24 results about "Aryne" patented technology

The invention is directed to a process for the preparation of an aromatic acid or a phenolic compound, said process comprising reacting a dienophile and a furanic compound comprising an acetal moiety in a Diels-Alders reaction to obtain an aromatic compound comprising said acetal moiety, followed by hydrolysis and oxidation of said acetal moiety into a hydroxide or carboxylate moiety to form the aromatic acid or phenolic compound, wherein said dienophile is selected from the group consisting of alkylenes, acetylenes, acrylates, maleates, fumarates, maleimides, propiolates, acetylene dicarboxylates, and benzynes and wherein said acetal moiety is bound directly to the 2-position of the furanic compound.

The invention relates to a synthesis method of an aminoacridine compound, and belongs to the technical field of organic synthesis. The synthesis method of the amino acridine compound comprises the following steps: reacting an aryne precursor derivative, polysubstituted o-aminobenzonitrile and fluorinion in the environment of acetonitrile and inert gas to obtain an aromatic diamine derivative, mixing the aromatic diamine derivative with a solvent, and reacting to obtain the amino acridine compound. And carrying out cyclization reaction under the action of acid to obtain the aminoacridine compound. The amino acridine compound is prepared by adopting a one-pot method, the process steps are simple, the experimental process is simplified, the raw materials are cheap and easy to obtain, and the product is easy to purify.

The application provides a method for simultaneously synthesizing thioether compounds and nitrile compounds, and belongs to the technical field of organic synthesis; the thioamide compound, fluoride and acetonitrile are mixed, then a phenylacetylene precursor is added, so that the thioether compound and the nitrile compound are simultaneously synthesized at room temperature; the method is simple and fast, does not need transition metal catalysis, has a wide substrate range, the fluoride source used is cheap and easy to obtain, and does not cause environmental pollution; the method has the advantages of simple process, mild reaction condition, good universality and the like, and the yield of the synthesized thioether compound and nitrile compound is very high, the thioether compound and the nitrile compound can reach 98% at most, and has extremely high industrial popularization value.

The invention discloses a method for preparing a heterocyclic compound containing indolone and 3-acylbenzofuran or indole structure, comprising the following steps: reacting palladium acetate, bis(diphenylphosphine) propane, TFBen, triethylenediamine, iodoaromatic compounds and o-hydroxyl / o-aminobenzyne compounds at 100°C for 24 hours, and after the reaction is complete, post-processing to obtain the heterocyclic compound containing indolone and 3-acylbenzofuran or indole structure. The reaction raw materials are cheap and easy to obtain, the substrate has good applicability and can be compatible with a variety of functional groups, TFBen is used as a carbonyl source, and the operation is simple. At the same time, the method can form multiple chemical bonds, including three C-C bonds and one C-O / C-N bond, through a one-step reaction, and provides a new method for the synthesis of carbonyl-containing bicyclic heterocyclic compounds.

The present invention discloses a functionalized isoquinolone and quinolone compounds and an efficient transition-metal-free approach for the synthesis of the same. The invention provides a highly functionalized isoquinolones from the reaction of dimethyl-2-((phenylamino)methylene) malonate with aryne precursors under mild. The reaction proceeds through insertion of aryne into the C−C σ-bond, which offers a novel and practical entry to access a wide range of isoquinolones with enhanced yields. The substrate scope is broad as the process can stands a variety of functional groups and the application of the developed process has been demonstrated in the total synthesis of antimalarial agent SJ000101247. Also, the highly functionalized quinolones are also useful in the synthesis of floxacins based compounds and derivatives e.g. ciprofloxacin, norfloxacin, G003967, etc.

The invention provides a synthesis method of aryl phosphate, and solves the problems of harsh reaction conditions, existence of potential safety hazards, high requirements on equipment, tedious process, low yield, high cost and the like which are not beneficial to industrial production in the existing synthesis method. The preparation method comprises the following main preparation steps: S1, reacting chloro phosphate with different types of amines to obtain phosphoramidate; s2, the phosphoramidate and different kinds of benzyne precursors are subjected to an arylation reaction under the fluoride condition, and aryl phosphate is obtained.By means of the one-pot method, the experimental operation process can be simplified, generation of by-product impurities is avoided, the yield is greatly improved through condition screening, and the obvious effect is achieved.

