The ice bath was removed, and the reaction was carried out at a constant temperature for 3 hours. The reaction was monitored by TLC until completion. Post-treatment: 5 mL of water was added, and the mixture was extracted with ethyl acetate (25 mL / time, 3 times). The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA (20:1) to obtain a white solid product with a yield of 92%. mp 120-121 °C; 1 H NMR (600MHz, dmso) δ7.43-7.29 (m, 1H), 7.17 (d, J=8.0Hz, 2H), 7.06-6.93 (m, 2H), 6.70-6.59 (m, 1H), 2.27 (s, 3H), 1.95-1.82 (m, 3H). 13 C NMR (150MHz, DMSO) δ171.77, 154.29, 144.66, 133.14, 132.65, 130.48, 117.07, 99.38, 20.57, 10.52.HRMS [ESI - for C 12 H 12 O3(MH) - ], m / z Calcd: 204.2250; Found: 204.2249.

[0104] Compound 1r: Under N2 protection, 231 mg of 4-ethylphenol, 1 g of 4A molecular sieve, and 31 mg of potassium iodide were added to a 100 mL three-necked flask containing 20 mL of THF. The mixture was cooled to 0 °C in an ice bath. 212 mg of potassium tert-butoxide was added and stirred for 10 minutes. Then, 250 mg of 5-chloro-3-methylfuran-2(5H)-one was added. The ice bath was removed, and the reaction was carried out at a constant temperature for 3 hours. The reaction was monitored by TLC until completion. Post-treatment: 5 mL of water was added, and the mixture was extracted with ethyl acetate (25 mL / time, 3 times). The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA (20:1) to obtain a white solid product with a yield of 88%. mp 129-130 °C; 1 H NMR (600MHz, dmso) δ7.38 (dt, J=3.8, 1.8Hz, 1H), 7.20 (dd, J=8.7, 2.3Hz, 2H), 7.08-6.97 (m, 2H), 6.65 (d, J=2.5Hz, 1H), 2.57 (q, J=7.6Hz, 2H), 1.92-1.83 (m, 3H), 1.16 (t, J=7.5Hz, 3H). 13 C NMR (150MHz, DMSO) δ171.75, 154.45, 144.64, 139.06, 133.11, 129.29, 117.04, 99.34, 27.75, 16.14, 10.50.HRMS [ESI - for C 13 H 14 O3[(MH) - ], m / z Calcd: 218.0943; Found: 218.0942.

[0105] Compound 1s: Under N2 protection, 257 mg of 2,3,5-trimethylphenol, 1 g of 4A molecular sieve, and 31 mg of potassium iodide were added to a 100 mL three-necked flask containing 20 mL of THF. The mixture was cooled to 0 °C in an ice bath. 212 mg of potassium tert-butoxide was added and stirred for 10 minutes. Then, 250 mg of 5-chloro-3-methylfuran-2(5H)-one was added. The ice bath was removed, and the reaction was carried out at a constant temperature for 3 hours. The reaction was monitored by TLC until completion. Post-treatment: 5 mL of water was added, and the mixture was extracted with ethyl acetate (25 mL / time, 3 times). The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA (20:1) to obtain a white solid product with a yield of 90%. mp 138-139 °C; 1H NMR (600MHz, dmso) δ7.41 (s, 1H), 6.88 (s, 1H), 6.76 (s, 1H), 6.54 (s, 1H), 2.25 (s, 3H), 2.19 (s, 3H), 2.03 (s, 3H), 1.91 (s, 3H). 13 C NMR (150MHz, cdcl3) δ171.53, 154.70, 142.56, 138.08, 136.03, 134.27, 126.03, 114.31, 100.09, 21.07, 19.96, 11.60, 10.58.HRMS [ESI - for C 14 H 16 O3[(MH) - ], m / z Calcd: 232.1099; Found: 232.1088.

[0106] Compound 1t: Under N2 protection, 274 mg of 6-hydroxyisoquinoline, 1 g of 4A molecular sieve, and 31 mg of potassium iodide were added to a 100 mL three-necked flask containing 20 mL of THF. The mixture was cooled to 0 °C in an ice bath. 212 mg of potassium tert-butoxide was added and stirred for 10 minutes. Then, 250 mg of 5-chloro-3-methylfuran-2(5H)-one was added. The ice bath was removed, and the reaction was carried out at a constant temperature for 3 hours. The reaction was monitored by TLC until completion. Post-treatment: 5 mL of water was added, and the mixture was extracted with ethyl acetate (25 mL / time, 3 times). The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA (20:1) to obtain a yellow oily product with a yield of 92%. mp 10-11 °C; 1 H NMR (600MHz, dmso) δ9.32 (s, 1H), 8.52 (d, J=5.8Hz, 1H), 7.87 (dd, J=10.1, 7. 0Hz, 2H), 7.67 (t, J=8.0Hz, 1H), 7.63-7.47 (m, 2H), 6.89 (s, 1H), 1.94 (s, 3H). 13 C NMR (150MHz, DMSO) δ171.64, 152.45, 150.98, 144.51, 143.51, 133.50, 129.45, 128.09, 122.71, 114.61, 114.24, 99.37, 10.64.HRMS [ESI - for C 14 H 11 NO3[(MH) - ], m / z Calcd: 241.0739; Found: 241.0726

[0107] Compound 1u: Under N2 protection, 206 mg of 4-aminophenol, 1 g of 4A molecular sieve, and 31 mg of potassium iodide were added to a 100 mL three-necked flask containing 20 mL of THF. The mixture was cooled to 0 °C in an ice bath. 212 mg of potassium tert-butoxide was added and stirred for 10 minutes. Then, 250 mg of 5-chloro-3-methylfuran-2(5H)-one was added. The ice bath was removed, and the reaction was carried out at a constant temperature for 3 hours. The reaction was monitored by TLC until completion. Post-treatment: 5 mL of water was added, and the mixture was extracted with ethyl acetate (25 mL / time, 3 times). The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA (20:1) to obtain a white solid product with a yield of 92%. mp 156-157 °C; 1 H NMR (600MHz, dmso) δ7.29 (s, 1H), 6.79 (dd, J=9.2, 3.2Hz, 2H), 6.51 (dd, J=9.2, 3.2Hz, 2H), 6.39 (s, 1H), 4.92 (s, 2H), 1.84 (s, 3H). 13 C NMR (150MHz, DMSO) δ171.90, 147.18, 145.21, 144.87, 133.01, 118.96, 115.04, 100.81, 10.52.HRMS [ESI - for C 11 H 11 NO3[(MH) - ], m / z Calcd: 205.0739; Found: 250.0736.

