872427-96-8

Basic information

• Product Name: (+/-)-(E)-1-hydroxy-1-(4-methoxyphenyl)hex-4-en-3-one
• Synonyms: (+/-)-(E)-1-hydroxy-1-(4-methoxyphenyl)hex-4-en-3-one
• CAS NO: 872427-96-8
• Molecular Weight: 220.268
• Mol File: 872427-96-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (+/-)-(E)-1-hydroxy-1-(4-methoxyphenyl)hex-4-en-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-(E)-1-hydroxy-1-(4-methoxyphenyl)hex-4-en-3-one(872427-96-8)
• EPA Substance Registry System: (+/-)-(E)-1-hydroxy-1-(4-methoxyphenyl)hex-4-en-3-one(872427-96-8)

Safety Data

• Hazardous Substances Data: 872427-96-8(Hazardous Substances Data)

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 3102-33-8 trans-3-penten-2-one 

Downstream Products

• 872428-15-4 (+/-)-4-(tert-butyldimethylsilyloxy)-1-cyclohexylidene-4-(4-methoxyphenyl)butan-2-one 
• 872428-14-3 (+/-)-(E)-5-(tert-butyldimethylsilyloxy)-5-(4-methoxyphenyl)-1-phenylpent-1-en-3-one 
• 872428-17-6 (+/-)-1-(tert-butyldimethylsilyloxy)-7-hydroxy-1-(4-methoxyphenyl)hept-4-en-3-one 
• 872428-01-8 (+/-)-(E)-1-(tert-butyldimethylsilyloxy)-1-(4-methoxyphenyl)hex-4-en-3-one 
• 123-11-5 4-methoxy-benzaldehyde 
• 3102-33-8 trans-3-penten-2-one 
• 847057-00-5 (S)-(E)-1-hydroxy-1-(4-methoxyphenyl)hex-4-en-3-one 

Relevant articles and documents

A catalytic asymmetric bioorganic route to enantioenriched tetrahydro- and dihydropyranones

A conceptually novel approach to hetero Diels-Alder adducts of carbonyl compounds is described using as the key steps an antibody-mediated kinetic resolution of hydroxyenones followed by a ring-closure process. Various β-hydroxyenones proved to be very good substrates for antibodies 84G3- and 93F3-catalyzed retro-aldol reactions, allowing the preparation of highly enantiomerically enriched (up to 99% ee) precursors of pyranones. An attractive feature of this methodology is the possibility to convert these acyclicenantioenriched β-hydroxyenones into tetrahydropyranones by a conventional Michael-type addition procedure or into the corresponding dihydropyranones using an alternative palladium-catalyzed oxidative ring closure. For the palladium-mediated cyclization, a biphasic system has been implemented that allows the direct preparation of enantiopure dihydropyranones from the corresponding racemic aldol precursors using a sequential antibody-resolution/palladium-cyclization strategy, without isolation of the intermediate enantioenriched hydroxyenones. This bioorganic route is best applied to the preparation of hetero Diels-Alder adducts otherwise derived from less nucleophilic dienes and unactivated dienophiles.