174226-56-3

Basic information

• Product Name: (S)-N-(4,4-diphenyl-3-butenyl)-prolinol
• Synonyms: (S)-N-(4,4-diphenyl-3-butenyl)-prolinol
• CAS NO: 174226-56-3
• Molecular Weight: 307.436
• Mol File: 174226-56-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (S)-N-(4,4-diphenyl-3-butenyl)-prolinol(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-N-(4,4-diphenyl-3-butenyl)-prolinol(174226-56-3)
• EPA Substance Registry System: (S)-N-(4,4-diphenyl-3-butenyl)-prolinol(174226-56-3)

Safety Data

• Hazardous Substances Data: 174226-56-3(Hazardous Substances Data)

Upstream product

• 6078-95-1 4,4-diphenyl-3-butenyl bromide 
• 23356-96-9 (S)-1-Pyrrolidin-2-yl-methanol 

Downstream Products

• 174226-61-0 (S)-N-(4,4-diphenyl-3-butenyl)pyrrolidine carboxaldehyde 

Relevant articles and documents

Evidence for a stepwise mechanism in formal hetero-Diels-Alder reactions of N-arylimines

In order to investigate the mechanism of Lewis acid-catalyzed cyclizations of ω-unsaturated N-arylimines, various prolinal-derived N-arylimines 17a-f were synthesized and treated with Lewis acids. Whereas imine 17a bearing a C-2 tether and imines 17d, f with terminal alkene or alkyne moieties could not be cyclized under these conditions, imine 17b with a C-3 tether gave three diastereomeric pyrrolo-[1',2':1,2]azepino[3,4-b]quinolines 18a-c and imine 17c gave two diasteromeric 7,7-diphenyl-indolizino-[3,4-b]quinolines 19a, b. High cis/trans-ratios were observed in both cases. Imine 17e bearing an internal alkyne underwent a cyclization/dehydrogenation to give the indolizino[3,4-b]quinoline 21. From these results a stepwise mechanism was concluded. The configuration of 19a was established by an X-ray crystal structure analysis.