The invention provides a method for synthesizing a benzimidazobenzothiazole compound, and belongs to the technical field of fine chemical synthesis. The preparation method comprises the following steps: mixing a 2-mercapto benzimidazole compound, fluoride, alkali, an additive, a molecular sieve and dichloromethane, then adding a benzyne precursor into the mixture, and synthesizing the benzimidazobenzothiazole compound at 110 DEG C; the method has the advantages of simplicity, convenience, rapidness, no need of transition metal catalysis, wide substrate range, cheap and easily available fluorine source, no environmental pollution and the like; the method has the advantages of being simple in process, good in universality and the like, the yield of the synthesized benzimidazobenzothiazole compound is as high as 90%, and the method has extremely high industrial popularization value.

The invention discloses a silicon aryne modified resin-based high-temperature-resistant wave-absorbing coating as well as a preparation method and application thereof, and relates to the technical field of wave-absorbing materials. The wave-absorbing coating is prepared from the following raw materials: an absorbent, a silicon aryne resin solution, a matrix resin solution, a diluent, a dispersing agent and an anti-settling agent, wherein the mass ratio of the absorbent to the silicon aryne resin solution to the matrix resin solution to the diluent to the dispersing agent to the anti-settling agent is (30 to 90) to (2.5 to 25) to (16.42 to 122.5) to (10 to 40) to (0.3 to 0.9) to (0.3 to 0.9). Intermolecular interaction and chemical bonding can be formed between the silicon aryne resin and the organic silicon resin, and the heat resistance, the flexibility and the impact resistance of the wave-absorbing coating can be greatly enhanced due to the synergistic effect between the silicon aryne resin and the organic silicon resin.

The invention discloses a protein / polypeptide-drug coupling method which comprises a method I or a method II. The method I comprises the following steps: carrying out mixed reaction on a salicylaldehyde derivative, a phenylboronic acid derivative and secondary amine, and then carrying out mixed reaction with lysine-containing polypeptide and / or protein to complete protein / polypeptide-drug coupling; the method II comprises the following steps: mixing a salicylaldehyde derivative, an aryne potassium trifluoroborate derivative and tryptophan-containing polypeptide and / or protein for reaction to complete protein / polypeptide-drug coupling; at least one of the salicylaldehyde derivative, the phenylboronic acid derivative and the aryne potassium trifluoroborate derivative comprises at least one drug molecule group capable of breaking and releasing drug molecules. The method is simple in condition, efficient in reaction and high in reaction site selectivity, coupling of various drugs and different polypeptides / proteins can be achieved, drug molecules can be released, and the pharmacodynamic activity of the drug molecules is reserved.

The invention discloses a method for synthesizing a benzofuran derivative through copper-catalyzed alkynylation reaction, and relates to the technical field of organic synthetic chemistry and medicinal chemistry. According to the method, halogenated anisole and terminal alkyne are used as raw materials, under the combined action of a copper catalyst and alkali, ethanol is used as a green solvent, an aryne intermediate is generated in situ through a Sonogashira coupling reaction, then an electrophilic reagent R-Se-X1 is directly added to induce cyclization without separation and purification, and a benzofuran skeleton is efficiently constructed. Compared with a traditional palladium catalysis system, the method has the advantages that the copper catalyst which is low in cost and easy to obtain is adopted, the problems of high cost and difficult recovery of precious metal (such as palladium) are solved, meanwhile, the use of cocatalysts of heavy metal (such as lead and antimony) is eliminated, and the economical efficiency and the environmental protection property of the process are remarkably improved. In addition, the reaction for synthesizing the aryne intermediate does not need inert gas protection, and the reaction conditions (heating and room temperature) are mild. In addition, the method provided by the invention also has excellent substrate universality.

The invention relates to preparation of a retardation film of a linear acrylate monomer with a side chain. The linear acrylate monomer with the side chain is an acrylate-terminated monomer containing a side chain group, and the ester group or amide side chain group contains at least one of naphthyl, benzofuryl, benzothienyl, benzothiazolyl and glycol ether. The polyphenyl ester derivative monomer containing the multi-substituted benzyne side chain group and different components are polymerized to obtain the phase difference delay film composition. The polysubstituted benzyne side chain in the linear acrylate monomer with the side chain has abundant substituent groups, so that the properties and characteristics of light transmission, solubility, film-forming property, refractivity and insulativity of the film are effectively regulated and controlled.

