34 results about "Cyclopentenone" patented technology

The invention provides a preparation method of 2-pentyl-2-cyclopentenone, and belongs to the technical field of organic synthesis. The preparation method comprises the following steps: carrying out a first-stage isomerization reaction on 2-pentylidene cyclopentanone and a first composite catalyst in a first atmosphere to obtain an intermediate, carrying out a second-stage isomerization reaction on the intermediate and a second composite catalyst in a second atmosphere, and controlling the volume ratio of nitrogen to hydrogen in the first atmosphere and the second atmosphere to obtain the 2-pentylidene cyclopentanone. In the first-stage isomerization reaction, the conversion rate of converting 2-pentylidene cyclopentanone into 2-pentyl-2-cyclopentenone is increased, and in the second-stage isomerization reaction, the use amount of hydrogen in the second atmosphere is reduced, the temperature of the second-stage isomerization reaction is increased, generation of by-products is inhibited, and the yield of 2-pentylidene cyclopentanone is increased. Further, the yield and the purity of the 2-pentyl-2-cyclopentenone can be improved. According to the preparation method, the first-stage isomerization reaction and the second-stage isomerization reaction are continuous reactions, intermittent reactions are not needed, and the preparation method is more suitable for industrial application.

The invention belongs to the technical field of organic matter preparation, and particularly relates to a preparation method of 2-pentylcyclopentyl-2-ketene. According to the method, methanol is used as a solvent, sulfonic acid type resin doped with lewis acid is used as a catalyst to catalyze the isomerization reaction of 2-pentylidene cyclopentanone, the catalyst and the methanol solvent can jointly promote the isomerization reaction of 2-pentylidene cyclopentanone, and the catalytic efficiency is high, so that the reaction yield is remarkably increased, and the catalyst cost is reduced; in addition, a fixed bed reactor continuous production mode is adopted, waste salt is prevented from being generated when the acid catalyst is quenched by processes such as HCl / HBr / p-toluenesulfonic acid, and methanol is used as a solvent, so that the byproduct dimethyl ether is simply separated from water and the solvent methanol. In addition, when the sulfonic acid type resin doped with the lewis acid is used for catalyzing the isomerization reaction of 2-pentylidene cyclopentanone, the stability is high, and the service life is long.

The application discloses a synthesis method of 3,3-difluorocyclopentylamine hydrochloride, and particularly relates to the technical field of chemical synthesis. The synthesis method comprises the following steps: taking 2-cyclopentenone and phthalimide as raw materials, and sequentially performing a Michael addition reaction, deoxygenation fluorination, removal of a phthaloyl protecting group, Boc protection and deprotection and salt formation reaction to obtain 3,3-difluorocyclopentylamine hydrochloride. The synthesis route and process design of the application are reasonable, the starting raw material is 2-cyclopentenone, the required reaction condition is mild, the post-treatment method is simple, the operability is strong, the raw material and reagent are cheap and easy to obtain, and the total yield can reach 43.6%, so the synthesis method has large-scale preparation value.

The invention relates to processes for preparing carbaprostacyclin analogues and intermediates prepared from the processes. The invention also relates to cyclopentenone intermediates in racemic or optically active form.

The present invention relates to catalysis field and is specifically related to a kind of preparation method of p-Xylene, the method including:Using 2,5-dimethylfurans and / or 2,5-hexanedione as raw material, the catalyst contains SCM-36 molecular sieves, and raw material and ethylene contact reaction prepare p-Xylene in the presence of alternatively organic solvent.Using SCM-36 molecular sieves as catalyst, under mild reaction conditions, 2,5-dimethylfurans and / or 2,5-hexanedione can be efficiently converted into p-Xylene, and conversion rate and product p-Xylene selectivity are very high.Meanwhile, in products obtained therefrom, key impurities (such as polyalkyl ethylbenzene, 2,5-hexanedione and 2-cyclopentenone) content is extremely low, greatly reducing separation energy consumption.In addition, the present invention has very high stability by using SCM-36 molecular sieves as catalyst, and is recycled four times without seeing catalyst performance significantly changed.

