149296-20-8

Basic information

• Product Name: 2-(2-Vinyl-benzyl)-malonic acid dimethyl ester
• CAS NO: 149296-20-8
• Molecular Weight: 248.279
• Mol File: 149296-20-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2-(2-Vinyl-benzyl)-malonic acid dimethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-Vinyl-benzyl)-malonic acid dimethyl ester(149296-20-8)
• EPA Substance Registry System: 2-(2-Vinyl-benzyl)-malonic acid dimethyl ester(149296-20-8)

Safety Data

• Hazardous Substances Data: 149296-20-8(Hazardous Substances Data)

Upstream product

• 149296-21-9 1-Chloromethyl-2-(2-mesyloxyethyl)benzene 
• 22570-84-9 2-chloromethylstyrene 
• 108-59-8 malonic acid dimethyl ester 

Downstream Products

• 149296-22-0 Dimethyl <(5-benzyloxy-4-oxo-4H-pyran-2-yl)methyl>-(2-ethenylbenzyl)propanedioate 
• 87057-53-2 Dimethyl <(5-hydroxy-4-oxo-4H-pyran-2-yl)methyl>-(2-ethenylbenzyl)propanedioate 

Relevant articles and documents

Cycloadditions of 4-pyrones. An approach to colchicine

The 4-pyrone, [5-acetoxy-4-oxo-4H-pyran-2-yl]carbonyl chloride was coupled with the malonate anion of bis(2,2,2-trichloroethyl) 2-ethenyl-3,4,5-trimethoxybenzylpropanedioate and analogs thereof. These adducts then underwent intramolecular thermal cyclizations (61-100% yield) to form the two fused seven member rings of the carbon skeleton of colchicine. The malonate moiety was deprotected and decarboxylated quantitatively to provide the desired ring system which contained a bridging ether, from C7a to C11 in the C ring, and a ketone at the 7 position. Removal of the bridging ether as H2O would yield the desired tropolone. Our attempts to remove the ether bridge were unsuccessful.