The invention relates to a silicon-hydrogen-terminated silicon-containing aryne resin and a preparation method and application thereof, the structural formula of the silicon-hydrogen-terminated silicon-containing aryne resin is as follows: in the formula, R1 and R2 are respectively and independently CH3, CH2 = CH, H or phenyl; n is equal to 1-9. The preparation method comprises the following steps: firstly, carrying out Grignard reaction on 1, 3-diacetylene benzene and a Grignard reagent to obtain a compound 1 as shown in a formula I; carrying out polymerization reaction on the compound 1 and a compound 2 as shown in a formula II to obtain a compound 3 as shown in a formula III; and then carrying out reduction reaction on the compound 3 and lithium aluminum hydride to obtain the silicon-hydrogen-terminated silicon-containing aryne resin. Compared with the prior art, the silicon-hydrogen-terminated silicon-containing aryne resin prepared by the invention has excellent heat resistance, has extremely high thermal decomposition temperature of 5% of cured substance weight loss in nitrogen and air, has excellent processability and has an extremely wide processable temperature window.

The application belongs to the technical field of biological medicine, and particularly relates to an N-heterocyclic carbene-gold (I)-phenyl alkyne complex and antibacterial application thereof. The N-heterocyclic carbene-gold (I)-phenyl alkyne complex has good bacteriostatic activity, and the minimum inhibitory concentration (MIC) is less than 5 muM. Meanwhile, it is found that the N-heterocyclic carbene-gold (I)-phenyl alkyne complex can enter cells, inhibit the growth and reproduction of intracellular bacteria by using the acidic environment in cells, and the cytotoxicity is significantly reduced compared with existing drugs, and has good application prospect.

The invention belongs to the field of catalysts, and particularly relates to chiral quaternary nitrogen guanidine salt derived from amino acid as well as a preparation method and application of the chiral quaternary nitrogen guanidine salt. The invention provides a compound shown in a formula I and a preparation method thereof. The compound has good catalytic performance in an asymmetric alkylation reaction and / or an arylation reaction. Experiments show that the catalytic performance of the compound disclosed by the invention in catalyzing the asymmetric arylation reaction in which benzyne participates is superior to that of the existing chiral quaternary ammonium salt catalyst or chiral quaternary phosphonium salt catalyst. Therefore, the method has a good application prospect. # imgabs0 #

The invention belongs to the technical field of lithium batteries, and particularly relates to acetylene carbon black with a high capacity retention ratio and a preparation method and application thereof. The invention provides a preparation method of acetylene carbon black with high capacity retention ratio, which comprises the following steps: introducing benzene and acetylene into a reactor for reaction to obtain acetylene carbon black, the volume ratio of the benzene to the acetylene is 1: (2-5). By controlling the benzyne ratio, the generated acetylene carbon black has raised sawtooth surface defects, the bonding strength among the acetylene carbon black, an adhesive and an active substance is enhanced, the electrolyte consumption caused by SEI membrane breaking due to volume expansion possibly caused in the active substance circulation process is relieved, and the service life of the electrolyte is prolonged. And the probability of mutual shedding between the active substance and the conductive agent is also reduced. The capacity retention ratio of the acetylene carbon black prepared by the invention in a lithium ion battery is far higher than that of Super P and other conductive carbon black.

To provide a novel combination therapy that exhibits excellent antitumor effects. [Solution] An antitumor agent containing futivatinib or a salt thereof as the active ingredient (not containing pembrolizumab as the active ingredient) administered in combination to cancer patients with an immune checkpoint inhibitor (excluding CD155 / TIGIT pathway antagonists) and at least one other antitumor agent.

The invention belongs to the technical field of biological medicines, and particularly relates to an N-heterocyclic carbene-gold (I)-benzyne complex and antibacterial application thereof. The N-heterocyclic carbene-gold (I)-benzyne complex disclosed by the invention has relatively good antibacterial activity, and the minimum inhibitory concentration (MIC) of the N-heterocyclic carbene-gold (I)-benzyne complex is less than 5 mu M. Meanwhile, research finds that the N-heterocyclic carbene-gold (I)-benzyne complex can enter cells and inhibit growth and reproduction of intracellular bacteria by utilizing an intracellular acid environment, the cytotoxicity is remarkably reduced compared with that of an existing drug, and the N-heterocyclic carbene-gold (I)-benzyne complex has a good application prospect.

Provided is a novel combination therapy that exhibits an excellent antitumor effect and combines an FGFR-inhibiting compound with an MEK inhibitor.　An antitumor agent contains (S)-1-(3-(4-amino-3-((3,5-dimethoxyphenyl)ethynyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)pyrrolidin-1-yl)prop-2-en-1-one or a salt thereof as an effective ingredient and is administered in combination with an MEK inhibitor.

