34 results about "Wittig reaction" patented technology

The application discloses a preparation method of beta-carotene, which comprises the following steps: 3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienyl triphenyl phosphonium salt (C15 phosphonium salt) cis-trans isomer and 2,7-dimethyl-2,4,6-octatriene-1,8-dial (C10) are dissolved in a water and a water incompatible solvent system, and Wittig reaction is generated under the action of an alkali. The reaction system can avoid that by-product inorganic salt is wrapped in the product, and the content of inorganic salt impurities in the product is reduced. In addition, the proportion of C15 phosphonium salt cis-trans isomer is controlled, a C15 phosphonium salt hydrolysis side reaction is inhibited, and the reaction yield is improved.

The invention relates to the technical field of chemical synthesis, and particularly discloses a compound with a peculiar smell removing function as well as a preparation method and application thereof. The chemical name of the compound is 2-ethoxy-3-((E)-methoxy-3-oxopropyl-1-alkene-1-yl) phenyl cinnamate, the smell of the compound is extremely light, sulfur-containing and nitrogen-containing compounds causing stink can be captured through a Michael addition reaction, and efficient peculiar smell removal is achieved. The preparation method comprises the following steps: (1) taking cinnamic acid as an initial raw material, and reacting with diethylamino sulfur trifluoride to prepare cinnamic acid acyl fluoride; (2) carrying out an esterification reaction on the cinnamic acid acyl fluoride and 2-methoxy-3-hydroxybenzaldehyde in the presence of 4-dimethylaminopyridine, so as to obtain 2-methoxy-3-formyl phenyl cinnamate; and (3) carrying out Wittig reaction on the 2-methoxy-3-formyl phenyl cinnamate and a phosphorus ylide reagent, so as to obtain the target compound.

The invention discloses a preparation method of beta-carotene. The preparation method comprises the following steps: dissolving an aqueous solution of 3-methyl-5-(2, 6, 6-trimethyl-1-cyclohexene-1-yl)-2, 4-pentadienyl triphenylphosphine salt (C15 phosphine salt) and 2, 7-dimethyl-2, 4, 6-octtriene-1, 8-dialdehyde (C10) cis-trans isomer in a solvent, carrying out wittig reaction under the action of alkali, and carrying out isomerization to obtain the product. By controlling the proportion of C10 cis-trans isomers of the reaction system, the content of the C25 aldehyde intermediate can be reduced, and the reaction yield and the product quality can be improved.

The invention relates to a synthetic method of chlorinated methyl styrene, which comprises the following steps: (1) in the presence of a reducing agent, carrying out selective reduction reaction on terephthalaldehyde or isophthalaldehyde to obtain p-hydroxymethylbenzaldehyde or 3-(hydroxymethyl) benzaldehyde; (2) in the presence of a chlorination reagent, carrying out chlorination reaction on the p-hydroxymethylbenzaldehyde or 3-(hydroxymethyl) benzaldehyde obtained in the step (1) to obtain p-chloromethylbenzaldehyde or 3-(chloromethyl) benzaldehyde; and (3) in the presence of alkali, carrying out Wittig reaction on the p-chloromethyl benzaldehyde or 3-(chloromethyl) benzaldehyde obtained in the step (2) to generate p-chloromethyl styrene or m-chloromethyl styrene. The method avoids the use of highly toxic chlorine or intermediates difficult to synthesize, has the advantages of short steps, mild conditions, high selectivity, high yield, environmental friendliness and the like, and has a good industrial application prospect.

This invention provides a method for preparing high-purity olaparib, belonging to the field of pharmaceutical synthesis technology. The method uses dimethyl (3-oxo-1,3-dihydroisobenzofuran-1-yl)phosphate as the starting material, reacting it with compound 2 via a Wittig reaction to generate compound 3. Compound 3 reacts with hydrazine hydrate to generate compound 4. Compound 4 is hydrolyzed and acidified to give compound 5. Compound 5 reacts with thionyl chloride to give compound 6. Compound 6 is then condensed with compounds 7 and 9 to obtain olaparib. This invention uses readily available raw materials, is simple to operate and process, has mild reaction conditions, achieves a total yield of up to 90%, a purity >99%, is environmentally friendly, and is suitable for industrial production.

