154675-31-7

Basic information

• Product Name: N-[1-(phenyl)propyl]-P,P-diphenylphosphinoylamide
• Synonyms: N-[1-(phenyl)propyl]-P,P-diphenylphosphinoylamide
• CAS NO: 154675-31-7
• Molecular Weight: 335.386
• Mol File: 154675-31-7.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: N-[1-(phenyl)propyl]-P,P-diphenylphosphinoylamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-[1-(phenyl)propyl]-P,P-diphenylphosphinoylamide(154675-31-7)
• EPA Substance Registry System: N-[1-(phenyl)propyl]-P,P-diphenylphosphinoylamide(154675-31-7)

Safety Data

• Hazardous Substances Data: 154675-31-7(Hazardous Substances Data)

Upstream product

• 98837-46-8 P,P-diphenyl-N-(phenylmethylene)phosphinic amide 
• 2386-64-3 ethylmagnesium chloride 
• 557-20-0 diethylzinc 
• 23517-42-2 propiophenone oxime 
• 17157-61-8 bis(diphenylphosphino)amine 
• 93-54-9 1-Phenyl-1-propanol 
• 5994-87-6 diphenylphosphinamide 
• 2157-50-8 propiophenone oxime 
• 93-55-0 1-phenyl-propan-1-one 
• 106651-13-2 P,P-diphenyl-N-(1-phenylpropylidene)phosphinic amide 
• 942066-05-9 N-[(1E)-1-phenylpropylidene]-P,P-diphenylphosphinic amide 
• 98837-46-8 N-benzylidenediphenylphosphinamide 

Downstream Products

• 3789-59-1 (R)-1-phenylpropylamine 
• 2941-20-0 1-phenylpropylamine 

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.

Enantioselective Hydrosilylation of Imines Catalyzed by Chiral Zinc Acetate Complexes

A series of zinc acetate complexes with optically pure diphenylethanediamine (DPEDA)-derived ligands have been employed as enantioselective catalyst for the hydrosilylation of various imines. High control of stereoselectivity (up to 97% ee) and excellent yields (up to 96%) were gained for a broad range of N-phosphinoylimines by using (R,R)-N,N′-dibenzyl-1,2-diphenylethane-1,2-diamine. This is the first successful application of an air-stable and environmentally friendly chiral Zn(OAc)2 complex instead of the previously used harmful diethylzinc in the asymmetric reduction of the C=N double bond.

METHODS FOR PREPARING DIORGANOZINC COMPOUNDS

There are provided methods for preparing the diorganozmc compounds of formula R2Zn (I or Ia), where R is a defined organic radical, and the two R groups can be the same or different The starting material is the zinc compound ZnX2 (II) or R2ZnX (IIa), where X is a defined anion and R2 is a defined organic radical. The zinc reagent of type II is combined with a Grignard reagent and also, when X is Cl or Br, with an alkali metal reagent (VI) to form the diorganozinc product (I or Ia). Also provided are methods for preparing the zinc alcoholates of formula Zn(OR1)2 by reaction of ZnX2, where X = Cl or Br, with an alkali metal reagent of the formula MOR1, where M = Na or K, and where R1 is a defined organic radical.