The application discloses a benzimidazole substituted cyclopentenone compound and a preparation method and application thereof, and the compound comprises a structural formula shown in formula I or a medicinal salt, an isomer, a medicinal derivative thereof; wherein R1 is a hydrogen atom, a chlorine atom or a fluorine atom; R2 is a hydrogen atom, a chlorine atom, a fluorine atom, a methyl group or a methoxy group; R3 is a hydrogen atom, a chlorine atom, a fluorine atom, a methyl group or a methoxy group; R4 is a hydrogen atom, a chlorine atom or a fluorine atom; R5 is a methyl group, an ethyl group or a propyl group; and R6 is a methyl group, an ethyl group or a propyl group. The compound has good antibacterial activity, and has strong antibacterial activity on various pathogenic microorganisms including gram-positive bacteria and fungi. The application has the advantages of rich raw materials, simple operation, mild conditions, simple post-treatment, good thermal stability and good application prospect.

The invention provides a method for preparing JP-10 aviation fuel, which comprises the following steps: A) carrying out rearrangement reaction on furfural in the presence of hydrogen and a first catalyst to prepare cyclopentenone; (B) carrying out self dimerization reaction on cyclopentenone under the condition of ultraviolet light to obtain a C10 four-membered ring oxygen-containing compound; and C) performing hydrodeoxygenation and rearrangement reaction on the C10 four-membered ring oxygen-containing compound under the action of hydrogen and a second catalyst to obtain the JP-10 aviation fuel, the second catalyst comprises a molecular sieve supported catalyst and / or an activated carbon supported catalyst. According to the method, a five-membered carbon ring molecule cyclopentenone is prepared through furfural molecule reconstruction, a four-membered tension carbon ring is constructed through green and efficient photocatalytic [2 + 2] cycloaddition, and finally a cycloalkane product is efficiently prepared through a skeleton rearrangement hydrodeoxygenation reaction through a metal-loaded molecular sieve catalyst. Wherein the maximum selectivity of the hanging tetrahydrodicyclopentadiene can reach 93%.

The present invention provides a method for preparing high-purity all-cis-jasmone, belonging to the technical field of organic chemistry. Sodium amide is prepared by reacting sodium with liquid ammonia, a catalyst is added, and the reaction is carried out with stirring. The solvent is removed under reduced pressure. Under the protection of an inert gas and under the condition of an ice-water bath, 2-formylmethyl-3-methyl-cyclopentene-2-one and toluene are added, and the reaction is carried out with heating and stirring. After cooling to room temperature, the product is collected by vacuum distillation to obtain high-purity all-cis-jasmone. The method of the present invention greatly improves the activity and reaction selectivity of the catalyst, enables the reaction to produce cis-jasmone, has a high yield, good selectivity, mild preparation conditions, a simple reaction method, and high product purity.

The application discloses a cyclopentenone derivative, a synthesis method and application thereof, uses 2-((Z)-3-iodoallyl)-malononitrile as raw material, and provides a synthesis method of the cyclopentenone derivative. 2+ The method uses formic acid as an additive, which can be used as a proton source for protonolysis of an intermediate on one hand, and can also be used as a reducing agent for Pd 2+ species on the other hand, so that efficient catalytic conversion effect is realized. The method is simple to operate, has good functional group compatibility, and provides a new idea for synthesizing polysubstituted cyclopentenone derivatives.

The present invention relates to a compound of formula (I) or a pharmaceutically acceptable salt and / or solvate thereof, for use as a drug, especially as an antibiotic. The present invention also relates to a pharmaceutical composition comprising said compound of formula (I) and at least one pharmaceutically acceptable excipient. The present invention further concerns a method of preparation of a compound of formula (I′).

The present invention discloses novel 5-substituted 4-hydroxycyclopent-2-en-1-one derivatives as active compounds in pharmaceutical compositions for cancer treatment. The present invention confers the cytotoxic effect of the above compounds on ovarian cancer, colorectal cancer, cervical cancer, hepatocellular carcinoma, lung cancer, bladder cancer, breast cancer, melanoma, lymphoma, leukemia, and myeloma malignant cells for inhibiting cell cycle progression in the G2 / M phase, reducing the expression of DNA replication licensing factors, and having a general cancer treatment effect. The present invention further discloses the use of the above compositions for the treatment of platinum-resistant tumors. Another aspect of the present invention is the synergistic effect of these compounds with existing cancer therapeutic agents as proteasome inhibitors. Finally, a method for synthesizing the active compounds of the above compositions is disclosed.

