1313870-27-7

Basic information

• Product Name: (R)-ethyl 6-methyl-2-oxo-4-phenyl-3,4-dihydro-2H-pyran-5-carboxylate
• Synonyms: (R)-ethyl 6-methyl-2-oxo-4-phenyl-3,4-dihydro-2H-pyran-5-carboxylate
• CAS NO: 1313870-27-7
• Molecular Weight: 260.29
• Mol File: 1313870-27-7.mol
• Article Data: 16

Chemical Properties

• CAS DataBase Reference: (R)-ethyl 6-methyl-2-oxo-4-phenyl-3,4-dihydro-2H-pyran-5-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-ethyl 6-methyl-2-oxo-4-phenyl-3,4-dihydro-2H-pyran-5-carboxylate(1313870-27-7)
• EPA Substance Registry System: (R)-ethyl 6-methyl-2-oxo-4-phenyl-3,4-dihydro-2H-pyran-5-carboxylate(1313870-27-7)

Safety Data

• Hazardous Substances Data: 1313870-27-7(Hazardous Substances Data)

Upstream product

• 2579-22-8 Phenylpropargyl aldehyde 
• 141-97-9 ethyl acetoacetate 
• 104-55-2 3-phenyl-propenal 
• 14371-10-9 (E)-3-phenylpropenal 
• 5443-49-2 α-bromocinnamaldehyde 
• 21947-71-7 cinnamic anhydride 
• 14804-59-2 3-bromo-3-phenylacrylaldehyde 
• 98-86-2 acetophenone 
• 104-53-0 3-phenyl-propionaldehyde 
• 92316-02-4 1-(3-phenyl-acryloyl)-1H-[1,2,4]triazole 
• 621-82-9 Cinnamic acid 
• 140653-89-0 (E)-benzylideneglyoxylic acid potassium salt 
• 100-52-7 benzaldehyde 
• 645-45-4 hydrocinnamic acid chloride 

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.

A Method for the Analysis of Free Carbenes Present after NHC-Organocatalyzed Transformations

In N-heterocyclic carbene (NHC) based organocatalysis, usually, the free carbene is generated in situ by treatment of the azolium salt with a base. Described herein is a method for the analysis of the NHC present in the reaction flask after the NHC-organocatalyzed reaction. For this, the reaction mixture was treated with elemental sulfur after the reaction and the thus-formed thiourea/thione derivative was isolated. Common NHC-catalyzed transformations such as benzoin reactions, Stetter reactions, homoenolate annulation reactions, and reactions proceeding via the α,β-unsaturated acylazolium intermediate have been studied. The results indicate that after the reactions, 28–84 % of the initial carbenes exist in the free form.