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236 results about "Regioselectivity" patented technology

In chemistry, regioselectivity is the preference of one direction of chemical bond making or breaking over all other possible directions. It can often apply to which of many possible positions a reagent will affect, such as which proton a strong base will abstract from an organic molecule, or where on a substituted benzene ring a further substituent will add.

Catalytic synthesis icariside D2 glycosyltransferase mutant with improved regioselectivity and activity

PendingCN120944841ABacteriaTransferasesBacillus licheniformisGlycosyltransferase activity
According to the invention, glycosyl transferase UGTBL1 derived from Bacillus licheniformis ZSP01 is taken as a research object, AlphaFold 2 is used for modeling, molecular docking, molecular dynamics simulation and other technologies, amino acid in an active pocket region of glycosyl transferase is analyzed, amino acid in a substrate channel is analyzed by software CAVER3.0, site-directed mutagenesis is carried out, and the glycosyl transferase UGTBL1 is obtained. The regioselectivity and the activity of the mutant for catalytically synthesizing the icariside D2 glycosyltransferase are improved.
Owner:NANJING TECH UNIV

Synthesis method of N-heterocyclic carbene catalyzed diunsaturated ester compound

The invention relates to a synthesis method of a diunsaturated ester compound catalyzed by N-heterocyclic carbene, and belongs to the field of organic synthesis. According to the preparation method, the synergistic effect of N-heterocyclic carbene and light is utilized, gamma-oxo unsaturated aldehyde and Katritzky salt are taken as starting raw materials, the Katritzky salt generates alpha-ester free radicals through a single electron transfer process under the illumination condition, the free radicals react with a nucleophilic trienol intermediate generated through catalysis of the N-heterocyclic carbene, and the alpha-ester free radicals react with the nucleophilic trienol intermediate to generate the gamma-oxo unsaturated aldehyde. Target products are obtained with good yield and high regioselectivity, so that a series of epsilon-alkylated diunsaturated ester compounds are efficiently synthesized. The method is simple and convenient to operate, green and efficient, has the advantages of no transition metal participation, wide substrate applicability and the like, provides a new way for synthesis of the diunsaturated ester compound, and has a wide application prospect.
Owner:HENAN ACADEMY OF SCI CHEM RES INST CO LTD +1

Method for biosynthesizing acetyl tetrapeptide-5, composition containing acetyl tetrapeptide and application of composition

The invention relates to the technical field of polypeptide biosynthesis, in particular to a method for biosynthesizing acetyl tetrapeptide-5, a composition containing the acetyl tetrapeptide-5 and application of the composition. According to the method, low-cost natural amino acid is used as a substrate, specific aminopeptidase or a mutant thereof is used as a biocatalyst, amino acid ligase and polyphosphatase are combined, and acetyl tetrapeptide-5 can be efficiently synthesized through a one-step enzymatic reaction. Compared with a traditional chemical synthesis method, the method has the advantages of low raw material cost, no use of an organic solvent, mild reaction conditions, high regioselectivity, environmental friendliness, low production cost and the like. The invention also provides a composition containing acetyl tetrapeptide-5 and dipeptide-15, the inhibition effect of the composition on grease secretion is obviously better than that of a single component, and the composition has a synergistic oil control effect under a specific ratio.
Owner:SHENZHEN READLINE BIOTECH CO LTD