The application discloses a chemical synthesis method of 7-ketolithocholic acid (3alpha-hydroxy-7-keto-5beta-cholestane-24-oic acid), and belongs to the field of organic chemical synthesis. The 7-ketolithocholic acid is synthesized from a plant source compound BA through steps of glycol or neopentyl glycol protection, oxidation, Wittig reaction, deprotection, reduction and hydrolysis. The raw material used for synthesizing the 7-ketolithocholic acid is cheap and easy to obtain, the synthesis steps are simple and convenient to operate, the yield is high, the environment is friendly, and the industrialized production is facilitated.

The method comprises the following steps: taking androstane-3-ketone-4-ene-17beta-carboxylic acid shown in a formula II as a raw material, carrying out decarboxylation hydroxylation, sulfonylation, elimination and double-bond oxidative cracking to prepare the exemestane intermediate shown in a formula VI, and then sequentially carrying out allylic oxidation, wittig reaction and 1, 2, 4-trimethyl-1, 3, 4-trimethyl-1, 3, 4-trimethyl-1, 3, 4-trimethyl-1, 3, 4-trimethyl-1, 3, 4-trimethyl-1, 3, 4-trimethyl-1, 3-trimethyl-1, 3, 4-trimethyl-1, 3, 4-trimethyl-1, 3-trimethyl-1, 3, 4-trimethyl-1, 3 the exemestane shown in the formula I is prepared through the step of 1, 2-site dehydrogenation. The method has the characteristics of simple process operation, mild conditions, high reaction yield and the like, and is suitable for industrial production.

The application belongs to the technical field of pharmaceutical synthesis chemistry, and particularly relates to a preparation method of a small molecule Id protein inhibitor AGX51. The preparation method takes a piperonal compound 5 as a starting raw material, and obtains an olefin product compound 4 through a Wittig reaction. The compound 4 is subjected to double bond epoxidation and ring-opening reaction under alkaline conditions to synthesize a compound 3. The compound 3 is subjected to a Pinacol rearrangement reaction to obtain a compound 2. The compound 2 is subjected to Wittig olefination and hydrolysis reaction in series to obtain the compound 1. The compound 1 is subjected to reduction amination and acylation reaction in sequence to complete the synthesis of AGX51 in one pot. The structure of the target product is confirmed by MS, 1 H NMR and 13 C NMR. The structures of intermediates are confirmed by 1 H NMR. Through the preparation method, the total yield of the small molecule Id protein inhibitor AGX51 is significantly improved.

The invention provides an olefine aldehyde intermediate and a synthetic method thereof, and a synthetic method of conopomorpha sinensis sex pheromone, and belongs to the field of compound synthesis. According to the synthesis method of the olefine aldehyde intermediate, provided by the invention, 1, 5-pentanediol is taken as a raw material, and the high-yield olefine aldehyde intermediate is obtained through transesterification, first oxidation reaction, Wittig reaction and Sagsa oxidation reaction; the yield of the olefine aldehyde intermediate can be further improved by limiting a catalytic system and an auxiliary agent of the Sagsa oxidation reaction. Results of the embodiment show that the synthesis method provided by the invention does not adopt alkyne compounds, the yield of the product in the Sagassa oxidation reaction stage can reach 81%, the total yield of the obtained olefine aldehyde intermediate can reach 48.5%, the sex pheromone of conopomorpha sinensis prepared by adopting the olefine aldehyde intermediate can reach 39.8%, and the yield is high.

