147198-49-0

Basic information

• Product Name: 4-benzyl-7-methoxy-3-phenyl-2H-1-benzopyran-2-one
• CAS NO: 147198-49-0
• Molecular Weight: 342.394
• Mol File: 147198-49-0.mol

Chemical Properties

• CAS DataBase Reference: 4-benzyl-7-methoxy-3-phenyl-2H-1-benzopyran-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-benzyl-7-methoxy-3-phenyl-2H-1-benzopyran-2-one(147198-49-0)
• EPA Substance Registry System: 4-benzyl-7-methoxy-3-phenyl-2H-1-benzopyran-2-one(147198-49-0)

Safety Data

• Hazardous Substances Data: 147198-49-0(Hazardous Substances Data)

Upstream product

• 77-78-1 dimethyl sulfate 
• 108-86-1 bromobenzene 
• 2555-28-4 4-methyl-7-methoxy-2H-1-benzopyran-2-one 
• 150-19-6 O-methylresorcine 
• 103-82-2 phenylacetic acid 
• 18439-96-8 1-(2-hydroxy-4-methoxyphenyl)-2-phenylethanone 

Relevant articles and documents

Palladium-catalyzed mono-γ-arylation of 7-methoxy-4-methylcoumarin

Herein, we report the selective mono-γ-arylation of 7-methoxy-4-methylcoumarin under palladium-catalyzed conditions. The Buchwald G3 pre-catalyst in conjunction with either the Xantphos or N-Xantphos ligand proves to be highly reactive, engaging aryl iodides, bromides, chlorides, and triflates to effect the desired transformation. A wide range of functionality is tolerated, including the ability to activate heteroaryl halides in the transformation. The initial scope of aryl halides and limitations of this methodology are presented.

Synthesis of 3-aryl-1-(4-methoxyphenyl)-2--2-propen-1-ones and benzopyran derivatives

Acylation of anisole (5) or m-methoxyphenol (6) with arylacetic acid (7 or 8) gives the corresponding deoxybenzoins (9-12) along with minor isomeric product 13 in one case.Acetylation of 4-hydroxy-4'-methoxydeoxybenzoin (10) with acetic anhydride in pyridine or its alkylation with N-(2-chloroethyl)diethylammonium/pyrrolidinium chloride furnishes the corresponding deoxybenzoin derivatives (14-16).Condensation of 9, 11, 15 and 16 with araldehydes affords the corresponding title compounds 2-propen-1-ones (17, 19 and 21-23). 1-(2-Hydroxy-4-methoxyphenyl)-2,3-diphenyl-2-propen-1-one (19) is isomerized using silica gel or hydrochloric acid to 2,3-trans-2,3-dihydro-7-methoxy-2,3-diphenyl-4H-1-benzopyran-4-one (24) which on sodium borohydride reduction provides a mixture of isomeric benzopyranols (25).Dehydration of 25 gives 7-methoxy-2,3-diphenyl-2H/4H-1-benzopyran (27).The isomeric 7-methoxy-2,4-diphenyl-2H/4H-1-benzopyran (28) is prepared by the reaction of 2,3-dihydro-7-methoxy-2-phenyl-4H-1-benzopyran-4-one (26) with phenylmagnesium bromide.Condensation of 11 with 7 in acetic anhydride/triethylamine furnishes 4-benzyl-7-methoxy-3-phenyl-2H-1-benzopyran-2-one (29).