42 results about "Enone" patented technology

The invention provides a preparation method of polar polyolefin, and belongs to the technical field of polyolefin. The preparation method comprises the following steps: in an inert atmosphere, under the action of a catalyst and a cocatalyst, copolymerizing C2-C6 olefin and an alkylated polar monomer in an organic solvent to prepare polar polyolefin, wherein the alkylated polar monomer is prepared by the following steps: dissolving an alkylating reagent in an organic solvent, adding a polar monomer, and mixing and stirring to obtain the alkylated polar monomer; the polar monomer comprises at least one of halogenated alpha-olefin, alpha-olefine acid, alpha-enol, alpha-olefine aldehyde, alpha-olefine ester and alpha-olefine ketone. The polar monomer is pre-protected by adding the alkylating reagent, so that effective copolymerization of C2-C6 olefin and the polar monomer is realized, and the performance of polyolefin is favorably improved.

The application belongs to the technical field of chemical synthesis, and particularly relates to a synthesis method of 2-aryl-2-cyclohexanedione enol ester compounds. The method uses a transition metal complex as a catalyst, and uses a phenyl boronic acid compound and an iodine onium compound as raw materials, first synthesizes a 3-hydroxy-2-aryl-2-cyclohexenone compound, and then synthesizes the 2-aryl-2-cyclohexanedione enol ester compound through acylation. The reaction condition is mild, no additional additives (such as alkali-sodium acetate, expensive silver salt-silver acetate, etc.) need to be added, the C-C bond can be efficiently and quickly constructed, the 2-aryl-2-cyclohexanedione cyclization derivative is obtained, the reaction operation is simple, the reaction time is short, the method has high efficiency and high safety, the substrate range is wide, the functional group tolerance is good, the method conforms to the concept of green chemistry and high atomic economy, and is very suitable for large-scale industrial production.

The invention discloses a method for separating and preparing megastigmatrienone isomers, and belongs to the technical field of isomer separation and preparation. The technical problem to be solved is that in the prior art, mg-level separation preparation of a megastigmatrienone single-configuration isomer cannot be rapidly realized. The key point of the technical scheme is as follows: the method comprises the following steps: (1) mixing megastigmatrienone with methanol to obtain a mixed solution; (2) separating the mixed solution by adopting a reversed-phase preparative chromatography to obtain an isomer of megastigmatrienone; wherein the chromatographic conditions in the reversed-phase preparative chromatography in the step (2) are as follows: a chromatographic column is a reversed-phase semi-preparative chromatographic column, the sample size is 100-800 [mu] L, the flow velocity is 0.1-0.8 mL / min, the detection wavelength is 308 nm, an eluent is methanol-THF-H2O in a ratio of 37.5: 7.5: 55, and isocratic elution is performed.

The present application relates to a kind of high 4-HBC mycobacterium genetic engineering bacteria and its construction method, and its application in the microbial fermentation preparation 22-hydroxy-23, 24-bis-norcholesta-4-en-3-ketone of 4-HBC.The high 4-HBC mycobacterium genetic engineering bacteria is constructed as follows: with mycobacterium as chassis, kshA1, kshA2, kstD1, kstD2, kstD3 gene is knocked out in turn, hsd4A gene is knocked out, ltp3, ltp4 gene is overexpressed, and the high 4-HBC mycobacterium genetic engineering bacteria is obtained.The genetic engineering bacteria provided in the present application can produce 4-HBC, greatly improve the production efficiency of steroidal drugs, help to improve the conversion rate of substrate, reduce production cost, and reaction condition is mild, environment-friendly, suitable for vigorous popularization and application, with higher economic benefit and social benefit.

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 discloses a method for the catalytic hydrolysis of 3,3'-oxybis(cyclohexane-2-en-1-one) using carbon materials. Under the action of a bio-carbon-supported potassium-magnesium oxide catalyst rich in strongly basic sites, 3,3'-oxybis(cyclohexane-2-en-1-one) undergoes a hydrolysis reaction to produce 1,3-cyclohexanedione. The raw material 3,3'-oxybis(cyclohexane-2-en-1-one) is a byproduct of the resorcinol process for preparing 1,3-cyclohexanedione, and is inexpensive and readily available. The catalytic hydrolysis of 3,3'-oxybis(cyclohexane-2-en-1-one) to produce 1,3-cyclohexanedione achieves value-added processing of byproducts from the CHD industry, reduces solid waste generation, lowers the production cost of 1,3-cyclohexanedione, and has significant socio-economic benefits.

