80485-50-3

Upstream product

• 13522-48-0 3-(phenylthio)-but-3-en-2-one 
• 127911-15-3 (5R)-5-isopropyl-2-methylcyclohexanone 
• 80485-53-6 phenyl α-bromovinyl sulfide 
• 77202-27-8 3-(phenylthio)-3-buten-2-ol 
• 931-59-9 benzenesulfenyl chloride 
• 1822-73-7 phenylthioethylene 

Downstream Products

• 91292-06-7 3,8-dimethyl-5α-isopropyl-3-phenylthio-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one 
• 24406-03-9 (-)-7-hydroxycalamenene 
• 91292-05-6 5α-isopropyl-8-methyl-3-phenylthio-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one 
• 91292-04-5 3,8-dimethyl-5α-isopropyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one 
• 76465-67-3 7-hydroxycalamenene 

Relevant academic research and scientific papers

Reactions of 3-Phenylthiobut-3-en-2-one. Part 4. Novel and Efficient Synthesis of 7-hydroxycalamenene, Ferruginol, and D-Homoestrone

The annelation reaction of 3-phenylthiobut-3-en-2-one with carvomenthone (1) gives 8a-hydroxy-4α-isopropyl-1-methyl-6-phenylthioperhydronaphthalen-7-one (2), which is converted into 7-hydroxycalamenene (4) by subsequent dehydration, methylation, and aroma

Reactions of 3-(Phenylthio)-3-buten-2-one with Cycloalkanones. A New Approach to Fused Phenols

Synthesis and properties of 3-(phenylthio)-3-buten-2-one (7) have been described.The butenone 7 reacted with lithium cycloalkanone enolates to give ketols 14 or diketones 15 in good yields, which were easily transformed into fused phenols 17 by the treatment with p-toluenesulfonic acid or sodium ethoxide, respectively.Oxidative elimination of the sulfenyl group of 14a afforded also 2-naphthol 17a.Tetrahydronaphthalene 23, a key intermediate of calamenene 1a and calamenenal 1b, was successfully synthesized by this approach by starting from l-carvone (19).Bicyclooctanone 25 was obtained in the reaction of 7 with kinetic enolate of 2-cyclohexen-1-one in 84percent yield.