Hydrosilylation reaction catalyst and preparation method thereof

The invention relates to the technical field of organic silicon catalysis, and discloses a hydrosilylation reaction catalyst and a preparation method thereof, the catalyst is prepared from a platinum complex catalyst solution, maleic anhydride, triphenyl borate, tetraethoxysilane, propylene carbonate and diethylene glycol dibutyl ether; the preparation method comprises the steps of solvent water removal, electronic relay adduct preassembly, active metal introduction, thermal induction aging and the like. An electron-deficient coordination center is constructed through a step-by-step process, the electron cloud density of the platinum center is reduced by utilizing the Lewis acid characteristic of triphenyl borate, and the solvent cage effect of propylene carbonate is matched, so that the high-temperature tolerance of the catalyst is improved, and the generation of platinum black is effectively inhibited; meanwhile, the solubilizing and bridging effects of diethylene glycol dibutyl ether are utilized, the compatibility problem of a high-polarity component and a non-polar silicone oil matrix is solved, and the obtained catalyst has high activity, high regioselectivity and excellent long-term storage stability.
Owner:江西宏柏新材料股份有限公司

Method for synthesizing benzodithiepinone derivative through metal-free catalysis

The invention discloses a method for synthesizing a benzodithiepinone derivative through metal-free catalysis, and belongs to the field of organic synthesis. According to the method, benzo disulfonylphenol ketone and alkyne are taken as raw materials, a dual-catalysis system composed of triethylene diamine and bis (diphenylphosphine) methane is adopted, a heating reaction is performed in a 1, 4-dioxane solvent, and the target seven-membered sulfur heterocycle (benzo [e] [1, 4] dithiepin-5-ketone compound) is obtained through separation and purification. According to the method, the problem of regioselective sulfuration of alkyne is effectively solved through a synergistic catalysis mechanism of organic amine and organic phosphine, and high-precision cyclization reaction of benzobissulfonylphenol ketone and alkyne is realized. The process is mild in reaction condition, free of inert gas protection, simple and convenient to operate and good in functional group tolerance, the atom economy can reach 100%, and an efficient and practical synthesis way is provided for construction of the benzo [e] [1, 4] dithiepin-5-ketone compound with a novel structure.
Owner:HUBEI NORMAL UNIV

A phosphine-containing porous organic polymer supported ruthenium catalyst and a method for preparing the same

This invention discloses a ruthenium catalyst supported on a phosphine-containing porous organic polymer and its preparation method. The phosphine-containing porous organic polymer serves as both a support and a solid ligand. The phosphine-containing porous organic polymer ligand is a random copolymer, and its structure can be represented by general formula I. The ruthenium catalyst supported on the phosphine-containing porous organic polymer according to this invention has a large specific surface area and contains a hierarchical porous structure, enabling efficient direct preparation of alcohols from olefins via reductive hydroformylation, and is easily recyclable. It exhibits excellent activity and regioselectivity in the direct preparation of alcohols from olefins via reductive hydroformylation, with an alcohol selectivity of nearly 90% and a high ratio of straight-chain alcohols to branched-chain alcohols.
Owner:QINGDAO INST OF BIOENERGY & BIOPROCESS TECH CHINESE ACADEMY OF SCI

Preparation method of 9-aryl xanthene compound

The invention relates to the technical field of organic synthesis, in particular to a preparation method of a 9-aryl xanthene compound. The preparation method of the 9-aryl xanthene compound comprises the following steps: adding a xanthene compound, an aromatic amine compound and a nitrogen-doped carbon material into an organic solvent, and reacting in an oxygen atmosphere; the 9-aryl xanthene compound is novel in structure and can be applied to the fields of medicines, agricultural chemicals, material science and the like, and the preparation method has the advantages of mild reaction conditions, simplicity and safety in operation, high raw material economy, wide substrate applicability and functional group compatibility, good chemical and regioselectivity and the like; a new way is provided for the construction of a novel xanthene derivative.
Owner:YANCHENG INST OF TECH

Cobalt-catalyzed dual migratory asymmetric nozaki-hiyama-kishi coupling system and its application in the preparation of chiral allylamine intermediates

