6129-15-3

Usage

Uses

Used in Polymer Synthesis:
(R)-(+)-N-(1-PHENYLETHYL)MALEIMIDE is used as a monomer in radical copolymerization with styrene to yield a ~1:1 copolymer with a high degree of polymerization (~98%). This copolymer is of interest due to its potential use in the development of advanced materials.
Used in Nonlinear Optical Materials:
(R)-(+)-N-(1-PHENYLETHYL)MALEIMIDE is used as a building block for the creation of vinyl copolymers with asymmetric main chains. These copolymers are valuable in the field of nonlinear optical materials, which have applications in areas such as optical communication and photonics.
Used in Organic Synthesis:
(R)-(+)-N-(1-PHENYLETHYL)MALEIMIDE serves as a dienophile in diastereoselective Diels-Alder reactions. This application is significant in organic synthesis, as it allows for the selective formation of specific stereoisomers, which is crucial for the development of pharmaceuticals and other specialty chemicals.

InChI:InChI=1/C12H11NO2/c1-9(10-5-3-2-4-6-10)13-11(14)7-8-12(13)15/h2-9H,1H3/t9-/m1/s1

Upstream product

• 33139-83-2 N-(1-phenylethyl)maleamidic acid 
• 618-36-0 rac-methylbenzylamine 
• 108088-06-8 C₁₂H₁₃NO₃ 
• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 108-31-6 maleic anhydride 
• 33139-83-2 N-(R)-(+)-1-phenylethylmaleamic acid 

Downstream Products

• 89143-22-6 1'-(1-Phenyl-ethyl)-[1,3']bipyrrolidinyl-2',5'-dione 
• 89143-34-0 1-(1-Phenyl-ethyl)-3-piperidin-1-yl-pyrrolidine-2,5-dione 
• 138118-39-5 4-Methoxy-2-(1-phenyl-ethyl)-3a,4,7,7a-tetrahydro-isoindole-1,3-dione 
• 138118-36-2 (3aS,7aR)-5-tert-Butyl-2-((R)-1-phenyl-ethyl)-3a,4,7,7a-tetrahydro-isoindole-1,3-dione 
• 1232046-26-2 (3aR,6aR)-5,6a-dihydro-1-phenyl-5-[(1R)-1-phenylethyl]-3-[4-(trifluoromethyl)phenyl]pyrrolo[3,4-c]pyrazole-4,6(1H,3aH)dione 
• 1354908-71-6 4-[(3aS,6aS)-3,4,5,6,6a-tetrahydro-3-(4-methylphenyl)-4,6-dioxo-5-[(1R)-1-phenylethyl]pyrrolo[3,4-c]pyrazol-1-yl]benzonitrile 
• 1354908-73-8 (3aS,6aS)-1-(4-chlorophenyl)-5,6a-dihydro-3-(4-nitrophenyl)-5-[(1R)-1-phenylethyl]pyrrolo[3,4-c]pyrazole-4,6(1H,3aH)dione 
• 1354908-53-4 (3aR,6aR)-5,6a-dihydro-1,3-diphenyl-5-[(1R)-1-phenylethyl]pyrrolo[3,4-c]pyrazole-4,6(1H,3aH)dione 
• 1354908-51-2 (3aS,6aS)-5,6a-dihydro-1,3-diphenyl-5-[(1R)-1-phenylethyl]pyrrolo[3,4-c]pyrazole-4,6(1H,3aH)dione 
• 1354908-66-9 (3aS,6aS)-5,6a-dihydro-3-(4-methoxyphenyl)-1-phenyl-5-[(1R)-1-phenylethyl]pyrrolo[3,4-c]pyrazole-4,6(1H,3aH)dione 
• 1354908-63-6 4-[(3aS,6aS)-1,3a,4,5,6,6a-hexahydro-4,6-dioxo-1-phenyl-5-[(1R)-1-phenylethyl]pyrrolo[3,4-c]pyrazol-3-yl]benzonitrile 

Relevant academic research and scientific papers

Synthesis and biological evaluation of novel pyrrolidine acid analogs as potent dual PPARα/γ agonists

The design, synthesis and structure-activity relationships of a novel series of 3,4-disubstituted pyrrolidine acid analogs as PPAR ligands is outlined. In both the 1,3- and 1,4-oxybenzyl pyrrolidine acid series, the preferred stereochemistry was shown to be the cis-3R,4S isomer, as exemplified by the potent dual PPARα/γ agonists 3k and 4i. The N-4-trifluoromethyl-pyrimidinyl pyrrolidine acid analog 4i was efficacious in lowering fasting glucose and triglyceride levels in diabetic db/db mice.

