30 results about "Allene" patented technology

The invention relates to organic electroluminescent materials and devices. Provided are metal complexes comprising a ligand LA wherein the ligand LA is a monodentate ligand comprising a carbon bent allene; wherein the ligand LA is coordinated to a metal M; wherein the metal M is optionally coordinated to one or more additional ligands; and wherein one or more ligands may be linked to form a multidentate ligand. Formulations comprising these compounds are also provided. Further provided are OLEDs and related consumer products utilizing these compounds.

The invention relates to the technical field of organic synthesis, in particular to a method for synthesizing a chiral allene compound from aromatic hydrocarbon and alkyne. A simple aromatic hydrocarbon compound and thianthrene-S-oxide are designed to construct an aryl thianthrene salt in situ under the action of an electrophilic activation reagent, then the aryl thianthrene salt constructed in situ under catalysis of a palladium catalyst and a chiral ligand is subjected to an asymmetric Heck reaction with alkyne, and the tri-substituted chiral allene compound is rapidly and efficiently constructed. The method is mild in condition, wide in substrate range and excellent in enantioselectivity and yield, and meanwhile, chiral allene fragments can be introduced into salicin and indometacin which have anti-inflammatory and analgesic activities.

The invention provides a method for synthesizing alpha-substituted allyl sulfone by cobalt-catalyzed reaction of sulfuryl allene and organic boric acid, which comprises the following steps: taking sulfuryl allene as shown in a formula I and organic boric acid as shown in a formula II as raw materials, taking a cobalt complex as a catalyst and an organic ligand, and reacting in the presence of an additive to prepare the alpha-substituted allyl sulfone as shown in a formula III. The invention aims to realize hydroarylation and hydroalkenylation of sulfuryl allene and organic boric acid by adopting an economical and effective means, a cheap cobalt catalysis system is used in the reaction process, and a new way is provided for synthesis of allyl sulfone compounds with highly specific 1, 2-regioselectivity.

The invention belongs to the technical field of organic chemistry, and discloses a β-alkynyl tetrahydropyridine compound and a synthesis method thereof, for solving the technical problem of high cost of the process for synthesizing β-alkynyl tetrahydropyridine structure from allene. By dissolving alkenyl allene compound 1 and phenylimine compound 2 in a solvent, adding copper trifluoromethanesulfonate, and heating the reaction to obtain β-alkynyl tetrahydropyridine compound. The present invention uses copper trifluoromethanesulfonate as a catalyst, and obtains β-alkynyl tetrahydropyridine compound by a one-step reaction, which has the advantages of simple operation, mild conditions, wide substrate range, etc., and has excellent application prospects.

The invention discloses a silicon-containing conjugated olefin compound as well as a preparation method and application thereof, the structural formula of the silicon-containing conjugated olefin compound is shown as (I), and the silicon-containing conjugated olefin compound is obtained by carrying out silicon-carbon bond breakage synthesis on an allenyl functionalized silicon hybrid quaternary compound in the presence of a ligand, a palladium catalyst and a reaction medium, the allene functionalized silicon hybrid quaternary compound is used as a reactant to directly perform intramolecular reaction under the action of a complex formed by a metal catalyst and a phosphine ligand, the reaction condition is mild, the method is simple, and the obtained crude product can be purified by a silica gel rapid chromatography to obtain a pure product. The method has the advantages of mild reaction conditions, wide substrate expansion range, simple preparation operation and the like, and the prepared compound has a certain application prospect in the anti-tumor field.

The invention relates to the technical field of chemical detection, in particular to a method for detecting the content of N, N, N ', N'-tetrapropyl-1, 3-propadiene-1, 4-diamine propionate, which comprises the following steps: (1) respectively dissolving a standard substance and a sample to be detected by using methanol to obtain a standard sample and a sample; (2) adopting a C8 reversed-phase chromatographic column, setting the detection wavelength to be 280-320 nm, selecting a mixed system of acetonitrile and a buffer salt solution as a mobile phase, performing sample injection detection, and calculating an average value of peak areas of N, N, N ', N'-tetrapropyl-1, 3-allene diene-1, 4-diamine propionate in chromatograms of a standard sample and a sample; and (3) calculating the content of N, N, N ', N'-tetrapropyl-1, 3-propadiene-1, 4-diamine propionate in the sample to be detected according to an external standard method formula. According to the method, the blank of detecting the content of the N, N, N ', N'-tetrapropyl-1, 3-propadiene-1, 4-diamine propionate by using a liquid chromatography method is filled.