[0108] Compound 1v: Under N2 protection, 243 mg of 3-chlorophenol, 1 g of 4A molecular sieve, and 31 mg of potassium iodide were added to a 100 mL three-necked flask containing 20 mL of THF. The mixture was cooled to 0 °C in an ice bath. 212 mg of potassium tert-butoxide was added and stirred for 10 minutes. Then, 250 mg of 5-chloro-3-methylfuran-2(5H)-one was added. The ice bath was removed, and the reaction was carried out at a constant temperature for 3 hours. The reaction was monitored by TLC until completion. Post-treatment: 5 mL of water was added, and the mixture was extracted with ethyl acetate (25 mL / time, 3 times). The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA (20:1) to obtain a white solid product with a yield of 91%. mp 143-144 °C; 1 H NMR (600MHz, dmso) δ7.41 (q, J=7.0Hz, 2H), 7.26-7.21 (m, 1H), 7.21-7.16 (m, 1H), 7.14-7.08 (m, 1H), 6.79-6.73 (m, 1H), 1.97-1.83 (m, 3H). 13C NMR (150MHz, cdcl3) δ171.27, 157.28, 142.21, 135.35, 134.97, 130.80, 124.09, 117.85, 115.46, 98.99, 10.87.HRMS [ESI - for C 11 H9ClO3[(MH) - ], m / z Calcd: 224.0240; Found: 224.0239.

[0109] Compound 1w: Under N2 protection, 308 mg of 3,4-dichlorophenol, 1 g of 4A molecular sieve, and 31 mg of potassium iodide were added to a 100 mL three-necked flask containing 20 mL of THF. The mixture was cooled to 0 °C in an ice bath. 212 mg of potassium tert-butoxide was added and stirred for 10 minutes. Then, 250 mg of 5-chloro-3-methylfuran-2(5H)-one was added. The ice bath was removed, and the reaction was carried out at a constant temperature for 3 hours. The reaction was monitored by TLC until completion. Post-treatment: 5 mL of water was added, and the mixture was extracted with ethyl acetate (25 mL / time, 3 times). The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA (20:1) to obtain a white solid product with a yield of 93%. mp 138-139 °C; 1 H NMR (600MHz, dmso) δ7.61 (dd, J=8.8, 3.0Hz, 1H), 7.44 (d, J=3.0Hz, 1H), 7.41-7.36 (m, 1H), 7.14 (dd, J=8.9, 3.0 Hz, 1H), 6.82-6.69 (m, 1H), 1.91-1.83 (m, 3H). 13 C NMR (150MHz, cdcl3) δ170.81, 155.23, 141.71, 134.87, 133.21, 130.91, 127.25, 119.17, 116.69, 98.78, 10.59.HRMS [ESI - for C 11 H8Cl2O3[(MH) - ], m / z Calcd: 257.9850; Found: 257.9843.

[0110] Compound 1x: Under N2 protection, 308 mg of 3,5-dichlorophenol, 1 g of 4A molecular sieve, and 31 mg of potassium iodide were added to a 100 mL three-necked flask containing 20 mL of THF. The mixture was cooled to 0 °C in an ice bath. 212 mg of potassium tert-butoxide was added and stirred for 10 minutes. Then, 250 mg of 5-chloro-3-methylfuran-2(5H)-one was added. The ice bath was removed, and the reaction was carried out at a constant temperature for 3 hours. The reaction was monitored by TLC until completion. Post-treatment: 5 mL of water was added, and the mixture was extracted with ethyl acetate (25 mL / time, 3 times). The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA (20:1) to obtain a white solid product with a yield of 93%. mp 147-149 °C; 1 H NMR (600MHz, dmso) δ7.41-7.36 (m, 1H), 7.38-7.31 (m, 1H), 7.23 (d, J=2.1Hz, 2H), 6.80 (s, 1H), 1.92-1.85 (m, 3H). 13 C NMR (150MHz, DMSO) δ171.38, 157.53, 144.07, 135.20, 133.56, 123.38, 116.28, 98.55, 10.54.HRMS [ESI - for C 11 H8C12O3[(MH) - ], m / z Calcd: 257.9850; Found: 257.9839.

[0111] Compound 1y: Under N2 protection, 308 mg of 2,3-dichlorophenol, 1 g of 4A molecular sieve, and 31 mg of potassium iodide were added to a 100 mL three-necked flask containing 20 mL of THF. The mixture was cooled to 0 °C in an ice bath. 212 mg of potassium tert-butoxide was added and stirred for 10 minutes. Then, 250 mg of 5-chloro-3-methylfuran-2(5H)-one was added. The ice bath was removed, and the reaction was carried out at a constant temperature for 3 hours. The reaction was monitored by TLC until completion. Post-treatment: 5 mL of water was added, and the mixture was extracted with ethyl acetate (25 mL / time, 3 times). The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA (20:1) to obtain a white solid product with a yield of 95%. mp 125-126 °C; 1 H NMR (600MHz, dmso) δ7.47-7.40 (m, 1H), 7.39 (d, J=3.4Hz, 3H), 6.77 (s, 1H), 1.96-1.84 (m, 3H). 13C NMR (150MHz, cdcl3) δ170.80, 153.39, 141.73, 134.99, 134.07, 127.62, 125.66, 123.77, 116.75, 99.59, 10.58.HRMS [ESI - for C 11 H8Cl2o3[(MH) - ], m / z Calcd: 257.9850; Found: 257.9853.

[0112] Compound 2a: Under N2 protection, 242 mg of 4-fluorothiophenol, 1 g of 4A molecular sieve, and 31 mg of potassium iodide were added to a 100 mL three-necked flask containing 20 mL of THF. The mixture was cooled to 0 °C in an ice bath. 212 mg of potassium tert-butoxide was added and stirred for 10 minutes. Then, 250 mg of 5-chloro-3-methylfuran-2(5H)-one was added. The ice bath was removed, and the reaction was carried out at a constant temperature for 3 hours. The reaction was monitored by TLC until completion. Post-treatment: 5 mL of water was added, and the mixture was extracted with ethyl acetate (25 mL / time, 3 times). The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA (20:1) to obtain a pale yellow solid product with a yield of 85%. mp 125-126 °C; 1 H NMR (600MHz, cdcl3) δ7.54-7.48 (m, 2H), 7.07-7.00 (m, 2H), 6.93 (q, J=1.6Hz, 1H), 6.03 (q, J=1.9Hz, 1H), 1.82 (t, J=1.8Hz, 3H). 13 C NMR (150MHz, cdcl3) δ172.45, 164.32, 162.66, 144.72, 136.85, 136.79, 132.12, 124.76, 116.35, 85.60, 10.37.HRMS [ESI - for C 11 H9FO2S[(MH) - ], m / zCalcd: 224.0307; Found: 224.0301

[0113] Compound 2b: Under N2 protection, 357 mg of 4-bromothiophenol, 1 g of 4A molecular sieve, and 31 mg of potassium iodide were added to a 100 mL three-necked flask containing 20 mL of THF. The mixture was cooled to 0 °C in an ice bath. 212 mg of potassium tert-butoxide was added and stirred for 10 minutes. Then, 250 mg of 5-chloro-3-methylfuran-2(5H)-one was added. The ice bath was removed, and the reaction was carried out at a constant temperature for 3 hours. The reaction was monitored by TLC until completion. Post-treatment: 5 mL of water was added, and the mixture was extracted with ethyl acetate (25 mL / time, 3 times). The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA (20:1) to obtain a yellow solid product with a yield of 82%. mp 118-119 °C; 1 H NMR (600MHz, cdcl3) δ7.50-7.44 (m, 2H), 7.41-7.35 (m, 2H), 6.95 (p, J=1.7Hz, 1H), 6.07 (p, J=1.9Hz, 1H), 1.86 (t, J=1.8Hz, 3H). 13 C NMR (150MHz, cdcl3) δ172.37, 144.45, 135.37, 132.42, 132.30, 129.32, 123.64, 85.41, 10.46.HRMS [ESI - for C 11 H9BrO2S[(MH) - ], m / z Calcd: 285.1550; Found: 285.1543.

