1415754-66-3

Basic information

• Product Name: 2,6-diethyl-2-(ethylthio)-3,5-dimethyl-2H-pyran-4(3H)-one
• CAS NO: 1415754-66-3
• Molecular Weight: 242.382
• Mol File: 1415754-66-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2,6-diethyl-2-(ethylthio)-3,5-dimethyl-2H-pyran-4(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-diethyl-2-(ethylthio)-3,5-dimethyl-2H-pyran-4(3H)-one(1415754-66-3)
• EPA Substance Registry System: 2,6-diethyl-2-(ethylthio)-3,5-dimethyl-2H-pyran-4(3H)-one(1415754-66-3)

Safety Data

• Hazardous Substances Data: 1415754-66-3(Hazardous Substances Data)

Upstream product

• 121811-29-8 ethyl 2-methyl-3-oxopentanoate 
• 1415754-48-1 3,3-bis(ethylthio)-2-methylpentanal 
• 1415754-60-7 7,7-bis(ethylthio)-5-hydroxy-4,6-dimethylnonan-3-one 
• 1415754-72-1 3,3-bis(ethylthio)-2-methylpentan-1-ol 
• 1415754-70-9 ethyl 3,3-bis(ethylthio)-2-methylpentanoate 

Relevant articles and documents

A versatile method for the synthesis of γ-pyrones

A versatile three-step procedure to annulate a γ-pyrone onto a methylene ketone was developed involving (i) aldol reaction with a dithiolane-protected β-ketoaldehyde, (ii) oxidation of the aldol adduct to a β-diketone, and (iii) treatment of the resulting dithiolane-protected 1,3,5-trione with 2-iodoxybenzoic acid (IBX) and trifluoromethanesulfonic acid (triflic acid; TfOH) in acetonitrile at ambient temperature to give the corresponding γ-pyrone. Cyclization proceeded with IBX alone, but significantly improved yields were obtained with added acid, particularly triflic acid. A dithiolane was more effective than a dithiane or acyclic dithioacetal protecting group. The method was amenable to the preparation of a variety of substituted γ-pyrones simply by altering the initial aldol reactants. Overall yields of 50%-60% were obtained in six examples. The method was applied to prepare a key fragment for the total synthesis of baconipyrones A and C and siphonarin B.