The present invention relates to a process for the preparation of Halogenated Alkenone Ethers of Formula (1) from a compound of Formula (2) using an iodide- based catalyst which enables superior process performance in terms of throughput, yield, and product purity when compared to the prior art, in addition to making the process more environmentally friendly by enabling the use of environmentally benign, inexpensive inorganic bases - in lieu of environmentally damaging organic bases, as were used in the prior art.

The application discloses a synthetic method of preparing a plant source cholesterin key intermediate 20-formyl-pregn-4-ene-3-ketone. The method takes plant source 21-hydroxy-20-methyl-pregn-4-ene-3-ketone, also known as bisnorol or BA, as raw material, and oxidizes BA into aldehyde through a phase transfer catalyst under oxygen environment. The preparation method has the advantages of high yield, mild reaction condition, fast reaction time, cheap and recyclable solvent, relatively simple operation and the like, solves the problems of high production cost and serious pollution in the prior art, has high industrial production value and good agricultural application prospect, and provides a new method for synthesizing medicinal auxiliary materials of plant source cholesterin. The reaction formula is as follows.

The present application relates to the technical field of organic synthesis, in particular to a synthesis method of polysubstituted pyrazole compounds, which comprises adding aryl diazonium salt 0.6 mmol, enone 0.9 mmol, 0.5 ml of acid and 0.3 mmol of electrolyte into a 10 ml three-necked bottle, and then adding 6 ml of solvent to dissolve; using a carbon rod as an anode and a platinum plate as a cathode, stirring the reaction, monitoring the reaction process by using thin layer chromatography, after the reaction is completed, extracting the mixture with ethyl acetate; drying the organic layer of the mixture with anhydrous sodium sulfate, rotary evaporating the solvent under reduced pressure, purifying the residue by column chromatography, and obtaining the target product; the method uses aryl diazonium salt as a double synthetic substrate under mild electrochemical conditions, continuously generates two free radicals by electrochemical reduction of aryl diazonium salt, directly synthesizes a series of polysubstituted pyrazole compounds, directly and orderly constructs polysubstituted pyrazole compounds without transition metal or external redox agent, is environment-friendly, efficient and high in atom economy.

The present invention relates to a chiral iridium hydride complex comprising a) a chiral (P, N)-ligand and b) a stabilized ketene ligand of formula (I), wherein R1 is selected from the group consisting of hydrogen, a C1-C500-alkyl group, a C2-C500-alkenyl group, a C1-C500-alkoxy group, a C2-C500-alkenyloxy group, a C1-C500-alkylamino group, a C2-C500-alkenyl amino group, a di-(C1-C500-alkyl) amino group, a di-(C2-C500-alkenyl) amino group, a N-(C1-C500-alkyl)-N-(C2-C500-alkenyl) amino group, a C3-C8-cycloalkyl group, a C3-C8-cycloalkyloxy group, a C3-C8-cycloalkylamino group, a N-(C1-C500-alkyl)-N-(C3-C8-cycloalkyl) amino group, and a pharmaceutically acceptable salt thereof; a C6-C14-aryl group, which may be substituted as further defined in the specification; r1a is selected from hydrogen, C1-C6-alkyl, C1-C6-alkylcarbonyl, or R1a and R1 together with the carbon atom to which R1a is attached and the carbonyl to which R1 is attached form a C5-C7-cycloalkanone ring wherein the C5-C7-cycloalkanone ring is unsubstituted or substituted by 1 to 4 substituents independently selected from C1-C6-alkyl and benzylidene, wherein the benzylidene group is unsubstituted or substituted by 1 to 5 substituents independently of one another selected from the group consisting of halogen, a C1-C500-alkyl group, a C1-C500-alkoxy group, a C1-C500-haloalkyl group, and a C1-C500-haloalkoxy group; r2 is selected from hydrogen, a C1-C500-alkyl group, a C1-C500-alkoxy group, a C1-C500-alkylamino group, a di-(C1-C500-alkyl) amino group, a C3-C8-cycloalkyl group, a C3-C8-cycloalkyloxy group, a C3-C8-cycloalkylamino group, an N-(C1-C500-alkyl)-N-(C3-C8-cycloalkyl) amino group, a C6-C14-aryl group, which may be substituted as further defined in the specification; and arrow represents a bond attached to an iridium atom; the present invention relates to chiral iridium hydride complexes, and to a method for producing optically active 4-substituted 1, 2, 3, 4-tetrahydroquinolines by enantioselective hydrogenation of the corresponding 4-substituted 1, 2-dihydroquinolines in the presence of such chiral iridium hydride complexes.

