1325642-75-8

Basic information

• Product Name: 1-(2-ethoxyethyl)-2-phenyl-1,4-dihydroindeno[1,2-b]pyrrole
• Synonyms: 1-(2-ethoxyethyl)-2-phenyl-1,4-dihydroindeno[1,2-b]pyrrole
• CAS NO: 1325642-75-8
• Molecular Weight: 303.404
• Mol File: 1325642-75-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1-(2-ethoxyethyl)-2-phenyl-1,4-dihydroindeno[1,2-b]pyrrole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-ethoxyethyl)-2-phenyl-1,4-dihydroindeno[1,2-b]pyrrole(1325642-75-8)
• EPA Substance Registry System: 1-(2-ethoxyethyl)-2-phenyl-1,4-dihydroindeno[1,2-b]pyrrole(1325642-75-8)

Safety Data

• Hazardous Substances Data: 1325642-75-8(Hazardous Substances Data)

Upstream product

• 70-11-1 α-bromoacetophenone 
• 22955-77-7 methyl 1-indanone-2-carboxylate 
• 110-76-9 2-ethoxy-1-ethanamine 
• 89506-40-1 2-(2-oxo-2-phenylethyl)-2,3-dihydro-1H-inden-1-one 

Relevant articles and documents

Synthesis of benzo[c]azocanones and indeno[1,2-b]pyrroles from oxoindanecarboxylates

Ethyl 1-oxo-indane-2-carboxylate with a 1,4-diketone motif gave a benzo[c]azocane-1-one derivative-an eight-membered ring lactam-in a bismuth-mediated ring-expansion reaction with methylamine (40% yield). Yields with other primary amines were significantly lower. The ester function in the heterocyclic product could be saponified to give the free carboxylic acid, which was further amidated with para-bromoaniline. The molecular structure of the latter was established by X-ray single-crystal analysis. Benzo[c]azocanones exist in two diastereoisomeric conformations, causing double signal sets in the NMR spectra. Slow interconversion between these conformers was proved by EXSY NMR spectroscopy. Moreover, a conformational analysis by DFT calculations revealed the two diastereoisomers to be boat conformers that interconvert through a twist conformer. The maximum barrier for this process was calculated to be approximately 70 kJ/mol. Reaction of the corresponding methyl 1-oxoindane-2-carboxylate with methylamine gave the benzo[c]azocanone in lower yield. A spirolactam and an indeno[1,2-b]pyrrole were formed as further products. When using an indanone-derived 1,4-diketone without an ester function, several primary amines could be used in a bismuth-catalyzed Paal-Knorr reaction to give indeno[1,2-b]pyrrole derivatives with up to quantitative yields in several cases. Attempts to synthesize a caprolactam derivative from a cyclobutanone derived β-oxo ester with 1,4-diketone motif were unsuccessful.