960283-15-2

Basic information

• Product Name: (4E)-ethyl 2-ethoxycarbonyl-3-methylene-5-phenyl-4-pentenoate
• Synonyms: (4E)-ethyl 2-ethoxycarbonyl-3-methylene-5-phenyl-4-pentenoate
• CAS NO: 960283-15-2
• Molecular Weight: 288.343
• Mol File: 960283-15-2.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (4E)-ethyl 2-ethoxycarbonyl-3-methylene-5-phenyl-4-pentenoate(CAS DataBase Reference)
• NIST Chemistry Reference: (4E)-ethyl 2-ethoxycarbonyl-3-methylene-5-phenyl-4-pentenoate(960283-15-2)
• EPA Substance Registry System: (4E)-ethyl 2-ethoxycarbonyl-3-methylene-5-phenyl-4-pentenoate(960283-15-2)

Safety Data

• Hazardous Substances Data: 960283-15-2(Hazardous Substances Data)

Upstream product

• 25364-76-5 1,3-diethyl 2-[(2E)-3-phenylprop-2-en-1-ylidene]propanedioate 
• 2181-42-2 trimethylsulphonium iodide 
• 1030268-21-3 trimethylsulfonium iodide 

Downstream Products

• 1223582-54-4 (8E)-1-tert-butyldimethylsilyoxy-6,6-diethoxycarbonyl-7-methylene-9-phenyl-8-nonene 

Relevant articles and documents

A dimethylsulfonium methylide mediated highly regioselective olefination of conjugated polyolefin 1,1-dioates to conjugated polyene-2-yl-malonates and their applications in Diels-Alder reactions

The reactions between dimethylsulfonium methylide and 1,3-diene- or 1,3,5-triene-1,1-dioates under specific conditions enable the highly regioselective tandem ylide addition-eliminative olefination to provide 1,3-butadien-2-yl- or 1,3,5-hexatriene-2-yl-malonates. Alkylation at malonate methine carbon of 1,3-butadien-2-ylmalonates with a suitable alkyl halide having in-built functionalities for a dienophile generation led to quick assembly of precursors for type 2 intramolecular Diels-Alder reaction. Syntheses of functionalized bicyclo[n.3.1] alkenes (n=5 or 6) with the double bond at the bridgehead position have been achieved via the IMDA. An asymmetric version of this reaction has been developed using a MacMillan's imidazolidinone catalyst, which provided a bicyclo[5.3.1] alkene with very high enantioselectivity. In situ methylation at malonate methine carbon of 1,3,5-hexatriene-2-yl-malonates followed by intermolecular Diels-Alder reaction with N-methylmaleimide provided the cycloadduct with complete regiocontrol and high diastereoselectivity.