This invention relates to the field of asymmetric catalytic hydrogenation, specifically to a method for preparing chiral chromone or chromane carboxylic acid compounds. The method involves preparing a chiral catalyst from a nickel compound and ligands. By controlling the combination of the nickel compound-ligand-solvent, enantioselective hydrogenation of the conjugated C=C bonds of the substrate chromone carboxylic acid compound is achieved, yielding the semi-reduced product chiral chromone carboxylic acid; or, further, the carbonyl group is reduced, and carbonyl reduction and dehydroxylation reactions are carried out at room temperature under trifluoroacetic acid and triethylsilane conditions to obtain the fully reduced product chiral chromane carboxylic acid. The catalytic system of this invention is simple to construct, and the selectivity can be controlled by the solvent system. It maintains high conversion and excellent enantioselectivity even under high S / C conditions, making it suitable for the efficient preparation of chiral chromone / chromane skeletal carboxylic acid compounds.

The invention discloses 6, 7-dihydrocyclopenta [b] pyridine-5-ketone and a synthesis method and application thereof.The method comprises the steps that a compound 1, namely 1, 3-cyclopentanedione, is added into an organic solvent I, ammonium acetate is added, the temperature is increased to 70-160 DEG C under inert gas protection, stirring reaction is conducted for 4-10 hours, after raw materials are consumed up, reaction liquid is subjected to first-time aftertreatment, and after the reaction liquid is subjected to second-time aftertreatment, a compound 2, namely 1, 3-cyclopentanedione is obtained; the compound 2 is 3-aminocyclopentyl-2-ketene; and adding the compound 2 obtained in the previous step, namely 3-aminocyclopentyl-2-ketene, into an organic solvent II, then adding p-methyl phenyl sulfonic acid hydrate, malonaldehyde and sulfate, heating to 60-150 DEG C under the protection of inert gas, stirring for 8-20 hours, and after the raw materials are completely consumed, carrying out secondary post-treatment on the reaction liquid to obtain a target compound 3, namely 6, 7-dimethoxy-2-(3-aminocyclopentyl-2-ketene). The invention relates to 2, 7-dihydrocyclopenta [b] pyridine-5-ketone.

The invention relates to a selective hydrogenation reduction method of a non-conjugated ketene compound, which comprises the following steps: in a nitrogen atmosphere, mixing a ketene compound shown as a formula (I), a hydrogen source, a catalyst, a ligand, a reducing agent and an organic solvent, and stirring at room temperature for 8-24 hours to obtain a reaction solution; and performing column chromatography separation and purification on the reaction liquid to obtain the alkyl ketone compound as shown in the formula (II). According to the method, iodoethane or bromoethane is used as a hydrogen source, and compared with the prior art, the method has the advantages of higher yield, mild reaction conditions, good selectivity, no need of high-pressure hydrogen, no pungent smell and environmental protection.

This invention provides a composition effective in suppressing the deterioration of citral flavor. [Solution] A citral flavor-suppressing composition containing one or more compounds selected from the group consisting of 8-methyl-4-methylenenona-7-en-2-one and 4,8-dimethylnona-3,7-dien-2-one as an active ingredient. Preferably, it contains at least 8-methyl-4-methylenenona-7-en-2-one. Alternatively, preferably, the unpleasant flavor is due to p-cresol and / or p-methylacetophenone.

