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WO1997024308A1 - Procede de preparation de composes carbonyle - Google Patents

Procede de preparation de composes carbonyle Download PDF

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Publication number
WO1997024308A1
WO1997024308A1 PCT/JP1996/003788 JP9603788W WO9724308A1 WO 1997024308 A1 WO1997024308 A1 WO 1997024308A1 JP 9603788 W JP9603788 W JP 9603788W WO 9724308 A1 WO9724308 A1 WO 9724308A1
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WO
WIPO (PCT)
Prior art keywords
group
substituted
methyl
substituent
oxocyclopentanecarboxylate
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP1996/003788
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English (en)
Japanese (ja)
Inventor
Toshiro Yamada
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Zeon Corp
Original Assignee
Nippon Zeon Co Ltd
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Filing date
Publication date
Application filed by Nippon Zeon Co Ltd filed Critical Nippon Zeon Co Ltd
Priority to JP52417997A priority Critical patent/JP4074341B2/ja
Publication of WO1997024308A1 publication Critical patent/WO1997024308A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
    • C07C45/676—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton by elimination of carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/317—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
    • C07C67/32—Decarboxylation

Definitions

  • the present invention relates to a method for producing a carbonyl group-containing compound. More specifically, the present invention relates to carbonyl group-containing compounds such as 2-substituted ester compounds and 2-monosubstituted ketone compounds which are useful as various fine chemical products such as pharmaceuticals, agricultural chemicals, fragrances and the like, and intermediates thereof. The present invention relates to a method for manufacturing the same.
  • ester compounds having a substituted ⁇ -position and having a carboxy group at the —position such as ⁇ -substituted malonic acid diester and ⁇ -substituted mono-jS-ketoester, are decarboxylated to obtain pharmaceuticals, agricultural chemicals and Various ester compounds and ketone compounds useful for fragrances and the like are manufactured.
  • Examples of the decarboxylation reaction of a mono-substituted malonic acid diester derivative include, for example, a method of reacting the substrate (starting material) with water at a high temperature of 200 to 260 ° C. (JP-A-53-12842).
  • a method of reacting the substrate (starting material) with an acid such as n-force bronic acid or glacial acetic acid at 195 has been reported.
  • the present inventors have conducted intensive studies in view of the above circumstances, and as a result, when a substrate is reacted with water in the presence of a phase transfer catalyst, the reaction proceeds at a low temperature, and the reaction conditions are mild. Therefore, they have found that the target compound can be obtained with high yield and high selectivity with almost no side reaction.
  • the present invention is selected from ⁇ -substituted malonic diesters and mono-substituted mono-keto esters; the S-carbonyl group-containing ester compound is reacted with water in the presence of a phase transfer catalyst. And a method for producing a carbonyl group-containing compound, which is characterized in that the compound is subjected to decarboxylation.
  • an ester compound having a carboxy group at the 9-position selected from a monosubstituted malonic acid diester and ⁇ -substituted mono ⁇ -ketoester is used.
  • the effect of the present invention can be improved. Is more prominent.
  • ⁇ -Substituted malonic acid diesters include, for example, those represented by the general formula (1)
  • R 1 represents a hydrogen atom or an organic residue
  • R 2 , R 3, and R 4 represent an organic residue
  • any of RR 2 , R 3, and R 4 combine to form a ring May be.
  • Examples of the ⁇ -substituted monoketoester include a compound represented by the general formula (2)
  • R 5 represents a hydrogen atom or an organic residue
  • R 6 , R 7 and R 8 represent an organic residue, and any one of R 5 , R 6 , R 7 and R 8 is bonded to form a ring May be formed.
  • the carbon number of the organic residue of R ′, R 2 , R 3 and R 4 in the general formula (1) or R 5 , R 6 , R 7 and R 8 in the general formula (2) is not particularly limited. However, it is usually in the range of 1 to 20, preferably 1 to 15, and more preferably 1 to 10.
  • Examples of the organic residue of RR 2 , R 3 , R 4 , R 5 , R e , R 7 and R 8 include a hydrocarbon group which may have a substituent. These organic groups may have an alkyl group which may have a substituent, an alkenyl group which may have a substituent, an alkynyl group which may have a substituent, or a group which may have a substituent.