The invention discloses a synthetic method of tea geometrid sex pheromone (3Z, 6Z, 9Z)-octadecatriene, which comprises the following steps: carrying out bromination on cis-3-hexene-1-alcohol in a bromination system, and carrying out salt forming reaction on the brominated cis-3-hexene-1-alcohol and triphenylphosphine to obtain cis-3-hexenyl triphenylphosphonium bromide; the preparation method comprises the following steps: generating an alkynyl metal intermediate from 3-butyne-1-alcohol under the action of an organic metal reagent, and carrying out alkylation reaction on the alkynyl metal intermediate and n-octane bromide to obtain 3-dodecanol; carrying out hydrogenation reaction under the action of a catalyst, and then carrying out oxidation reaction under the action of an oxidizing agent to obtain cis-3-dodecenal; the preparation method comprises the following steps: dispersing cis-3-hexenyl triphenyl phosphonium bromide in an ether solvent, and carrying out Wittig reaction on the cis-3-hexenyl triphenyl phosphonium bromide and cis-3-dodecenal under the action of alkali to obtain the (3Z, 6Z, 9Z)-octadecatriene. The synthesis method only needs six-step reaction, the reaction condition is mild, the raw materials are cheap and easy to obtain, the yield is high, and large-scale production is easy.

The invention relates to a preparation method of sacubitril, which comprises the following steps: (1) reacting (S)-1-([1, 1 '-biphenyl]-4-yl)-3-chloropropane-2-ol with succinimide under the condition of triphenylphosphine and DEAD (Diethylaminoethyl Adenine) to obtain (R)-1-(1-([1, 1'-biphenyl]-4-yl)-3-chloropropane-2-yl) pyrrolidine-2, 5-diketone; (2) adding water and an alkaline reagent into the product in the step (1) to obtain (R)-4-(([1, 1 '-biphenyl]-4-yl)-3-hydroxypropyl-2-yl)-amino-4-oxobutyric acid; (3) carrying out oxidation and wittig reaction on the product obtained in the step (2) to prepare (4R)-5-[1, 1 '-biphenyl]-4-yl-4-[(3-carboxyl-1-oxopropyl) amino]-2-methyl-2-pentenoic acid-1-ethyl ester; (4) performing palladium-carbon catalytic reaction on the product obtained in the step (3) for alkali adjustment to prepare a sacubitril sodium salt aqueous solution; and (5) performing free extraction on the sacubitril sodium salt, concentrating, adding acetone and isopropanol to prepare a mixed solution, and reacting with valsartan and sodium hydroxide to prepare the sacubitril valsartan sodium. The method is simple and convenient to operate, can obtain the product with high purity and high yield, and is suitable for industrial production.

The application provides a synthesis method and antitumor application of several furanopyrimidine-ibuprofen hybrid derivatives, which are linked by aza-wittig reaction, intramolecular cyclization, substitution reaction, hydrolysis and acidification reaction and the like, and a fused triazole, a hydrazide, a bis-hydrazide and an oxadiazole are used as a bond bridge key, so that different series of furanopyrimidine-ibuprofen hybrid derivatives are synthesized in a simple and efficient manner. The CCK8 method in vitro pharmacodynamics test proves that the target compound has proliferation inhibition activity on A549 lung cancer cells and HepG2 liver cancer cell lines. Test results show that the target compound shows good proliferation inhibition activity on the two kinds of cells, and the structural formula is as follows:

The invention discloses a composite absorbent for capturing carbon dioxide in flue gas and application of the composite absorbent, and relates to the technical field of carbon dioxide composite absorbents. The flue gas CO2 trapping composite absorbent and the matched macromolecular anti-degradation agent disclosed by the invention have efficient absorptivity, strong degradation resistance and industrial suitability, the material takes aminoethylethanolamine as a main absorbent and is matched with a 2-amino-2-methyl-1-propanol auxiliary absorbent and an N-methylpiperazine activator, and high CO2 selectivity is realized through mass ratio optimization; the anti-degradation agent is prepared by compounding a bismuth reagent and a macromolecular anti-degradation agent, the macromolecular anti-degradation agent is subjected to a Witt ig reaction, a thiol click reaction and other multi-step processes, active units such as hindered phenol, benzotriazole and acetaldoxime are integrated, free radicals can be removed, metal ions can be passivated, NOx can be neutralized, the amine degradation rate is reduced, and an efficient, stable and economical solution is provided for CO2 trapping.

