189569-63-9

Basic information

• Product Name: 1-Indolizinecarboxylic acid, 3-(2-phenylethenyl)-, methyl ester, (E)-
• CAS NO: 189569-63-9
• Molecular Formula: C18H15NO2
• Molecular Weight: 277.323
• Mol File: 189569-63-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1-Indolizinecarboxylic acid, 3-(2-phenylethenyl)-, methyl ester, (E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Indolizinecarboxylic acid, 3-(2-phenylethenyl)-, methyl ester, (E)-(189569-63-9)
• EPA Substance Registry System: 1-Indolizinecarboxylic acid, 3-(2-phenylethenyl)-, methyl ester, (E)-(189569-63-9)

Safety Data

• Hazardous Substances Data: 189569-63-9(Hazardous Substances Data)

Upstream product

• 100-42-5 styrene 
• 316375-85-6 methyl indolizine-1-carboxylate 
• 922-67-8 propynoic acid methyl ester 

Relevant articles and documents

Dehydrogenative Heck coupling of biologically relevant N-heteroarenes with alkenes: Discovery of fluorescent core frameworks

A Pd/Cu-catalyzed dehydrogenative Heck coupling is established that allows direct alkenylation of various biologically relevant N-heteroarenes with alkenes. The resulting π-extended alkenylated N-heteroarenes exhibit interesting fluorescent properties and have proven to be potentially useful fluorescent probes for bioimaging. The Royal Society of Chemistry 2012.

Indolizines 4. The synthesis of new 3-vinylindolizines.

New 3-vinylindolizines have been synthesized by two methods.The first strategy calls for the Wittig olefination of 3-acylindolizines with methylenetriphenylphosphorane or methoxymethylenetriphenylphosphorane.The best yields are obtained when the ylid is formed at room temperature and the condensation in refluxing THF.The required 3-acylindolizines were obtained by direct acylation of indolizines or by 1,3-dipolar cyclo-additions to acylmethylpyridinium ylids.The following 3-isopropenylindolizines were made with good yields: unsubstituted (18, 85percent), 2-methyl (10, 98percent), 2-C6H5 (17, 95percent), 1-COOMe (20, 98percent), 1-COOMe-2-C6H5 (22, 91 percent), 1,2-di-COOMe (24, 58percent).Also synthesized are the following 3-α-styrylindolizines: 2-C6H5 (19, 99percent), 1-COOMe (21, 93percent), 1-COOMe-2-C6H5 (23, 87percent), 1,2-diCOOMe (25, 66percent). 3-(α-Methyl-β-methoxyvinyl)indolizines E (26, 40percent) and Z (27, 40percent) were also obtained.The second strategy involves the 1,3-dipolar cyclo-addition of dipolarophiles to allylpyridinium ylids.The following new 3-vinylindolizines have been synthesized: 1-carbomethoxy-3-vinylindolizine (30, 21percent), 1,2-dicarbomethoxy-3-vinylindolizine (31, 16percent), 1-carbomethoxy-3-β-styrylindolizine (33, 43percent), 3-β-styrylindolizine (34, 17percent), 1-carbomethoxy-3-(β-carbomethoxy)vinylindolizine 38 (31percent).