1072-87-3

Usage

Uses

Used in Polymer and Resin Production:
3-Methylpyrrole-2,5-dione is used as a key component in the production of various polymers and resins. Its chemical properties allow it to contribute to the formation and stability of these materials, enhancing their performance in different applications.
Used in Pharmaceutical and Agrochemical Synthesis:
3-Methylpyrrole-2,5-dione serves as an important intermediate in the synthesis of pharmaceuticals and agrochemicals. Its unique structure enables it to be incorporated into the development of new drugs and agricultural products, potentially improving their efficacy and safety.
Used in Organic Chemistry as a Dienophile:
3-Methylpyrrole-2,5-dione is utilized as a dienophile in the Diels-Alder reaction, an organic chemical reaction that creates cyclic compounds. Its reactivity in this process allows for the formation of complex molecular structures, which can be further used in various chemical and pharmaceutical applications.
It is important to handle 3-methylpyrrole-2,5-dione with care, as prolonged exposure or ingestion can cause irritation or harm to the respiratory system and skin, and it is considered toxic if swallowed or inhaled.

InChI:InChI=1/C5H5NO2/c1-3-2-4(7)6-5(3)8/h2H,1H3,(H,6,7,8)

Upstream product

• 625-82-1 2,4-dimethyl-1H-pyrrole 
• 6641-34-5 (3-methyl-2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-urea 
• 498-23-7 citraconic acid 
• 616-02-4 citraconic acid anhydride 
• 26608-34-4 Etioporphyrin III 
• 5522-66-7 3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester 
• 81971-99-5 deuteroporphyrin IX dimethyl ester 
• 2644-60-2 χ-phylloporphyrin-XV 
• 7564-40-1 N-carbamylcitraconimide 

Downstream Products

• 73383-82-1 1-Benzyl-3-methyl-2,5-dihydropyrrole-2,5-dione 
• 84165-67-3 7-Carbamoyl-7-methyl-5-oxo-1,2,3,5,6,7-hexahydro-indolizine-8-carboxylic acid ethyl ester 
• 84165-61-7 (4-Methyl-2,5-dioxo-pyrrolidin-3-yl)-pyrrolidin-(2Z)-ylidene-acetic acid ethyl ester 
• 69636-49-3 2,3-dichloro-2-methylsuccinimide 
• 165606-93-9 3-(dichloromethylene)-4,4-dichloro-2,5-pyrrolidinedione 
• 339152-94-2 3-chloro-4-dichloromethyl-pyrrole-2,5-dione 
• 69636-50-6 3-chloro-4-methyl-1H-pyrrole-2,5-dione 
• 940055-61-8 3-(2-aminobenzylamino)-3-methylpyrrolidine-2,5-dione 
• 150254-86-7 (+/-)-(E)-3-(4-Methoxyphenyl)-N-<4-(3-methyl-2,5-dioxo-1-pyrrolidinyl)butyl>-2-propenamide 
• 128866-07-9 (+/-)-(E)-3-(4-Hydroxyphenyl)-N-[4-(3-methyl-2,5-dioxo-1-pyrrolidinyl)butyl]-2-propenamide 
• 50656-76-3 (R)-(-)-5-hydroxy-3-methyl-3-pyrrolin-2-one 
• 209802-54-0 (E)-pulchellalactam 
• 209802-54-0 (Z)-pulchellalactam 

Relevant academic research and scientific papers

Synthesis of aminal-type Lilium candidum alkaloids and lilaline; determination of their relative configuration by the concerted use of NMR spectroscopy and DFT conformational analysis

We hereby report the synthesis of six racemic alkaloids isolated from Lilium candidum L. Their common structural feature is a five-membered lactam ring which is, in the case of the flavonoid alkaloid lilaline, attached to the molecule's aromatic core, while in the case of the other five compounds, it is connected to the nitrogen atom of a pyrrolinone ring by an aminal function. The syntheses of these natural products were achieved via Mannich-type alkylations through cyclic N-acyliminium ions as intermediates. Besides the synthesis, the so far unexplored stereochemistry of these natural products was determined by a combination of NMR-based proton–proton distance measurements and theoretical conformational analyses carried out at the DFT level.

Recombinant Cyanobacteria for the Asymmetric Reduction of C=C Bonds Fueled by the Biocatalytic Oxidation of Water

A recombinant enoate reductase was expressed in cyanobacteria and used for the light-catalyzed, enantioselective reduction of C=C bonds. The coupling of oxidoreductases to natural photosynthesis allows asymmetric syntheses fueled by the oxidation of water. Bypassing the addition of sacrificial cosubstrates as electron donors significantly improves the atom efficiency and avoids the formation of undesired side products. Crucial factors for product formation are the availability of NADPH and the amount of active enzyme in the cells. The efficiency of the reaction is comparable to typical whole-cell biotransformations in E. coli. Under optimized conditions, a solution of 100 mg prochiral 2-methylmaleimide was reduced to optically pure 2-methylsuccinimide (99 % ee, 80 % yield of isolated product). High product yields and excellent optical purities demonstrate the synthetic usefulness of light-catalyzed whole-cell biotransformations using recombinant cyanobacteria.