  • alkyl group which may have a substituent examples include methyl, ethyl, n-propyl, isopropyl, n-butyl, methallyl, sec-butyl, t-butyl, n-amyl, isoamino, ⁇ —Hexyl, iso Hexyl, 3-methylpentyl, 2-methylpentyl, 1-methylpentyl, n-heptyl, isoheptyl, n-octinole, 2-ethylhexylene, n-noninole, n-tesinole, n-doasinole, n —Te trateshinore, n—Penyu Decyl, n—Kutadecyl, n—Eicosyl.
  • alkyl groups are substituents that do not adversely affect the decarboxylation reaction, for example, an alkoxy group, a halogen atom, a formyl group, an amino group, an N-substituted amino group, an N-substituted amide group, an acyl group, and an acyloxy group.
  • any substituent such as an alkylthio group.
  • an alkyl group having 1 to 10 carbon atoms having no substituent is preferable, and an alkyl group having 1 to 6 carbon atoms having no substituent is particularly preferable.
  • alkenyl groups have a substituent that does not adversely affect the decarboxylation reaction, such as an alkoxy group, a halogen atom, a formyl group, an amino group, an N-substituted amino group, an N-substituted amide group, an acyl group, A substituent such as an acyloxy group or an alkylthio group; It may be.
  • an unsubstituted alkenyl group having 2 to 10 carbon atoms is preferable, and an alkenyl group having no substituent and having 3 to 8 carbon atoms is particularly preferable.
  • these alkynyl groups are substituents which do not adversely affect the decarboxylation reaction, for example, alkoxy
  • a substituent such as a halogen atom, a formyl group, an amino group, an N-substituted amino group, an N-substituted amide group, an acyl group, an acyloxy group, or an alkylthio group.
  • alkynyl groups an unsubstituted alkynyl group having 2 to 10 carbon atoms is preferable, and an alkynyl group having no substituent and having 3 to 8 carbon atoms is particularly preferable.
  • Aralkyl and alkylidene groups are substituents that do not adversely affect the decarboxylation reaction, such as alkyl, alkoxy, halogen, formyl, amino, N-substituted It may have a substituent such as a amino group, an N-substituted amide group, an acyl group, an acyloxy group, an alkylthio group, etc.
  • an aryl group, an aralkyl group and an aryl group which may have a substituent Specific examples of the alkylidene group include, for example, phenyl group, 4-methylphenyl group, benzyl group, 2-methylbenzyl group, 3-methylbenzyl group, 4-methylbenzyl group, 4- (1-ethoxyquincarbylethyl) benzyl Group, 4-fluorobenzyl group, 4 monobromobenzyl group, 4 — Benzyl benzyl group, 4-fluoro benzylidene group, 4- benzylidene group, and the like. Of these, benzyl, 4-chlorobenzyl, 4-fluorobenzyl, 4-chlorobenzylidene and the like are preferred.
  • R 9 is a hydrogen atom or an organic residue
  • R 1 D is an organic residue
  • X is an oxycarbonyl group
  • Z is a carbonyloxy group or a carbonyl group
  • n is an integer of 1 to 6.
  • Specific examples of the organic residue of R 9 and R 1 Q in the formula are the same as the specific examples of the organic residue of R 1 in the general formula (1).
  • Z is a carbonyloxy group or a carbonyl group, preferably a carbonyl group.
  • n is preferably 3, 4 or 5, more preferably 3 or 4.
  • Preferred examples of such a cyclic compound include, for example, methyl 1-methyl-12-oxocyclopentanecarboxylate, ethyl 1-methyl-12-oxocyclopentenecarboxylate, 1-methyl-2-oxocyclopentanecarboxylate Aryl, 1-ethyl-2-oxomethyl pentanecarboxylate, 1-isopropyl-1-oxocyclopentanecarboxylate Methyl, 1-butyl-12-oxocyclopentanecarboxylate, methyl 1-pentyl-2-oxocyclopentenecarboxylate, 1-pentyl-2-ethyl oxocyclopentenecarboxylate, 1-pentyl-2-oxocyclo Propyl pentanecarboxylate, 1-Pentyl-2-oxoquinone Mouth Isopropyl pentanecarboxylate, 1-Pentyl-2-oxocyclopentyl carb
  • 1-methyl-2-O Kiso cyclopentanecarboxylic acid methyl 1-methyl-2-O Kiso cyclopentanecarboxylic acid Echiru, 1 Echiru 2 O Kiso cyclopentanecarboxylic acid methyl, 1-isopropyl Methyl pill 2-oxocyclopentanecarboxylate, 1-pentyl-2-methyl oxocyclopentanecarboxylate, 1-pentyl-12-oxocyclopentanecarboxylate, 1-hexyl_2-oxocyclopentanecarboxylate Methyl, 1- (2-butenyl) 1,2-oxoxene methyl pentanecarboxylate, 1- (2-butenyl) -1,2-oxonechloropentanecarboxylate, 1- (2-pentenyl) 1,2-oxocyclopentanecarboxylate Methyl acid, 1- (2-pentenyl
  • 1-ethyl-2-oxocyclopentanecarboxylate Methyl acrylate, methyl 1-isopropyl-2-oxocyclopentanecarboxylate, methyl 1-pentyl-12-oxocyclopentanecarboxylate, 1-Hexyl-1-2-oxoxn-methyl pentanecarboxylate, 1- (2-butenyl) -12-oxo-oxo-methyl pentanecarboxylate, 1- (2-pentenyl) -1-Methyl 2-oxone-clopentanecarboxylate, 1- (2-Hexenyl) methyl 2-oxocyclopentanecarboxylate, 1- (2-butynyl) methyl 2-oxocyclopentanecarboxylate, 1- (2-pentynyl) _2-oxocyclopentanecarboxylic acid Methyl, 3- (2-pentynyl) -1,2-o
