202258-17-1

Basic information

• Product Name: 7-(6-Benzenesulfonyl-5-hydroxy-4,4-dimethyl-hexyl)-3-isopropyl-4-methoxy-bicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile
• CAS NO: 202258-17-1
• Molecular Weight: 469.645
• Mol File: 202258-17-1.mol

Chemical Properties

• CAS DataBase Reference: 7-(6-Benzenesulfonyl-5-hydroxy-4,4-dimethyl-hexyl)-3-isopropyl-4-methoxy-bicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 7-(6-Benzenesulfonyl-5-hydroxy-4,4-dimethyl-hexyl)-3-isopropyl-4-methoxy-bicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile(202258-17-1)
• EPA Substance Registry System: 7-(6-Benzenesulfonyl-5-hydroxy-4,4-dimethyl-hexyl)-3-isopropyl-4-methoxy-bicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile(202258-17-1)

Safety Data

• Hazardous Substances Data: 202258-17-1(Hazardous Substances Data)

Upstream product

• 128291-71-4 7-(4,4-Dimethyl-hex-5-enyl)-3-isopropyl-4-methoxy-bicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile 
• 3112-85-4 methylphenylsulfonate 
• 162888-68-8 7-(4,4-Dimethyl-5-oxo-pentyl)-3-isopropyl-4-methoxy-bicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile 

Downstream Products

• 202258-21-7 7-((E)-6-Benzenesulfonyl-4,4-dimethyl-hex-5-enyl)-3-isopropyl-4-methoxy-bicyclo[4.2.0]octa-1,3,5-triene-7-carboxylic acid methyl ester 
• 162888-69-9 1-(4,4-Dimethyl-6-phenylsulfonylhex-5-enyl)-4-isopropyl-5-methoxy-1,2-dihydrobenzocyclobutene-1-carbonitrile 

Relevant articles and documents

Synthesis of pisiferol revisited; control of stereochemistry in an intramolecular Diels-Alder reaction

Thermolysis of 4(X=H) gives 6a and 6b(X=H) in a ratio of 1:4 whereas 4 (X=SO2Ph) gives more of trans-ring junction product 6a(X=SO2Ph) suitable for the synthesis of pisiferol [ratio 6a: 6b(X=S)2Ph) = 1.5:1].

Control of stereochemistry in an intramolecular Diels-Alder reaction by the phenylsulfonyl group; an improved synthesis of pisiferol

Thermolysis of 4a (X = H) gives 6a and 6b (X = H) in a ratio of 1:4 whereas 4b (X = SO2Ph) gives more of the trans-ring junction product 6a (X = SO2Ph) suitable for the synthesis of pisiferol [ratio 6a:6b (X = SO2Ph) = 1.5:1]. Base catalysed elimination of the phenylsulfonyl group from 6a (X = SO2Ph) gives 18 which is hydrogenated to 6a (X = H), an intermediate in the synthesis of pisiferol. Both 6a and 6b (X = SO2Ph) have ring B in a half-boat conformation.