1352755-81-7

Basic information

• Product Name: (S)-5-acetyl-6-methyl-4-phenyl-3,4-dihydro-2H-pyran-2-one
• Synonyms: (S)-5-acetyl-6-methyl-4-phenyl-3,4-dihydro-2H-pyran-2-one
• CAS NO: 1352755-81-7
• Molecular Weight: 230.263
• Mol File: 1352755-81-7.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: (S)-5-acetyl-6-methyl-4-phenyl-3,4-dihydro-2H-pyran-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-5-acetyl-6-methyl-4-phenyl-3,4-dihydro-2H-pyran-2-one(1352755-81-7)
• EPA Substance Registry System: (S)-5-acetyl-6-methyl-4-phenyl-3,4-dihydro-2H-pyran-2-one(1352755-81-7)

Safety Data

• Hazardous Substances Data: 1352755-81-7(Hazardous Substances Data)

Upstream product

• 33603-90-6 (2Z)-2-bromo-3-phenyl-2-propenal 
• 123-54-6 acetylacetone 
• 102-92-1 Cinnamoyl chloride 
• 38986-89-9 3-phenylacryloyl fluoride 
• 645-45-4 hydrocinnamic acid chloride 
• 104-55-2 3-phenyl-propenal 
• 92316-02-4 1-(3-phenyl-acryloyl)-1H-[1,2,4]triazole 
• 98-86-2 acetophenone 
• 14804-59-2 3-bromo-3-phenylacrylaldehyde 
• 5443-49-2 α-bromocinnamaldehyde 
• 104-53-0 3-phenyl-propionaldehyde 

Downstream Products

• 108056-65-1 methyl (S)-(-)-5-oxo-3-phenylhexanoate 

Relevant articles and documents

Enantioselective Synthesis of 3,4-Dihydropyran-2-ones via Phase-Transfer-Catalyzed Addition-Cyclization of Acetylacetone to Cinnamic Thioesters

Herein, we present the first example of synthesis of 3,4-dihydropyran-2-ones from cinnamic thioesters via a stereoselective phase-transfer-catalyzed domino Michael-cyclization reaction with acetylacetone. The reaction proceeded under the catalysis of Cinchona-derived quaternary ammonium phenoxide that, in combination with inorganic bases, provided 3,4-dihydropyran-2-ones in yields of up to 93% and enantioselectivities of up to 88% enantiomeric excess.

Oxidative NHC catalysis: direct activation of β sp3 carbons of saturated acid chlorides

The first activation of saturated acid chlorides by oxidative N-heterocyclic carbene catalysis has been successfully utilized to synthesize enantio-enriched spirooxindole lactones and δ-lactones. The reaction involves the transformation of the β sp3 carbon of saturated acid chlorides into an electrophilic carbon as a key step. The product was obtained in excellent yield and stereoselectivity.

Aerobic Oxidation/Annulation Cascades through Synergistic Catalysis of RuCl3 and N-Heterocyclic Carbenes

Cooperative catalysis combining a transition metal with an N-heterocyclic carbene is challenging due to strong binding of NHCs towards late transition metals. We report the first example of synergistic catalysis by a chiral NHC and a coordinatively unsaturated ruthenium compound. RuCl3 was found to mediate efficient aerobic oxidation of homoenolates generated from enals and the N-heterocyclic carbene. The resulting α,β-unsaturated acylazolium intermediate reacts selectively with 1,3-dicarbonyl compounds or ketones at either the β- or γ-carbon, yielding polysubstituted chiral lactones in high yield and with excellent enantioselectivity (up to 98 % yield, 94 % ee). This protocol can be applied to structurally sophisticated substrates.