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Usage

Uses

Used in Organic Chemistry:
1-Cinnamoylpyrrole is used as a precursor for the synthesis of various organic compounds, leveraging its unique structure and reactivity to facilitate the creation of new chemical entities.
Used in Material Science:
1-Cinnamoylpyrrole is utilized as a building block in the development of new materials, capitalizing on its specific properties to enhance material performance and functionality.
Used in Pharmaceutical Development:
1-Cinnamoylpyrrole is employed as a potential component in the design and synthesis of new pharmaceuticals, with its unique structure offering opportunities for the creation of novel therapeutic agents.
Used in Research and Development:
1-Cinnamoylpyrrole is used as a subject of ongoing research to explore its potential uses and properties, contributing to the advancement of knowledge in chemistry and related fields.

Upstream product

• 696-59-3 cis,trans-2,5-dimethoxytetrahydrofuran 
• 621-79-4 cinnamamide 
• 864953-57-1 diethyl 2-oxo-2-(pyrrol-1-yl)ethylphosphonate 
• 100-52-7 benzaldehyde 
• 1370360-36-3 N-(2,4,4-trimethoxybutyl)cinnamamide 
• 109-97-7 pyrrole 
• 102-92-1 Cinnamoyl chloride 
• 54582-33-1 1,1'-carbonyldiimidazole 
• 627546-31-0 1-(1H-pyrrol-1-yl)-2-(triphenylphosphoranylidene)ethanone 

Downstream Products

• 627546-30-9 (2S,3R)-trans-2,3-epoxy-3-phenyl-1-pyrrol-1-yl-propan-1-one 
• 864953-64-0 (S)-3-methoxyamino-3-phenyl-1-pyrrol-1-yl-propan-1-one 
• 880175-74-6 (2R,3S)-2,3-epoxy-3-phenyl-1-pyrrol-1-yl-2-propan-1-one 
• 836598-15-3 (3S)-3-cyano-3-phenyl-1-pyrrol-1-ylpropan-1-one 
• 959937-02-1 [(1S,2S)-2-phenylcyclopropyl]pyrrol-1-ylmethanone 
• 1012919-13-9 dipropyl 2-(3-oxo-1-phenyl-3-(1H-pyrrol-1-yl)propyl)malonate 
• 1021867-79-7 4-nitro-3-phenyl-1-pyrrol-1-yl-butan-1-one 
• 1071992-26-1 3-phenyl-1-pyrrol-1-yl-5-hexene-1-one 
• 1349195-07-8 (1S,2R,3R)-5-methylene-2-phenyl-3-(1H-pyrrole-1-carbonyl)cyclopentanecarbonitrile 
• 1349194-96-2 ((1S,2S)-4-methylene-2-phenylcyclopentyl)(1H-pyrrol-1-yl)methanone 
• 1360768-91-7 (2S,3S)-1'-methyl-3-phenyl-3H-spiro[furan-2,3'-indoline]-2',5(4H)-dione 
• 1374418-71-9 (2R,3R)-1'-methyl-3-phenyl-3H-spiro[furan-2,3'-indoline]-2',5(4H)-dione 
• 1608108-51-5 ((1S,2S,3R)-4-methylene-2-phenyl-3-((trimethylsilyl)ethynyl)cyclopentyl)(1H-pyrrol-1-yl)methanone 
• 1608108-53-7 ((1S,2S,3R)-3-(3-((tert-butyldimethylsilyl)oxy)prop-1-yn-1-yl)-4-methylene-2-phenylcyclopentyl)(1H-pyrrol-1-yl)methanone 

Relevant academic research and scientific papers

α,β-Unsaturated N-Acylindoles: An Alternative Class of Michael Acceptors and Their Application in Asymmetric Borylation

Copper(I)-catalyzed enantioselective borylation of α,β-unsaturated N-acylindoles as well as N-acylpyrroles was efficiently achieved by means of bis(pinacolato)diboron (B2pin2), affording the enantioenriched products in excellent yields with up to 99% ee. The present work provides an alternative class of Michael acceptors, that is, α,β-unsaturated N-acylindoles, for potential asymmetric transformations.

Bifunctional Thiourea-Catalyzed Stereoablative Retro-Sulfa-Michael Reaction: Concise and Diastereoselective Access to Chiral 2,4-Diarylthietanes

Owing to the chiral recognition capacity of bifunctional thioureas, a stereoablative retro-sulfa-Michael reaction has been developed. Utilization of a biphasic system enabled us to render the process catalytic. The usefulness of this methodology was further illustrated by the diastereoselective synthesis of all possible stereoisomers of 2,4-diarylthiethanes.

A practical preparation of highly versatile N-acylpyrroles from 2,4,4-trimethoxybutan-1-amine

A novel method for the preparation of N-acylpyrrole is described. The method involves condensation of carboxylic acids with 2,4,4-trimethoxybutan-1- amine, followed by acid-mediated cyclization to form the pyrrole ring. The preparative procedure is highly

Palladium-catalyzed conjugate allylation reactions of α,β- unsaturated N- acylpyrroles

(Chemical Equation Presented) Conjugate allylation reactions of α,β-unsaturated N-acylpyrroles using allylboronic ester are catalyzed by a palladium complex that is ligated by a bidentate N-heterocyclic carbene. A variety of functional groups are tolerate

Catalytic asymmetric epoxidation of α,β-unsaturated N-acylpyrroles as monodentate and activated ester equivalent acceptors

Catalytic asymmetric epoxidation of α,β-unsaturated N-acylpyrroles as monodentate and activated ester equivalent acceptors is described. A Sm(O-i-Pr)3/(R)-H8-BINOL complex promoted the epoxidation reaction to afford products in high yield (up to quant) and high enantiomeric excess (up to >99.5% ee). Reaction proceeded smoothly using cumene hydroperoxide (CMHP) with low explosive hazard, and completed within 0.2-0.5 h with 5 mol % catalyst. Catalyst loading was successfully reduced to as little as 0.02 mol %. The N-acylpyrrole properties as well as efficient synthesis of α,β-unsaturated N-acylpyrroles are also described.

Sequential Wittig olefination-catalytic asymmetric epoxidation with reuse of waste Ph3P(O): Application of α,β-unsaturated N-Acyl pyrroles as ester surrogates

Waste not, want not: Efficient one-pot access to optically active epoxides with 96 to 99.5% ee from a variety of aldehydes is described. In a sequential process, the Ph3P(O) by-product of a Wittig reaction acts as a modulator for the samarium catalyst in the asymmetric epoxidation of the conjugated N-acyl pyrrole Wittig product (see scheme). The N-acyl pyrrole functionality is key to the high reactivity and selectivity observed. R = alkyl, aryl, vinyl.

Remarkably stable tetrahedral intermediates: Carbinols from nucleophilic additions to N-acylpyrroles

Sufficiently stable intermediates formed in the reaction of N-acylpyrroles (1) with hydride and Grignard reagents can undergo further synthetic transformations and chromatographic purification to enable the generation of pyrrolecarbinols 2 in 76-95% yields [Eq. (1)].