94450-91-6

Basic information

• Product Name: 2H-Pyran-2-one, tetrahydro-4-[(2-methylphenyl)methyl]-3-(phenylthio)-, trans-
• CAS NO: 94450-91-6
• Molecular Formula: C19H20O2S
• Molecular Weight: 312.433
• Mol File: 94450-91-6.mol

Chemical Properties

• CAS DataBase Reference: 2H-Pyran-2-one, tetrahydro-4-[(2-methylphenyl)methyl]-3-(phenylthio)-, trans-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-Pyran-2-one, tetrahydro-4-[(2-methylphenyl)methyl]-3-(phenylthio)-, trans-(94450-91-6)
• EPA Substance Registry System: 2H-Pyran-2-one, tetrahydro-4-[(2-methylphenyl)methyl]-3-(phenylthio)-, trans-(94450-91-6)

Safety Data

• Hazardous Substances Data: 94450-91-6(Hazardous Substances Data)

Upstream product

• 931-59-9 benzenesulfenyl chloride 
• 882-33-7 diphenyldisulfane 
• 94451-06-6 2-(phenylthio)-2-penten-5-olide 
• 89-92-9 2-methylbenzyl bromide 
• 56812-61-4 2-methylbenzylmagnesium bromide 
• 89036-08-8 2-(phenylthio)-5-pentanolide 
• 542-28-9 3,4,5,6-tetrahydro-2H-pyran-2-one 

Relevant articles and documents

An Useful Synthetic Method for 3-Substituted δ-Lactones. Synthesis of (+/-)-Secocrispiolide

2-Phenylthio-2-penten-5-olide (1) acted as a reactive Michael acceptor toward some typical carbon nucleophiles to give 3-substituted 2-phenylthio-5-pentanolides (2) which were convertible both to 3-substituted 5-pentanolides by reductive desulfurization and to 3-substituted 2-penten-5-olides by sulfenic acid syn elimination of the sulfoxides 4 derived from 2.The Pummerer rearrangement of 4 provided 3-substituted 2-phenylthio-2-penten-5-olides and/or 2-hydroxy-2-penten-5-olides. (+/-)-Secocrispiolide was synthesized via the adduct obtained by the Michael reaction of 1 with the Grignard reagent prepared from 2,6-dimethylbenzyl bromide and magnesium.

THE MICHAEL REACTION OF 2-(PHENYLTHIO)-2-PENTEN-5-OLIDE WITH SOME BENZYLIC GRIGNARD REAGENTS. SYNTHESIS OF SECOCRISPIOLIDE

The electrophilic reactivity of 2-(phenylthio)-2-penten-5-olide toward some benzylic Grignard reagents was investigated, and 2-methylene-3-(2,6-dimethylbenzyl)-5-pentanolide (secocrispiolide) was synthesized from one of the Michael adducts.