PendingCN122355967APtru catalystPropylamine
The application discloses a kind of using cobalt catalyst by unreported double migration coupling strategy, realizes migration asymmetric nitrogen hetero Nozaki-Hiyama-Kishi (aza-NHK) reaction, and the selective preparation α-chiral (E)-allyl amine starting from simple and easy to obtain ortho halogen phenyl ethylene or corresponding E / Z-alkyl bromide or its mixture belongs to the field of organic chemistry and medicinal chemistry.The application under the action of metal cobalt source, ligand, organic additive, inorganic additive etc., makes cyclic sulfonamide and ortho alkenyl substituted aryl halide or alkenyl halide react in organic solvent, to obtain a series of polysubstituted olefins with excellent regioselectivity, stereoselectivity and good yield, which can be used as active drug molecules and important synthetic intermediates.The application uses cheap transition metal cobalt as catalyst, and uses ortho alkenyl substituted aryl iodine and cyclic sulfonamide as raw material, and the reaction condition is warm, simple operation, and good functional group compatibility.
Owner:NANJING UNIV

A method for synthesizing nitrogen-containing heteroarene carboxylic acid compounds based on nitrogen-containing heteroarene carbon-hydrogen bond carboxylation reaction

The application discloses a method for synthesizing nitrogen-containing heteroarene carboxylic acid compounds based on nitrogen-containing heteroarene carbon-hydrogen bond carboxylation reaction and belongs to the technical field of organic synthesis, and specifically comprises the following steps: adding a reaction substrate, an organic catalyst, a base and an additive into a reaction container, then adding a solvent under a CO2 atmosphere, and stirring and reacting at room temperature or under heating in a light irradiation condition; and performing post-treatment on a reaction product, separating and purifying the reaction product, and obtaining nitrogen-containing heteroarene carboxylic acid compounds and derivatives thereof. The scheme has the characteristics of mild reaction condition, wide reaction substrate range, good yield and good regioselectivity, and cheap and easily-obtained raw materials, can efficiently realize nitrogen-containing heteroarene carbon-hydrogen bond carboxylation reaction, synthesize important nitrogen-containing heteroarene carboxylic acid compounds, and has a good application prospect.
Owner:SICHUAN UNIV

Method for preparing chiral alcohol through asymmetric reduction of large steric hindrance rigid ketone based on aldehyde ketone reductase and mutant thereof

The invention belongs to the technical field of biosynthesis, and particularly relates to a method for preparing chiral alcohol through asymmetric reduction of large steric hindrance rigid ketone based on aldehyde ketoreductase and a mutant thereof. Comprising the following steps: adding a recombinant Escherichia coli wet cell for expressing aldehyde ketoreductase, a recombinant Escherichia coli wet cell for expressing formate dehydrogenase, a buffer solution, a substrate, a cosolvent, ammonium formate and coenzyme into a reaction container, reacting at a certain temperature, and after the reaction is completed, extracting, separating and carrying out rotary evaporation to obtain a product alcohol. The biological catalysis method is mild in reaction condition, environmentally friendly and high in regioselectivity and stereoselectivity, chiral resolution and heavy metal residues in products are avoided, and the defects of a chemical method are exactly overcome.
Owner:杭州微远生物科技有限公司

Diketopiperazine heterodimer as well as biosynthesis method and application thereof

The invention discloses a diketopiperazine heterodimer as well as a biosynthesis method and application thereof, and belongs to the technical field of bioengineering. The biosynthesis method of the diketopiperazine heterodimer comprises the following steps: S1, culturing a recombinant cell containing P450 dimerization enzyme or a mutant thereof, and performing induced expression to obtain a whole-cell culture; and S2, adding a cyclic dipeptide substrate containing tryptophan into the whole-cell culture, carrying out a catalytic reaction, and separating and purifying the obtained product to obtain the diketopiperazine heterodimer. According to the invention, the P450 dimerization enzyme or the mutant thereof is used for catalyzing the biosynthesis of the tryptophan-containing diketopiperazine into the diketopiperazine heterodimer with different regioselectivity / stereoselectivity, the biosynthesis method is green and environment-friendly, the efficiency is high, and the variety of the diketopiperazine heterodimer is greatly expanded.
Owner:HUBEI UNIV