This invention relates to a method for synthesizing squaric acid, the method comprising the following steps: (1) reacting alkyl vinyl ether, trichloroacetyl chloride, and zinc to obtain 2,2-dichloro-3-alkoxycyclobutanone; (2) subjecting 2,2-dichloro-3-alkoxycyclobutanone to chlorination with chlorine to obtain 2,2,4,4-tetrachloro-3-alkoxycyclobutanone; (3) subjecting 2,2,4,4-tetrachloro-3-alkoxycyclobutanone to elimination reaction with a base to obtain 2,4,4-trichloro-3-alkoxycyclobuten-1-one; and (4) subjecting 2,4,4-trichloro-3-alkoxycyclobuten-1-one to hydrolysis to obtain the squaric acid. The synthesis method provided by this invention avoids the use of the prohibited raw material perchloro-1,3-butadiene and has lower energy consumption, meeting the needs of green and clean production.

The present invention provides an estetrol synthesis process, and relates to the technical field of steroid compound synthesis processes, and the method comprises the following steps: taking estrone as an initial raw material, firstly carrying out 3-site hydroxyl protection, and then carrying out an oxidative dehydrogenation reaction in the presence of a metal catalyst and in an oxygen atmosphere to prepare a key intermediate ketene, then 17-site carbonyl reduction, 17-site hydroxyl protection, 15, 16-site double bond dihydroxylation, 3-site protecting group removal and hydrolysis reaction are sequentially carried out, and finally the target product estetrol is obtained. The method adopts metal catalysis to directly oxidize to construct cycloenone, effectively avoids the problem of poor stability of partial intermediates in the prior art, has the advantages of simple process, short reaction steps, greenness, environmental protection and the like, and is suitable for industrial production.

The invention discloses ketene reductase and a method for preparing (R)-4-propyl-dihydrofuran-2-ketone by using the ketene reductase, the amino acid sequence of the ketene reductase has at least 95%, 96%, 97%, 98% or 99% identity compared with the amino acid sequence shown in SEQ ID NO: 1, and at least one or more amino acid residue differences of W106, Y72, T29, P286, T28, P26 and homologous sites thereof exist. When the ketene reductase disclosed by the invention is used for preparing (R)-4-propyl-dihydrofuran-2-ketone, the reaction time is relatively short, the conversion rate of a substrate is relatively high, and the ee value of (R)-4-propyl-dihydrofuran-2-ketone is relatively high, so that the ketene reductase is more efficient and suitable for industrial production.

This invention provides a method for synthesizing milobalin benzylsulfonic acid, comprising the following steps: a chiral enone undergoes a condensation reaction with cyanoacetate in the presence of ammonium acetate to obtain an unsaturated cyano ester; next, the unsaturated cyano ester undergoes a condensation reaction with nitromethane to obtain a nitro ester; the nitro ester is then deesterified at high temperature to obtain a chiral nitro nitrile, which is then reduced to a chiral amino nitrile; subsequently, the chiral amino nitrile is hydrolyzed to obtain the free base of milobalin; finally, the free base of milobalin is salted with benzylsulfonic acid to obtain milobalin benzylsulfonic acid. This invention stereospecifically constructs a chiral cyclobutane quaternary carbon center to obtain a chiral nitro ester with a single stereoconfiguration, avoiding the chiral isomer waste generated by chiral isomer resolution, eliminating the need for chiral column separation or chiral resolution, significantly reducing production costs, and simultaneously avoiding the environmental pollution caused by residual heavy metal titanium in the product and solid waste heavy metal titanium.

The present disclosure provides engineered enone reductase enzymes (EREDs), polypeptides having ERED activity, and polynucleotides encoding these enzymes, as well as vectors and host cells comprising these polynucleotides and polypeptides. Methods for producing ERED enzymes are also provided. The present disclosure also provides engineered ketoreductase enzymes (KREDs), polypeptides having KRED activity, and polynucleotides encoding these enzymes, as well as vectors and host cells comprising these polynucleotides and polypeptides. Methods for producing KRED enzymes are also provided. The present disclosure further provides compositions comprising the ERED and KRED enzymes and methods of using the engineered ERED and KRED enzymes. The present disclosure finds particular use in the production of pharmaceutical compounds.

