10420-33-4

Usage

Uses

Used in Pharmaceutical Industry:
Dimethyl acetylsuccinate is used as a key intermediate in the preparation of β-carbolines via diastereoand enantioselective Bronsted acid catalyzed N-acyliminium cyclization cascades of tryptamines and keto acids/esters. This application is significant for the development of novel pharmaceuticals with potential therapeutic properties.
Used in Chemical Synthesis:
Dimethyl acetylsuccinate is used as a building block in the synthesis of complex organic molecules, such as 2-oxofuro[2,3-b]pyrroles and 19-methyl-15-oxa-20-azatricyclo[12.3.3.0(1,14)]icos-18-en-18-carboxylates. These synthesized compounds can be further utilized in various chemical and pharmaceutical applications, showcasing the versatility of dimethyl acetylsuccinate in different industries.

InChI:InChI=1/C8H12O5/c1-5(9)6(8(11)13-3)4-7(10)12-2/h6H,4H2,1-3H3

Upstream product

• 108-24-7 acetic anhydride 
• 624-48-6 dimethyl cis-but-2-ene-1,4-dioate 
• 7039-93-2 2,5-Dihydrofuran-2,5-dimethoxy-2-methylfuran-3-carbonsaeuremethylester 
• 112799-49-2 5-Methoxy-2-methylfuran-3-carbonsaeuremethylester 
• 186581-53-3 diazomethane 
• 21634-63-9 methyl methyl-2-(1-methylethenyl)-2-hexenoate 
• 67-56-1 methanol 
• 107-25-5 methoxyethene 
• 201230-82-2 carbon monoxide 
• 123-63-7 paracetaldehyde 
• 105-57-7 diethyl acetal 
• 94-36-0 dibenzoyl peroxide 
• 6141-58-8 methyl 2-methyl-3-furancarboxylate 

Downstream Products

• 62214-19-1 (4-hydroxy-2-mercapto-6-methyl-5-pyrimidinyl)-acetic acid 
• 162498-48-8 (4-chloro-2,6-dimethyl-pyrimidin-5-yl)-acetic acid methyl ester 
• 5536-40-3 (2,6-dimethyl-4-hydroxy-pyrimidin-5-yl)-acetic acid 
• 1189155-54-1 (5-methoxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-acetic acid methyl ester 
• 111526-25-1 (1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-acetic acid methyl ester 
• 1011416-46-8 (3-methyl-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-4-yl)-acetic acid methyl ester 
• 162498-46-6 (4-chloro-6-methyl-pyrimidin-5-yl)-acetic acid methyl ester 
• 229498-64-0 (5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)-acetic acid methyl ester 
• 664365-94-0 methyl 2-[7-[2-(4-fluorophenyl)-2-oxoethoxy]-4,8-dimethyl-2-oxo-2H-3-chromenyl]acetate 
• 500204-29-5 methyl 2-[7-[2-(3-methoxyphenyl)-2-oxoethoxy]-4,8-dimethyl-2-oxo-2H-3-chromenyl]acetate 
• 664366-00-1 methyl 2-[7-[2-(4-methoxyphenyl)-2-oxoethoxy]-4,8-dimethyl-2-oxo-2H-3-chromenyl]acetate 
• 664365-98-4 methyl 2-[7-[2-(4-bromophenyl)-2-oxoethoxy]-4,8-dimethyl-2-oxo-2H-3-chromenyl]acetate 
• 664365-96-2 methyl 2-[7-[2-(4-chlorophenyl)-2-oxoethoxy]-4,8-dimethyl-2-oxo-2H-3-chromenyl]acetate 

Relevant academic research and scientific papers

Synthetic method of dimethyl acetyl succinate

The invention relates to a synthetic method of dimethyl acetyl succinate. The synthetic method comprises the following steps: esterification reaction; acetylation reaction: adding dimethyl maleate andmethanol into a reactor, starting stirring, dropwise adding acetic anhydride into the reactor, adding sodium borohydride solid powder at the same time, and performing a constant-temperature reactionto obtain an acetyl compound solution; extracting: adjusting the pH value of the acetyl compound solution by using a sodium carbonate solution; adding the solution into a rotary evaporator, evaporating excessive methanol and part of water in the solution, putting the rest part into a separating funnel, standing for layering, separating out a water phase, washing an organic phase with purified water, evaporating residual water in the organic phase in vacuum, and slowly cooling to the normal temperature to obtain a dimethyl acetyl succinate solid. Acetic anhydride is used as an acylating agent for acetylation reactions, the optimal reaction conditions are selected, the reaction yield is increased to 96.71%, the reaction process is carried out under a normal pressure, and the influence of thepurity of dimethyl maleate on the yield of DMAS is reduced.

Alkoxycarbonylcarbene Transfer to Acyclic Tertiary Enaminones

Copper-catalyzed alkoxycarbonylcarbene transfer from methyl or tert-butyl diazoacetate to acyclic enaminoesters 6a,b and enaminocarboxanilide 13 yields vicinal push-pull-substituted cyclopropanes 7a,b, 8, and 14. In contact with dry silica gel, the latter compounds undergo facile ring-opening leading to enaminoesters 9,10, and 15. Treatment with aqueous acid transforms 9 and 10 into 2-acylsuccinates 11 and 12, and 15 into pyrrolinone 16. Methoxycarbonylcarbene transfer to enaminoketones 1a-c does not yield isolable cyclopropanes, but after hydrolytic work-up α-acyl-γ-ketoesters 2a-c are obtained.

THE PHOTOCHEMISTRY OF METHYL GERANATE, A MODEL CHROMOPHORE FOR INSECT JUVENILE HORMONE ANALOGS

The irradiation of methyl geranate (3) in ether using 254 nm lamps produces methyl 5-methyl-2-isopropenyl-4-hexenoate (13), 1,6,6-trimethyl-endo-5-carbomethoxybicyclo-hexane (11), methyl 2-isopropenyl-5-methylcyclopentanecarboxylate (12) and methyl (3Z)-3,7-dimethyl-3,6-octadienoate (14).Photolysis run in water or in ether in the presence of base generates two additional dienes: methyl 3-methylene-7-methyl-6-octaenoate (16) and methyl (3E)-3,7-dimethyl-3,6-octadienoate (17).The photolysis of methyl (2E, 6E)-3,7-dimethyl-2,6-nonadienoate (4a) in ether procedures all Z/E isomers, 4a - 4d.

4-(Phenylthio)-pyrrole-3-carboxylic Acid Esters

Dihydro(dimethoxy)methylfurancarboxylic acid esters 4A/4B have been applied to the synthesis of the title compounds.With amines as catalysts they react with thiophenols to give the addition products 12a-d, which upon heating with acids eliminate methanol to form the furancarboxylic acid esters 13a-b and 17, whereas reactions with ammonia or amines lead to the pyrrolecarboxylic acid esters 20a-e.Reactions of 4 with 2-aminothiophenol yield the fused pyrrole and pyrrolidine derivatives 15 and 16.Compounds 20b and e were transformed to the benzothiopyranopyrrole carboxylic acid esters 23a and b.