100420-10-8

Basic information

• Product Name: 4-phenyl-1-(pyrrolidin-1-yl)butan-1-one
• Synonyms: 4-phenyl-1-(pyrrolidin-1-yl)butan-1-one
• CAS NO: 100420-10-8
• Molecular Weight: 217.311
• Mol File: 100420-10-8.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 4-phenyl-1-(pyrrolidin-1-yl)butan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-phenyl-1-(pyrrolidin-1-yl)butan-1-one(100420-10-8)
• EPA Substance Registry System: 4-phenyl-1-(pyrrolidin-1-yl)butan-1-one(100420-10-8)

Safety Data

• Hazardous Substances Data: 100420-10-8(Hazardous Substances Data)

Upstream product

• 123-75-1 pyrrolidine 
• 1370291-65-8 potassium 3-phenylpropanoyltrifluoroborate 
• 1821-12-1 4-Phenylbutyric acid 
• 1008-76-0 4,5-dihydro-5-phenyl-2(3H)-furanone 
• 2051-95-8 succinylbenzene 
• 99802-88-7 4-hydroxy-4-phenyl-1-(pyrrolidine-1-yl)butan-1-one 
• 18496-54-3 phenylbutyric acid chloride 

Downstream Products

• 3056-71-1 N-phenyl-4-phenylbutyramide 

Relevant articles and documents

Synthesis of secondary and tertiary amides without coupling agents from amines and potassium acyltrifluoroborates (KATs)

Although highly effective for most amide syntheses, the activation of carboxylic acids requires the use of problematic coupling reagents and is often poorly suited for challenging cases such as N-methyl amino acids. As an alternative to both secondary and tertiary amides, we report their convenient synthesis by the rapid oxidation of trifluoroborate iminiums (TIMs). TIMs are easily prepared by acid-promoted condensation of potassium acyltrifluoroborates (KATs) and amines and are cleanly and rapidly oxidized to amides with hydrogen peroxide. The overall transformation can be conducted either as a one-pot procedure or via isolation of the TIM. The unique nature of the neutral, zwitterionic TIMs makes possible the preparation of tertiary amides via an iminium species that would not be accessible from other carbonyl derivatives and can be conducted in the presence of unprotected functional groups including acids, alcohols and thioethers. In preliminary studies, this approach was applied to the late-stage modifications of long peptides and the iterative synthesis of short, N-methylated peptides without the need for coupling agents.

Chemoselective α,β-Dehydrogenation of Saturated Amides

We report a method for the selective α,β-dehydrogenation of amides in the presence of other carbonyl moieties under mild conditions. Our strategy relies on electrophilic activation coupled to in situ selective selenium-mediated dehydrogenation. The α,β-unsaturated products were obtained in moderate to excellent yields, and their synthetic versatility was demonstrated by a range of transformations. Mechanistic experiments suggest formation of an electrophilic SeIV species.

Chemoselective Intermolecular Cross-Enolate-Type Coupling of Amides

A new approach for the synthesis of 1,4-dicarbonyl compounds is reported. Chemoselective activation of amide carbonyl functionality and subsequent umpolung via N-oxide addition generates an electrophilic enolonium species that can be coupled with a wide range of nucleophilic enolates. The method conveys broad functional group tolerance on both components, does not suffer from formation of homocoupling byproducts and avoids the use of transition metal catalysts.