The present disclosure features materials and methods for the synthesis of polyurethanes by chain-growth copolymerization of a first reactant having an oxirane or thiirane moiety and at least one allene reactant in the presence of a Lewis acid, wherein the first allene reactant is an isocyanate or isothiocyanate. The features also reside in polyurethanes copolymers and terpolymers according to formula (I): (I), wherein An is a halogen atom or a carboxylate or alkoxide moiety; each X and X’ is independently an oxygen or sulfur atom; each R1 and R2 is independently a hydrogen atom or an alkyl group, including straight-chain, branched, saturated, unsaturated, aromatic, cyclic alkyl groups and alkyl groups containing heteroatoms, R3 is an electron-deficient group, m and o are independently selected from integers ≥ 1, and n is 0 or an integer ≥ 1. Both X and X’ can be the same, or X and X’ can be different.

The present invention discloses a method for preparing trans-olefins by chromium-catalyzed semi-hydrogenation of allenes. The method uses an allene compound as a raw material, a cyclic (alkyl)(amino)carbene chromium complex with a diphenylphosphine-substituted side arm as a catalyst, and hydrogen as a hydrogen source, and undergoes a full reaction to obtain the trans-olefin. The method has mild preparation conditions, low cost, a wide range of raw material sources, simple operation, good regio- and stereoselectivity, and can be carried out without the need for a directing group.

The invention relates to a method for synthesizing cis-propenylphosphonic acid through a continuous flow hydrogenation reaction catalyzed by porous organic polymer supported palladium, and belongs to the technical field of synthesis of medical intermediates. According to the method, allene phosphonic acid is taken as a raw material, porous organic polymer supported palladium is taken as a catalyst, cis-propenylphosphonic acid is synthesized through continuous hydrogenation reaction in a micropacked bed reactor, the reaction temperature is 10-70 DEG C, the hydrogen pressure is 0.1-0.5 MPa, the reaction conversion rate can reach 99%, the reaction selectivity can reach 88%, and the activity of the catalyst is not obviously reduced after continuous reaction for 300 hours. According to the synthesis method provided by the invention, by virtue of the micro-packed bed reactor, the reaction speed is high, the safety is high, the reaction selectivity is good, continuous production of cis-propenylphosphonic acid can be realized, and the production cost of fosfomycin is reduced.

The present invention discloses a method for preparing allene compounds, comprising: S1, subjecting compound I to a substitution reaction with iodobenzene diacetate to obtain compound II; S2, subjecting compound II to a Suzuki coupling reaction with compound VIII to obtain compound III; S3, subjecting compound III to an acyl chloride reaction to obtain compound IV; S4, subjecting compound IV to a Friedel-Crafts acylation reaction with AlCl3 to obtain compound V; S5, subjecting compound V to a substitution reaction with Tf2O to obtain compound VI; and S6, subjecting compound VI to a palladium-catalyzed reaction to obtain compound VII; wherein R1 is methyl, ethyl, propyl, isopropyl, cyclopropyl, butyl, or other alkyl groups; and R2 is methyl, ethyl, propyl, isopropyl, cyclopropyl, butyl, or other alkyl groups. The preparation method of the present invention can be used to artificially synthesize allenes and allene compounds, facilitating industrial production. The structural formulas of compounds I, II, III, IV, V, VI, VII, and VIII are as follows:

The application discloses a method for preparing alpha, gamma-unsaturated dienone, which is prepared by isomerization reaction of allene ketone under the action of a catalyst, wherein the catalyst comprises a hydroxyl-functionalized quaternary ammonium salt basic ionic liquid with a structure shown in formula (I); R1, R2, R3 and R4 are independently selected from substituted or unsubstituted alkane, alkene, alkyne and aromatic hydrocarbon, and at least one of R1, R2, R3 and R4 comprises a hydroxyl substituent; and Y is a group alkaline in water. The application catalyzes the isomerization reaction of allene ketone by using the catalyst comprising the hydroxyl-functionalized quaternary ammonium salt basic ionic liquid, and then alpha, gamma-unsaturated dienone is prepared, so that the application has the advantages of small catalyst consumption, high selectivity and yield, low reaction temperature, less pollution, and high yield and selectivity of the catalyst after recycling and multiple reuse.

The invention relates to a polysubstituted bicyclo [2.1. 1] hexane compound and a preparation method thereof, and belongs to the technical field of organic chemistry. According to the method, the bicyclo [1.1. 1] butanone and the allene amine are used as starting materials, the lutetium trifluoromethanesulfonate is used as a catalyst, the 4A molecular sieve is used as an additive, the bicyclo [2.1. 1] hexane compound is obtained through reaction in 1, 2-dichloroethane at room temperature, the reaction condition is mild, the substrate application range is wide, and the method has good scientific significance and application prospects.