The invention belongs to the technical field of medicine preparation, and particularly relates to a preparation method of Milsartan potassium. Comprising the following steps: (1) mixing azilsartan, alkali, ethyl acetate and N, N '-carbonyldiimidazole, heating, adding 4-hydroxymethyl-5-methyl-1, 3-dioxole-2-ketone, and reacting to obtain a product 1; and (2) cooling the product 1, mixing with potassium isooctanoate, stirring, crystallizing, carrying out suction filtration, and washing to obtain the product 1. The method provided by the invention has the advantages of few steps, easily available raw materials, simple post-treatment and less generation of three wastes, and is suitable for industrial production.

The invention discloses a preparation method of 3-bromo-2-cyclopentene-1-ketone, which comprises the following steps: by taking 1, 3-cyclopentanedione (compound III) as a raw material, reacting with paratoluensulfonyl chloride under the action of alkali and a phase transfer catalyst to obtain a compound II; and finally, carrying out substitution reaction on the compound I and brominated inorganic salt under the action of a phase transfer catalyst to generate a final product 3-bromo-2-cyclopentene-1-ketone (compound I). According to the method, by adopting the phase transfer catalyst and an adaptive mixed solvent system, the problems of dissolution and mass transfer caused by polarity difference in the reaction are effectively solved, the reaction conditions are mild, and the operation is simple and convenient; in addition, according to the method, product separation and purification are simple, a high-purity product can be obtained without column chromatography, the two-step total yield reaches 87.45%, the liquid phase purity exceeds 99%, and the whole process is environmentally friendly, suitable for large-scale production and good in industrial application prospect.

The application discloses a method for preparing cyclopentenone substances by furan alcohol rearrangement-hydrogenolysis, and belongs to the field of fine organic chemicals. In the method, furan alcohol compounds (furfuryl alcohol, 5-methyl furan alcohol and 2,5-dihydroxymethyl furan) are mixed with water solvent in different concentrations, a cobalt disulfide (CoS2) catalyst is added, and the mixture is reacted in a hydrogen environment with a pressure of 0.5-1.5 MPa at a reaction temperature of 160-200 DEG C. The method can obtain 2-cyclopentenone / 3-methyl-2-cyclopentenone, and has the advantages of simple process, convenient operation, cheap and easily obtained catalyst and multiple recycling, and is easy to be industrialized. When the conversion rate of furfuryl alcohol for synthesizing 2-cyclopentenone reaches 100%, the yield reaches 90%; when the conversion rate of 5-methyl furan alcohol and 2,5-dihydroxymethyl furan for synthesizing 3-methyl-2-cyclopentenone reaches 100%, the yields reach 80% and 78% respectively.

A method for preparing a dithiocyclopentenone derivative and an application thereof, a bactericide and a bactericidal method are provided. The chemical structural formula of the dithiocyclopentenone derivative is shown as:where R1 is selected from phenyl or substituted phenyl, pyridyl, thiazolyl, thienyl or piperazinyl; and R2 is selected from H, —CH3 or —CH2CH3.

The invention belongs to the technical field of drug synthesis, and particularly relates to a preparation method of a Milsartan potassium side chain, which comprises the following steps: by taking 4-chloromethyl-5-methyl-1, 3-dioxole-2-ketone as a starting material and a hydrophobic solvent as a solvent, reacting with sodium formate under the catalysis of TBAB (Tetrabutylammonium Bromide) to obtain an ester; and carrying out transesterification on the esterified product and an alcohol solvent under the action of a catalyst to obtain the Milsartan potassium side chain.

The invention discloses a preparation method of 2-cyclopentenone, which comprises the following steps: taking cyclopentanone (compound V) as an initial raw material, and carrying out bromination reaction to obtain 2-bromocyclopentanone (compound IV); then carrying out carbonyl protection to obtain 2-bromo-1, 1-dimethoxy cyclopentane (a compound III); then carrying out elimination reaction to obtain 3, 3-dimethoxy cyclopent-1-ene (a compound II); according to the method, the total yield can reach 75.46%, the raw materials are cheap and easy to obtain, the use of dangerous reagents is avoided, the post-treatment is mild and efficient, and the method is suitable for industrial large-scale production.

