109 results about "Propargyl bromide" patented technology

The invention discloses a cyclodextrin chiral stationary phase, the structure of which is shown in the general formula (I), wherein X is -OCH3 or -OCH2CH3, n is equal to 1-7, and R is -H, -CH3, -COCH3, -COC6H5 and -CONHC6H5. The preparation method of the stationary phase comprises the following steps: a silane coupling agent, sodium azide and a catalyst are added into an organic solvent, then spheroidal silicon is added for preparing azide silica gel derivant; oligomeric ethylene glycol, sodium hydride and propargyl bromide are added into tetrahydrofuran for preparing bialkynyl oligomeric ethylene glycol; monosubstituted nascent and derivative cyclodextrin containing azid groups is prepared; finally, the click chemistry reaction method is used for bonding the cyclodextrin. The cyclodextrin chiral stationary phase has the advantages that the selectivity of the bonding reaction is high, and the surface bonded amount is large; the chiral separation ability is strong, thereby being especially suitable for the chiral separation of a high efficiency liquid chromatography in the reversed-phase mode; the preparation method is simple and has less steps, the bonding reaction is the click chemistry reaction, the reaction condition is mild, and the reaction is carried out in the water solution.

The core structure of 2-(1',2',3'-triazole-4'-benzyloxy)-1,3,4,6-O-acetyl-D-glucose with an anti-colorectal carcinoma activity is that a 1,2,4-triazole derivative substitutes 2-site of 1,3,4,6-O- acetyl-D-glucose. The above compound has a good activity of inhibiting colorectal carcinoma cells, and can be used as an anti-colorectal carcinoma medicine. A synthesis method of the above compound comprises the following steps: 2-amino-D-glucose hydrochloride and an azidation reagent are used as raw materials to generate a 2-azido-1,3,4,6-O-acetyl-D-glucose intermediate under an alkaline condition; 3-propargyl bromide and phenylcarbinol react under the action of sodium hydride to generate phenyl propargyl ether; and the 2-azido-1,3,4,6-O-acetyl-D-glucose intermediate and phenyl propargyl ether undergo a click reaction in a solvent under the catalysis of monovalent copper to generate 2-(1',2',3'-triazole-4'-benzyloxy)-1,3,4,6-O-acetyl-D-glucose.

The invention relates to a benzoin oxime derivative and a preparation method thereof. A structural formula of the benzoin oxime derivative is shown in the specification. The preparation method comprises the following steps: reacting malonate with propargyl bromide in anhydrous acetonitrile under the catalysis of sodium hydride to obtain a white solid product; by taking triethylamine as alkali, reacting the white solid product with phenylethynyl bromine or substituted phenylethynyl bromine in anhydrous acetonitrile under the catalysis of Pd(PPh3)2Cl2/CuI to obtain a light brown solid product; reacting the light brown solid product with benzoin oxime in toluene at 95-105 DEG C to obtain the benzoin oxime derivative. A brand new synthetic method of polysubstituted benzoin oxime is provided, and a series of new benzoin oxime derivatives are generated. Compared with normal benzoin oxime derivatives, the benzoin oxime derivative prepared by virtue of the preparation method has relatively complex and diverse structures by virtue of multiple cycles, and presents relatively wide application prospects in chemical industry production and clinic medicines.

The invention provides a dibenzo selenophene derivative and a preparation method thereof. The preparation method comprises the following steps that sodium hydride is used as a catalyst, malonic ester and propargyl bromide are added into an acetonitrile solvent, and a reaction is performed in an ice-water bath for 8-14 h to obtain a compound a; on the oxygen-free and water-free conditions, the compound a and a substituted complex of phenyl acetylene bromide are subjected to a reaction in an acetonitrile solvent under the effect of a catalyst and alkali at the temperature of 20-30 DEG C for 8-14 h to obtain a compound b; the compound b and diphenyl diselenide are subjected to a reaction at the temperature of 95-105 DEG C, and after separation and purification, the dibenzo selenophene derivative can be obtained. Compared with the prior art, the novel polysubstitution dibenzo selenophene synthesis method is provided, a series of novel selenophene derivatives are generated, multi-loops exist in the obtained dibenzo selenophene derivative compared with a common selenophene derivative, the structure is more complex and diversified, and wider application prospect is represented in chemical production and clinic medicine.