Non-specific peroxidase HecUPO, coding gene thereof, recombinant microorganism, steroid 16 alpha-hydroxylation method and application

The invention discloses a non-specific peroxidase HecUPO derived from Hypoxylon sp. (strain EC38), wherein the amino acid sequence of the non-specific peroxidase HecUPO is as shown in SEQ ID NO: 1. The enzyme can efficiently catalyze testosterone to generate 16 alpha-hydroxylation reaction to generate C16 alpha-hydroxytestosterone, the conversion rate reaches 70%, the separation yield reaches 82%, no by-product is generated, and the C16 alpha-hydroxytestosterone has excellent regioselectivity. The invention also discloses a gene for coding the HecUPO, a recombinant plasmid pPICZA-HecUPO containing the gene, a recombinant pichia pastoris engineering bacterium and an application of the recombinant pichia pastoris engineering bacterium in steroid hydroxylation. The non-specific peroxidase HecUPO disclosed by the invention has the advantages of being high in catalytic efficiency, specific in regioselectivity, simple in reaction system, green, environmentally friendly and the like, and a new enzymology resource is provided for fixed-point hydroxylation modification of steroid drugs.
Owner:HUBEI UNIV

Gas separation membrane, gas separation module, gas separation apparatus, and polyimide compound

Provided are a polyimide compound including a repeating unit having an aromatic diamine component having a specific structure in which a side-chain benzylic position is regioselectively brominated, a gas separation membrane having a gas separation layer containing the polyimide compound, and a gas separation module and a gas separation apparatus each having the gas separation membrane.
Owner:YESTAR ADVANCED MATERIALS (HK) CO LTD

A method for migrating C(sp²)-H / C(sp³)-H cross-coupling catalyzed by metal / photoredox catalysis

This invention discloses a migration C(sp²)-H / C(sp³)-H cross-coupling reaction achieved using metal / photoredox catalysis, belonging to the fields of organic chemistry and medicinal chemistry. Under the action of a nickel source, photocatalyst, ligands, base, and additives, this invention enables the reaction of alkanes with ortho-alkenyl-substituted aryl halides or ortho-pyridine-substituted aryl halides in an organic solvent under light irradiation, yielding a series of polysubstituted olefins or polysubstituted aromatic compounds with excellent regioselectivity, stereoselectivity, and good yields, which can serve as active pharmaceutical molecules. This invention uses inexpensive transition metal nickel as a catalyst, readily available alkanes and haloaromatics as raw materials, and features mild and simple conditions, good functional group compatibility, and easy operation.
Owner:SHANGHAI FULE PHARM TECH CO LTD

The invention relates to 2apos; synthesis method of-O-methyladenosine

The invention discloses a synthesis method of 2 '-O-methyladenosine, and belongs to the technical field of nucleoside synthesis and medicinal chemistry. According to the method, xylose which is rich in source is taken as an initial raw material, eight-step reaction including acetalation protection, acetylation, glycosylation, deacetylation, methylation, deacetalation protection, Mitsunobu reaction and secondary deacetylation is performed, reaction conditions of each step are accurately controlled, and finally, a target product is synthesized. The method has the advantages of high methylation reaction regioselectivity, mild reaction conditions, cheap and easily available raw materials and controllable cost, and overcomes the problems of poor methylation reaction regioselectivity, harsh reaction conditions and high cost in the existing synthesis method. The obtained product has important application value in the fields of research and development of antiviral drugs, design of nucleic acid probes and the like.
Owner:NANJING UNIV OF SCI & TECH

