5656-61-1

Basic information

• Product Name: 3H-Naphtho[1,8-bc]furan, 4,5-dihydro-
• Synonyms: 3H-Naphtho[1,8-bc]furan, 4,5-dihydro-
• CAS NO: 5656-61-1
• Molecular Formula: C11H10O
• Molecular Weight: 158.2
• Mol File: 5656-61-1.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3H-Naphtho[1,8-bc]furan, 4,5-dihydro-(CAS DataBase Reference)
• NIST Chemistry Reference: 3H-Naphtho[1,8-bc]furan, 4,5-dihydro-(5656-61-1)
• EPA Substance Registry System: 3H-Naphtho[1,8-bc]furan, 4,5-dihydro-(5656-61-1)

Safety Data

• Hazardous Substances Data: 5656-61-1(Hazardous Substances Data)

Upstream product

• 13185-18-7 8-methoxy-1-tetralone 
• 7695-47-8 8-hydroxy-1,2,3,4-tetrahydro-1-naphthalenone 
• 175886-14-3 ethyl 2-(8-oxo-5,6,7,8-tetrahydro-1-naphthyloxy)acetate 
• 57044-13-0 (8-Oxo-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-acetic acid 

Relevant articles and documents

Furan Derivatives. IV. On the Effects of Substituents in the Syntheses of 4,5-Dihydro-3H-naphthofurans

The reaction of (8-oxo-5,6,7,8-tetrahydro-1-naphthyloxy)acetic acids with acetic anhydride and sodium acetate give a mixture of 4,5-dihydro-3H-naphthofurans and lactones.The relative yiels of 4,5-dihydro-3H-naphthofurans and lactones varied according to kinds of substituents on the benzene ring of (8-oxo-5,6,7,8-tetrahydro-1-naphthyloxy)acetic acids.Substituents which make the methylene group approach closer to the carbonyl carbon atom of (8-oxo-5,6,7,8-tetrahydro-1-naphthyloxy)acetic acids by a steric effect seem to favor the production of 4,5-dihydro-3H-naphthofurans.On the other hand, substituents which make the methylene group separate from the carbonyl carbon atom seem to favor the production of lactones.An electron-withdrawing chlorine atom on the benzene ring of (8-oxo-5,6,7,8-tetrahydro-1-naphthyloxy)acetic acids also favors the production of 4,5-dihydro-3H-naphthofurans.

Photocyclization Reactions. Part 3 [1]. Synthesis of Naphtho[1,8-bc]-furans and Cyclohepta[cd]benzofurans Using Photocyclization of 8-Alkoxy-1,2,3,4-tetrahydro-1-naphthalenones and 4-Alkoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ones

Photocyclization reactions were carried out on 8-alkoxy-1,2,3,4-tetrahydro-1-naphthalenones (six-membered ring ketones) 4a-g and 4-alkoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ones (seven-membered ring ketones) 5a-e in acetonitrile. Irradiation of 4a-f gave rearranged naphthyl alcohols 8a-f as major products. In the case of 4g, 2a,3,4,5-tetrahydronaphtho[1,8-bc]furan-2a-ol 6g was obtained. In contrast, irradiation of 5a-e afforded 2,2a,3,4,5,6-hexahydrocyclohepta[cd]benzofuran-2a-ols 9a-e in good yields. The difference in reactivities between 4a-g and 5a-e is attributed to the conformation of six- and seven-membered rings. Conformational and substituent effects in cyclization step of 1,5-biradicals are discussed along with reaction pathways.