18 results about "Axial chirality" patented technology

This invention discloses an axially chiral 1,4'-biquinolinone and its derivatives, and a synthetic method thereof. The method uses MBH carbonate and quinoline-2(1 H Using β-ketones as raw materials, (DHQD)₂PYR as catalyst, and DME as solvent, a centrally chiral β-substituted allyl intermediate was synthesized; then, using iron powder as a reducing agent and acetic acid as solvent, enantiomeric enriched centrally chiral γ-lactam compounds were obtained; finally, using DBN as a base and DME as solvent, enantiomeric enriched compounds were obtained. (S) -Axial chiral 1,4'-biquinolinone or its derivatives. The method of this invention has mild reaction conditions, readily available raw materials, high enantioselectivity of the product, and excellent yield. The synthesized 1,4'-biquinolinone or its derivatives can be further used to synthesize novel substituted quinolinone phosphonate compounds, and to synthesize drugs with antibacterial, antimalarial, anticancer, antitumor, or herbicidal activities, showing broad application prospects.

The application relates to the technical field of organic chemical synthesis, and discloses an axially chiral porphyrin compound with a long-chain ester structure and a preparation method and application thereof. The compound has a structure shown in formula (I), formula (I), wherein R is n is 6, 8, 10, 12, 14 or 16. The method provided by the application has great significance for the study of an axially chiral long-chain compound family, and proves that the chain length of a raw material greatly influences the liquid crystal properties of an obtained axially chiral long-chain compound, and can inspire the synthesis of an axially chiral porphyrin compound with a longer chain.

The application discloses a method for constructing a cycloalkene-quinolinone axial chiral compound through a Heck reaction. The method uses a quinolinone compound containing central chirality as a substrate, uses palladium acetate (Pd(OAc)2) and 4,5-bisdiphenylphosphine-9,9-dimethylxanthene (Xantphos) as a catalyst, uses silver phosphate (Ag3PO4) as an alkali, and uses toluene as a solvent to prepare a cycloalkene-quinolinone axial chiral compound. The compound can be reacted with diisobutylaluminum hydride to realize conversion of a functional group. The method has mild reaction conditions, raw materials are easy to obtain, the product has excellent enantioselectivity, and has excellent yield, and thus provides a new method for synthesizing a cycloalkene-quinolinone axial chiral compound.

This invention belongs to the field of chemical catalysis technology, and discloses a class of bridged carboxylic acid-containing bifunctionalized phosphine ligands or their racemates or enantiomers, as well as their preparation methods and applications. The bridged carboxylic acid-containing bifunctionalized phosphine ligands or their racemates or enantiomers of this invention have the structures shown in Formulas I-V: wherein, R 1 R' is a C1-C5 straight-chain alkyl group; R' is any one of substituted or unsubstituted aryl, substituted or unsubstituted alkyl, or substituted or unsubstituted cycloalkyl. The bridged carboxylic acid-containing bifunctionalized phosphine ligand of this invention, with biphenyl as its backbone, achieves complete transfer of facet chirality to axial chirality through a desymmetry reaction via precise chiral recognition and control. The resulting chiral ligand exhibits advantages such as high reactivity, good enantioselectivity, and a wide substrate adaptability. It is particularly effective in palladium-catalyzed asymmetric C-H bond-activated arylization reactions of halogenated compounds and can be applied to asymmetric C-H bond-activated arylization reactions.

This invention discloses a method for the kinetic resolution of oxaspirone via organocatalytic hydrogenolysis. Using chiral phosphate CPA as a catalyst, Hantzsch ester as a hydrogen source, and racemic oxaspirone 2,4-dien-6-one rac-1 as a substrate, a series of axially chiral biaryl phenolic compounds 2 are synthesized via asymmetric hydrogenolysis, and the central chiral oxaspirone 1 is recovered. This invention offers advantages such as simple and practical operation, readily available raw materials, high resolution coefficient, and good enantioselectivity. Some of the axially chiral biaryl products have structures similar to axially chiral cannabinol, possessing potential medicinal value.

This invention provides a method for preparing chiral N-tert-butylsulfonamide compounds. The method uses N-tert-butylsulfonylimide as a starting material, employs Mn(CO)₅Br and a chiral PNN ligand as catalysts, and an alcohol as a solvent. A hydrogenation reaction occurs in this homogeneous catalytic system, yielding axially chiral diaryl nitrophenol compounds in high yield (99%) and with high ee values ​​(>99%). This reaction has the advantages of high efficiency, mild conditions, and environmental friendliness. The obtained chiral N-tert-butylsulfonamide can be deprotected with a sulfonyl protecting group to obtain the corresponding chiral primary amine.