Method for efficiently synthesizing methyl 2-chloro-3-oxovalerate

The invention belongs to the technical field of organic synthetic chemistry, and discloses a method for efficiently synthesizing methyl 2-chloro-3-oxovalerate. According to the method, high-selectivity chlorination is performed on a beta-site C-H bond of methyl 3-oxovalerate under a mild condition by taking sodium chloride as a chlorine source and adopting a dual-catalysis system consisting of engineered halogenase and a visible light-sensitive catalyst under visible light irradiation. The engineered halogenase is a HalB triple mutant, and the affinity and regioselectivity of a substrate are remarkably improved; the photosensitive catalyst is a ruthenium bipyridine complex and synergistically drives generation of chlorine free radicals. According to the invention, a brand new biological-photochemical synergistic catalysis platform is constructed by organically combining the substrate recognition capability of the engineered halogenase and an electron transfer mechanism driven by visible light catalysis, so that the contradiction among selectivity, mildness and atomic efficiency of a traditional chlorination method is solved; and the method can be expanded to precise synthesis of other beta-functionalized ketone ester compounds.
Owner:INNER MONGOLIA HUAZHOU PHARM CO LTD

Preparation method of chiral nitrogen heterocyclic compound

The invention belongs to the technical field of biochemistry, and particularly relates to a method for catalytically synthesizing a chiral nitrogen heterocyclic compound by a biological enzyme. The invention develops a method for obtaining a chiral nitrogen heterocyclic compound with high enantioselectivity by catalyzing an easily-obtained N-acyloxy amine compound as a nazein precursor to carry out C (sp3)-H amination cyclization reaction by taking an enzyme containing heme as a catalyst. The enzyme catalysis method is mild in reaction condition, simple in technical requirement, wide in substrate universality, high in product enantioselectivity and green, efficient and economical in synthesis process. The nitrogen-containing heterocyclic compound prepared by the method disclosed by the invention has the advantages of better reaction yield, excellent regioselectivity, wide substrate range and good functional group compatibility, and can be applied to synthesis and modification of some drug intermediates.
Owner:BEIJING UNIV OF CHEM TECH

Preparation method of GLP-1 agonist intermediate and compound

The invention discloses a method for preparing a GLP-1 agonist intermediate 5-bromine-4-fluorine-1-methyl-1H-indazole, according to the method, 2, 6-difluorobenzonitrile which is low in price is used as a starting raw material, the regioselectivity of bromination reaction is improved and the yield is increased by optimizing the reaction, and the whole reaction synthesis operation is simple, the safety risk is low, and the method is suitable for industrial production. The method is more suitable for industrial production, and a new way is provided.
Owner:CHENGDU BOTENG PHARM CO LTD

Alpha-fluoro alpha, beta-unsaturated amide derivative as well as synthesis method and application thereof

The invention discloses an alpha-fluoro alpha, beta-unsaturated amide derivative as well as a synthesis method and application thereof. The preparation method comprises the following steps: by taking amyl-1, 1, 2-trifluoro-1, 4-diene which is simple and convenient to prepare and a cheap and abundant amine compound as raw materials, an allyl palladium chloride dimer as a transition metal catalyst, 1, 4-bis (diphenylphosphine) butane as a ligand and 2, 5-di-tert-butylbenzoquinone as an oxidant, reacting in an organic solvent at a proper temperature under a nitrogen condition, thereby obtaining the 1, 1, 2-trifluoro-1, 4-diene compound. The alpha-fluoro alpha, beta-unsaturated amide derivative is obtained with good yield, and the structural formula of the derivative is shown in the specification. The synthesis method disclosed by the invention has the characteristics of simplicity and convenience in operation, mild conditions, greenness, economy, wide substrate compatibility, high chemical selectivity and high regioselectivity, and solves the technical problem that the synthesis conditions of the alpha-fluoro-alpha, beta-unsaturated amide derivative are complicated and harsh. Meanwhile, the alpha-fluoro drug molecules can be efficiently and highly selectively obtained, and the method has a wide application prospect.
Owner:SOUTH CHINA UNIV OF TECH