The invention discloses a method for preparing rasagiline which has simple and convenient operation and is suitable for industrialized production. In the method, primary amine group on 1-indan amine is protected by o-Nos, and the 1-indan amine removes the protecting group after the 1-indan amine is substituted by propargyl chloride (or propargyl bromide); compared with the prior method, two steps of reactions are added in the method, but after the 1-indan amine is protected by the o-Nos, the reaction specificity of the 1-indan amine and the propargyl chloride (or the propargyl bromide) is greatly improved; and the protecting group can be easily removed after reaction without other side effects, so a single product is generated. Besides, raw materials and reaction reagent used in the method is cheap and easily obtained. The method has the advantages of simple and easy operation, mild reaction condition, easy control, good reaction selectivity, total yield improvement and cost reduction, and has excellent industrialized prospect.

The invention discloses 2-(1',2',3'-triazolyl-4'-oxymethylenepyridyl)-1,3,4,6-O-acetyl-D-glucose with anti-rectal cancer activity. The 2-(1',2',3'-triazolyl-4'-oxymethylenepyridyl)-1,3,4,6-O-acetyl-D-glucose has a core structure of 1,3,4,6-O-acetyl-D-glucose subjected to 1,2,4-triazole derivative 2-site substitution. The above compound has good rectal cancer cell inhibition activity and can be used as a drug for resisting rectal cancer. A compound synthesis method comprises that 2-amino-D-glucose hydrochloride and an azidation reagent as raw materials undergo a reaction under alkaline conditions to produce a 2-azido-1,3,4,6-O-acetyl-D-glucose intermediate, 3-propargyl bromide and aromatic methanol undergo a reaction under the action of sodium hydride to produce aromatic propargyl ether, and the 2-azido-1,3,4,6-O-acetyl-D-glucose intermediate and the aromatic propargyl ether undergo a click reaction in a solvent in the presence of monovalent copper as a catalyst to produce 2-(1', 2', 3'-triazolyl-4'-oxymethylenepyridyl)-1,3,4,6-O-acetyl-D-glucose.

The invention discloses a florescent ion probe reagent for zinc ion detection, which contains triazole phenanthroline bridge type bis(beta-cyclodextrin), adopts phenanthroline as a probe molecule and takes the nitrogen atom on the phenanthroline ring and the nitrogen atom on the triazole ring as bonding sites of bivalent zinc ions. A preparation method comprises the following steps of: firstly synthesizing a 2,9-dipropargyl-1,10-phenanthroline intermediate from 2,9-dihydroxymethyl-1,10-phenanthroline, 3-propargyl bromide and the like; and then synthesizing a target product from the intermediate, uni-6-deoxy-6-azido-beta-cyclodextrin, sodium ascorbate and the like. As a water-soluble zinc ion florescent probe, the synthesis path of the cyclodextrin derivative is simple, the production cost is low, and the florescent ion probe reagent is suitable for amplification synthesis and practical production application; the zinc ion identifying operation is simple and practical and has high sensitivity, and the zinc ion is displayed by a fluorescence spectrum; and as a zinc ion florescent probe, the florescent ion probe reagent disclosed by the invention can effectively detect zinc ions in cells and has broad application prospects.

The invention discloses a series of alkynyl quaternary ammonium salt multifunctional surfactants and a preparation method thereof. A structural formula of quaternary ammonium salt is shown in the description, wherein R represents a C4-C22 linear, branched or cycloalkyl, aryl or alkenyl group. The preparation method comprises the following steps: (1) carrying out alkylation on ethanol amine under alkaline and acetonitrile reflux conditions by virtue of bromo-hydrocarbon; and (2) carrying out further alkylation on tertiary amine under an ethanol reflux condition by virtue of propargyl bromide, so as to obtain alkynyl quaternary ammonium salt, namely reddish brown semitransparent viscous liquid or solid. The alkynyl quaternary ammonium salt multifunctional surfactants have very high surface activity, good corrosion resistance and excellent viscoelasticity, the preparation method is simple and feasible, the raw material cost is low, the operation is easy, the yield is high, and the surfactants are environmentally friendly.