[0114] Compound 2c: Under N2 protection, 23 mg of 2-methylthiophenol, 1 g of 4A molecular sieve, and 31 mg of potassium iodide were added to a 100 mL three-necked flask containing 20 mL of THF. The mixture was cooled to 0 °C in an ice bath. 212 mg of potassium tert-butoxide was added and stirred for 10 minutes. Then, 250 mg of 5-chloro-3-methylfuran-2(5H)-one was added. The ice bath was removed, and the reaction was carried out at a constant temperature for 3 hours. The reaction was monitored by TLC until completion. Post-treatment: 5 mL of water was added, and the mixture was extracted with ethyl acetate (25 mL / time, 3 times). The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA, 20:1) to obtain a yellow oily product with a yield of 88%. mp14-15℃; 1H NMR (600MHz, cdcl3) δ7.57-7.54 (m, 1H), 7.25-7.19 (m, 2H), 7.17 (td, J=7.1, 2.4Hz, 1 H), 6.98 (p, J=1.7Hz, 1H), 6.09 (p, J=1.9Hz, 1H), 2.46 (s, 3H), 1.85 (t, J=1.8Hz, 3H). 13C NMR (150MHz, cdcl3) δ172.61, 144.68, 141.22, 134.89, 131.84, 130.62, 129.70, 129.15, 126.68, 85.80, 21.04, 10.45.HRMS [ESI - for C 12 H 12 02S[(MH) - ], m / z Calcd: 220.0558; Found: 220.0549.

[0115] Compound 2d: Under N2 protection, 265 mg of 4-methoxythiophenol, 1 g of 4A molecular sieve, and 31 mg of potassium iodide were added to a 100 mL three-necked flask containing 20 mL of THF. The mixture was cooled to 0 °C in an ice bath. 212 mg of potassium tert-butoxide was added and stirred for 10 minutes. Then, 250 mg of 5-chloro-3-methylfuran-2(5H)-one was added. The ice bath was removed, and the reaction was carried out at a constant temperature for 3 hours. The reaction was monitored by TLC until completion. Post-treatment: 5 mL of water was added, and the mixture was extracted with ethyl acetate (25 mL / time, 3 times). The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA (20:1) to obtain a yellow solid product with a yield of 89%. mp 123-124 °C; 1 H NMR (600MHz, cdcl3) δ7.44-7.41 (m, 2H), 6.91 (p, J=1.6Hz, 1H), 6.86-6.82 (m, 2H), 5.99 (p, J=1.9Hz, 1H), 3.80 (s, 3H), 1.79 (t, J=1.8Hz, 3H). 13 C NMR (150MHz, cdcl3) δ172.72, 160.74, 145.13, 136.90, 131.65, 119.61, 114.61, 85.93, 55.34, 10.35.HRMS [ESI - for C 12 H 12 O3S[(MH) - ], m / z Calcd: 236.0507; Found: 236.0493.

[0116] Compound 2e: Under N2 protection, 314 mg of 4-tert-butylthiophenol, 1 g of 4A molecular sieve, and 31 mg of potassium iodide were added to a 100 mL three-necked flask containing 20 mL of THF. The mixture was cooled to 0 °C in an ice bath. 212 mg of potassium tert-butoxide was added and stirred for 10 minutes. Then, 250 mg of 5-chloro-3-methylfuran-2(5H)-one was added. The ice bath was removed, and the reaction was carried out at a constant temperature for 3 hours. The reaction was monitored by TLC until completion. Post-treatment: 5 mL of water was added, and the mixture was extracted with ethyl acetate (25 mL / time, 3 times). The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA (20:1) to obtain a yellow solid product with a yield of 81%. mp 135-136 °C; 1 H NMR (600MHz, cdcl3) δ7.47-7.42 (m, 2H), 7.36-7.32 (m, 2H), 6.95-6.93 (m, 1H), 6.07 (p, J=1.9Hz, 1H), 1.81 (t, J=1.8Hz, 3H), 1.30 (d, J=0.7Hz, 9H). 13 C NMR (150MHz, cdcl3) δ172.69, 152.53, 144.87, 133.70, 131.83, 126.57, 126.15, 85.98, 34.66, 31.16, 10.35.HRMS [ESI - forC 15 H 18 O2S[(MH) - ], m / z Calcd: 262.1028; Found: 262.1019.

[0117] Compound 2f: Under N2 protection, 302 mg of 2-naphthiophenol, 1 g of 4A molecular sieve, and 31 mg of potassium iodide were added to a 100 mL three-necked flask containing 20 mL of THF. The mixture was cooled to 0 °C in an ice bath. 212 mg of potassium tert-butoxide was added and stirred for 10 minutes. Then, 250 mg of 5-chloro-3-methylfuran-2(5H)-one was added. The ice bath was removed, and the reaction was carried out at a constant temperature for 3 hours. The reaction was monitored by TLC until completion. Post-treatment: 5 mL of water was added, and the mixture was extracted with ethyl acetate (25 mL / time, 3 times). The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA (20:1) to obtain a yellow solid product with a yield of 90%. mp 124-125 °C; 1H NMR (600MHz, cdcl3) δ8.05 (d, J=1.8Hz, 1H), 7.86-7.76 (m, 3H), 7.56 (dd, J=8.5, 1.9Hz, 1H), 7. 52 (dt, J=6.2, 3.4Hz, 2H), 7.01 (t, J=1.6Hz, 1H), 6.19 (p, J=1.9Hz, 1H), 1.82 (t, J=1.8Hz, 3H). 13 C NMR (150MHz, cdcl3) δ172.63, 144.72, 133.47, 133.24, 133.01, 132.16, 130. 24, 128.77, 127.79, 127.75, 127.71, 126.97, 126.79, 85.99, 10.43.HRMS [ESI - for C 15 H 18 O2S[(MH) - ], m / z Calcd: 256.0558; Found: 256.0846.