The invention belongs to the field of medicinal chemistry, and particularly provides a synthesis method of a key intermediate of suzertraline, 3, 4-difluoro-2-methoxybenzaldehyde is used as a starting material, and 3, 4-difluoro-2-methoxyphenylacetic acid is obtained through Wittig reaction, demethylation and aldehyde group oxidation. Compared with the prior art, the synthesis yield of the synthesized target compound is high, the synthesis process is simple to operate, the use of an expensive catalyst is avoided, the method is environment-friendly, the production is efficient, the synthesis purity is high, and factory amplification-scale production is facilitated.

The invention provides a synthesis method of cefepime starting material oxidation impurities, and belongs to the field of medicinal chemistry. The cefepime is prepared by modifying a 7-site amino side chain of D-7-ACA, oxidizing a 3-site hydroxyl, carrying out wittig reaction with a starting material, and then carrying out deprotection. When the starting material is subjected to wittig reaction, the ylide generated by the starting material can be oxidized to generate oxidized impurities. The method comprises the following steps: reacting a cefepime starting material with a strong base to generate a ylide intermediate, and continuously introducing new oxygen into the ylide intermediate to prepare the cefepime starting material oxide impurity. The preparation and separation method of the cefepime starting material oxidation impurity provided by the invention has the advantages of simplicity in operation, environmental friendliness, low cost and high purity of the obtained impurity, and lays a good foundation for quality research and control of cefepime.

The invention discloses a synthesis method of a diene liquid crystal monomer, which comprises the following steps: S1, Grignard addition reaction: carrying out Grignard addition reaction on substituted cyclohexyl N-methoxy-N-methyl benzamide and a substituted cyclohexyl methyl chloride Grignard reagent to obtain a ketone intermediate; s2, the ketone intermediate sequentially reacts with 5, 5-dibromobarbituric acid for a bromination reaction, then sodium formate is added into an alcohol solvent for a hydroxylation reaction, then sodium borohydride is added for a reduction reaction, and a vicinal diol intermediate is obtained; and S3, carrying out an orthoformate reaction on the vicinal diol intermediate obtained in the step S2 and triethyl orthoformate in a fluorine-containing alcohol solvent, then heating to reflux, and carrying out an elimination reaction to obtain the target diene liquid crystal monomer. According to the invention, a traditional double bond construction strategy of multiple Wittig reactions is abandoned, a new synthesis route which takes the Grignard reaction as a starting point and finally constructs a diene structure by a one-pot method through a low-temperature orthoformate / elimination reaction carried out in a specific fluorine-containing solvent is designed, the route is simple, the total yield is high, and the overall cost is lower.

The invention discloses synthesis and antitumor activity research of a novel drug small molecular formula (1) containing an adamantane structure. According to the invention, 1-bromoadamantane is used as an initial raw material, 2-(4-((3R, 5R, 7R)-adamantane-1-yl)-2-nitrophenoxy) acetic acid is generated through a typical Friedel-Crafts alkylation reaction, an NBS bromination reaction and the like, and then an important intermediate compound 5 is synthesized through a Wittig reaction and a hydrolysis reaction. And carrying out coupling reaction on the intermediate compound 6 and different amine compounds to obtain eight target compounds 7a-7h: formula (1). A CCK-8 experiment is carried out on a target compound to obtain a conclusion that the target compound 7a-7f and 5-fluorouracil are tested at the concentration of 20 mu M, and the result shows that the compound 7c has the best inhibition effect on HeLa and A549 cells, and the compound 7e has the better inhibition effect on Hep G2 cells. IC50 value calculation is carried out on a target compound under various concentrations, the IC50 value of 7c on HeLa and A549 cells is minimum and the inhibition effect is best, and the IC50 value of 7e on Hep G2 cells is minimum and the inhibition effect is best.