The application provides a synthetic intermediate of entecavir and a preparation method of entecavir. The preparation method of the synthetic intermediate of entecavir comprises the following steps: S1. 4-[(tert-butyldimethylsilyloxymethylsilyl)oxy]-2-cyclopentenone is used as raw material, and a compound III is obtained by reaction under the condition of imidazole and formaldehyde. S2. Michael addition reaction is carried out between the compound III and a lithium reagent in-situ generated from potassium tert-butoxide, sec-butyllithium and methyl tert-butyl ether to obtain a compound IV, i.e. the synthetic intermediate of entecavir. The synthetic intermediate of entecavir is prepared through two steps, and the entecavir is prepared through five steps. The process steps are simple, the raw materials used in each step are cheap and easy to obtain, the process is simple, the product is easy to purify, the total yield is high, and the industrial production is easy to realize.

This invention discloses a method for synthesizing 2-pentylcyclopentenone and the catalyst used. The method uses 2-pentylcyclopentenone and hydrogen as raw materials, and performs a hydroisomerization reaction in the presence of a catalyst to obtain 2-pentylcyclopentenone. The catalyst is a supported catalyst and includes a support, an active metal, a rare earth metal oxide, and a modifier. The active metal and rare earth metal oxide are supported on the support. The support includes zinc aluminate with a spinel structure. The modifier contains phosphorus and / or nitrogen. This synthesis method achieves high conversion of 2-pentylcyclopentenone, high selectivity and high purity of the target product 2-pentylcyclopentenone, and the process is relatively simple, suitable for industrial production. The catalyst exhibits high catalytic activity and high stability.

The invention relates to processes for preparing carbaprostacyclin analogues and intermediates prepared from the processes. The invention also relates to cyclopentenone intermediates in racemic or optically active form.

The invention discloses a preparation method of 2-bromo-2-cyclopentenone, which comprises the following steps: taking cyclopentanone (compound III) as a starting raw material, firstly carrying out bromination reaction to obtain 2, 2-dibromocyclopentanone (compound II), and finally carrying out elimination reaction to obtain the product 2-bromo-2-cyclopentenone (compound I), the total yield can reach 82.59%, the raw materials in the route are low in cost and easy to obtain, and the method is suitable for industrial production. The use of dangerous reagents is avoided, the post-treatment is mild and efficient, and the method has great large-scale production potential and economic value.

The present invention relates to a compound of formula (I) or a pharmaceutically acceptable salt and / or solvate thereof for use as a drug, in particular as an antibiotic. The present invention also relates to a pharmaceutical composition comprising said compound of formula (I) and at least one pharmaceutically acceptable excipient. The present invention further relates to a process for preparing a compound of formula (I'). [Formula 1] TIFF2023554322000083.tif2618(I) [Case 2] TIFF2023554322000084.tif2517(I')

The invention relates to the technical field of microbial fermentation and biological medicine, in particular to a halogenated cyclopentenone compound as well as a preparation method and application thereof. The invention provides a halogenated cyclopentenone compound, which is obtained by carrying out fermentation culture, extraction and separation on mangrove forest plant artemisinin endophytic fungi Perconia macrospinosa F35, and the chemical structure of the halogenated cyclopentenone compound is identified by modern spectrum technologies such as nuclear magnetic resonance, high-resolution mass spectrum, ultraviolet spectrum and the like. Activity research shows that the series of halogenated cyclopentenone can effectively inhibit the activity of key virulence factor tyrosine phosphatase MptpA and MptpB of mycobacterium tuberculosis, shows good anti-tuberculosis activity by inhibiting pathogenic signal channels of pathogenic bacteria, and has wide application potential and development value in the field of anti-tuberculosis drugs.

The present invention relates to a process for preparing benzoprostacyclin analogs and intermediates prepared by the process, as well as benzoprostacyclin analogs prepared therefrom. The present invention also relates to cyclopentenone intermediates in racemic or optically active form.

The invention discloses a simple and convenient synthesis method of methyl dihydrojasmonate. The methyl dihydrojasmonate is synthesized under the action of trimethylchlorosilane; according to the method, a Reformatsky reagent generated by 2-methyl bromoacetate and activated zinc powder in situ and 2-amyl-2-cyclopentenone are subjected to a Michael addition reaction, and methyl dihydrojasmonate is directly obtained. The method has the main advantages that 2-pentyl-2-cyclopentenone is used as a raw material, methyl dihydrojasmonate can be obtained only through one-step reaction, and the yield reaches up to 97%. Compared with the traditional production method of methyl dihydrojasmonate, the method provided by the invention has the advantages of short route steps, high efficiency and high atom economy, and is suitable for industrial production of methyl dihydrojasmonate.