The invention provides a method for constructing a substituted pyrimidone skeleton through reaction of gem-difluoroallene and benzamidine hydrochloride compounds, and relates to the technical field of organic synthesis. The method for constructing the substituted pyrimidone skeleton through the reaction of the gem-difluoro allene and the benzamidine hydrochloride compound provided by the invention comprises the following steps: mixing the gem-difluoro allene, the benzamidine hydrochloride compound, alkali and a solvent, heating to react, and after the reaction is finished, performing post-treatment to obtain the substituted pyrimidone compound. The pyrimidone core heterocyclic ring is efficiently constructed by utilizing the special electrophilicity brought by two fluorine atoms in gem-difluoroallene molecules and through a defluorination cyclization mechanism promoted by alkali. The method has the advantages that a noble metal catalyst is not needed, raw materials are easy to obtain, operation is easy and convenient, reaction conditions are mild, one-step synthesis is achieved, functional group compatibility is good, and a new strategy is provided for green and efficient synthesis of pyrimidone compounds.

The present invention discloses a method for synthesizing allene carboxylic acid based on CO2, which belongs to the field of organic synthesis technology. The method comprises the following steps: dissolving a 1,3-enyne substrate, an iodide, a formate, a hydrogen transfer catalyst, a photocatalyst and an alkali in a solvent, introducing CO2 under normal pressure and room temperature, reacting by blue light irradiation, and separating and purifying after acidification to obtain an allene carboxylic acid compound. The present invention is based on the photocatalytic CO2 participation in the 1,4-carbon carboxylation reaction of 1,3-enyne, thereby realizing the synthesis of allene carboxylic acid. The method has mild reaction conditions, good regioselectivity, good functional group tolerance, and makes up for many deficiencies of the prior art. The method provides an efficient and green innovative path for drug molecule modification, functional material development and CO2 resource utilization, and at the same time expands new ideas for green chemical synthesis and carbon cycle technology.

The invention discloses an allene ketone compound with a structure as shown in a formula (I), or pharmaceutically acceptable salt or stereoisomer thereof, and application thereof. The invention provides an allenone compound which can covalently modify and mark amino acid residues in protein or polypeptide, especially cysteine residues. The method can be used for identifying, analyzing and identifying potential tumor treatment targets and active sites with medicinal values; and the compound has certain anti-tumor activity and can be used for anti-tumor drugs. (I)

The invention belongs to the technical field of organic synthesis methodology, and particularly relates to a method for synthesizing allene nitrile compounds based on a visible light / metal copper dual-catalysis strategy and application of the allene nitrile compounds. According to the method, substituted sulfonium salt and substituted enyne are used as raw materials, trimethylsilyl cyanide is used as a cyano source, alkali is used as an additive, and an organic solvent is added; and reacting in inert gas at a certain temperature, and preparing the allene nitrile compound under the dual catalytic action of the photocatalyst and the metal copper / ligand catalyst. The method does not need harsh reaction conditions, the reaction can be completed in one step, the reaction conditions are mild, and the method is green and environment-friendly. The allene nitrile compound and the derivative thereof prepared by the method are expected to serve as lead compounds to be applied to the research and development fields of anti-cancer, antiviral and antibacterial drugs and the like.

The invention relates to a preparation method of an all-carbon-tetra-substituted olefin compound and application of the all-carbon-tetra-substituted olefin compound as a nematicide, and belongs to the technical field of forestry pest control. The compound is constructed through free radical fluorine sulfonylation reaction of FSO2Cl on allene, a multifunctional structure containing aldehyde groups, tetra-substituted olefin and allyl sulfonyl fluoride is efficiently synthesized by utilizing a bi-1, 2-carbon migration strategy, and the compound has excellent synthesis modifiability. A biological activity research shows that the compound has a remarkable killing effect on pine wood nematode and can be used for effectively preventing and treating a destructive forestry disease, namely pine wood nematode disease. According to the invention, the limitation of stereoselective synthesis of traditional tetra-substituted olefin is broken through, meanwhile, the metabolic stability and biological activity of the compound are enhanced by introducing the sulfonyl fluoride group, and an innovative solution is provided for developing a novel environment-friendly nematicide.

This invention provides a cobalt-catalyzed method for synthesizing α-substituted allyl sulfones by reacting sulfonyl allenes with organoboronic acids. Using sulfonyl allenes of Formula I and organoboronic acids of Formula II as raw materials, a cobalt complex as a catalyst, and an organic ligand, the reaction yields α-substituted allyl sulfones of Formula III in the presence of additives. This invention aims to achieve the hydroarylation and hydroalkenylation of sulfonyl allenes with organoboronic acids using an economical and efficient method. The reaction process utilizes an inexpensive cobalt catalytic system, providing a new route for the synthesis of allyl sulfone compounds with highly specific 1,2-regioselectivity.

