199609-59-1

Basic information

• Product Name: 3-Bromo-2-hydroxy-7-(4-methoxy-phenyl)-cyclohepta-2,4,6-trienone
• Synonyms: 3-Bromo-2-hydroxy-7-(4-methoxy-phenyl)-cyclohepta-2,4,6-trienone
• CAS NO: 199609-59-1
• Molecular Weight: 307.144
• Mol File: 199609-59-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3-Bromo-2-hydroxy-7-(4-methoxy-phenyl)-cyclohepta-2,4,6-trienone(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Bromo-2-hydroxy-7-(4-methoxy-phenyl)-cyclohepta-2,4,6-trienone(199609-59-1)
• EPA Substance Registry System: 3-Bromo-2-hydroxy-7-(4-methoxy-phenyl)-cyclohepta-2,4,6-trienone(199609-59-1)

Safety Data

• Hazardous Substances Data: 199609-59-1(Hazardous Substances Data)

Upstream product

• 130163-29-0 2-methoxy-7-(4-methoxy-phenyl)-cycloheptatrienone 
• 92254-30-3 α-(4-methoxyphenyl)tropolone 
• 5720-07-0 4-methoxyphenylboronic acid 
• 1728-86-5 2-bromo-7-methoxytropone 

Downstream Products

• 199609-69-3 Acetic acid 6-acetoxy-2-(4-methoxy-phenyl)-7-oxo-cyclohepta-1,3,5-trienyl ester 

Relevant articles and documents

Monoaryl- and bisaryldihydroxytropolones as potent inhibitors of inositol monophosphatase

The first successful preparation of mono- and disubstituted 3,7- dihydroxytropolone involves a four-step synthetic scheme. Thus, bromination of 3,7-dihydroxytropolone (8) followed by permethylation of the resultant products furnished gram quantities of intermediates 13-18. Single or double Suzuki coupling reactions between these permethylated monobromo- and dibromodihydroxytropolone derivatives and a variety of boronic acids delivered the expected products whose deprotection yielded the desired compounds 1a-u and 26a-n, usually in fair to good yields. Tropolones 1 and 26 were found to be potent inhibitors of inositol monophosphatase with IC50 values in the low-micromolar range. The results are discussed in the context of the recently described novel mode of inhibition of the enzyme by 3,7- dihydroxytropolones.