[0118] Compound 2g: Under N2 protection, 273mg of 4-chlorothiophenol, 1g of 4A molecular sieve, and 31mg of potassium iodide were added to a 100mL three-necked flask containing 20mL THF. The mixture was cooled to 0℃ in an ice bath. 212mg of potassium tert-butoxide was added and stirred for 10 minutes. Then, 250mg of 5-chloro-3-methylfuran-2(5H)-one was added. The ice bath was removed, and the reaction was carried out at a constant temperature for 3 hours. The reaction was monitored by TLC until completion. Post-treatment: 5mL of water was added, and the mixture was extracted with ethyl acetate (25mL / time, 3 times). The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA (20:1) to obtain a white solid product with a yield of 88%. mp 147-148℃; 1 H NMR (600MHz, cdcl3) δ7.48-7.44 (m, 2H), 7.33-7.30 (m, 2H), 6.95 (p, J=1.7Hz, 1H), 6.07 (p, J=1.9Hz, 1H), 1.86 (t, J=1.8Hz, 3H). 13 C NMR (150MHz, cdcl3) δ172.38, 144.51, 135.52, 135.08, 132.35, 129.33, 128.56, 85.48, 10.43.HRMS [ESI - for C 11 H9O2S[(MH) - ], m / z Calcd: 240.0012; Found: 240.0003.

[0119] Compound 2h: Under N2 protection, 261 mg of 2,5-dimethylthiophenol, 1 g of 4A molecular sieve, and 31 mg of potassium iodide were added to a 100 mL three-necked flask containing 20 mL of THF. The mixture was cooled to 0 °C in an ice bath. 212 mg of potassium tert-butoxide was added and stirred for 10 minutes. Then, 250 mg of 5-chloro-3-methylfuran-2(5H)-one was added. The ice bath was removed, and the reaction was carried out at a constant temperature for 3 h. The reaction was monitored by TLC until completion. Post-treatment: 5 mL of water was added, and the mixture was extracted with ethyl acetate (25 mL / time, 3 times). The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA (20:1) to obtain a yellow solid product with a yield of 85%. mp 124-125 °C; 1 H NMR (600MHz, cdcl3) δ7.38 (d, J=1.8Hz, 1H), 7.11 (d, J=7.7Hz, 1H), 7.05 (dd, J=7.8, 1.8Hz, 1H) , 6.99 (p, J=1.5Hz, 1H), 6.09 (q, J=1.9Hz, 1H), 2.41 (s, 3H), 2.30 (s, 3H), 1.86 (t, J=1.8Hz, 3H). 13 C NMR (150MHz, cdcl3) δ172.68, 144.68, 137.78, 136.41, 135.11, 131.84, 130.37, 129.55, 85.97, 20.72, 20.50, 10.42.HRMS [ESI - for C 13 H 14 O2S[(MH) - ], m / z Calcd: 234.0715; Found: 234.0709.

[0120] Compound 2i: Under N2 protection, 288 mg of 4-isopropylthiophenol, 1 g of 4A molecular sieve, and 31 mg of potassium iodide were added to a 100 mL three-necked flask containing 20 mL of THF. The mixture was cooled to 0 °C in an ice bath. 212 mg of potassium tert-butoxide was added and stirred for 10 minutes. Then, 250 mg of 5-chloro-3-methylfuran-2(5H)-one was added. The ice bath was removed, and the reaction was carried out at a constant temperature for 3 hours. The reaction was monitored by TLC until completion. Post-treatment: 5 mL of water was added, and the mixture was extracted with ethyl acetate (25 mL / time, 3 times). The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA (20:1) to obtain a yellow oily product with a yield of 89%. mp 5-6 °C; 1H NMR (600MHz, cdcl3) δ7.46-7.42 (m, 2H), 7.21-7.16 (m, 2H), 6.93 (q, J=1.8Hz, 1H), 6.12 -6.03 (m, 1H), 2.89 (p, J=7.2Hz, 1H), 1.81 (d, J=2.0Hz, 3H), 1.23 (dd, J=7.2, 2.0Hz, 6H). 13 C NMR (150MHz, cdcl3) δ172.71, 150.29, 144.92, 134.40, 131.81, 127.26, 126.71, 85.98, 33.84, 23.59, 10.35.HRMS [ESI - for C 12 H 12 O5S[(MH) - ], m / z Calcd: 268.0405; Found: 268.0394.

[0121] Compound 3a: 200 mg of 5-hydroxy-3-methyl-2(5H)-furanone and 214 mg of DMAP were added to a 100 mL round-bottom flask containing 10 mL of DCM. The mixture was cooled to 0 °C in an ice bath, and 246 mg of benzoyl chloride dissolved in DCM was added dropwise. After the addition was complete, the ice bath was removed, and the reaction was carried out at a constant temperature for 3 h. The reaction was monitored by TLC until completion. Post-treatment: Extraction was performed with 10 mL of saturated sodium chloride aqueous solution. The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA 10:1) to obtain a white solid product with a yield of 89%. mp 122-126 °C; 1 H NMR (600MHz, cdcl3) δ 8.18-7.97 (m, 2H), 7.61 (q, J=5.8Hz, 1H), 7.46 (t, J=7.6Hz, 2H), 7.16-7.07 (m, 1H), 7.06-6.99 (m, 1H), 2.20-1.93 (m, 3H). 13 C NMR (150MHz, cdcl3) δ171.07, 164.74, 142.12, 134.57, 133.99, 130.05, 128.58, 128.43, 93.03, 10.64.HRMS [ESI-] forC 12 H 10 O4[(MH)-], m / zCalcd: 218.21; Found: 218.18.

[0122] Compound 3b: 200 mg of 5-hydroxy-3-methyl-2(5H)-furanone and 214 mg of DMAP were added to a 100 mL round-bottom flask containing 10 mL of DCM. The mixture was cooled to 0 °C in an ice bath, and 306 mg of 4-chlorobenzoyl chloride dissolved in DCM was added dropwise. After the addition was complete, the ice bath was removed, and the reaction was carried out at a constant temperature for 3 h. The reaction was monitored by TLC until completion. Post-treatment: Extraction was performed with 10 mL of saturated sodium chloride aqueous solution. The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA (10:1) to obtain a white solid product with a yield of 91%. mp 142-145 °C; 1 H NMR (600MHz, cdcl3) δ7.97 (td, J=6.4, 2.8Hz, 2H), 7.50-7.36 (m, 2H), 7.14-7.05 (m, 1H), 7.03-6.95 (m, 1H), 2.08-1.95 (m, 3H). 13 C NMR (150MHz, cdcl3) δ170.87, 163.91, 141.86, 140.63, 134.73, 131.40, 128.99, 126.88, 93.08, 10.62.HRMS [ESI - forC 12 H9ClO4[(MH) - ], m / zCalcd: 252.65; Found: 252.62.

