16206-31-8

Basic information

• Product Name: ethyl 2,5-dimethyl-4-phenyl-1H-pyrrole-3-carboxylate
• CAS NO: 16206-31-8
• Molecular Formula: C₁₅H₁₇NO₂
• Molecular Weight: 243.301
• Mol File: 16206-31-8.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 415.9°C at 760 mmHg
• Flash Point: 205.3°C
• Density: 1.105g/cm³
• Vapor Pressure: 3.99E-07mmHg at 25°C
• Refractive Index: 1.561
• CAS DataBase Reference: ethyl 2,5-dimethyl-4-phenyl-1H-pyrrole-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 2,5-dimethyl-4-phenyl-1H-pyrrole-3-carboxylate(16206-31-8)
• EPA Substance Registry System: ethyl 2,5-dimethyl-4-phenyl-1H-pyrrole-3-carboxylate(16206-31-8)

Safety Data

• Hazardous Substances Data: 16206-31-8(Hazardous Substances Data)

Upstream product

• 91473-89-1 5--4,5-dihydro-2,5-dimethyl-4-phenyl-3-furancarbonsaeure-ethylester 
• 4187-87-5 1-Phenyl-2-propyn-1-ol 
• 141-97-9 ethyl acetoacetate 
• 1539-44-2 2,6-dimethyl-4-phenyl-pyridine-3,5-dicarboxylic acid diethyl ester 
• 5303-65-1 3-aminobutanoic acid ethyl ester 
• 579-07-7 1-Phenylpropane-1,2-dione 
• 1165-06-6 Diethyl 2,6-dimethyl-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate 
• 705-60-2 (2-nitroprop-1-enyl)benzene 
• 201230-82-2 carbon monoxide 
• 105-36-2 ethyl bromoacetate 
• 75-05-8 acetonitrile 
• 626-34-6 ethyl aminocrotonate 
• 591-51-5 phenyllithium 
• 231609-65-7 ethyl 3-(1-(N-methoxy-N-methylcarbamoyl)ethylamino)crotonate 

Relevant articles and documents

Transaminase-Mediated Amine Borrowing via Shuttle Biocatalysis

Shuttle catalysis has emerged as a useful methodology for the reversible transfer of small functional groups, such as CO and HCN, and goes far beyond transfer hydrogenation chemistry. While a biocatalytic hydrogen-borrowing methodology is well established, the biocatalytic borrowing of alternative functional groups has not yet been realized. Herein, we present a new concept of amine borrowing via biocatalytic shuttle catalysis, which has no counterpart in chemo-shuttle catalysis and allows efficient intermolecular amine shuttling to generate reactive intermediates in situ. By coupling this dynamic exchange with an irreversible downstream step to displace the reaction equilibrium in the forward direction, high conversion to target products can be achieved. We showcase the potential of this amine-borrowing methodology using a biocatalytic equivalent of both the Knorr-pyrrole synthesis and Pictet-Spengler reaction.

Chemo-Enzymatic Synthesis of Pyrazines and Pyrroles

Herein we report the biocatalytic synthesis of substituted pyrazines and pyrroles using a transaminase (ATA) to mediate the key amination step of the ketone precursors. Treatment of α-diketones with ATA-113 in the presence of a suitable amine donor yielded the corresponding α-amino ketones which underwent oxidative dimerization to the pyrazines. Selective amination of α-diketones in the presence of β-keto esters afforded substituted pyrroles in a biocatalytic equivalent of the classical Knorr pyrrole synthesis. Finally we have shown that pyrroles can be prepared by internal amine transfer catalyzed by a transaminase in which no external amine donor is required.

Iron-catalyzed tandem one-pot addition and cyclization of the blaise reaction intermediate and nitroolefins: Synthesis of substituted NH-pyrroles from nitriles

The iron-catalyzed addition and cyclization of the Blaise reaction intermediate and nitroolefins to synthesize highly functionalized NH-pyrroles in a tandem one-pot manner from nitriles has been developed. This reaction shows good functional group tolerance and affords a broad spectrum of substituted NH-pyrroles in good yields. Copyright