  • carbonyl group-containing compounds produced by decarboxylation from these substrates are as follows:
  • R 1 represents a hydrogen atom or an organic residue
  • R 2 and R 3 represent an organic residue
  • any of F, R 2 and R 3 may combine to form a ring
  • R 5 represents a hydrogen atom or an organic residue
  • R 6 and R 7 represent an organic residue
  • any of R 5 , R 6 and R 7 may combine to form a ring. No.
  • the ketone compound represented by is generated.
  • R 9 is a hydrogen atom or an organic residue
  • Z is a carbonyloxy group or a carbonyl group
  • n is an integer of 1 to 6.
  • phase transfer catalyst is not particularly limited as long as it is generally used in the synthesis reaction.
  • quaternary salts such as quaternary ammonium halides and quaternary phosphonium halides
  • Polyethers such as crown ethers and polyoxyalkylene glycols; amino alcohols; and quaternary salts are particularly preferred.
  • Quaternary salts consist of a cation (positive ion) formed by the bonding of four carbon-containing substituents to a heteroatom such as a nitrogen atom and a phosphorus atom, and a counter ion (negative ion).
  • the hetero atom is not particularly limited as long as it is an atom belonging to Group 5B of the periodic table, but a nitrogen atom and a phosphorus atom are preferable.
  • the number of carbon atoms of the four carbon-containing substituents of the hetero atom is not particularly limited, but is usually 1 to 30, and more preferably 1 to 20.
  • the substituent is not particularly limited as long as it includes a carbon directly bonded to a hetero atom, and examples thereof include an alkyl group, an aryl group, an aralkyl group, an alkenyl group, and an alkynyl group.
  • These carbon-containing substituents include a substituent that does not affect the reaction of an alkoxy group, a halogen atom, an alkylthio group, and the like; a reaction of a carbonyl group, a sulfonyl group, a sulfinyl group, and the like within the carbon-containing substituent structure. Or a divalent substituent that does not affect the above. Further, the carbon-containing substituents may be bonded to each other to form a ring.
  • the carbon The contained substituent is preferably an alkyl group, an aryl group, an aralkyl group and the like. The four substituents may be used alone or in combination of two or more.
  • carbon-containing substituent examples include alkyl groups such as methyl, ethyl, propyl, butyl, octyl, peraryl, hexadecyl, etc .; phenyl, 2-methylphenyl, 4-methylphenyl, 4-methylphenyl and the like.
  • Aralkyl groups such as benzyl and 2-methylbenzyl groups; aralkyl groups such as monomethylbenzyl group, 2-methoxybenzyl group and 4-methoxybenzyl group; substituents are cyclically bonded to a nitrogen atom Pyridinium, picolinium and the like in such cases. These substituents may have a substituent that does not affect the reaction.
  • anion examples include halide, hydroxyide, hydroxysulfate and the like, and preferably halide.
  • the halide is not particularly limited, but specific examples thereof include fluoride, bromide, chloride, and iodide, and are preferably bromide and chloride.
  • quaternary salts include, for example, quaternary ammonium halides, quaternary phosphonium halides, quaternary ammonium hydroxides, quaternary phosphonium hydroxides, and quaternary ammonium hydroxides.
  • phase transfer catalyst examples include, for example, tetramethylammonium bromide, tetramethylammonium chloride, and tetraethyl.
  • Ammonium bromide Tetrapropylammonium bromide, Tetrabutylammonium bromide, Tetrabutylammonium chloride, Cetyltrimethylammonium bromide, Benzyltriethyl Quaternary ammonium halides such as ammonium chloride and trioctylmethylammonium chloride; tetrabutylphosphonium bromide, benzyltriphenylphosphonium chloride, Quaternary phosphonium halides such as butyl triphenylphosphonium bromide; 15—crown-5, 18—crown-6, dibenzo-18—crown-18, dibenzo124—crown 18-Dicyclohexyl — 18-Crown ethers such as 18-crown; poly
  • tetramethylammonium bromide tetramethylammonium bromide, tetramethylammonium bromide, tetraethylammonium bromide, tetrapropylammonium bromide, tetrabutylammonium bromide , Tetrabutylammonium chloride, cetyltrimethylammonium bromide, benzyltriethylammonium chloride, trimethylbenzylammonium bromide, and trioctylmethylammonium chloride.
  • Particularly preferred are tetrabutylphosphonium bromide, benzyltriphenylphosphonium bromide and butyltriphenylphosphonium bromide.
  • phase transfer catalysts may be used alone or in combination of two or more. They can be used together.