The invention discloses a preparation method of thioester and epithioester compounds, and belongs to the technical field, the preparation method of the thioester compounds comprises the following steps: in an organic solvent, under the participation of alkali, reacting an alpha-carbonyl alkenyl ester compound with a thiol or thiophenol compound at 0-50 DEG C to obtain the thioester compounds; the preparation method of the episulfide compound comprises the following steps: reacting a sulfydryl-containing carboxylic acid compound with an allene ketone compound or an alkyne amide compound in dichloroethane at 0-70 DEG C to obtain a sulfydryl-containing alkenyl ester compound; then, in an organic solvent, the alkenyl ester compound containing sulfydryl reacts at the temperature of 0-50 DEG C under the participation of alkali and / or an additive, and the episulfide compound is obtained; the method for preparing thioester and epithioester provided by the invention has the advantages of low cost, simple operation, mild reaction conditions, wide substrate adaptability, no racemization of products and the like.

The present invention relates to methods of treating chronic degenerative conditions of the central nervous system related to oxidative stress, comprising administering a composition comprising allene oxide synthase (AOS), or a functional equivalent variant thereof.

The invention belongs to the technical field of novel synthesis of copper-catalyzed high-molecular polymers, and discloses a synthesis method of a copper-catalyzed allene sulfonyl amidine polymer, which comprises the following steps of: accurately weighing 1 molar equivalent of binary sulfonyl azide monomer SA, 1 molar equivalent of binary secondary amine monomer Nu, 2 molar equivalent of 1, 3-diyne monomer DY and 3 molar equivalent of organic alkali DIPEA, dissolving in a solvent, and uniformly stirring; adding 0.1 mol equivalent of catalyst CuI in the reaction process, stirring for 24 hours at room temperature, and stopping the reaction; and settling the reaction solution by using a settling agent, centrifuging, repeating for three times, collecting a precipitated product, and drying the product to constant weight. The invention provides a one-step synthesis strategy for efficiently preparing polyallene sulfonyl amidine by taking 1, 3-diyne, binary sulfonyl azide and binary secondary amine as monomers based on copper catalysis for the first time.

The invention discloses a 3, 4, 4-triaryl-3-allyl-1-ketone compound as well as a preparation method and application of the 3, 4, 4-triaryl-3-allyl-1-ketone compound. The structural formula of the 3, 4, 4-triaryl-3-allyl-1-ketone compound provided by the invention is as shown in a formula I which is described in the specification. The preparation method comprises the following steps: in the presence of a catalyst and hydrogen, carrying out catalytic coupling reaction on three iodobenzene compounds, allene and aldehyde compounds to obtain the compound as shown in the formula I, the 3, 4, 4-triaryl-3-allyl-1-ketone compound disclosed by the invention is novel in structure and can be used for synthesizing medicine and material intermediates.

The present invention relates to the field of catalytic hydrogenation, and more particularly to the hemihydrogenation of allenes to corresponding alkenes in the presence of a homogeneous catalyst system, wherein the homogeneous catalyst system comprises a cobalt salt, a bidentate diphosphine ligand, and a weakly coordinating or non-coordinating monoanion or reducing agent.

The invention discloses a synthesis method of 3-allenyl-2-hydroxyl-1-aryl-1-acetone, and the synthesis method comprises the following steps of: synthesizing 3-allenyl-2-hydroxyl-1-aryl-1-acetone; the method comprises the following steps of: adding alkali into an organic solvent under the action of lewis acid and a chiral palladium catalyst by taking a 2-hydroxy aryl ethanone compound as shown in a formula (I) and an allene carbonate compound as shown in a formula (II) as raw materials, reacting at-20 DEG C to 30 DEG C, and after the reaction is finished, carrying out post-treatment to obtain the compound shown in the formula (I). In the formula (I), the formula (II) and the formula (III), Ar is phenyl, naphthyl, thienyl or substituted phenyl; r is phenyl or substituted phenyl. According to the invention, the synthesis of the 3-allenyl-2-hydroxy-1-aryl-1-acetone with a discontinuous chiral center is realized through a synergistic catalysis method of the lewis acid and the chiral palladium catalyst for the first time. The method has the advantages of simple and easily available raw materials, simple operation, mild reaction conditions, strong substrate applicability, good functional group compatibility, excellent stereoselectivity and the like.

