90909-25-4

Basic information

• Product Name: 3-methoxycarbonyl-2,3-dihydrothiin-4-one
• CAS NO: 90909-25-4
• Molecular Weight: 172.205
• Mol File: 90909-25-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 3-methoxycarbonyl-2,3-dihydrothiin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-methoxycarbonyl-2,3-dihydrothiin-4-one(90909-25-4)
• EPA Substance Registry System: 3-methoxycarbonyl-2,3-dihydrothiin-4-one(90909-25-4)

Safety Data

• Hazardous Substances Data: 90909-25-4(Hazardous Substances Data)

Upstream product

• 25012-75-3 3-methoxycarbonylthian-4-one S-oxide 
• 4160-61-6 3-methoxycarbonyltetrahydropyran-4-one 

Relevant articles and documents

THE SYNTHESIS OF THIATHROMBOXANE ANALOGUES

Thiathromboxane analogues (2) and (19) have been prepared by an extremely short and efficient synthetic route which can also be employed to make simple 2,3-dialkylated thian-4-ones.The cornerstone of the synthetic strategy is the organocopper conjugate addition - enolate alkylation reactions of 3-methoxycarbonyl-5,6-dihydrothiin-4-one (1b).

Pummerer Rearrangements Using Chlorotrimethylsilane

Attempted Pummerer rearrangement of 3-methoxycarbonylthian-4-one S-oxide in refluxing acetic anhydride gives unexpected products in which β-carbon oxidation and ring contraction has taken place.Treatment of 3-methoxycarbonylthian-4-one with N-chlorosuccinimide gives similar rearrngement products.These rearrangements are rationalised by the intermediacy of a common thiiranium ion.Chlorotrimethylsilane in refluxing tetrachloromethane efficiently effects the expected Pummerer rearrangement of 3-methoxycarbonylthian-4-one S-oxide into the corresponding α,β-unsaturated sulphides.Reactions of this reagent with related sulphoxides are also described.