[0123] Compound 3c: 200 mg of 5-hydroxy-3-methyl-2(5H)-furanone and 214 mg of DMAP were added to a 100 mL round-bottom flask containing 10 mL of DCM. The mixture was cooled to 0 °C in an ice bath, and 277 mg of 4-fluorobenzoyl chloride dissolved in DCM was added dropwise. After the addition was complete, the ice bath was removed, and the reaction was carried out at a constant temperature for 3 h. The reaction was monitored by TLC until the reaction was completed. Post-treatment: Extraction was performed with 10 mL of saturated sodium chloride aqueous solution. The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA 10:1) to obtain a white solid product with a yield of 85%. mp 143-144 °C; 1 H NMR (600MHz, cdcl3) δ8.06 (dd, J=8.8, 5.6Hz, 2H), 7.18-7.05 (m, 3H), 7.02 (d, J=2.6Hz, 1H), 2.09-1.96 (m, 3H). 13 C NMR (150MHz, cdcl3) δ170.93, 167.21, 165.51, 163.75, 141.94, 134.68, 132.70, 124.67, 115.93, 115.78, 93.03, 10.61.HRMS [ESI- forC 12 H9FO4[(MH) - ], m / zCalcd: 236.20; Found: 236.16.

[0124] Compound 3d: 200 mg of 5-hydroxy-3-methyl-2(5H)-furanone and 214 mg of DMAP were added to a 100 mL round-bottom flask containing 10 mL of DCM. The mixture was cooled to 0 °C in an ice bath, and 270 mg of 4-methylbenzoyl chloride dissolved in DCM was added dropwise. After the addition was complete, the ice bath was removed, and the reaction was carried out at a constant temperature for 3 h. The reaction was monitored by TLC until the reaction was completed. Post-treatment: Extraction was performed with 10 mL of saturated sodium chloride aqueous solution. The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA 10:1) to obtain a white solid product with a yield of 92%. mp 124-125 °C; 1 H NMR (600MHz, cdcl3) δ7.97-7.90 (m, 2H), 7.27 (s, 2H), 7.12 (s, 1H), 7.06-6.99 (m, 1H), 2.43 (s, 3H), 2.04 (s, 3H). 13 C NMR (150MHz, cdcl3) δ171.14, 164.76, 144.95, 142.25, 134.47, 130.10, 129.30, 125.65, 125.65, 92.95, 21.71, 10.63.HRMS [ESI - forC 13 H 12 O4[(MH)-], m / zCalcd: 232.24; Found: 232.18.

[0125] Compound 3e: 200 mg of 5-hydroxy-3-methyl-2(5H)-furanone and 214 mg of DMAP were added to a 100 mL round-bottom flask containing 10 mL of DCM. The mixture was cooled to 0 °C in an ice bath, and 333 mg of 2-naphthoyl chloride dissolved in DCM was added dropwise. After the addition was complete, the ice bath was removed, and the reaction was carried out at a constant temperature for 3 h. The reaction was monitored by TLC until completion. Post-treatment: Extraction was performed with 10 mL of saturated sodium chloride aqueous solution. The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA 10:1) to obtain a white solid product with a yield of 94%. mp 135-136 °C; 1H NMR (600MHz, cdcl3) δ8.62 (s, 1H), 8.04 (dd, J=8.7, 2.2Hz, 1H), 7.96 (d, J=8.1Hz, 1H), 7.90 (t, J=7.3Hz, 2H), 7.63 (t, J=7.5Hz, 1H), 7.57 (t, J=7.7Hz, 1H), 7.19 (s, 1H), 7.12-7.04 (m, 1H), 2.06 (d, J=2.4Hz, 3H). 13 C NMR(150MHz,cdcl3)δ171.07,64.91,142.15,135.96,134.62,132.38,132.02,1 29.46,128.84,128.46,127.81,126.92,125.61,125.08,93.16,10.66.HRMS[ESI - forC 16 H 12 O4[(MH)-], m / zCalcd: 268.27; Found: 268.22.

[0126] Compound 3f: 200 mg of 5-hydroxy-3-methyl-2(5H)-furanone and 214 mg of DMAP were added to a 100 mL round-bottom flask containing 10 mL of DCM. The mixture was cooled to 0 °C in an ice bath, and 306 mg of 3-chlorobenzoyl chloride dissolved in DCM was added dropwise. After the addition was complete, the water bath was removed, and the reaction was carried out at a constant temperature for 3 h. The reaction was monitored by TLC until the reaction was completed. Post-treatment: Extraction was performed with 10 mL of saturated sodium chloride aqueous solution. The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA 10:1) to obtain a white solid product with a yield of 81%. mp 149-151 °C; 1 H NMR (600MHz, cdcl3) δ8.02 (d, J=2.2Hz, 1H), 7.94 (d, J=7.7Hz, 1H), 7.59 (d, J=7.9Hz, 1H), 7.42 (ddt, J=10.2, 4.8, 2.2Hz, 1H), 7.10 (s, 1H), 7.03 (d, J=2.6Hz, 1H), 2.06-2.02 (m, 3H). 13 C NMR (150MHz, cdcl3) δ170.78,164.81,145.92,135.1,134.85,133.56,131.87,131.06,128.47,85.20,10.40.HRMS[ESI - forC 12 H9C1O4[(MH) -], m / zCalcd: 252.65; Found: 252.

[0127] Compound 3g: 200mg of 5-hydroxy-3-methyl-2(5H)-furanone and 214mg of DMAP were added to a 100mL round-bottom flask containing 10mL DCM. The mixture was cooled to 0℃ in an ice bath, and 277mg of 2-fluorobenzoyl chloride dissolved in DCM was added dropwise. After the addition was complete, the ice bath was removed, and the reaction was carried out at a constant temperature for 3h. The reaction was monitored by TLC until the reaction was completed. Post-treatment: Extraction was performed with 10mL of saturated sodium chloride aqueous solution. The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA 10:1) to obtain a white solid product with a yield of 84%. mp 162-163℃; 1 H NMR (600MHz, cdcl3) δ7.95 (t, J=7.6Hz, 1H), 7.58 (q, J=7.1Hz, 1H), 7.25-7.08 (m, 3H), 7.03 (s, 1H), 2.03 (s, 3H). 13 C NMR (150MHz, cdcl3) δ170.98,163.15,162.34,162.31,161.41,141.94,135.69,135.63,1 34.65,132.34,124.17,124.15,117.25,117.11,117.02,116.95,92.95,10.63.HRMS[ESI - forC 12 H9FO4[(MH)-], m / zCalcd: 236.20; Found: 236.17.

[0128] Compound 3h: 200 mg of 5-hydroxy-3-methyl-2(5H)-furanone and 214 mg of DMAP were added to a 100 mL round-bottom flask containing 10 mL of DCM. The mixture was cooled to 0 °C in an ice bath, and 365 mg of 4-trifluoromethylbenzoyl chloride dissolved in DCM was added dropwise. After the addition was complete, the ice bath was removed, and the reaction was carried out at a constant temperature for 3 h. The reaction was monitored by TLC until the reaction was completed. Post-treatment: Extraction was performed with 10 mL of saturated sodium chloride aqueous solution. The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA 10:1) to obtain a yellow oily product with a yield of 85%. mp 16-17 °C; 1 H NMR (600MHz, cdcl3) δ8.16 (d, J=7.9Hz, 2H), 7.73 (d, J=7.9Hz, 2H), 7.12 (s, 1H), 7.04 (s, 1H), 2.05 (s, 3H). 13C NMR (150MHz, cdcl3) δ170.76,163.62,141.66,135.54,134.92,131.68,130.45,125.64,93.21,92.31,10.65.HRMS [ESI - for C 13 H9F3O4[(MH) - ], m / zCalcd: 286.21; Found: 286.18.