The invention belongs to the technical field of organic materials and discloses a dihydroxy fluorescence chain extender based on a carbazole derivative and preparation and application thereof. The method comprises the following steps: (1) under alkaline condition, an organic solvent is used as a reaction medium, carbazole and propargyl bromide react and subsequent processing is carried out to obtain an intermediate 9-propynyl carbazole; the molar ratio of carbazole to propargyl bromide is 1: 1.1-2; and (2) in the atmosphere of inert gas and in the presence of a catalyst and a reducing agent, the intermediate 9-propynyl carbazole and dihydroxy azide react in a solvent, and subsequent processing is carried out to obtain the dihydroxy fluorescence chain extender based on the carbazole derivative. The chain extender has high yield, has high fluorescence intensity and good anti-ultraviolet stability, and is used in manufacturing of a fluorescence WPU emulsion.

The invention discloses a chrysin non-natural amino acid derivative or pharmacologically-acceptable hydrate and salt thereof. The chrysin non-natural amino acid derivative comprises a stereoisomer ora tautomer. The chrysin non-natural amino acid derivative comprises the following preparation steps: preparing 5-hydroxy-7-propargylflavone by chrysin and propargyl bromide under the action of alkali;preparing (L/D)-N3-Boc amino acid methyl ester by (L/D)-halogenated-Boc amino acid methyl ester and NaN3 under the action of CuI/L-proline sodium; reacting the 5-hydroxy-7-propargylflavone and the (L/D)-N3-Boc amino acid methyl ester under the action of CuSO4.5H2O/sodium ascorbate, removing Boc groups and hydrolyzing to prepare the chrysin amino acid derivative. The chrysin non-natural amino acidderivative disclosed by the invention has an anti-cancer effect and can be used in preparation of an anti-cancer drug.

The invention relates to a preparation method of glycopolymer with lateral chains containing heterogeneous sugar units. The preparation method includes: using 2-amino-2-methyl-1,3-propanediol as the raw material, using BOC to perform amino protection, then allowing the 2-amino-2-methyl-1,3-propanediol to have Williamson etherification reaction with propargyl bromide to prepare a compound with terminal alkyne, using an acetyl protected carbohydrate compound containing azido as the raw material to prepare a compound containing heterogeneous sugar through click chemical reaction, removing BOC protection, polymerizing with RAFT, using modification after polymerization to prepare glycopolymer with lateral chains containing heterogeneous sugar units, and then removing OAc protection to prepare glycopolymer containing heterogeneous sugar units. Compared with the prior art, the preparation method is simple in polymer monomer synthesizing method and controllable in polymer lateral chain structure, and the prepared glycopolymer is controllable in molecular weight, narrow in molecular weight distribution, good in water solubility and applicable to fields such as high polymer materials and biological medicine.

The invention discloses a preparation method of a ligand, a fluorescent probe, and a preparation method and an application of the fluorescent probe. The ligand is DATP, and is obtained by reacting a compound 1, NaN3, tetrabutylammonium hydrogen sulfate, bis(2-pyridylmethyl)amine, propargyl bromide, CuI, and a CH2Cl2 and CF3COOH mixed solvent. The fluorescent probe adopts DATP and Ni<2+> as cores,Eu<3+> and Ni<2+> are linked with the ligand through a Ni-N coordination bond, and Tb<3+> is linked with the ligand trough Tb-O and Tb-N coordination bonds. The fluorescent probe of the invention is prepared with DATP as the core, and a Eu<3+>/Tb<3+> complex can be used in time-resolved fluorescence detection to effectively eliminate interference from samples and short-lived fluorescence such as scattered light, so the prepared fluorescent probe has the advantages of good water solubility, extremely high sensitivity, excellent selectivity to histidine, simple preparation method and mild conditions, and is suitable for detecting histidine in biological systems.