Disclosed is a photosensitive resin composition comprising 20 to 60 parts by mass of an olefinic compound monomer, 20 to 60 parts by mass of an acrylate-based prepolymer, and 1 to 5 parts by mass of a photopolymerization initiator, the acrylate-based prepolymer comprising a rigid prepolymer having a functionality of 3 to 5 and a flexible prepolymer having a functionality of 2, the rigid prepolymer with the functionality of 3-5 and the flexible prepolymer with the functionality of 2 comprise one or a combination of more of epoxy acrylate, urethane acrylate and polyester acrylate, and the mass ratio of the rigid prepolymer with the functionality of 3-5 to the flexible prepolymer with the functionality of 2 is 0: 1-0.8: 1; the photopolymerization initiator comprises an oxime ester compound and a ketene compound, and finally the photosensitive resin composition which is wide in spectral response, high in curing speed and low in curing shrinkage rate and improves the curing depth regulation and control precision, the elongation at break and the tensile strength is obtained.

The invention relates to silicon-containing three-dimensional center silacyclohexenone skeleton borane as well as a preparation method and application thereof, the silicon-containing three-dimensional center silacyclohexenone skeleton borane has a structural formula as shown in a formula (I), and substituent groups R1 and R2 are respectively aryl or alkyl. According to the synthesis method of the compound, metal copper is used as a catalyst, and under the combined action of a chiral phosphine ligand and alkali, silacyclohexenone and a diborane compound are subjected to a hydroboration reaction to synthesize the compound. The synthesis method provided by the invention is simple to operate, mild in reaction condition, high in substrate universality, high in product yield and high in enantioselectivity. The synthesized compound is an important silicon-containing stereo center heterocyclic compound and can be widely applied to various fields of organic synthesis, medicine, material chemistry and fine chemical engineering.

The present application relates to the field of biological chemical industry, in particular to an alcohol dehydrogenase mutant and application thereof, the mutant is obtained by mutating one or more sites selected from 62, 108, 130, 132, 134, 182, 206, 287, 303, 313, 314 of the alcohol dehydrogenase with the amino acid sequence of SEQ ID NO: 4, the mutation is to mutate the amino acid of the site into one of A, G, V, L, I, P, F, Y, W, S, T, C, M, N, Q, D, E, K, R, H, the alcohol dehydrogenase mutant and application of the present application increase the substrate feeding amount, realize high conversion rate (> 99%) of the substrate, have good product ee value (> 98%), and it is determined that the old yellow enzyme (belongs to enone reductase) YqjM from Bacillus subtilis has the best catalytic activity, and shows good industrial application performance.

The invention discloses a preparation method of 4-(2-furyl)-3-butene-2-ketone, and relates to the technical field of heterocyclic compound preparation, and the preparation method comprises the following steps: mixing and stirring dichloromethane, pyridine vinyl ethyl ether, 2-furaldehyde and supported primary amine hydrochloride, adding a sodium bicarbonate solution, collecting an organic phase, adding a stabilizer and anhydrous sulfuric acid, stirring, filtering, washing, and drying to obtain the 4-(2-furyl)-3-butene-2-ketone. Silica gel column chromatography is used, and 4-(2-furyl)-3-butene-2-ketone is prepared; according to the method, the conversion rate of pyridine is increased by adding the supported primary amine hydrochloride; the added stabilizer can inhibit olefinic bonds in the product from generating peroxide due to oxidation, can chelate trace iron ions, copper ions and other metal ions, has good dispersibility in an organic phase, can significantly prolong the storage stability of the product, and can cooperate with the supported primary amine hydrochloride to ensure the high selectivity and conversion rate of the reaction. The loss of a target product is avoided, and the yield and the purity of the product are remarkably improved.

The application discloses a preparation method of a gamma-pyrone compound, which comprises the following steps: using a dibromo enone compound with a chemical structure general formula as shown in formula (I) and a non-terminal alkyne compound with a structure general formula as shown in formula (II) as raw materials, reacting under the action of a catalyst and an additive in an organic solvent at 100-120 DEG C for 10-24 hours to obtain a gamma-pyrone compound with a structure general formula as shown in formula (III). The dibromo enone compound and the non-terminal alkyne compound used in the method have the advantages of simple synthesis process operation, easy preparation, high conversion rate and wide substrate application range; the gamma-pyrone compound is successfully prepared by using the dibromo enone compound and the non-terminal alkyne compound as raw materials, and has the characteristics of simple and easy operation, low cost, green environmental protection, high atom economy and high yield. Since the gamma-pyrone compound is widely distributed in biological and pharmaceutical active molecules, the gamma-pyrone compound has wide application prospects.