The application discloses a novel method for preparing an intermediate of an aryl abietane diterpene Plebein C, and specifically comprises the following steps: substituting a carbonyl alpha position of 4,4-dimethyl-2-cyclohexen-1-ketone to obtain compound I; protecting the compound I by TBS to obtain compound II; performing a Luche reduction reaction on the compound II to obtain compound III; performing an iodination reaction on 3-hydroxy-4-methoxybenzaldehyde to obtain compound IV; performing a Wittig reaction on the compound IV to obtain compound V; performing a Mitsunobu reaction between the compound III and the compound V to obtain compound VI; performing a radical cyclization reaction on the compound VI to obtain compound VII; performing an oxidation on a benzyl position of the compound VII to obtain compound VIII; and finally performing an oxidation and a ring closure on the compound VIII to obtain a five-ring intermediate compound IX of a Plebein C molecule; the preparation method has the advantages of simple synthetic route, low-cost and easily-obtained reagents, high yield, favorability for industrial preparation of the intermediate, and strong popularization potential.

This invention relates to a method for synthesizing Fmoc-α-methyl-L-glutamic acid (5-tert-butyl ester). It primarily addresses the technical problems of existing synthesis methods, such as demanding conditions, cumbersome operations, low yields, and unsuitability for industrial production. The preparation steps of this invention are as follows: (1) Synthesizing Cbz-(S)-2-formylalanine methyl ester according to literature methods; (2) Reaction of Cbz-(S)-2-formylalanine methyl ester with (tert-butyloxycarbonylmethylene)triphenyl via Wittig reaction; (3) Selective hydrolysis of the methyl ester; (4) Hydrogenation of the double bond and the Cbz protecting group to obtain α-methyl-L-glutamic acid (5-tert-butyl ester); (5) Reaction of α-methyl-L-glutamic acid (5-tert-butyl ester) with Fmoc-OSu to obtain the final product. This invention has the advantages of high yield, low cost, simple operation and purification, good economic benefits, and is more suitable for industrial production.

The invention relates to a large Stokes shift cholinesterase near-infrared fluorescent probe and a construction method thereof.Quinoline is used as a core skeleton, and a conjugated system is constructed through a D-pi-A electronic regulation strategy: aryl, alkenyl or amido is introduced to the 4th site / 6th site to regulate the emission wavelength; the construction method comprises the following steps: synthesizing a fluorophore main skeleton through a Wittig reaction / Heck reaction, connecting a recognition unit through a substitution reaction, and introducing the electron-withdrawing group through a Najing condensation reaction. Stokes shift breaks through 100 nm, and excitation light interference can be inhibited. According to the probe, a recognition unit simulating acetylcholine / butyrylcholine'dumbbell-shaped 'conformation is covalently connected to a quinoline nitrogen atom through a benzyl bromide group, the recognition unit comprises an aromatic cavity adaptive to AChE / BChE substrate pocket hydrophobicity and an active site for catalyzing ester bond hydrolysis, an enzymatic reaction triggers intramolecular electron rearrangement and C-N bond breakage, a fluorescence quenching state is relieved, and the quinoline nitrogen atom can be detected. And "off-on" type signal conversion is realized.

The synthesis method comprises the following steps: by taking 3, 5-dimethoxyacetophenone as shown in a formula I as a raw material, carrying out Wittig reaction to obtain mixed-configuration trisubstituted olefin as shown in a formula b, carrying out asymmetric hydroboration reaction by taking pinacolborane as a boron source and a chiral CoCl2-TIP complex as a catalyst under the action of a reducing agent, and carrying out recrystallization to obtain the actinomycete ketone key intermediate. The preparation method comprises the following steps: preparing a chiral alkyl boron compound as shown in a formula c, deprotecting an aldehyde acetal group of the chiral alkyl boron compound as shown in the formula c to form an aldehyde group, carrying out intramolecular electrophilic addition reaction to form a ring, carrying out dehydration elimination to prepare a dihydronaphthalene compound as shown in a formula d, and oxidizing to prepare a key intermediate compound of actinomycete ketone as shown in a formula II. The method has the advantages of mild reaction conditions, simple operation, good reaction conversion rate, total yield of 67.2%, and high enantiomer selectivity of 92%. According to the invention, the reaction steps are shortened, the reaction yield is increased by more than 10 times, and good enantioselectivity is still maintained.