  • the amount of the phase transfer catalyst to be used is appropriately selected depending on the reaction conditions, and is usually 0.001 to 20% by weight, preferably 1% by weight, based on the monosubstituted malonic acid diester or ⁇ -substituted mono) ⁇ -ketoester.
  • the range is from 0.1 to 10% by weight, more preferably from 0.1 to 5% by weight.
  • the amount of water used is usually 1 mol or more, preferably 1 to 100 mol, more preferably 1 to 50 mol, and still more preferably 1 mol of ⁇ -substituted malonic acid diester or ⁇ -substituted mono- ⁇ -ketoester. Is in the range of 1.5 to 5 moles.
  • the method of introducing water into the reactor may be a method of adding water in the form of droplets or a method of adding water in the form of water vapor. It is recommended to introduce it in a form.
  • a solvent can be used if necessary.
  • the solvent is not particularly limited as long as it is stable and hard to volatilize, but nonpolar hydrocarbons, nonprotonic polar solvents and the like are usually used. Of these, non-protonic polar solvents are most preferred in terms of compatibility with the substrate and water.
  • Non-polar solvents include, for example, aliphatic hydrocarbons such as ⁇ -decane, ⁇ -tridecane, ⁇ -tetradecane, ⁇ _octadecane; alicyclic rings such as tert-butylcyclohexane, bicyclohexyl, etc.
  • Formula hydrocarbons xylene, 1,3,4,5-tetramethylbenzene, cumene, naphthalene, tetralin, butylbenzene, cyclohexylbenzene, pentylbenzene, dipentylbenzene, dodecylbenzene, biphenyl
  • aromatic hydrocarbons such as
  • Non-protonic polar solvents include, for example, sulfones such as getyl sulfone and diphenyl sulfone; sulfoxides such as dimethyl sulfoxide, methyl sulfoxide and diphenyl sulfoxide; trimethylamine, N , N, N ', N'-Tertiary amines such as tetramethylethylenediamine, N, N-dimethylaniline, N, N-Jetylaniline: N, N-dimethylformamid N-substituted amides, such as N, N-ethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone, N-phenyl-l-prolactam, etc .; N-substituted ureas such as N ', N'-tetramethylurea, 1,3-dimethyl-2-imidazolidinone; 1-nitrodecane, nitro-benz
  • solvents are used alone or in combination of two or more.
  • the amount of the solvent used is not particularly limited, but is usually 0 to 3 liters, preferably 0 to 2 liters per 100 g of the ⁇ -substituted malonic acid diester or ⁇ -substituted 1 / 3-ketoester. Torr, more preferably in the range of 0 to 1 liter.
  • the decarboxylation reaction can be performed according to a conventional method, for example, by blowing steam into a substrate or a solution in which the substrate is dissolved in a solvent.
  • the reaction temperature is usually 1 2 0-250. (, Preferably 150 to 200.C, more preferably 150 to 190 ° C, and the reaction time is usually 1 to 20 hours, preferably 1 to 10 hours, more preferably 2 to 8 hours.
  • This reaction can be carried out in a batch system under high pressure, but usually a method is employed in which the reaction is carried out while gradually supplying water under normal pressure in an open system. , The target can be separated.
  • Example 1 except that methyl 1- (2-pentynyl) 1-2-oxocyclopentanecarboxylate was replaced with methyl 1--(4-cyclobenzyl) -1,3-dimethyl_2-oxocyclopentanecarboxylate When the reaction was carried out in the same manner as in 1, 5- (4-chlorobenzyl) -1,2,2-dimethyl-1-cyc Mouth pentanone was obtained in a yield of 95%.
  • Example 2 Same as Example 1 except that methyl 1- (2-pentynyl) 1-2-year-old oxocyclopentanecarboxylate was replaced with methyl 11- (4-cyclobenzyl) -13-isopropyl-12-oxoxane methyl pentanecarboxylate As a result, 2-isopropyl-15- (4-chlorobenzyl) -11-cyclopentapentanone was obtained in a yield of 90%.
  • Example 1 was repeated except that methyl 1- (2-pentynyl) -12-oxocyclopentanecarboxylate was replaced with methyl 3- (4-cyclobenzenebenzylidene) 1-1-isopropyl-12-oxocyclopentanecarboxylate.
  • 2- (4-chlorobenzylidene) -15-isopropyl-11-cyclopentanone was obtained in a yield of 79%.
  • the reaction was carried out in the same manner as in Example 1 except that tetrabutylphosphonium bromide was not used.
  • the yield of the target product was 5%, and the conversion of the raw materials was less than 10%.
  • the desired ester or ketone compound can be obtained with good selectivity and high yield by decarboxylating the ⁇ -substituted malonic acid diester or ⁇ -substituted-3-ketoester under mild conditions. . Therefore, the method of the present invention can be advantageously used for the production of fragrance components, pharmaceuticals, agricultural chemicals, industrial chemicals and intermediates thereof on an industrial scale by utilizing such characteristics.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