The invention discloses a radioactive drug and a preparation method thereof. The compound is fluo-polyethylene glycol-triazole ring-methylene-2metridazloe, and the structural general formula of the compound is disclosed in the specification, wherein n is 1-10, and F is 18F. The preparation method comprises the following steps of: adding 2-metridazloe, propargyl bromide and K2CO3 to CH3CN; heating for refluxing; adding a product obtained after sufficient reaction, a product obtained by adding di-p-tolyl-sulphonate of polyethylene glycol and NaN3 to DMF (Dimethyl Formamide) and heating with boiled water, CuI and Et3N to THF (Tetrahydrofuran); and finally carrying out a clink reaction on the two products to finally obtain a [18F]FPEGn-TAN solution.

The invention discloses a method for synthesis and purification of the bonding agent N-propargyl diethanol amine. The structure of the compound is shown in the description. The bonding agent N-propargyl diethanol amine is expected to be applied to energetic binder type propellants. The method comprises the steps of adding 3-propargyl bromide to a diethanol amine tetrahydrofuran solution dropwise with triethylamine as the acid-binding agent under the ice-bath condition, conducting filtration after three hours of reaction, conducting filtrate concentration and reduced pressure distillation in sequence, and collecting the product. The method has the advantages of being high in yield and environmentally friendly.

The invention discloses a benzodihydropyran ring derivative and a preparation method thereof. The malonate and propargyl bromide are used as initial raw materials to synthesize a benzodihydropyran ring derivative through a three-step reaction; and the raw material is simple and easy to obtain, the synthesis method is convenient and fast, and an efficient and fast synthesis path is provided for the preparation of the benzodihydropyran ring derivative.

The invention discloses an amino acid compound containing a diaziridine group and a synthesis method thereof. The method comprises the following steps: with ethyl acetoacetate as a raw material, performing a reaction under the action of lithium diisopropylamide; performing a reaction with propargyl bromide to generate 3-oxoheptyl-6-acetylenic acid ethyl ester; then hydrolyzing the reaction productto generate 3-oxoheptyl-6-acetylenic acid, so as to obtain 3-oxoheptyl-6-acetylenic acid; then performing a reaction with hydroxylamine-O-sulfonic acid in an ammonia gas methanol solution; performingiodine elementary substance oxidation to generate 2-(3-(butyl-3-acetylene-1-yl)-3H-diaziridine-3-yl)acetic acid; then carrying out a reaction on 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride and N-hydroxysuccinimide to generate 2,5-dioxopyrrolidine-1-yl-2-(3-(butyl-3-yl-1-yl)-3H-diaziridine-3-yl)acetate, and then carrying out a reaction with amino acid molecules to generate the targetproducts. The compound synthesized by the invention contains diaziridine groups and amino acid molecules with biological activity, and can be used in biological activity test and analysis.

The invention discloses an acyl chloride and alkyne addition product and a preparing method thereof. The preparing method includes the steps that sodium hydride is used as a catalyst, diisopropyl malonate and propargyl bromide are added into anhydrous acetonitrile, the mixture is put in an ice-water bath and stirred for reacting, and a white solid product is obtained after purification and separation; the product phenyl ethynyl bromide is mixed in an anhydrous oxygen-free catalytic system of Pd(PPh3)2Cl2/CuI, triethylamine is used as alkali, anhydrous acetonitrile is used as solvent, a light brown solid product is obtained through stirring reacting at the room temperature as well as purification and separation, the light brown solid product reacts with adamantanecarbonyl-chloride in methylbenzene, and the acyl chloride and alkyne addition product is obtained through purification and separation. Compared with the prior art, the prepared beta-chloro-alpha, beta unsaturated ketone does not need a metal catalyst, is high in yield and more complex and verified in structure and will show broader application prospects in chemical industry production and clinic medicine.