Synthesis method of chiral trifluoromethyl allyl tertiary alcohol compound

The invention relates to a synthesis method of a chiral trifluoromethyl allyl tertiary alcohol compound, which comprises the following steps: under the protection of nitrogen, taking alkyne and trifluoromethyl ketone as raw materials, taking metal cobalt salt and an organic ligand as catalysts, taking Hanus ester as a reducing agent, and reacting in the presence of excessive organic solvent, photosensitizer and organic alkali to obtain the chiral trifluoromethyl allyl tertiary alcohol compound. And carrying out illumination reaction to obtain the chiral trifluoromethyl allyl tertiary alcohol compound. The method has the advantages of simple and easily available reaction raw materials and reagents, mild and easily controlled conditions, high atom economy, no need of noble metal catalysis, wide substrate application range, high regioselectivity, stereoselectivity and enantioselectivity, and wide application prospect.
Owner:LANZHOU INSTITUTE OF CHEMICAL PHYSICS CHINESE ACADEMY OF SCIENCES

Alpha-carbonyl gamma-chiral methyl carboxylate compound and analogue thereof, and preparation method and application of alpha-carbonyl gamma-chiral methyl carboxylate compound and analogue thereof

The invention discloses an alpha-carbonyl gamma-chiral methyl carboxylate compound and an analogue thereof as well as a preparation method and application of the alpha-carbonyl gamma-chiral methyl carboxylate compound. The alpha-carbonyl gamma-chiral methyl carboxylate compound comprises a compound as shown in a formula I or a formula II, wherein R1 is selected from H, phenyl, t-butyloxycarboryl or meta-position cyano substituted phenyl; r2 is selected from H, alkyl with 1-6 carbon atoms, hydroxyl, tertiary butyl, benzyl or benzhydryl. According to the alpha-carbonyl gamma-chiral methyl carboxylate compound provided by the invention, ester groups with different steric hindrances are selected, so that a Dieckmann condensation reaction with high regioselectivity is realized under a low-temperature condition; the product obtained by the reaction does not need to be subjected to chiral resolution to obtain a single component, the purification step is simplified, and the method is suitable for being widely used in actual production.
Owner:ZHONGSHAN INST FOR DRUG DISCOVERY SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI

Process for the preparation of a fully substituted 5,5'-bioxazole compound and use thereof

The application relates to a transition metal-catalyzed N-(1-arylvinyl)amide for constructing a fully substituted 5,5'-oxazole compound through a multiple cross-dehydrogenative coupling strategy. Specifically, under the condition of an inert solvent, through the joint promotion of a transition metal catalyst and a silver salt oxidant, multiple dehydrogenation 1,1-bifunctionalization of olefins is realized. The method has good regioselectivity and chemical selectivity. Notably, the application reports the first case of a transition metal-catalyzed simple construction of a fully substituted 5,5'-oxazole compound skeleton based on a multiple dehydrogenation cyclization strategy. The substrate of the conversion has a wide application range and strong functional group tolerance. The applicant also realizes the modification of drug molecules such as propyl sulfone. Further, the obtained 5,5'-oxazole molecules are subjected to fluorescence testing, and the fluorescence quantum yield reaches 83.14%, indicating that the novel skeleton has great application potential in luminescent materials.
Owner:ANQING BAIYI BIOTECHNOLOGY CO LTD

Film forming method and film forming apparatus

A film forming method includes: (A) preparing a substrate having a first film and a second film in different regions of a substrate surface; (B) selectively forming a film-formation inhibiting film that inhibits formation of a target film on a surface of the second film; and (C) selectively forming the target film on the surface of the first film by using the film-formation inhibiting film, wherein the target film includes at least silicon (Si) and oxygen (O), and wherein (C) includes: (Ca) supplying a metal catalyst-containing gas to the surface of the substrate to adsorb metal catalysts to the surface of the first film; (Cb) supplying a plasmarized gas to the surface of the substrate to remove at least a portion of the metal catalysts adsorbed to a surface of the film-formation inhibiting film in (Ca); and (Cc) supplying a silanol group-containing gas to the surface of the substrate.
Owner:TOKYO ELECTRON LTD