The application discloses an axially chiral cyclopentenyl and indole-naphthyl compound and a preparation method and application thereof, and the structural formula of the compound is shown in formula 3 and formula 5. The formula 3 compound is obtained by stirring and reacting formula 1 and formula 2 compounds under the action of a chiral phosphoric acid catalyst. The formula 5 compound is obtained by synthesizing the formula 3 compound in two steps. Through biological activity testing, the formula 3 compound has significant cytotoxic activity on PC-3 cancer cells. Through model reaction verification, the formula 5 compound can be used as a chiral ligand or a chiral organic catalyst, and is respectively applied to catalyzing asymmetric allyl coupling reaction and catalyzing asymmetric (4+1) cycloaddition reaction. The method for preparing the axially chiral cyclopentenyl and indole-naphthyl compound is simple in operation, mild in reaction condition, economical and easy in raw material, high in optical purity of the prepared axially chiral compound, high in yield and good in application prospect.

The application relates to the technical field of chemical synthesis, and particularly discloses an indole pyrazole C-N axis chiral compound and a synthesis method thereof. The structural formula of the indole pyrazole C-N axis chiral compound is shown in formula (I), the compound is a kind of axis chiral compound with high resistance to selection, R1 is a substituted or unsubstituted phenyl, naphthyl or alkyl, R2 is a phenyl, R3 is a substituted or unsubstituted phenyl, and R4 is an ethyl. The compound shown in formula (I) can inhibit the growth of cancer cells, thereby interfering with the malignant behavior of the cancer cells.

This invention discloses an N-N axial chiral phase-transfer catalyst, its synthesis method, and its applications, belonging to the field of asymmetric catalytic synthesis technology. Using chiral 2,4-pentanediol and N-Boc-indolephenol as starting materials, this invention efficiently constructs an N-N axial chiral biscarbazole cyclic ether skeleton through a five-step reaction involving Mitsunobu etherification, deBoc protection, PIDA oxidative cyclization, radical bromoxymethylation, and intramolecular quaternization. This method eliminates the need for complex chiral resolution and noble metal coupling, employs mild reaction conditions, uses readily available and inexpensive starting materials, achieves high overall yield, and yields a product with an axial chirality ee value ≥98%. The resulting catalyst possesses excellent conformational rigidity, chiral induction ability, and phase-transfer performance, exhibiting broad substrate applicability. It also possesses bisindole ring bioactivity, making it widely applicable in asymmetric catalytic synthesis in pharmaceuticals, fine chemicals, and other fields, and providing new directions for the development of antibacterial and antitumor biomaterials.

The application belongs to the field of bioengineering and biocatalysis technology, and particularly relates to an alcohol dehydrogenase mutant and application thereof. The application discloses an alcohol dehydrogenase mutant CcPAR-M1 (V158L), and an amino acid sequence of the mutant is shown as SEQ ID No. 3. The mutant can be used for catalyzing asymmetric reduction reaction of a biaryl aldehyde substrate through dynamic kinetic resolution to generate R an axially chiral biaryl dimethanol compound. By using the biocatalytic system disclosed in the application, the highest yield of the target product can reach 96%, and the enantiomeric excess value can reach 99% ee at most. The method provides a green, efficient and excellent stereoselective biocatalytic strategy for construction of the axially chiral biaryl dimethanol compound.

The present invention relates to the field of asymmetric catalysis and organic synthesis, and specifically provides a general method for generating axial chirality by means of a chiral companion strategy. The features and concept of the method are: a chiral aromatic tertiary amine compound without a nitrogen chiral center is subjected to intramolecular chiral oxidation to induce the formation of a new aromatic tertiary amine N-oxide (NO) chiral center. Due to the structural rigidity of the chiral aromatic tertiary amine N-oxide compound, when the steric hindrance of different substituents Rb and Rs connected to ortho positions of an aromatic ring is relatively large, the rotation of the aromatic ring is hindered, and new rotation-hindered axial chirality is generated while an aromatic tertiary amine chiral N-oxide center is formed. By means of the method and by regulating the structural and functional characteristics of the different substituents Rb and Rs, various axial chiral ligands, chiral small-molecule catalysts, pharmaceutical and agrochemical intermediates, and chiral synthons can be prepared. The present invention has important scientific and application values for the design, synthesis, and application of chiral ligands, chiral catalysts, especially ligands and catalysts containing axial chirality, and chiral compounds having special functions.

