84583-07-3

Basic information

• Product Name: methyl 3-methyl-4-oxotetrahydro-2H-thiopyran-3-carboxylate
• CAS NO: 84583-07-3
• Molecular Formula: C₈H₁₂O₃S
• Molecular Weight: 188.2441
• Mol File: 84583-07-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 283.3°C at 760 mmHg
• Flash Point: 131.5°C
• Density: 1.187g/cm³
• Vapor Pressure: 0.00319mmHg at 25°C
• Refractive Index: 1.503
• CAS DataBase Reference: methyl 3-methyl-4-oxotetrahydro-2H-thiopyran-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 3-methyl-4-oxotetrahydro-2H-thiopyran-3-carboxylate(84583-07-3)
• EPA Substance Registry System: methyl 3-methyl-4-oxotetrahydro-2H-thiopyran-3-carboxylate(84583-07-3)

Safety Data

• Hazardous Substances Data: 84583-07-3(Hazardous Substances Data)

Upstream product

• 4131-74-2 Dimethyl 3,3'-thiodipropionate 
• 4160-61-6 3-methoxycarbonyltetrahydropyran-4-one 
• 84583-06-2 Potassium salt of 3-Carbomethoxytetrahydrothiopyran-4-one 
• 74-88-4 methyl iodide 
• 127956-09-6 methyl 3-phenylselenomethyl-1-thiacyclohexan-4-one-3-carboxylate 

Downstream Products

• 84583-08-4 3-methyldihydro-2H-thiopyran-4(3H)-one 

Relevant articles and documents

Free Radical Ring-Expansion Leading to Novel Six- and Seven-Membered Heterocycles

Free radical promoted ring-expansion of nitrogen-, oxygen- and sulfur-containing heterocyclic β-keto esters is described.Treatment of the derived phenylselenomethyl derivatives with tri-n-butyltin hydride leads to smooth one-carbon ring expansion.

Enzymes in Organic Synthesis. 27. Horse Liver Alcohol Dehydrogenase Catalyzed Oxidoreductions of 3-Alkylthiopyran Ketones and Alcohols

The stereospecificity of horse liver alcohol dehydrogenase (HLADH) toward S-heterocyclic substrates has been studied further.While 3-methyl- and 3-ethyltetrahydrothiopyran-4-ones (1) and -4-ols (2,3) are not good substrates, the ketones 1 and trans alcohols 3 do undergo highly stereoselective enzyme-mediated oxidoreductions in preparative-scale (up to 2 g of substrate) reactions.In contrast, HLADH-catalyzed oxidations of the cis alcohols 2 are too slow to be preparatively viable.Reductions of the racemic ketones 1 occur with high enantiomeric- and stereoselectivity,with the 3S enantiomers being converted in excellent yields to the corresponding 3S,4S trans alcohols 3 of 78-90 percent ee.The unreactive 3R ketone enantiomers of 58-66 percent ee are recovered from the same reactions.Oxidations of the racemic trans alcohols 3 are also markedly stereoselective, permitting the unreactive (3R,4R)-3 enantiomers of 65-85 percent ee to be isolated in good yields.