206446-98-2

Basic information

• Product Name: 2-Pentanone, 4-hydroxy-5-phenyl-
• CAS NO: 206446-98-2
• Molecular Formula: C11H14O2
• Molecular Weight: 178.231
• Mol File: 206446-98-2.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 2-Pentanone, 4-hydroxy-5-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Pentanone, 4-hydroxy-5-phenyl-(206446-98-2)
• EPA Substance Registry System: 2-Pentanone, 4-hydroxy-5-phenyl-(206446-98-2)

Safety Data

• Hazardous Substances Data: 206446-98-2(Hazardous Substances Data)

Upstream product

• 122-78-1 phenylacetaldehyde 
• 67-64-1 acetone 
• 1118-84-9 allyl acetoacetate 
• 1833-53-0 2-(Trimethylsilyloxy)propene 
• 100303-82-0 1-methoxy-2-phenylethanol 
• 61077-65-4 1-phenylpent-4-en-2-ol 
• 101-41-7 benzeneacetic acid methyl ester 

Downstream Products

• 3318-61-4 1-phenyl-2,4-pentanedione 

Relevant articles and documents

Selective access to all four diastereomers of a 1,3-amino alcohol by combination of a keto reductase- and an amine transaminase-catalysed reaction

The biocatalytic synthesis of chiral amines has become a valuable addition to the chemists' toolbox. However, the efficient asymmetric synthesis of functionalised amines bearing more than one stereocentre, such as 1,3-amino alcohols, remains challenging. By employing a keto reductase (KRED) and two enantiocomplementary amine transaminases (ATA), we developed a biocatalytic route towards all four diastereomers of 4-amino-1-phenylpentane-2-ol as a representative molecule bearing the 1,3-amino alcohol functionality. Starting from a racemic hydroxy ketone, a kinetic resolution using an (S)-selective KRED provided optically active hydroxy ketone (86% ee) and the corresponding diketone. Further transamination of the hydroxy ketone was performed by either an (R)- or an (S)-selective ATA, yielding the (2R,4R)- and (2R,4S)-1,3-amino alcohol diastereomers. The remaining two diastereomers were accessible in two subsequent asymmetric steps: the diketone was reduced regio- and enantioselectively by the same KRED, which yielded the (S)-configured hydroxy ketone. Eventually, the subsequent transamination of the crude product with (R)- and (S)-selective ATAs yielded the remaining (2S,4R)- and (2S,4S)-diastereomers, respectively.

Decarboxylative aldol reactions of allyl β-keto Esters via heterobimetallic catalysis

Mild and selective heterobimetallic-catalyzed decarboxylative aldol reactions involving allyl β-keto esters have been developed. The reaction is promoted by Pd(0)- and Yb(III)-DIOP complexes at room temperature and involves the in situ formation of a ketone enolate from allyl β-keto esters followed by addition of the enolate to aldehydes. The reaction is a new example of heterobimetallic catalysis in which the optimized reaction conditions require the addition of both metals. Copyright