The disclosure relates to engineered enone reductase polypeptides having improved properties, polynucleotides encoding the engineered polypeptides, related vectors, host cells, and methods for making the engineered enone reductase polypeptides. The disclosure also provides methods of using the engineered enone reductase polypeptides for chemical transformations.

The invention discloses a method for catalyzing hydrolysis of 3, 3 '-oxybis (cyclohex-2-ene-1-ketone) by using a carbon material, and under the action of a biochar loaded potassium magnesium oxide catalyst rich in strongly basic sites, the 3, 3'-oxybis (cyclohex-2-ene-1-ketone) is subjected to a hydrolysis reaction to generate 1, 3-cyclohexanedione. The raw material 3, 3 '-oxybis (cyclohex-2-ene-1-ketone) used in the method is a byproduct of 1, 3-cyclohexanedione prepared by a resorcinol method, and is low in cost and easy to obtain. According to the method, 1, 3-cyclohexanedione is prepared from 1, 3 '-oxybis (cyclohex-2-ene-1-ketone) through a catalytic hydrolysis reaction, so that by-product value increase of the CHD industry is realized, the solid waste output is reduced, the production cost of 1, 3-cyclohexanedione is reduced, and the method has relatively high social and economic effects.

This invention discloses a method for the highly selective oxidation of cyclohexene to cyclohexenone using rare-earth-based perovskite, relating to the field of cyclohexene oxidation for cyclohexenone preparation technology. It addresses the problems of existing methods being either not environmentally friendly enough, having insufficiently mild reaction conditions, or having long reaction times. This invention involves adding cyclohexene, a rare-earth-based perovskite catalyst, and a liquid-phase reaction medium to a photoreaction tube, heating the resulting mixture to 60–80°C and maintaining the temperature, intermittently introducing oxygen as an oxidant, and reacting fully under light and stirring conditions to obtain the product. This invention is simple and convenient to operate, and can complete the catalytic oxidation in a short time under mild reaction conditions with low temperature and no pressure required. The reaction process is green and mild, with high cyclohexene conversion and high selectivity for cyclohexenone, and low production cost, making it suitable for large-scale production.

The invention discloses novel spiro polyphenyl ether as well as a preparation method and application thereof. The preparation method comprises the following steps: 1) carrying out condensation reaction on 3, 5-dimethyl-4-hydroxybenzaldehyde (ketone) and aliphatic ketone under the promotion of inorganic base to obtain ketene; 2) performing catalytic hydrogenation on ketene in an organic solvent; 3) treating the hydrogenated product with acid to carry out double-spiro cyclization reaction to obtain spiro diphenol; 4) mixing 2, 6-dimethylphenol, spiro diphenol, organic amine and a phase transfer catalyst in a good solvent of polyphenyl ether, adding a hydrogen peroxide solution, and carrying out an oxidative copolymerization reaction to obtain an oxidative copolymerization reaction product solution; 5, organic acid is used for quenching the reaction solution, part of the organic solvent is removed, the reaction solution is concentrated, then a poor solvent is added, and a product is separated out and purified. The spiro polyphenyl ether prepared through the method has the advantages of being low in number-average molecular weight, few in biphenyl and quinone impurities, good in mechanical performance, chemical resistance and dielectric performance and the like, and is suitable for preparing copper-clad plates.

The invention discloses a preparation method of a di (ketene glycol) monomer (DETOSU), which adopts a DETOSU precursor as a raw material, selects LiHMDS and other specific alkali reagents, adopts a charging sequence of firstly adding the DETOSU precursor and then adding the alkali reagents, reduces the content of unilateral heterogeneous byproducts to a controllable range on the basis of ensuring medium and above reaction yield, and has the advantages of mild reaction conditions, high yield, low cost and high yield. The adoption of an n-butyllithium flammable and explosive reagent or a pentacarbonyl iron highly toxic product is avoided, and the method is more suitable for industrial large-scale production.

The invention provides a whole-cell integrated catalyst. The whole-cell integrated catalyst comprises escherichia coli whole cells for expressing alcohol dehydrogenase and monatomic palladium immobilized on the surfaces of the whole cells. The invention also provides another whole-cell integrated catalyst. The catalyst also comprises a silicon film coated on the whole cell immobilized with monatomic palladium. The catalyst provided by the invention can be used for catalyzing a ketene substrate to generate chiral alcohol with high optical purity.