1202-10-4

Basic information

• Product Name: 2,6-diethyl-3,5-dimethyl-4H-pyran-4-one
• Synonyms: 2,6-diethyl-3,5-dimethyl-4H-pyran-4-one;2,6-Diethyl-3,5-dimethyl-4-pyranone;3,5-Dimethyl-2,6-diethyl-4H-pyran-4-one;2,6-diethyl-3,5-dimethyl-pyran-4-one;2,6-diethyl-3,5-dimethylpyran-4-one;4H-Pyran-4-one, 2,6-diethyl-3,5-dimethyl-;Mixture of (2R,3S)- and (2R,3R)-6-Ethyl-2,3-Dihydro-2,3,5-trimethyl-4H-pyran-4-one
• CAS NO: 1202-10-4
• Molecular Formula: C₁₁H₁₆O₂
• Molecular Weight: 180.25
• Mol File: 1202-10-4.mol
• Article Data: 4

Chemical Properties

• Melting Point: 38.7 °C
• Boiling Point: 140-150 °C(Press: 10 Torr)
• Appearance: /
• Density: 0.9887 g/cm3(Temp: 50 °C)
• CAS DataBase Reference: 2,6-diethyl-3,5-dimethyl-4H-pyran-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-diethyl-3,5-dimethyl-4H-pyran-4-one(1202-10-4)
• EPA Substance Registry System: 2,6-diethyl-3,5-dimethyl-4H-pyran-4-one(1202-10-4)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 1202-10-4(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 31, p. 5619, 1990 DOI: 10.1016/S0040-4039(00)97913-9

Upstream product

• 123-62-6 propionic acid anhydride 
• 13460-50-9 metaboric acid 
• 1415754-49-2 6-(2-ethyl-1,3-dithiolan-2-yl)-5-hydroxy-4-methylheptan-3-one 
• 1415754-59-4 C₁₄H₂₆O₂S₂ 
• 1415754-60-7 7,7-bis(ethylthio)-5-hydroxy-4,6-dimethylnonan-3-one 
• 1413945-57-9 2-(2-ethyl-1,3-dithian-2-yl)propanal 
• 1415754-48-1 3,3-bis(ethylthio)-2-methylpentanal 
• 121811-29-8 ethyl 2-methyl-3-oxopentanoate 
• 1228104-09-3 2-(2-ethyl-1,3-dithiolan-2-yl)propanal 
• 96-22-0 pentan-3-one 
• 1415754-72-1 3,3-bis(ethylthio)-2-methylpentan-1-ol 
• 1415754-70-9 ethyl 3,3-bis(ethylthio)-2-methylpentanoate 
• 1413945-54-6 2-(2-ethyl-1,3-dithian-2-yl)propan-1-ol 
• 1413945-52-4 ethyl 2-(2-ethyl-1,3-dithian-2-yl)propanoate 

Downstream Products

• 151831-92-4 4,5-Diethyl-3-<3-(2'-furyl)-2,2-bis(phenylsulfonyl)propyl>-6-methyl-2H-pyran-2-one 
• 151832-04-1 2,6-Diethyl-3-<3-(2'-furyl)-2,2-bis(phenylsulfonyl)propyl>-5-methyl-4H-pyran-4-one 
• 1114889-20-1 C₃₄H₃₈O₄ 

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.

Mild conditions for cyclization of β-triketides to the corresponding γ-pyrones carrying adjacent chiral centers toward biomimetic synthesis of fully substituted γ-pyrone-containing natural products

Related to synthetic study on γ-pyrone-containing natural products, conversions of β-triketides having unstable substituents to the corresponding γ-pyrones have successfully been accomplished by the new methods under conditions using (CH3)2S+C1 or Ph3P+CX3 (or Ph3P+X, X =C1, Br) as the oxygen acceptors.