An unexpected formation of the novel 7-oxa-2-azabicyclo[2.2.1]hept-5-ene skeleton during the reaction of furfurylamine with maleimides and their bioprospection using a zebrafish embryo model

An unexpected intramolecular cyclization during the reaction of furfurylamine with maleimides is reported as a novel strategy for the efficient green synthesis of the 7-oxa-2-azabicyclo[2.2.1]hept-5-ene skeleton. Under the same reaction conditions, 7-oxabicyclo[2.2.1]hept-5-enes were synthesized when furfurylamine was N-protected by the acetyl group. Both types of bicycloheptenes were screened using the zebrafish model system for genetics and developmental biology. The Royal Society of Chemistry 2013.

Heat-resistant poly(N-(1-phenylethyl)maleimide-co-styrene) microspheres prepared by dispersion polymerization

This article reports on a novel type of polymeric microsphere consisting of poly(N-(1-phenylethyl)maleimide-co-styrene) (poly(N-PEMI-co-St)) and showing remarkable heat resistance. Such microspheres were prepared by dispersion polymerization with 2,2′-azo

Synthesis and stereochemistry of some novel dihydropyrrolo[3,4-c]pyrazoles

Eleven novel dihydropyrrolo[3,4-c]pyrazole derivatives were obtained by the reaction of chiral (1R)-N-(1-phenylethyl)maleimide and C,N-aryl-substituted nitril-imines. The reaction afforded the cycloadducts as a regioisomeric mixture which can be separable in some cases. The structure and stereochemistry of cycloadducts were assigned on the basis of infrared (IR), 1H and 13C nuclear magnetic resonance (NMR), mass and X-ray spectra, optical rotation measurements, and CHN analyses.

A facile synthesis of N-substituted maleimides

A simple and efficient method for the synthesis of N-substituted maleimides from the corresponding maleamic acids under the phase transfer catalysis has been described.

A flexible approach to methyl (5S)-5-alkyltetramate derivatives

Regioselective Grignard reagent additions to 3-methoxymaleimides and subsequent diastereoselective reductive dehydroxylation of the resulting N,O-acetals were studied. On the basis of these studies, a flexible and highly regio- and diastereoselective approach to methyl 5-alkyltetramate derivatives was disclosed. The method is the first direct and flexible asymmetric cationic synthon-based approach, and allows for the synthesis of various methyl (5S)-5-alkyltetramate derivatives that are otherwise inaccessible by the commonly used methods based on α-amino acids. Georg Thieme Verlag Stuttgart.

Base-induced alcoholysis of N-arylmaleimides: Facile in situ oxa-Michael addition to alkyl maleanilates: Two-step one-pot rapid access to alkoxysuccinic acids

A simple, efficient and general two-step, one-pot approach to alkoxysuccinic acids is described. The potassium carbonate-catalyzed reactions of alcohols with N-p-tolylmaleimide (4) followed by an acid-induced hydrolysis of intermediate products furnished alkoxysuccinic acids 1a-f in 90-98% yields. All the intermediates from the reaction of imide 4 with alcohols have been isolated and characterized, proving that the in situ formed alkyl maleanilates 3 are the actual Michael acceptors.

Solvent free N-alkyl and N-arylimides preparation from anhydrides catalyzed by TaCl5-silica gel

The first Lewis acid catalyzed and solvent free procedure for the preparation of imides from the corresponding anhydrides is described involving TaCl5-silica gel as Lewis acid under microwave irradiation.

Use of readily available monomers in the synthesis of vinyl copolymers with optical activity arising from the configuration of stereogenic carbon atoms in the main chain

The present work was aimed at synthesising vinyl copolymers with optical activity arising only from the configuration of the stereogenic carbon atoms in the main chain. By copolymerising optically active diesters of fumaric acid with styrene, backbones wi

7-oxabicycloheptane carboxylic acid prostaglandin analog intermediates useful in the preparation of anti-thrombotic and anti-vasospastic compounds and method for preparing same

A method is provided for preparing carboxylic acid intermediates of the structure STR1 wherein an aldehyde of the structure STR2 is prepared and subjected to a Horner-Emmons reaction to form the ester of the structure STR3 and the ester is hydrogenated to the carboxylic acid which may be used in making the final anti-thrombotic--anti-vasospastic compounds.