87567-89-3

Basic information

• Product Name: 1,3-Cyclohexadiene-1-carboxylic acid, 3-methyl-5,6-dioxo-, methyl ester
• CAS NO: 87567-89-3
• Molecular Formula: C9H8O4
• Molecular Weight: 180.16
• Mol File: 87567-89-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1,3-Cyclohexadiene-1-carboxylic acid, 3-methyl-5,6-dioxo-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Cyclohexadiene-1-carboxylic acid, 3-methyl-5,6-dioxo-, methyl ester(87567-89-3)
• EPA Substance Registry System: 1,3-Cyclohexadiene-1-carboxylic acid, 3-methyl-5,6-dioxo-, methyl ester(87567-89-3)

Safety Data

• Hazardous Substances Data: 87567-89-3(Hazardous Substances Data)

Upstream product

• 6049-93-0 2,3-dihydroxy-5-methylbenzoic acid 
• 17746-75-7 3-bromo-5-methylsalicylic acid 
• 87567-91-7 2,3-dihydroxy-5-methylbenzoic acid methyl ester 

Downstream Products

• 87568-18-1 6-chloro-2,3-dihydroxy-5-methylbenzoic acid methyl ester 
• 87567-90-6 2-chloro-3-methyl-5,6-dioxo-1,3-cyclohexadiene-carboxylic acid methyl ester 

Relevant articles and documents

Quassinoid Synthesis via o-Quinone Diels-Alder Reactions

The reaction of 3,5-disubstituted o-quinones (2a, 2c) and 4-chloro-3,5-disubstituted o-quinones (2b, 2d) with simple dienes was investigated as a potential route to the quassinoid skeleton.Quinones 2a and 2c reacted in high yield at the 3,4-position with only a small excess of diene.Attempted equilibration of cis-fused cycloadducts to the trans-fused system failed due to the intervention of a stable enol form, as in 20.Compound 2c with ethyl 3,5-hexadienoate gave 15a, which upon reduction and lactonization provided BCD-ring tricyclic quassinoid analogues 18a and 19a.Again isomerization to the BC trans-fused system was not possible.The chloroquinones showed some preference for Diels-Alder reaction at the 5,6-position, but the additions were characterized generelly by low yields, side reactions, and lessened stereoselectivity.