131213-18-8

Basic information

• Product Name: dimethyl (2E)-2-(2-methoxybenzylidene)cyclopentane-1,1-dicarboxylate
• Synonyms: dimethyl (2E)-2-(2-methoxybenzylidene)cyclopentane-1,1-dicarboxylate
• CAS NO: 131213-18-8
• Molecular Weight: 304.343
• Mol File: 131213-18-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: dimethyl (2E)-2-(2-methoxybenzylidene)cyclopentane-1,1-dicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: dimethyl (2E)-2-(2-methoxybenzylidene)cyclopentane-1,1-dicarboxylate(131213-18-8)
• EPA Substance Registry System: dimethyl (2E)-2-(2-methoxybenzylidene)cyclopentane-1,1-dicarboxylate(131213-18-8)

Safety Data

• Hazardous Substances Data: 131213-18-8(Hazardous Substances Data)

Upstream product

• 529-28-2 4-iodoanisol 
• 130905-55-4 dimethyl 4-pentenylmalonate 
• 108-59-8 malonic acid dimethyl ester 
• 766-51-8 2-Chloroanisole 
• 93185-10-5 dimethyl 2-(pent-4'-enyl)malonate 
• 578-57-4 2-bromoanisole 

Relevant articles and documents

Pd-catalyzed intramolecular addition of active methylene compounds to alkynes with subsequent cross-coupling with (hetero)aryl halides

We report an efficient protocol for tandem Pd-catalyzed intramolecular addition of active methylene compounds to alkynes, followed by subsequent cross-coupling with (hetero)aryl bromides and chlorides. The reaction proceeds under mild conditions, providing excellent functional group tolerance, including unprotected OH, NH2 groups, enolizable ketones, or a variety of heterocycles. Mechanistic studies point towards a catalytic cycle involving oxidative addition, intramolecular nucleophilic addition to the Pd(ii)-activated alkyne, and reductive elimination, with 5-exo-dig cyclization being the rate limiting step.

Stereospecific synthesis of arylidene and allylidene cyclopentanes by a palladium-catalyzed cylisation

Vinyl and aryl halides react with ε-acetylenic β-diesters, β-keto esters and βsulfonylesters in the presence of a Pd(o) catalyst leading in good yields to the title compounds. The acetylenic homolog containing an additional carbon leads in the same conditions to a cyclohexane, but this process then competes with the arylation of the terminal acetylenic carbon.