1206-49-1

Usage

Uses

Used in Pharmaceutical Industry:
1-(2,6-Dimethyl-phenyl)-pyrrole-2,5-dione is used as a building block in organic synthesis for the development of new pharmaceuticals, leveraging its potential biological activities such as antitumor, antiviral, and antibacterial properties. Its versatility as an intermediate allows for the creation of a wide range of medicinal compounds.
Used in Agrochemical Industry:
In the agrochemical sector, 1-(2,6-Dimethyl-phenyl)-pyrrole-2,5-dione is utilized as a key intermediate in the synthesis of various agrochemicals, contributing to the development of effective products for pest and disease control in agriculture, potentially through its demonstrated biological activities.
Used in Organic Synthesis Research:
DMPD is employed as a versatile intermediate in organic synthesis research, where its chemical properties are explored and harnessed to create new compounds and materials for various applications, taking advantage of its solubility in organic solvents and its reactivity in chemical reactions.

InChI:InChI=1/C12H11NO2/c1-8-4-3-5-9(2)12(8)13-10(14)6-7-11(13)15/h3-7H,1-2H3

Upstream product

• 87-62-7 2,6-dimethylaniline 
• 198220-53-0 C₁₂H₁₃NO₃ 
• 108-31-6 maleic anhydride 

Downstream Products

• 112313-19-6 (1S,2S,6R,7R)-4-(2,6-Dimethyl-phenyl)-4-aza-tricyclo[5.2.2.0^2,6]undec-10-ene-3,5,8-trione 
• 112313-19-6 (1R,2S,6R,7S)-4-(2,6-Dimethyl-phenyl)-4-aza-tricyclo[5.2.2.0^2,6]undec-10-ene-3,5,8-trione 
• 1352335-34-2 (R)-1-(1-(2,6-dimethylphenyl)-2,5-dioxopyrrolidin-3-yl)cyclohexanecarbaldehyde 
• 1352335-29-5 (S)-1-(1-(2,6-dimethylphenyl)-2,5-dioxopyrrolidin-3-yl)cyclohexanecarbaldehyde 
• 1352335-25-1 (R)-2-(1-(2,6-dimethylphenyl)-2,5-dioxopyrrolidin-3-yl)-2-methylpropanal 
• 1352335-21-7 (S)-2-(1-(2,6-dimethylphenyl)-2,5-dioxopyrrolidin-3-yl)-2-methylpropanal 
• 1264932-11-7 ethyl 10-(2,6-dimethylphenyl)-9,11-dioxo-6,9,10,11-tetrahydro-5H-pyrrolo[3',4':3,4]pyrrolo[2,1-a]isoquinoline-8-carboxylate 

Relevant academic research and scientific papers

Unusual regio- and stereo-selectivity in Diels-Alder reactions between bulky N-phenylmaleimides and anthracene derivatives

Unusual regio- and stereo-selectivity in Diels-Alder (D-A) reactions were achieved between bulky N-phenylmaleimides and anthracene derivatives. Using multiple substituents with steric hindrance on both diene and dienophile, a noticeable shift toward 1,4-addition was successfully obtained. The substrate scope in this reaction was broad and the highest yield of anti-1,4-adducts was over 90%. Novel structures of anti-1,4-adducts were confirmed by single crystal X-ray diffraction analysis. This study not only provides the first reported method of synthesizing anti-1,4-adducts and achieving otherwise unattainable regio- and stereo-selectivity, but also elucidates the importance of combining the steric effects of two reactants to shift products toward 1,4-adducts. Moreover, the resulting 1,4-adducts could be further functionalized through their halogen groups via carbon-carbon coupling reactions.

Chemical reactivity and antimicrobial activity of N-substituted maleimides

Several N-substituted maleimides containing substituents of varying bulkiness and polarity were synthesised and tested for antimicrobial and cytostatic activity. Neutral maleimides displayed relatively strong antifungal effect minimum inhibitory concentrations (MICs in the 0.54 g ml-1 range); their antibacterial activity was structure dependent and all were highly cytostatic, with IC50 values below 0.1 g ml-1. Low antimicrobial but high cytostatic activity was noted for basic maleimides containing tertiary aminoalkyl substituents. Chemical reactivity and lipophilicity influenced antibacterial activity of neutral maleimides but had little if any effect on their antifungal and cytostatic action. N-substituted maleimides affected biosynthesis of chitin and β(1,3)glucan, components of the fungal cell wall. The membrane enzyme, β(1,3)glucan synthase has been proposed as a putative primary target of N-ethylmaleimide and some of its analogues in Candida albicans cells.

Thermal Cycloaddition of N-Arylmaleimides to Phenols: the Convenient Synthesis of Bicyclooct-2-en-5-one and Tricyclo2,8>octan-2-one Derivatives from Phenols

Monohydric phenols undergo 2,5-thermal cycloaddition of N-substituted maleimides to give bicyclooct-2-en-5-ones.Homopolymers of the maleimides are also concurrently formed, except in the case of N-(2,6-dimethylphenyl)maleimide: this is the preferred addend and gave a 63percent yield of the 2,5-adduct as a mixture of exo and endo isomers.U.v. irradiation in acetone of the diester (16) derived from the endo adduct of phenol and N-phenylmaleimide gave the tricyclo2,8>octan-3-one (17) in quantitative yield.