The application discloses a preparation method of 4-oxo-beta-apo-12'-carotenal and products and applications thereof. The preparation method comprises the following steps: S1, under the protection of inert gas, 4-oxo-vinyl-beta-ionol is dissolved in a first organic solvent to prepare 4-oxo-C15 halide with a halogenating agent; S2, triphenylphosphine is added to the system in S1 to prepare 4-oxo-C15 phosphonium salt; S3, under the protection of inert gas, 8,8-dimethoxy-2,7-dimethyl-2,4,6-octatriene aldehyde, lye and a second organic solvent are added to the system in S2 to generate Wittig reaction; the system is adjusted to be acidic, and a hydrolysis reaction is performed to obtain 4-oxo-beta-apo-12'-carotenal. The method has the advantages of easy raw material, simple reaction and more than 95% of all-trans content of the product.

The application belongs to the technical field of organic synthesis, and particularly relates to a preparation method of spilanthol amide (2E, 6Z, 8E)-N-isobutyl-2, 6, 8-decatrienamide. The synthesis route of spilanthol amide is too long, and the operation is complex, so that the industrialized production is not easy. In view of the above problems, the application provides a preparation method of spilanthol amide (2E, 6Z, 8E)-N-isobutyl-2, 6, 8-decatrienamide. The target product is successfully synthesized through seven steps of quaternary phosphonium salt reaction, Wittig reaction, Wittig-horner reaction, dehydration condensation and the like, with cheap and easily obtained 4-bromobutyric acid ethyl ester as raw material. Each reaction condition is simple, and the operation is convenient, so that the method is suitable for industrialized scale production.

The application discloses a preparation method of 2-methyl-4-chloro-2-butenoic acid ethyl ester, which comprises the following steps: taking an ethoxycarbonyl ethyl triphenyl phosphonium salt aqueous solution and a monochloroacetaldehyde aqueous solution as raw materials, and performing a Wittig reaction under the action of an alkali to obtain 2-methyl-4-chloro-2-butenoic acid ethyl ester, wherein the content of alkali metal ions in the 2-methyl-4-chloro-2-butenoic acid ethyl ester is 1-3 ppm. The method has the advantages of high reaction yield, simple and mild process conditions, moderate residual amount of metal ions in the product, good storage stability of the product and the like.

The invention discloses a preparation process of latanoprost, bemeprost and intermediates of the latanoprost and the bemeprost. Specifically, the invention provides a preparation method of a compound as shown in a formula IV, which comprises the following steps: in the presence of alkali and a solvent, carrying out wittig reaction on a compound as shown in a formula III and 4-carboxybutyl triphenylphosphonium bromide to generate the compound as shown in the formula IV, wherein the molar ratio of the compound shown in the formula III to the alkali is 1: (11-20); the reaction temperature of the wittig reaction is-40 DEG C to-5 DEG C. The preparation process provided by the invention has the advantages of high product purity, high yield and simple separation, and is suitable for industrial production.

This invention provides a method for synthesizing 7-ketolithocholic acid or its intermediates, which is prepared via a novel intermediate I-1. The method uses phytosterol degradation product dichlorol as a starting material and proceeds through oxidation, Knoevenagel reaction (or Wittig reaction), hydrogenation, esterification, ketal protection, allylic oxidation, deketal protection, and hydrogenation to obtain 7-ketolithocholic acid or its intermediates. The method of this invention uses readily available raw materials, has high yield, and employs simple and mild reaction conditions, making it suitable for industrial production.