The invention relates to the synthesis and anti-hepatoma activity study of a 1-substitution phenyl-3-methyl-4-(2-fluorine-4-chlorine-5-propargyloxyphenyl)-5-methylmercapto-1H pyrazole compound (A). The compound (A) is prepared through the following steps of reducing 2-chlorine-4-fluorine-5-nitro phenyl ethyl carbonate with iron powder, carrying out diazotization and Meerwein arylation reaction and reacting with carbon disulfide and dimethyl sulfate to obtain 2-chlorine-4-fluorine-5-(1,1-dimethylthio-3-oxo-1-alkene-2-group) phenyl ethyl carbonate (5), hydrolyzing the (5), then reacting with propargyl bromide to obtain 4,4-dimethylthio-3-(2-fluorine-4-chlorine-5-propargyloxyphenyl) butane-3-alkene-2-ketone (6), and finally with ethyl alcohol as a solvent, reacting (6) with different substituted phenylhydrazine hydrochlorides under reflux condition to generate the compound (A). Test results indicate that both the degrees of the compound A for inhibiting HepG2 cancer cells and promoting cell apoptosis are greater than or equal to control drug cyclophosphamide.

Relating to a plasticizer preparation method, the invention discloses a method for turning biomass cardanol into a chloroprene rubber internal plasticizer by click chemistry. The method includes: firstly reacting cardanol with propargyl bromide to prepare propargyl ether cardanol and chloroprene rubber with an azido structure, then carrying out click chemistry reaction to realize reaction of the propargyl ether cardanol and chloroprene rubber with an azido structure, thus realizing internal plasticization of chloroprene rubber. The method for internal plasticization of chloroprene rubber withthe natural biomass raw material by click chemistry reaction disclosed by the invention has the advantages that: the cardanol raw material is sufficient, the chemical reaction process is simple, the product has obvious plasticization effect, excellent thermal stability and near zero migration of plasticizer, therefore the chloroprene rubber internal plasticizer is a new product conforming to the green and environment-friendly circular economy concept and has very broad market prospects.

The present invention belongs to the technical field of organic synthesis, and specifically discloses 6-substituted-1-((1-substituted phenyl-1,2,3-triazole-4-yl)methyl)-4-carbonylquinoline-3-carboxylic compounds or a pharmaceutical salt thereof, and preparation and application thereof. The general formula is shown in the specification, wherein R, R1, R2, R3, R4 and R5 are the same or different, each being selected from one of H, halogen, nitro, amino, hydroxyl, C1-C4 alkyl, C1-C4 haloalkyl, C1-C4 alkoxyl, C1-C4 carboxyl and formyl. The preparation comprises: performing condensation between substituted phenyl as a raw material and diethyl ethoxymethylene malonate to produce an intermediate I, and performing Gould-Jacobs cyclization to produce an intermediate II; performing ''click chemistry'' between substituted phenyl azide and propargyl bromide to produce an intermediate III; and performing an N-alkylation reaction, alkaline hydrolysis and acidification between the intermediate II and the intermediate III to obtain a target product IV. The inventive compound or the pharmaceutically salt thereof has an excellent antitumor effect.

The invention discloses a free radical nano-capture material. The free radical nano-capture material is amphiphilic phenol. The chemical composition general formula of the free radical nano-capture material is (C6H5OH)na-(C6H5O-PEG)nb and the structural formula of the free radical nano-capture material is shown in the description. According to the invention, linear phenol is prepared through acid catalysis, alkynyl functional groups are introduced to a phenolic chain through propargyl bromide, alkynyl and azide groupa chemically reacts through click by using methoxypolyethylene glycol with azide groups at the terminal, and finally, the nanoscale free radical nano-capture material-amphiphilic phenol is obtained; a preparation method provided by the invention is simple, the prepared free radical nano-capture material can form micelle in water and reserved phenolic hydroxyl of the free radical nano-capture material has an obvious capture effect on free radicals.