344248-49-3

Basic information

• Product Name: N-(1-naphthalen-1-yl-ethyl)-P,P-diphenylphosphinamide
• Synonyms: N-(1-naphthalen-1-yl-ethyl)-P,P-diphenylphosphinamide
• CAS NO: 344248-49-3
• Molecular Weight: 371.419
• Mol File: 344248-49-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: N-(1-naphthalen-1-yl-ethyl)-P,P-diphenylphosphinamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(1-naphthalen-1-yl-ethyl)-P,P-diphenylphosphinamide(344248-49-3)
• EPA Substance Registry System: N-(1-naphthalen-1-yl-ethyl)-P,P-diphenylphosphinamide(344248-49-3)

Safety Data

• Hazardous Substances Data: 344248-49-3(Hazardous Substances Data)

Upstream product

• 941-98-0 1'-naphthacetophenone 
• 100485-51-6 (E)-1-(naphthalen-1-yl)ethanone oxime 
• 1079-66-9 chloro-diphenylphosphine 
• 1956-40-7 1-(1-naphthalenyl)ethanone oxime 
• 942066-01-5 N-[(E)-1-(1-naphthyl)ethylidene]diphenylphosphinic amide 
• 82572-09-6 C₂₄H₂₀NOP 

Downstream Products

• 40280-57-7 hydrochloride of <1-(1-naphthyl)ethyl>amine 
• 42882-31-5 (RS)-1-(1-naphthyl)ethylamine 

Relevant articles and documents

Enantioselective Hydrogenation of Activated Aryl Imines Catalyzed by an Iron(II) P-NH-P′ Complex

Chiral amines are key building blocks in synthetic chemistry with numerous applications in the agricultural and pharmaceutical industries. Asymmetric imine hydrogenation, particularly with iridium catalysts, is well developed. However, imine reduction still remains challenging in the context of replacing such a precious metal with a cheap, nontoxic, and environmentally friendly substitute such as iron. Here, we report that an unsymmetrical iron P-NH-P′ catalyst that was previously shown to be effective for the asymmetric hydrogenation of aryl ketones is also a very effective catalyst for the asymmetric hydrogenation of prochiral aryl imines activated with N-diphenylphosphinoyl or N-tosyl groups. The P-NH-P′ abbreviation stands for (S,S)-PPh2CHPhCHPhNHCH2CH2PiPr2. Density functional theory results suggest that, surprisingly, the NH group on the catalyst activates and orients the imine to hydride attack by hydrogen bonding to the PO or SO group on the imine nitrogen, as opposed to the imine nitrogen itself. This may explain why N-Ph and N-Bu imines are not hydrogenated.

Highly enantioselective Pd-catalyzed asymmetric hydrogenation of activated imines

(Chemical Equation Presented) Pd/bisphosphines complexes are highly effective catalysts for asymmetric hydrogenation of activated imines in trifluoroethanol. The asymmetric hydrogenation of N-diphenylphosphinyl ketimines 3 with Pd(CF3CO2)/(S)-SegPhos indicated 87-99% ee, and N-tosylimines 5 could gave 88-97% ee with Pd-(CF3CO 2)/(S)-SynPhos as a catalyst. Cyclic N-sulfonylimines 7 and 11 were hydrogenated to afford the useful chiral sultam derivatives in 79-93% ee, which are important organic synthetic intermediates and structural units of agricultural and pharmaceutical agents.

A Study of the Synthesis of Optically Active Amines from Prochiral N-Phosphinylimines

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