The invention discloses a method for preparing a high-density low-freezing-point aviation oil component by taking furfuryl alcohol and methyl pentanone alcohol as raw materials, and belongs to the technical field of sustainable biomass liquid fuel. The method comprises the following steps: carrying out hydrogenation reaction on methyl pentanone alcohol to obtain 2-methyl-2, 4-pentanediol; the preparation method comprises the following steps: carrying out a dehydration reaction on 2-methyl-2, 4-pentanediol to obtain 2-methyl-1, 3-pentadiene; the furfuryl alcohol is subjected to water phase reforming, and 4-hydroxy-2-cyclopentenone is obtained; the preparation method comprises the following steps: carrying out Diels-Alder reaction on 2-methyl-1, 3-pentadiene and 4-hydroxy-2-cyclopentenone, so as to obtain an aviation oil component precursor; performing hydrodeoxygenation reaction on the aviation oil component precursor to obtain an aviation oil component; wherein the precursor can be prepared by carrying out a cascade dehydration Diels-Alder reaction on 2-methyl-2, 4-pentanediol and 4-hydroxy-2-cyclopentenone, and the precursor can be prepared by carrying out a cascade dehydration Diels-Alder reaction on the 2-methyl-2, 4-pentanediol and the 4-hydroxy-2-cyclopentenone; the furfuryl alcohol can also be prepared from furfuryl alcohol and 2-methyl-1, 3-pentadiene through a cascade water phase reforming Diels-Alder reaction. The reaction operation is simple, the condition is mild and controllable, the selectivity is high, and the obtained aviation oil component is high in density and low in freezing point.

The invention provides a benzocyclopentenone compound as shown in a formula (I), or a tautomer, a stereoisomer or pharmaceutically acceptable salt thereof, and application of the benzocyclopentenone compound or the tautomer, the stereoisomer or the pharmaceutically acceptable salt. In-vivo and in-vitro experiment results show that the compound disclosed by the invention has an excellent protection effect on cerebral cortex neuronal cells, and particularly, the survival rate of the cerebral cortex neuronal cells can be remarkably improved under the condition of hypoxia and hypoglycemia; an excellent brain protection effect is achieved, and the cerebral infarction area can be greatly reduced; the compound can be used for preventing and treating nerve injury, degenerative diseases and ischemic diseases. # imgabs0 #

The invention relates to processes for preparing benzoprostacyclin analogues and intermediates prepared from the process, and the benzoprostacyclin analogues prepared therefrom. The invention also relates to cyclopentenone intermediates in racemic or optically active form.

The invention discloses novel 5-substituted 4-hydroxy-cyclopent-2-en-1-one derivatives as active compounds in pharmaceutical compositions for the treatment of cancer. The invention confers cytotoxic effects of the said compounds on ovarian, colorectal, cervical, hepatocellular, lung, bladder and breast carcinomas, melanoma, lymphoma, leukemia and myeloma malignant cells, for the inhibition of cell cycle progression at the G2 / M phase, for reducing the expression of DNA replication licensing factors and for having general cancer treatment effects. It further discloses the use of the said compositions for the treatment of platinum-resistant tumors. Another aspect of the invention is the synergetic effects of these compounds with existing cancer treatment medicaments as the proteasomal inhibitors. Finally, the synthetic methods of the active compounds of the said com-positions are disclosed.

The application discloses a synthesis method of an entecavir intermediate, which comprises the following steps: taking 4-hydroxy-2-cyclopentenone as raw material, and reacting with tert-butyldimethylsilylchloride in the presence of alkali to prepare compound (II); then, the compound (II) is reacted with imidazole and formaldehyde to obtain compound (III); then, the compound (III) is reacted with acetyl chloride in the presence of alkali to obtain compound (IV); then, a free radical initiator is added into the compound (IV), and then addition reaction occurs under the irradiation of ultraviolet light to obtain compound (V); finally, the compound (V) is reacted with tert-butyldimethylsilylchloride in the presence of alkali, and the entecavir intermediate is obtained. The entecavir intermediate prepared by the method is an important raw material for synthesizing the antiviral drug entecavir. Compared with the prior art, the method has the advantages of cheap and easily available raw material, simple process, short synthesis route, easy product purification, high total yield and easy industrialized production.