[0129] Compound 3i: 200 mg of 5-hydroxy-3-methyl-2(5H)-furanone and 214 mg of DMAP were added to a 100 mL round-bottom flask containing 10 mL of DCM. The mixture was cooled to 0 °C in an ice bath, and 277 mg of 3-fluorobenzoyl chloride dissolved in DCM was added dropwise. After the addition was complete, the ice bath was removed, and the reaction was carried out at a constant temperature for 3 h. The reaction was monitored by TLC until completion. Post-treatment: Extraction was performed with 10 mL of saturated sodium chloride aqueous solution. The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA 10:1) to obtain a white solid product with a yield of 88%. mp 162-163 °C; 1 H NMR (600MHz, cdcl3) δ7.85 (dt, J=7.8, 1.3Hz, 1H), 7.72 (ddd, J=9.1, 2.6, 1.5Hz, 1H), 7.45 (td, J=8.0, 5. 4Hz, 1H), 7.32 (tdd, J=8.2, 2.6, 1.0Hz, 1H), 7.13-7.09 (m, 1H), 7.05-7.01 (m, 1H), 2.04 (t, J=1.6Hz, 3H). 13 C NMR (150MHz, cdcl3) δ170.89, 163.66, 161.71, 141.72, 134.78, 130.55, 125.92, 121.06, 116.73, 93.03, 10.58.HRMS [ESI - forC 12 H9FO4[(MH)-], m / zCalcd: 236.20; Found: 236.17.

[0130] Compound 3j: 200 mg of 5-hydroxy-3-methyl-2(5H)-furanone and 214 mg of DMAP were added to a 100 mL round-bottom flask containing 10 mL of DCM. The mixture was cooled to 0 °C in an ice bath, and 309 mg of 3,4-difluorobenzoyl chloride dissolved in DCM was added dropwise. After the addition was complete, the ice bath was removed, and the reaction was carried out at a constant temperature for 3 h. The reaction was monitored by TLC until completion. Post-treatment: Extraction was performed with 10 mL of saturated sodium chloride aqueous solution. The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA 10:1) to obtain a white solid product with a yield of 83%. mp 155-156 °C; 1 H NMR (600MHz, cdcl3) δ7.89-7.81 (m, 2H), 7.24 (dd, J=8.1, 1.8Hz, 1H), 7.08 (p, J=1.5Hz, 1H), 7.01 (p, J=1.7Hz, 1H), 2.03 (t, J=1.6Hz, 3H). 13 CNMR (150MHz, cdcl3) δ170.79, 162.89, 155.08, 153.46, 151.07, 149.32, 141.59, 134.88, 127.28, 119.26, 93.05, 10.72.HRMS [ESI - forC 12 H8F2P4[(MH) - ], m / zCalcd: 254.19; Found: 254.11.

[0131] Compound 3k: 200 mg of 5-hydroxy-3-methyl-2(5H)-furanone and 214 mg of DMAP were added to a 100 mL round-bottom flask containing 10 mL of DCM. The mixture was cooled to 0 °C in an ice bath, and 384 mg of 4-bromobenzoyl chloride dissolved in DCM was added dropwise. After the addition was complete, the ice bath was removed, and the reaction was carried out at a constant temperature for 3 h. The reaction was monitored by TLC until completion. Post-treatment: Extraction was performed with 10 mL of saturated sodium chloride aqueous solution. The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA 10:1) to obtain a white solid product with a yield of 82%. mp 124-125 °C; 1 H NMR (600MHz, cdcl3) δ7.93-7.87 (m, 2H), 7.64-7.57 (m, 2H), 7.14-7.06 (m, 1H), 7.02 (p, J=1.6Hz, 1H), 2.04 (d, J=1.6Hz, 3H). 13C NMR (150MHz, cdcl3) δ170.91, 164.08, 141.88, 134.75, 132.01, 131.50, 129.36, 127.32, 93.08, 10.66.HRMS [ESI - forC 12 H9BrO4[(MH)-], m / zCalcd: 297.10; Found: 297.03.

[0132] Compound 3l: 200 mg of 5-hydroxy-3-methyl-2(5H)-furanone and 214 mg of DMAP were added to a 100 mL round-bottom flask containing 10 mL of DCM. The mixture was cooled to 0 °C in an ice bath, and 270 mg of 3-methylbenzoyl chloride dissolved in DCM was added dropwise. After the addition was complete, the ice bath was removed, and the reaction was carried out at a constant temperature for 3 h. The reaction was monitored by TLC until the reaction was completed. Post-treatment: Extraction was performed with 10 mL of saturated sodium chloride aqueous solution. The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA 10:1) to obtain a white solid product with a yield of 86%. mp 166-168 °C; 1 H NMR (600MHz, cdcl3) δ7.84 (d, J=10.3Hz, 2H), 7.42 (d, J=7.7Hz, 1H), 7.34 (t, J=7.8Hz, 1H), 7.12 (s, 1H), 7.03 (s, 1H), 2.40 (s, 3H), 2.03 (s, 3H). 13 C NMR (150MHz, cdcl3) 6171.20, 164.39, 164.23, 142.33, 134.41, 132.24, 120.63, 113.89, 92.90, 55.49, 10.63.HRMS [ESI - forC 13 H 12 O4[(MH) - ], m / zCalcd: 232.24; Found: 232.12.

[0133] Compound 3m: 200 mg of 5-hydroxy-3-methyl-2(5H)-furanone, 214 mg of DMAP, and 335 mg of EDCI were added to a 100 mL round-bottom flask containing 10 mL of DCM. The mixture was cooled to 0 °C in an ice bath, and 298 mg of 4-chloromethylbenzoic acid dissolved in DCM was added dropwise. After the addition was complete, the ice bath was removed, and the reaction was carried out at a constant temperature for 3 h. The reaction was monitored by TLC until completion. Post-treatment: Extraction was performed with 10 mL of saturated sodium chloride aqueous solution. The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA 10:1) to obtain a white solid product with a yield of 88%. mp 123-125 °C; 1 H NMR (600MHz, cdcl3) δ 8.11-7.99 (m, 2H), 7.49 (d, J=7.9Hz, 2H), 7.12 (s, 1H), 7.06-6.99 (m, 1H), 4.62 (s, 2H), 2.10-1.96 (m, 3H). 13 C NMR (150MHz, cdcl3) 6171.01, 164.25, 143.45, 141.92, 134.65, 130.57, 128.71, 92.98, 45.12, 10.59.HRMS [ESI - forC 13 H 11 ClO4[(MH) - ], m / zCalcd: 266.68; Found: 266.59.