The invention relates to the technical field of organic synthesis preparation, in particular to a preparation method and application of p-tert-pentyloxystyrene. The preparation method comprises the following steps: (1) carrying out condensation reaction on an alcohol substance and / or an ester substance and 4-fluorobenzaldehyde to prepare an intermediate compound I; (2) carrying out substitution reaction on the intermediate compound I and sodium tert-amyl alcohol in a reaction solvent, and after the reaction is finished, carrying out hydrolysis reaction to prepare an intermediate compound II; the reaction solvent comprises tert-amyl alcohol; and (3) carrying out wittig reaction on the intermediate compound II to prepare the p-tert-pentyloxy styrene. The preparation method has the advantages of simple and easily controlled synthesis steps, high efficiency, convenience, easily available raw materials, high intermediate and product yield, high product purity, easy purification and the like; the prepared p-tert-pentyloxy styrene has an irreplaceable effect in the fields of polymer synthesis, electronic materials, daily chemical spices, medicine research and development and the like, particularly has a good application prospect in the fields of high-performance polymers and microelectronic materials, and is wide in product application prospect.

The invention provides an asymmetric synthesis method of (R)-glabridin, which comprises the following steps: synthesizing 5-hydroxy-6-hydroxymethyl-2, 2-dimethylchroman-4-ketone by using 2, 6-dihydroxyacetophenone as a raw material, then carrying out nuclear substitution reaction, Wittig reaction, asymmetric hydrogenation reaction, protecting group removal and carbonyl reduction reaction, and finally dehydrating under an acidic condition to obtain the (R)-glabridin. The chiral center is constructed by a method of catalyzing asymmetric hydrogenation through a chiral metal catalyst, the addition amount is as low as 0.5 mol%, the reaction selectivity is good (eegt, 98%), the conversion rate is high (the yield gt, 89%), and the problem of low construction efficiency of the chiral center in asymmetric synthesis of glabridin is solved. The asymmetric synthesis route of (R)-glabridin provided by the invention is novel and efficient, the reaction conditions are mild, and technical support is provided for industrial large-scale production.

The invention belongs to the technical field of biopesticides, and discloses a method for asymmetrically synthesizing sex pheromone of beeswax borers. The method comprises the following steps: by taking (R)-epoxypropane (2) as a raw material, firstly, reacting the (R)-epoxypropane (2) with pent-4-alkenyl magnesium bromide (3) to prepare (R)-octyl-7-ene-2-alcohol (4); then carrying out THP protection and NaIO4 oxidation synthesis to obtain (R)-6-[(tetrahydro-2H-pyran-2-yl) oxy] heptanoic acid (6); then introducing a chiral methyl group by utilizing a chiral induction strategy to prepare oxazolidinone imide 9; then, carrying out NaBH4 reductive cracking, Dess-Martin oxidation and Wittig reaction, so as to obtain THP protected dienol 12; and finally, carrying out deprotection and Pd / C catalytic hydrogenation to prepare the sex pheromone (2R, 6R, 10R)-6, 10, 14-trimethylpentadecan-2-ol (1) of the beewax borers. The method has the advantages of high total yield, simple synthetic route and the like.

The invention provides a method for preparing an internal olefin (1, 2-disubstituted olefin) compound through visible light catalysis, which comprises the following steps of: mixing an organic silicon salt compound, brominated vinyl triphenylphosphine, a photosensitizer, an aldehyde compound, an alkaline substance and an organic solvent in an inert gas atmosphere, stirring and reacting for 12-48 hours at 25-35 DEG C under illumination, adding tetrahydrofuran into the obtained reaction liquid A, and reacting for 2-4 hours at the temperature of 25-35 DEG C to obtain the internal olefin (1, 2-disubstituted olefin) compound. Stirring and reacting for 10-24 hours at the temperature of 50-70 DEG C without illumination to obtain reaction liquid B, and post-treating the reaction liquid B to obtain the internal olefin (1, 2-disubstituted olefin) compound. According to the method, the polysubstituted olefin which is difficult to prepare by the existing method can be synthesized, the photooxidation reduction reaction and the wittig reaction are fused in a catalytic cycle, a ylide reagent does not need to be prepared, one-pot synthesis is realized, the catalyst is cheap and easy to obtain, the toxicity is low, the reaction conditions are mild, the energy consumption is saved, the yield is high, the substrate universality is strong, and the operation is simple.