Single-molecule fluorescent probe based on phenothiazine structure as well as preparation method and application of single-molecule fluorescent probe

The invention belongs to the technical field of fluorescent probes, and particularly relates to a single-molecule fluorescent probe based on a phenothiazine structure as well as a preparation method and application of the single-molecule fluorescent probe. The preparation method comprises the following steps: firstly introducing an alkyl chain to a nitrogen atom of a raw material to obtain the phenothiazine structure-based single-molecule fluorescent probe, then carrying out regioselective formylation on the raw material to obtain the phenothiazine structure-based single-molecule fluorescent probe, then treating the raw material by adopting aluminum trichloride to realize O-demethylation, and finally carrying out intramolecular cyclization reaction on the raw material and 1H-benzimidazole-2-acetonitrile to obtain the phenothiazine structure-based single-molecule fluorescent probe. The single-molecule fluorescent probe based on the phenothiazine structure prepared by the invention is compatible with orthogonal chemical reaction activity and maintains controllable electron transfer, so that different chemical events are converted into specific optical signals, and selective and mechanism specific fluorescent response to phosgene, copper ions and hypochlorite is realized.
Owner:PUTIAN UNIV

Method for synthesizing alpha-substituted allyl sulfone through reaction of cobalt-catalyzed sulfuryl allene and organic boric acid

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.
Owner:NORTHWEST UNIV

Synthesis method of cedrene cis-diol

The present patent application concerns a synthesis method of cedrene cis-diol of formula I comprising the following steps: a) providing α-cedrene of formula II and carrying out the regioselective and stereospecific reaction of α-cedrene of formula II to give cedrene epoxide of formula III, b) carrying out the stereospecific isomerization reaction of cedrene epoxide of formula III to give cedranone of formula IV, c) carrying out the regioselective and stereospecific hydroxylation reaction of cedranone of formula IV to give hydroxycedranone of formula V, d) carrying out the stereoselective reduction reaction of hydroxy cedranone of formula V to give cedrene cis-diol of formula I, characterized in that: in stage a) of the stereospecific epoxidation reaction, the reaction is carried out using a lipase enzyme and hydrogen peroxide, and the reaction temperature is comprised between 20 °C and 35 °C, and the cedrene epoxide of formula III is used as is, i.e. without the need for purification, in the next stereospecific isomerization step b); in stage b) of stereospecific isomerization reaction, the reaction is carried out using a Brönsted acid, and the reaction temperature is comprised between 20 °C and 85 °C, and cedranone of formula IV is purified by distillation; in stage c) of regioselective and stereospecific hydroxylation reaction, the reaction is carried out in the presence of a strong base, and the reaction temperature is comprised between 20 °C and 30 °C, and the hydroxycedranone of formula V is purified by crystallization; in stage d) of stereoselective reduction reaction, the reaction involves the following two sub-steps: dl) adding a Lewis acid, followed by d2) adding a reducing agent, and the reaction temperature is comprised between -5 and 0 °C, and the cedrene cis-diol of formula I is purified by crystallization; in each of the aforementioned steps a)-d) the compounds of formula III, IV, V and I are obtained respectively in a diastereomeric mixture with a diastereoisomeric ratio > 99:1.
Owner:POLITECNICO DI MILANO

Method for constructing alpha-aza-aromatic hydrocarbon substituted allyl ketone compound through dipole reversal alpha-position amination reaction of phosphine-catalyzed acetylenic ketone