[0134] Compound 3n: 200 mg of 5-hydroxy-3-methyl-2(5H)-furanone, 214 mg of DMAP, and 335 mg of EDCI were added to a 100 mL round-bottom flask containing 10 mL of DCM. The mixture was cooled to 0 °C in an ice bath, and 266 mg of 4-methoxybenzoic acid dissolved in DCM was added dropwise. After the addition was complete, the ice bath was removed, and the reaction was carried out at a constant temperature for 3 h. The reaction was monitored by TLC until completion. Post-treatment: Extraction was performed with 10 mL of saturated sodium chloride aqueous solution. The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA 10:1) to obtain a white solid product with a yield of 90%. mp 153-154 °C; 1 H NMR (600MHz, cdcl3) δ 8.04-7.94 (m, 2H), 7.16-7.07 (m, 1H), 7.06-6.99 (m, 1H), 6.96-6.89 (m, 2H), 3.87 (d, J=2.8Hz, 3H), 2.09-1.95 (m, 3H). 13C NMR (150MHz, cdcl3) δ171.20, 164.39, 164.23, 142.33, 134.41, 132.24, 120.63, 113.89, 92.90, 55.49, 10.63.HRMS [ESI - forC 13 H 12 O5[(MH)-], m / zCalcd: 248.24; Found: 248.16.

[0135] Compound 3o: 200 mg of 5-hydroxy-3-methyl-2(5H)-furanone, 214 mg of DMAP, and 335 mg of EDCI were added to a 100 mL round-bottom flask containing 10 mL of DCM. The mixture was cooled to 0 °C in an ice bath, and 296 mg of 4-nitrobenzoic acid dissolved in DCM was added dropwise. After the addition was complete, the ice bath was removed, and the reaction was carried out at a constant temperature for 3 h. The reaction was monitored by TLC until completion. Post-treatment: Extraction was performed with 10 mL of saturated sodium chloride aqueous solution. The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA 10:1) to obtain a white solid product with a yield of 90%. mp 177-179 °C; 1 H NMR (600MHz, cdcl3) δ 8.34-8.29 (m, 2H), 8.25-8.20 (m, 2H), 7.13 (p, J = 1.4Hz, 1H), 7.05 (p, J = 1.7Hz, 1H), 2.05 (t, J = 1.6Hz, 3H). 13 C NMR (150MHz, cdcl3) δ171.02, 164.25, 143.45, 142.03, 134.66, 130.49, 128.65, 93.06, 45.13, 10.66.HRMS [ESI - forC 12 H9NO6[(MH) - ], m / zCalcd: 263.21; Found: 263.16.

[0136] Compound 3p: 200 mg of 5-hydroxy-3-methyl-2(5H)-furanone, 214 mg of DMAP, and 335 mg of EDCI were added to a 100 mL round-bottom flask containing 10 mL of DCM. The mixture was cooled to 0 °C in an ice bath, and 375 mg of 4-phenoxybenzoic acid dissolved in DCM was added dropwise. After the addition was complete, the ice bath was removed, and the reaction was carried out at a constant temperature for 3 h. The reaction was monitored by TLC until completion. Post-treatment: Extraction was performed with 10 mL of saturated sodium chloride aqueous solution. The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA 10:1) to obtain a white solid product with a yield of 79%. mp 152-153 °C; 1 H NMR (600MHz, cdcl3) δ8.03-7.98 (m, 2H), 7.44-7.38 (m, 2H), 7.22 (ddt, J=8.6, 7.4, 1.2Hz, 1H), 7. 11 (p, J=1.4Hz, 1H), 7.09-7.05 (m, 2H), 6.99 (m, 2H), 6.98 (d, J=2.0Hz, 1H), 2.03 (t, J=1.5Hz, 3H). 13 C NMR (150MHz, cdcl3) δ171.20, 164.39, 164.23, 142.33, 134.41, 132.25, 127.32, 120.64, 113.89, 92.90, 55.50, 10.64.HRMS [ESI - forC 18 H 14 O5[(MH) - ], m / zCalcd: 310.30; Found: 310.21.

[0137] Compound 3q: 200 mg of 5-hydroxy-3-methyl-2(5H)-furanone, 214 mg of DMAP, and 335 mg of EDCI were added to a 100 mL round-bottom flask containing 10 mL of DCM. The mixture was cooled to 0 °C in an ice bath, and 319 mg of 3,5-dimethoxybenzoic acid dissolved in DCM was added dropwise. After the addition was complete, the ice bath was removed, and the reaction was carried out at a constant temperature for 3 h. The reaction was monitored by TLC until completion. Post-treatment: Extraction was performed with 10 mL of saturated sodium chloride aqueous solution. The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA 10:1) to obtain a white solid product with a yield of 85%. mp 152-153 °C; 1 H NMR (600MHz, cdcl3) δ7.17 (d, J=2.4Hz, 1H), 7.03 (p, J=1.7Hz, 1H), 6.69 (t, J=2.4Hz, 1H), 3.83 (s, 4H). 13C NMR (150MHz, cdcl3) δ171.06, 164.57, 160.79, 142.06, 134.61, 130.17, 107.61, 106.79, 93.16, 55.64, 10.66.HRMS [ESI - forC 13 H 11 O6[(MH) - ], m / zCalcd: 263.23; Found: 263.17.

[0138] Compound 3r: 200 mg of 5-hydroxy-3-methyl-2(5H)-furanone, 214 mg of DMAP, and 335 mg of EDCI were added to a 100 mL round-bottom flask containing 10 mL of DCM. The mixture was cooled to 0 °C in an ice bath, and 240 mg of 4-aminobenzoic acid dissolved in DCM was added dropwise. After the addition was complete, the ice bath was removed, and the reaction was carried out at a constant temperature for 3 h. The reaction was monitored by TLC until completion. Post-treatment: Extraction was performed with 10 mL of saturated sodium chloride aqueous solution. The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA 10:1) to obtain a white solid product with a yield of 79%. mp 160-161 °C; 1 HNMR (600MHz, cdcl3) δ7.87-7.82 (m, 2H), 7.10 (t, J=1.5Hz, 1H), 7.00 (q, J=1.6Hz, 1H), 6.66-6.60 (m, 2H), 4.17 (s, 2H), 2.01 (t, J=1.6Hz, 3H). 13 C NMR (150MHz, cdcl3) δ171.37, 164.59, 151.85, 142.59, 134.22, 132.32, 117.42, 113.79, 92.80, 10.63.HRMS [ESI - forC 12 H 11 NO4[(MH) - ], m / zCalcd: 233.22; Found: 233.08.