The invention discloses an open-chain imine axially chiral compound and a synthesis method thereof. According to the method, MBH carbonate and a (2-methoxynaphthalene-1-yl) (phenyl) methylenimine derivative are taken as raw materials, palladium acetate and a chiral phosphoramidite ligand are taken as catalysts, lithium carbonate is taken as alkali, methylbenzene is taken as a solvent, and the enantiomer-enriched open-chain imine axially chiral compound is obtained. The compound can react with m-chloroperoxybenzoic acid to realize efficient conversion from axial chirality to central chirality. The method has the advantages of mild reaction conditions, easily available raw materials, high product enantioselectivity and excellent yield, and provides a simple and efficient way for preparation and conversion application of open-chain imine axially chiral compounds.

The application discloses a kind of chiral N -(4-indolyl)imidazole and its N’ Functional imidazole salt derivatives; the application is obtained by chiral resolution N -(1,3,5,7-tetramethyl-2-ethyl-4-indolyl)-4,5-dimethyl imidazole R a type and S a type isomers, then react with halogenated hydrocarbon, first obtain axially chiral N Chiral nitrogen heterocyclic carbene precursor imidazole salt of arylimidazole skeleton; the chiral N -(4-indolyl)imidazole salt can be applied in asymmetric catalytic reaction as catalyst or ligand.

The application discloses an axially chiral phthalazine compound and a synthesis method and application thereof, and belongs to the technical field of pharmaceutical intermediates. The compound structure is shown in the following formula: or. The application takes a diazo compound as raw material, takes a chiral phosphorus catalyst as a catalyst, takes a Bronsted acid and an organic base as co-catalysts, takes silane as a reducing agent, takes an organic solvent as a solvent, takes 4A molecular sieve as an additive, and obtains the product through one-step reaction, column chromatography purification under a mild reaction temperature, has the advantages of high enantioselectivity and yield, and has the advantages of mild reaction condition, wide applicability of substrate range, simple operation and safety. The obtained axially chiral phthalazine compound has an antitumor effect, and is an important chemical, chemical and pharmaceutical intermediate.

This invention discloses a bipyrrole-based axially chiral phase transfer catalyst, its preparation method, and its application, belonging to the technical field of axially chiral phase transfer catalysts. The axially chiral compound (S)-1,9-diphenyl-5-((S)-1-phenylethyl)-5,6-dihydro-4H-dipyrrolo[1,2-b:2',1'-g][1,2,5]triazacycloheptane-3,7-dicarboxylic acid diethyl ester is used as a nucleophile to attack the partially positively charged carbon atom in the benzyl bromide reagent, replacing its bromide ion to generate a quaternary ammonium ion intermediate. The bromide ion attack causes the C-N bond to break, and the phenylethyl group on the quaternary ammonium ion intermediate detaches, forming a chiral tertiary amine with a benzyl group. Subsequently, it undergoes a quaternization reaction with excess benzyl bromide to obtain the chiral phase transfer catalyst. The prepared catalyst exhibits good catalytic activity in the [3+2] cycloaddition reaction of 2-(morpholine-4-carbonyl)allyl benzenesulfinate with phenylacryloylbenzene. The preparation method is simple and has broad application prospects.

This invention discloses an axially chiral bipyridine ligand, its preparation method, and its uses. The axially chiral bipyridine ligand has the structure of general formula (Ⅰ): the axially chiral bipyridine ligand contains a binaphthalene structure, wherein part A is selected from A-1, A-2, or A-3; part B is a hydrogen atom or is the same as part A. The complex catalyst formed in situ in the reaction system of the axially chiral bipyridine ligand and copper salt in this invention exhibits high catalytic activity, good to excellent enantioselectivity, and good substrate universality in the asymmetric ring-opening iodination, thioesterification, and hydrolysis of cyclic diaryliodonium salts to synthesize highly optically pure, diverse substituted 1,1'-bi-2-iodobenzene compounds, 1,1'-bi-2'-iodo-2-thioester compounds, and 1,1'-bi-2'-iodo-2-phenol compounds, respectively, showing great promise for industrial applications. This invention belongs to the field of asymmetric synthetic chemistry.