60925-76-0

Usage

Uses

Used in Organic Synthesis:
(S)-(-)-N-(1-PHENYLETHYL)MALEIMIDE is used as a dienophile in Diels-Alder reactions for the formation of cyclic compounds, which are crucial in the synthesis of complex organic molecules.
Used in Enzymatic Reactions:
(S)-(-)-N-(1-PHENYLETHYL)MALEIMIDE serves as a substrate in enzymatic reactions, where enzymes catalyze specific chemical transformations, contributing to the synthesis of various organic compounds.
Used in Pharmaceutical Preparation:
(S)-(-)-N-(1-PHENYLETHYL)MALEIMIDE is utilized as a reagent in the preparation of pharmaceuticals, playing a key role in the development of new drugs and therapeutic agents.
Used in Agrochemical Synthesis:
It is also employed in the synthesis of agrochemicals, contributing to the development of pesticides and other agricultural chemicals that protect crops and enhance agricultural productivity.
Used in the Synthesis of Biologically Active Compounds:
(S)-(-)-N-(1-PHENYLETHYL)MALEIMIDE acts as a building block in the synthesis of various biologically active compounds, which have potential applications in medicine, biotechnology, and other fields.

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-/m0/s1

Upstream product

• 3886-69-9 (R)-1-phenyl-ethyl-amine 
• 108-31-6 maleic anhydride 
• 33139-83-2 N-(R)-(+)-1-phenylethylmaleamic acid 
• 541-59-3 maleiimide 
• 1517-69-7 (R)-1-phenylethanol 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 33139-84-3 (Z)-3-((S)-1-Phenyl-ethylcarbamoyl)-acrylic acid 
• 108088-06-8 C₁₂H₁₃NO₃ 
• 618-36-0 rac-methylbenzylamine 
• 33139-83-2 N-(1-phenylethyl)maleamidic acid 

Downstream Products

• 335117-41-4 3-Benzylsulfanyl-1-((S)-1-phenyl-ethyl)-pyrrolidine-2,5-dione 
• 335117-25-4 5-Hydroxy-1-((S)-1-phenyl-ethyl)-5-phenylethynyl-1,5-dihydro-pyrrol-2-one 
• 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 

Relevant academic research and scientific papers

Maleimide-based metal-free ligation with dienes: A comparative study

A brief literature survey reveals that metal-free ligation such as the maleimide-based cycloaddition with electron-rich (hetero)dienes is a widespread tool for the assembly of (bio)molecular systems with applications in biotechnology, materials science, polymers and bio-organic chemistry. Despite their everyday use, only scattered data about their kinetics as well as the stabilities of corresponding products under physiological conditions, are accessible. These key parameters are yet, of paramount importance to ensure the rapid and effective preparation of stable compounds. Herein is reported a systematic study regarding the different classes of dienes used in chemoselective ligation, including their accessibility and stability, as well as comparative kinetic experiments and products stability assays. We took advantage of these data to develop a double labeling strategy from the combined use of cyclopentadiene and oxazole dienes.

Cp?Co(III)-Catalyzed C-H Alkylation with Maleimides Using Weakly Coordinating Carbonyl Directing Groups

A novel protocol for ortho-C-H alkylation of aromatic and heteroaromatic ketones and esters under Cp?Co(III) catalysis has been developed for the first time. The reaction proceeds through initial cyclometalation via weak chelation-assisted C-H bond activation, followed by coordination of activated alkene, insertion between Co-C, and protodemetalation.

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.

Synthesis and reactivity of (1S)-N-(1-phenylethyl)maleimide towards nucleophiles: An application to preparation of chiral pyrroloisothiochroman and pyrrolobenzo[d]thiepine based on π-cationic cyclization

Chiral pyrroloisothiochroman and pyrrolo[d]thiepine were obtained efficiently in four steps from N-alkylated maleimides via, successively, sulfurization, regioselective reduction followed by π-cationic cyclization of the N-acyliminium ion intermediates. These latter, in addition, led to conjugate enamides as a consequences of the dehydration reaction.