The first experimental demonstration of side chain extension of geoporphyrins in sediments

To investigate the formation process of high carbon number (>C 32) sedimentary porphyrins, heating experiments of several porphyrins were performed. Chromic acid oxidation of the heating products of protoporphyrin IX dimethyl ester afforded 2-methyl-3-npropylmaleimide as the predominant product among the side-chain extension products formed. On the other hand, saturated substituents of etioporphyrin were also extended on heating to slowly form normal and branched homologs. These results may suggest that the transalkylation of porphyrin side chains proceeds mainly by a regioselective mechanism involving alkyl radical addition to a vinyl group of chlorophylls or their diagenetic products.

Pyrrolidine(thi)ones Substituted by Heterocyclic Substituents in The 3-Position

Pyrrolidine(thi)one compounds substituted by heterocyclic substituents in the 3-position, their preparation and use in pharmaceutical compositions, in particular as immunomodulators for treatment and/or inhibition of inflammatory and autoimmune diseases and haematological-oncological diseases.

Asymmetric bioreduction of C=C bonds using enoate reductases OPR1, OPR3 and YqjM: Enzyme-based stereocontrol

Three cloned enoate reductases from the "old yellow enzyme" family of flavoproteins were investigated in the asymmetric bioreduction of activated alkenes. 12-Oxophytodienoate reductase isoenzymes OPR1 and OPR3 from Lycopersicon esculentum (tomato), and YqjM from Bacillus subtilis displayed a remarkably broad substrate spectrum by reducing α,β-unsaturated aldehydes, ketones, maleimides and nitroalkenes. The reaction proceeded with absolute chemoselectivity-only the conjugated C=C bond was reduced, while isolated olefins and carbonyl groups remained intact-with excellent stereoselectivities (ees up to >99%). Upon reduction of a nitroalkene, the stereochemical outcome could be determined via choice of the appropriate enzyme (OPR1 versus OPR3 or YqjM), which furnished the corresponding enantiomeric nitroalkanes in excellent ee. Molecular modelling suggests that this "enzyme-based stereocontrol" is caused by subtle differences within the active site geometries.

Asymmetric bioreduction of activated C=C bonds using Zymomonas mobilis NCR enoate reductase and old yellow enzymes OYE 1-3 from yeasts

The asymmetric bioreduction of C=C-bonds bearing an electron-withdrawing group, such as an aldehyde, ketone, imide, nitro, carboxylic acid, or ester moiety by a novel enoate reductase from Zymomonas mobilis and Old Yellow Enzymes OYE 1-3 from yeasts furnished the corresponding saturated products in up to >99%ee. Depending on the substrate type, stereocontrol was achieved by variation of the substrate structure, by switching the (E/Z) geometry of the alkene or by choice of the appropriate enzyme. This substrate- or enzyme-based stereocontrol allowed access to the opposite enantiomeric products. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Method for the preparation of dicarboxylic imides

The present invention relates to a method for the preparation of a carboxylic imide having the general formula [in-line-formulae]R1—(CO)—(NR3)—(CO)—R2 , ??(I)[/in-line-formulae] wherein a carboxylic anhydride having the general formula [in-line-formulae]R1—(CO)—O—(CO)—R2 ??(II)[/in-line-formulae] is reacted with urea or a urea derivative of the form (R3HN)—(CO)—(NR3H) in a solvent. In particular, the method can be used for the preparation of thalidomide.

Convenient synthesis of pulchellalactam, a CD45 protein tyrosine phosphatase inhibitor from the marine fungus Corollospora pulchella, and its related compounds

Convenient synthesis of pulchellalactam (1a) and its related compounds was accomplished. Total yields of (Z)-pulchellalactam and (E)-pulchellalactam were 55% for 5 steps and 43% for 8 steps from commercially available and inexpensive citraconic anhydride, respectively.

A new maturity indicator of sedimentary organic matter based on thermal fission of allylic bond in porphyrins

A 3-ethyl-4-methylpyrrole unit in etioporphyrin was shown to be converted to a 3,4-dimethylpyrrole unit by the action of heat, which was proved to be catalyzed by Na-montmorillonite. Time courses of the reaction could be followed by analyzing 2-ethyl-3-me

First synthesis of (R)-(-)-5-hydroxy-3-methyl-3-pyrrolin-2-one (jatropham) by lipase-catalyzed kinetic resolution

Jatropham, (R)-(-)-5-hydroxy-3-methyl-3-pyrrolin-2-one, is synthesized in three steps from citraconic anhydride. Highly regioselective reduction of citraconimide gives racemic jatropham in high yield. Kinetic resolution of racemic jatropham using lipase is also described. (C) 1999 Elsevier Science Ltd.