Il est possible de préparer des composés carbonyle tels que des cétones ou des esters en mettant à réagir des β-carbonyle esters sélectionnés parmi des diesters d'acides maloniques à substitution α et d'esters α-substitués-β-céto avec de l'eau en présence d'un catalyseur de transfert de phase afin de mener à bien la décarboxylation.
PCT/JP1996/003788 1995-12-29 1996-12-25 Procede de preparation de composes carbonyle Ceased WO1997024308A1 (fr)

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JP52417997A JP4074341B2 (ja) 1995-12-29 1996-12-25 カルボニル基含有化合物の製造方法

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JP35254695 1995-12-29
JP7/352546 1995-12-29

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WO1997024308A1 true WO1997024308A1 (fr) 1997-07-10

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7935669B2 (en) * 2001-12-13 2011-05-03 Firmenich Sa Compounds for a controlled release of active molecules
WO2015075981A1 (fr) * 2013-11-22 2015-05-28 株式会社クレハ Procédé de préparation d'un composé carbonylé
JP2019069907A (ja) * 2017-10-06 2019-05-09 信越化学工業株式会社 （７ｅ）−７，９−デカジエン酸エステルの製造方法。
WO2023108601A1 (fr) * 2021-12-13 2023-06-22 浙江九洲药业股份有限公司 Procédé de synthèse de loxoprofène et de ses analogues

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS505321A (fr) * 1973-04-09 1975-01-21
JPS5225709A (en) * 1975-08-20 1977-02-25 Sumitomo Chem Co Ltd Process for preparaion of alpha-substituted acetones
JPS5673045A (en) * 1979-11-19 1981-06-17 Dainippon Ink & Chem Inc Preparation of farnesylacetic acid ester
JPH0578282A (ja) * 1991-09-18 1993-03-30 Kureha Chem Ind Co Ltd ３−（無置換または置換ベンジル）−１−アルキル−２−オキソシクロペンタンカルボン酸アルキルエステル誘導体、その製造方法、殺菌剤及び中間体としての利用

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS505321A (fr) * 1973-04-09 1975-01-21
JPS5225709A (en) * 1975-08-20 1977-02-25 Sumitomo Chem Co Ltd Process for preparaion of alpha-substituted acetones
JPS5673045A (en) * 1979-11-19 1981-06-17 Dainippon Ink & Chem Inc Preparation of farnesylacetic acid ester
JPH0578282A (ja) * 1991-09-18 1993-03-30 Kureha Chem Ind Co Ltd ３−（無置換または置換ベンジル）−１−アルキル−２−オキソシクロペンタンカルボン酸アルキルエステル誘導体、その製造方法、殺菌剤及び中間体としての利用

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7935669B2 (en) * 2001-12-13 2011-05-03 Firmenich Sa Compounds for a controlled release of active molecules
WO2015075981A1 (fr) * 2013-11-22 2015-05-28 株式会社クレハ Procédé de préparation d'un composé carbonylé
JP2019069907A (ja) * 2017-10-06 2019-05-09 信越化学工業株式会社 （７ｅ）−７，９−デカジエン酸エステルの製造方法。
WO2023108601A1 (fr) * 2021-12-13 2023-06-22 浙江九洲药业股份有限公司 Procédé de synthèse de loxoprofène et de ses analogues

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