PendingCN121248504ASteroidsPtru catalystKetone
The invention discloses a method for constructing an alpha-aza-aromatic hydrocarbon substituted propenone compound through dipole reversal alpha-position amination reaction of phosphine-catalyzed acetylenic ketone, and relates to a preparation method of the propenone compound. The reaction of the method can be carried out under the following conditions: small organic molecule triphenylphosphine is used as a catalyst, the temperature is 25-50 DEG C, dichloromethane is used as a solvent, acetylenic ketone and an N-heterocyclic aromatic compound are used as reaction substrates, the corresponding functionalized alkenyl ketone compound is obtained, and the highest conversion rate can reach 99%. The method has the advantages of mild reaction conditions, no use of a metal catalyst, environmental friendliness, wide substrate application range, high yield, simple operation, good regioselectivity and commercially available catalyst, and in addition, the target product alpha-aza-arene substituted propenone has potential biological activity and medicinal value.
Owner:Chaoyang Normal University

Method for synthesizing perfluoropyridine substituted glycine derivative through photooxidation reduction catalysis

PendingCN120923414AOrganic chemistryPhotoredox catalysisFine chemical
The invention relates to the fields of medicine, organic chemical industry and fine chemical industry, and particularly discloses a method for synthesizing a perfluoropyridine substituted glycine derivative through photooxidation reduction catalysis. According to the method, an N-arylglycine derivative and perfluoropyridine are taken as initial raw materials, and various alpha-(perfluoro-4-pyridine) phenylglycine derivatives and N-(perfluoro-4-pyridyl) phenylglycine derivatives can be efficiently synthesized under the condition that visible light and a photosensitizer participate in catalysis. Accurate regulation and control of reaction region selectivity are realized by regulating and controlling the type and proportion of the additive alkali, and alpha-C (sp3)-H and N-H substituted polyfluoro heteroarylation products are respectively obtained. The method has the advantages of mild reaction conditions, no metal participation, no need of additional oxidant, high reaction yield and the like. In addition, the method is simple to operate, excellent in regioselectivity and good in substrate functional group compatibility, and a new thought can be provided for polyfluorinated heteroarylation modification of amino acid.
Owner:CHANGZHOU UNIV

An n-amino-alpha-amino acid compound and a method for synthesizing the same

The application provides an N-amino-alpha-amino acid compound and a synthesis method thereof, and the synthesis method is as follows: hydrazone reaction substrates, a photocatalyst, a reducing agent and alkali are added into a reaction container, then organic solvents are added under a CO2 atmosphere, stirring reaction is carried out under light conditions at 20-70 DEG C for 0.1-48 h, and then the reaction product is separated and purified to obtain the N-amino-alpha-amino acid compound; the synthesis method can synthesize important N-amino-alpha-amino acid compounds under mild reaction conditions, has the characteristics of wide reaction substrate range, good yield and good regioselectivity, cheap and easily obtained raw materials and easily derivable products, and can effectively solve the problems of limitations and the need to use metal reducing agents in the synthesis of alpha-aryl-substituted alpha-amino acid products in the prior art.
Owner:SICHUAN UNIV

Phosphine-free cobalt-(II) complexes for dehydrogenative c-c coupling reactions using alcohols: synthesis and applications thereof

The invention provides a newly developed, inexpensive, and bench-stable Cobalt (II)-complexes encompassing phosphine-free N,N-bidentate ligand system. Particularly, the present invention utilizes Co(II)-complexes as catalyzing system for the sole purpose of studying the C-alkylation reaction through borrowing hydrogen strategy. The present invention also provides a catalytic methodology for selective alkylation, alkenylation of fluorene, and inactivated bulky indene utilizing alcohol under mild and benign conditions. In the present invention, fluorene and indene are alkylated using a range of substrates as an alkylating agent, such as primary and secondary aromatic, heteroaromatic, and aliphatic alcohols. The present invention indicates a sophisticated catalytic process with yields that range from high to exceptional yields and excellent regioselectivity of the C3-alkylated indenes.
Owner:INDIAN INSTITUTE OF SCIENCE EDUCATION & RESEARCH (IISER) TIRUPATI