The invention discloses a synthesis method and application of a chiral homoallylamine compound, and belongs to the technical field of synthesis of drug intermediates, and the synthesis method comprises the following steps: under the protection of inert gas, dissolving a copper salt catalyst, a phosphine ligand, imine, allene silane and tert-butyl alcohol in tetrahydrofuran, stirring and mixing; adding phenyl silane, and reacting at 20-30 DEG C for 12-20 hours; after the reaction is finished, adding a saturated ammonium fluoride methanol solution to quench the reaction; and continuously stirring the mixture, carrying out reduced pressure rotary evaporation to remove the solvent, and separating a crude product by column chromatography to obtain a target product. When THF is used as a solvent and copper acetate is used as a catalyst, the chiral homoallylamine compound can be obtained at room temperature with the highest yield of 78% and diastereoselectivity greater than 20: 1.

The invention discloses a method for synthesizing a 1, 5-diene drug skeleton intermediate, and the method adopts a metallized porous organic polymer catalyst Cu (at) POL-bpy to realize efficient and accurate construction of the 1, 5-diene drug skeleton intermediate through a boryl-allylation coupling reaction of allene, and provides a new strategy for preparation of a 1, 5-diene drug. The method is low in cost and high in catalytic efficiency, the catalyst still keeps stable catalytic activity after being continuously recycled, and the good industrial application prospect is shown.

The invention discloses an allene compound synthesized by coupling three electrophilic reagents and a preparation method and application thereof. The method comprises the following steps: under the protection of gas, reacting simple and easily available aryl iodide, propargyl alcohol derivative, alkyl bromide or aryl bromide in an organic solvent at 110-120 DEG C under the synergistic catalysis of a palladium catalyst and C5-site amide substituted norbornene or C2-site ethyl ester substituted norbornene to obtain a series of allene compounds. The method has the advantages of cheap and easily available raw materials, mild reaction conditions, good substrate universality, high yield and simple preparation process, and can be used for rapidly obtaining a high-value chiral skeleton.

The application relates to the technical field of organic synthesis, and particularly relates to a method for synthesizing chiral diene compounds from aromatic hydrocarbons and alkynes. A simple aromatic hydrocarbon compound is designed to be in-situ constructed into an arylthianthrene onium salt under the action of an electrophilic activation reagent, then a palladium catalyst and a chiral ligand are used to catalyze the asymmetric Heck reaction of the arylthianthrene onium salt constructed in-situ and alkynes, so that a trisubstituted chiral diene compound is quickly and efficiently constructed. The method has mild conditions, a wide substrate range, excellent enantioselectivity and yield, and can introduce a chiral diene fragment into salicylate and indometacin which have anti-inflammatory and analgesic activities.

The invention discloses a preparation method of a trisubstituted allene compound. The present invention relates to the hydroarylation of 1, 3-enyne with aryl halides under electrochemical conditions, which strategy focuses on the generation of aryl radicals from aryl halides via cathodic single electron transfer (SET) electroreduction promoted by an organic redox mediator, thereby avoiding the need for metal catalysts. The aryl radicals generated in situ will undergo selective addition to the distal (olefin) carbon of the 1, 3-enyne. And expensive transition metal catalysts and harsh reaction conditions are not needed. The high reduction potential of aryl halides is avoided, so that aryl radicals can be generated under mild electrochemical conditions, and degradation of sensitive functional groups, which is often observed at high voltages, is prevented. In addition, water can be used as a benign and abundant proton source, and the method is easily suitable for using low-cost and commercially available D2O as a deuterium donor, and can efficiently synthesize deuterium-labeled allene.

The invention discloses a method for synthesizing allene carboxylic acid based on CO2, and belongs to the technical field of organic synthesis, and the method comprises the following steps: dissolving a 1, 3-eneyne substrate, iodide, formate, a hydrogen transfer catalyst, a photocatalyst and alkali in a solvent, introducing CO2 under the conditions of normal pressure and room temperature, carrying out blue light irradiation reaction and acidification treatment, and then carrying out separation and purification to obtain the allene carboxylic acid. The allene carboxylic acid compound is prepared. According to the method disclosed by the invention, the synthesis of allene carboxylic acid is realized on the basis that CO2 participates in 1, 4-carbon carboxylation reaction of 1, 3-enyne through photocatalysis. The method has the advantages of mild reaction conditions, good regioselectivity and good functional group tolerance, and makes up for many defects in the prior art. The method provides an efficient and green innovative path for drug molecule modification, functional material development and CO2 resource utilization, and expands a new thought for green chemical synthesis and a carbon cycle technology.