The application belongs to the field of catalysts, and particularly relates to a chiral quaternary nitrogen guanidine salt derived from an amino acid, a preparation method thereof and application thereof. The application provides a compound shown in formula I and a preparation method thereof. The compound has good catalytic performance in asymmetric alkylation reaction and / or arylization reaction. Experiments show that the catalytic performance of the compound in asymmetric arylization reaction participated by benzene alkyne is superior to that of existing chiral quaternary ammonium salt catalysts or chiral quaternary phosphonium salt catalysts. Therefore, the application has good application prospect.

A method for producing a biaryl compound, including the steps of: generating a benzyne compound from a precursor of the benzyne compound; generating a fused ring compound containing a 1,4-epoxy-1,4-dihydrobenzene ring by subjecting the benzyne compound and a furan compound to a Diels-Alder reaction; and generating a biaryl compound by subjecting the fused ring compound and a halogenated aryl compound to a cross-coupling reaction.

The invention provides silicon aryne resin and a preparation method thereof. The silicon aryne resin is prepared from the following raw material components in parts by weight: 12 to 16 parts of magnesium chips, 60 to 65 parts of bromoethane, 30 to 36 parts of diacetylene benzene, 0.5 to 1.0 part of vinyl trichlorosilane, 18 to 21 parts of methyl vinyl dichlorosilane, 172 to 198 parts of methyl tetrahydrofuran, 18 to 21 parts of acetic acid and 250 to 350 parts of deionized water. The invention also provides a silicon aryne resin composite material and a preparation method thereof, and the silicon aryne resin composite material is prepared by alternately arranging quartz glass fiber yarns and hollow quartz glass fiber yarns on a yarn collecting frame at intervals according to the quantity ratio of 1: 1, and then sequentially dewaxing, dipping in a silicon aryne resin solution, baking and curing. The molecular structure of the silicon aryne resin contains aromatic rings, silane, alkynyl and other structural groups, and the resin can form a spatial network structure with high aromatic ring content after being cured, and has excellent high temperature resistance.

The present invention discloses a method for preparing an indomethacin ester derivative. The indomethacin ester derivative is shown in formula (I). The preparation method of the derivative is to use a 2-(trimethylsilyl)phenyl trifluoromethanesulfonate compound as a benzylene precursor and cesium fluoride as a base to achieve a reaction with indomethacin under conditions without the addition of an external condensing agent or metal catalyst. The method is simple to operate and has concise steps, providing a safe, efficient, and practical synthesis method for the preparation of valuable indomethacin ester derivatives. The indomethacin ester derivatives prepared by the present invention are expected to be used in the preparation of COX-2 inhibitors or non-steroidal anti-inflammatory drugs.

The invention discloses a method for electrochemical synthesis of a 3, 4-dihydroisoquinoline-1 (2H)-ketone compound, and the method comprises the following steps: dissolving a 1, 2, 3-benzotriazinone compound, a benzyne compound and an electrolyte salt in a solvent to obtain a reaction solution, placing an anode and a cathode in the reaction solution, introducing a direct current, and carrying out electrochemical reaction to obtain the 3, 4-dihydroisoquinoline-1 (2H)-ketone compound. And after the reaction is finished, carrying out post-treatment to obtain the 3, 4-dihydroisoquinoline-1 (2H)-ketone compound. The method has the characteristics that synthesis is performed through an electrochemical method, a transition metal catalyst is not needed, the use of a chemical oxidation reducing agent is avoided, and the method is green, environment-friendly, high in safety, simple to operate, mild in reaction condition, easy to control and the like.

The invention discloses a preparation method of m-dibutylaminophenol, and relates to the technical field of carbocyclic compound preparation, the m-dibutylaminophenol comprises the following raw materials: 2-chlorophenol, 2, 6-di-tert-butyl-4-methylphenol, zinc chloride, tetrabutylammonium bromide, sodium amide, potassium tert-butoxide, an activated 3A molecular sieve, di-n-butylamine and triethylamine; according to the invention, 2-chlorophenol is used as a core reaction substrate, the structure arrangement of ortho-position chlorine atoms and hydroxyl is highly adaptive, hydrogen chloride can be accurately removed under the action of strong alkali to generate a benzyne intermediate, and a stable benzene ring skeleton is provided for a target product; through the synergistic effect of the activated 3A molecular sieve, the 2, 6-di-tert-butyl-4-methylphenol and the potassium tert-butoxide, the total impurity content is greatly reduced, the product purity and color are remarkably optimized, and the synchronous improvement of the reaction efficiency and the product quality is realized.