32744-30-2

Basic information

• Product Name: 2-phenyl-4,5-dihydro-3H-naphtho<1,8-bc>furan
• CAS NO: 32744-30-2
• Molecular Weight: 234.298
• Mol File: 32744-30-2.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-phenyl-4,5-dihydro-3H-naphtho<1,8-bc>furan(CAS DataBase Reference)
• NIST Chemistry Reference: 2-phenyl-4,5-dihydro-3H-naphtho<1,8-bc>furan(32744-30-2)
• EPA Substance Registry System: 2-phenyl-4,5-dihydro-3H-naphtho<1,8-bc>furan(32744-30-2)

Safety Data

• Hazardous Substances Data: 32744-30-2(Hazardous Substances Data)

Upstream product

• 100-44-7 benzyl chloride 
• 2882-19-1 ethyl 2-phenyl-2-bromoacetate 
• 88058-45-1 8-benzyloxy-1,2,3,4-tetrahydro-1-naphthalenone 
• 7695-47-8 8-hydroxy-1,2,3,4-tetrahydro-1-naphthalenone 

Relevant articles and documents

Photocyclization Reactions. Part 4 [1]. Synthesis of Naphtho[1,8-bc]-furans and Cyclohepta[cd]benzofurans Using Photocyclization of Ethyl 2-(8-Oxo-5,6,7,8-tetrahydro-1-naphthyloxy)acetates and Ethyl 2-(5-Oxo-6,7,8,9-tetrahydro-5H-benzocyclohepten-4-yloxy)acetates

Photocyclization reactions were carried out on ethyl 2-(8-oxo-5,6,7,8-tetrahydro-1-naphthyloxy)acetates 1a-e and ethyl 2-(5-oxo-6,7,8,9-tetrahydro-5H-benzocyclohepten-4-yloxy)acetates 2a-e in acetonitrile. Irradiation of 1a-e gave naphtho[1,8-bc]furanols 3a-e and naphtho[1,8-bc]furans 4a-e in 33-83% yields and ethyl acrylates 5b-d were produced in 3-25% yields during irradiation of 1b-d. On the other hand, 2a-e afforded cyclohepta[cd]benzofuranols 6a-e and cyclohepta[cd]benzofurans 7a-e in 44-87% yields. Ethyl acrylates 8b-d were also produced in 7-43% yields from irradiation of 2b-d. Substituent effects on photocyclization and reaction pathways are discussed.

Conformational Effects in Photocyclization of Six and Seven-membered Ring Alkoxyketones

Irradiation of 8-alkoxytetrahydro-1-naphthalenones 5 gave rearranged naphthyl alcohols 11 as major products and in contrast, 4-alkoxytetrahydrobenzocyclohepten-5-ones 6 afforded tetrahydrocycloheptabenzofurans 14 in good yields; the difference in reactivities is attributed to the conformation of six- and seven-membered rings.