[0139] Compound 3s: 200 mg of 5-hydroxy-3-methyl-2(5H)-furanone, 214 mg of DMAP, and 335 mg of EDCI were added to a 100 mL round-bottom flask containing 10 mL of DCM. The mixture was cooled to 0 °C in an ice bath, and 263 mg of 4-ethylbenzoic acid dissolved in DCM was added dropwise. After the addition was complete, the ice bath was removed, and the reaction was carried out at a constant temperature for 3 h. The reaction was monitored by TLC until completion. Post-treatment: Extraction was performed with 10 mL of saturated sodium chloride aqueous solution. The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA (10:1) to obtain a white solid product with a yield of 82%. mp 144-146 °C; 1 HNMR (600MHz, cdcl3) δ7.99-7.93 (m, 2H), 7.28 (d, J=8.1Hz, 2H), 7.12 (p, J=1.4Hz, 1H), 7 .03 (p, J=1.6Hz, 1H), 2.71 (q, J=7.6Hz, 2H), 2.03 (t, J=1.6Hz, 3H), 1.26 (t, J=7.6Hz, 3H). 13 C NMR (150MHz, cdcl3) δ171.14, 164.78, 151.11, 142.24, 134.47, 130.22, 128.12, 125.84, 92.96, 29.00, 15.06, 10.64.HRMS [ESI-] forC 14 H 14 O4[(MH) - ], m / zCalcd: 246.26; Found: 246.11.

[0140] Compound 3t: 200 mg of 5-hydroxy-3-methyl-2(5H)-furanone, 214 mg of DMAP, and 335 mg of EDCI were added to a 100 mL round-bottom flask containing 10 mL of DCM. The mixture was cooled to 0 °C in an ice bath, and 350 mg of 4-methylsulfonylbenzoic acid dissolved in DCM was added dropwise. After the addition was complete, the ice bath was removed, and the reaction was carried out at a constant temperature for 3 h. The reaction was monitored by TLC until completion. Post-treatment: Extraction was performed with 10 mL of saturated sodium chloride aqueous solution. The organic phase was collected, dried over anhydrous Na2SO4, and purified by column chromatography (PE:EA 10:1) to obtain a white solid product with a yield of 82%. mp 127-129 °C; 1 H NMR (600MHz, cdcl3) 68.33-8.16 (m, 1H), 8.09-7.92 (m, 1H), 3.13-3.05 (m, 2H), 2.05 (dt, J=3.4, 1.6Hz, 2H). 13C NMR (150MHz, cdcl3) δ170.72, 163.27, 145.27, 141.58, 135.03, 133.17, 130.99, 127.69, 93.28, 44.25, 10.68.HRMS [ESI - forC 13 H 12 06S[(MH)-], m / zCalcd: 296.29; Found: 296.13.

[0141] Example 2: Experiment on the induction of germination of orobanche and strigophyte seeds by compounds 1a-1y, 2a-2i, and 3a-3t

[0142] The germination rates of *Striga asiatica* seeds and *Orobanche deserticola* seeds at a concentration of 10 ppm for compounds 1a-1y, 2a-2i, 3a-3t provided by this invention and the control drug strigolactone GR24 are as follows:

[0143] Biological experiments were conducted in petri dishes to determine the germination rates of the target compound on *Striga asiatica* seeds and *Orobanche deserticola* seeds.

[0144] Reagent preparation: Accurately weigh 10 mg of each target compound and dissolve it in 1 mL of DMDO to obtain a stock solution with a concentration of 10,000 ppm. Each concentration solution is then serially diluted from the stock solution. Positive control solutions are obtained by serially diluting the pre-prepared stock solutions.

[0145] Seed pretreatment: Orobanche and Strelitzia seeds were surface-sterilized by soaking in 1% NaClO for 2 minutes and then in 75% alcohol for 2 minutes. After thorough rinsing with sterile deionized water, they were air-dried. A 9cm layer of ordinary filter paper was placed at the bottom of a petri dish and moistened with sterile water. 9mm diameter glass fiber filter paper was then placed on top of the petri dish, and Orobanche and Strelitzia seeds were evenly scattered on the glass fiber filter paper, with approximately 50-100 seeds per sheet. The mixture was then incubated at 25℃ in the dark for 7 days.

[0146] Petri dish germination test: Filter paper was appropriately cut and laid flat on a petri dish, ensuring close contact with the surface. Pre-cultured *Orobanche deserticola* and *Striga asiatica* seeds were transferred to the treated petri dishes. 1 mL of 10 ppm compounds 1a-1y, 2a-2i, and 3a-3t, along with the control drug GR24, were added. 2% DMSO served as a negative control, and GR24 as a positive control. Each treatment was repeated in triplicate. After these steps, the seeds were uniformly transferred to an artificial climate incubator (22℃, 60% humidity) and cultured for 7 days. Germination of *Orobanche deserticola* and *Striga asiatica* seeds was observed and statistically analyzed using a stereomicroscope. The germination rate of *Orobanche deserticola* and *Striga asiatica* was calculated using the following formula:

[0147]

[0148] The germination effects of target compounds 1a-1y, 2a-2i, 3a-3t at a concentration of 10 ppm and the control drug GR24 on *Orobanche deserticola* and *Striga asiatica* are shown in Table 1.

[0149] Table 1

[0150]

[0151]

[0152] Although the present invention has been described in detail above with general descriptions and specific embodiments, modifications or improvements can be made to it, which will be obvious to those skilled in the art. Therefore, all such modifications or improvements made without departing from the spirit of the present invention fall within the scope of protection claimed by the present invention.

Claims

1. 5-Hydroxy-3-methylfuran-2(5H)-one derivative, characterized in that, The structure is shown in Equation I: In Equation I, R is 1s; .

2. The method for preparing the 5-hydroxy-3-methylfuran-2(5H)-one derivative according to claim 1, characterized in that, The preparation method of compound I includes: adding a phenolic derivative to a tetrahydrofuran solution of 5-chloro-3-methylfuran-2(5H)-one, cooling to 0-5℃ and then adding a catalytic amount of potassium tert-butoxide, reacting at room temperature to obtain the target compound; The phenolic derivative has the structure R-OH, where R is 1s.

3. The method according to claim 2, characterized in that, Includes the following steps: Step 1: Add 118.6 mmol of methylmalonic acid and 118.6 mmol of glyoxal to a reaction flask containing water, add 10 drops of concentrated sulfuric acid, and heat under reflux at 110-115 °C for 10-12 h to obtain intermediate I, namely 5-hydroxy-3-methyl-2-( 5H )-Furfuralone; Step 2: Add intermediate I to a reaction flask containing DCM, slowly add SOCl2, then add DMF, and heat under reflux at 90-95℃ for 1-2 h to obtain intermediate II, namely 5-chloro-3-methylfuran-2-( 5H )-ketone; Step 3: Under N2 protection, add the phenolic derivative and potassium iodide to a reaction flask containing THF, cool to 0-5℃, add potassium tert-butoxide and stir for 10-15 min, then add intermediate II and react at room temperature for 3-5 h to obtain the target compound.

4. The following applications of the 5-hydroxy-3-methylfuran-2(5H)-one derivative of claim 1: It is used to induce the germination of seeds of strigophytes and broomrape plants.

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