126927-02-4

Basic information

• Product Name: (+)-(S)-N-hydroxy-2-(phenylmethoxy)-1-phenylethanamine
• Synonyms: (+)-(S)-N-hydroxy-2-(phenylmethoxy)-1-phenylethanamine
• CAS NO: 126927-02-4
• Molecular Weight: 243.305
• Mol File: 126927-02-4.mol

Chemical Properties

• CAS DataBase Reference: (+)-(S)-N-hydroxy-2-(phenylmethoxy)-1-phenylethanamine(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-(S)-N-hydroxy-2-(phenylmethoxy)-1-phenylethanamine(126927-02-4)
• EPA Substance Registry System: (+)-(S)-N-hydroxy-2-(phenylmethoxy)-1-phenylethanamine(126927-02-4)

Safety Data

• Hazardous Substances Data: 126927-02-4(Hazardous Substances Data)

Upstream product

• 127001-23-4 (+)-(S)-2-(phenylmethoxy)-N-<(2-chlorobenzoyl)oxy>-1-phenylethanamine 
• 127001-22-3 (S)-1-phenyl-2-(phenylmethoxy)ethylamine 
• 20989-17-7 (2S)-2-phenylglycinol 
• 100-39-0 benzyl bromide 
• 2935-35-5 (S)-2-phenylglycine 
• 15028-39-4 L-2-phenylglycine methyl ester hydrochloride 

Downstream Products

• 127001-25-6 (-)-(S)-N-benzylidene-2-(phenylmethoxy)-1-phenylethanamine N-oxide 
• 127001-26-7 (-)-(S)-N-(4-methoxybenzylidene)-2-(phenylmethoxy)-1-phenylethanamine N-oxide 
• 127001-27-8 (-)-(S)-N-hexylidene-2-(phenylmethoxy)-1-phenylethanamine N-oxide 
• 364778-86-9 (1S)-(Z)-2-benzyloxy-N-(3-methyl-1-butylidene)-1-phenylethylamine N-oxide 
• 126927-34-2 N-<2'-(phenylmethoxy)-1'-phenylethyl>-N-hydroxy-2,2-dimethyl-3-octanamine 
• 103621-10-9 2-<(1-phenylethyl)amino>-2-phenylethanol 
• 126927-07-9 N-<2'-(phenylmethoxy)-1'-phenylethyl>-N-hydroxy-1-phenylethanamine 
• 126927-16-0 N-<2'-(phenylmethoxy)-1'-phenylethyl>-N-hydroxy-1-phenyl-2-propen-1-amine 
• 126927-18-2 N-<2'-(phenylmethoxy)-1'-phenylethyl>-N-hydroxy-3-buten-1-amine 
• 126927-09-1 N-<2'-(phenylmethoxy)-1'-phenylethyl>-N-hydroxy-1-phenyl-1-propanamide 
• 126927-32-0 N-<2'-(phenylmethoxy)-1'-phenylethyl>-N-hydroxy-1-nonen-4-amine 
• 126927-30-8 N-<2'-(phenylmethoxy)-1'-phenylethyl>-N-hydroxy-1-octen-3-amine 
• 126927-13-7 (1R,1'S)--N-hydroxy-2,2-dimethyl-1-phenyl-1-propanamine 
• 126948-80-9 (1S,1'S)--N-hydroxy-2,2-dimethyl-1-phenyl-1-propanamine 

Relevant articles and documents

Diastereoselective addition of terminal alkynes to chiral nitrones: Asymmetric synthesis of propargylic N-hydroxylamines

1,3-Asymmetric induction in the Et2Zn-catalyzed addition of terminal alkynes was studied with nitrones bearing a chiral auxiliary on their nitrogen atom. The obtained propargylic N-hydroxylamines were generally isolated in good yields and with satisfactory to excellent diastereoselectivities.

(1S)-(Z)-2-benzyloxy-N-(3-methyl-1-butylidene)-1-phenylethylamine N-oxide

The preparation and crystal structure of (1S)-(Z)-2-benyloxy-N-(3-methyl-1-butylidene)-1-phenylethylamine N-oxide was described. A dihedral angle of 11.16 (2)° was observed between the C5/N1/C6 and N1/C6/H11 planes. There were three bonds originating from the N atom, to an oxygen atom, to a Csp2 and to a Csp3 atom. The nitrogen atom substituent of the nitrone function adopted a conformation which minimizes the 1,3-allylic strain.

Enantioselective Synthesis of Primary Amines via Grignard Additions to Stereogenic N-(α-Phenyl-β-(benzyloxy)ethyl)nitrones

Addition of a wide range of Grignard to C-aryl- and C-alkyl-N-(α-phenyl-β-(benzyloxy)ethyl)nitrones (4-7) occurred with high diastereoselectivity (90:10 to 97:3 ratios) and good yields (56 - 97percent).Notable exceptions are allyl- and (o-methoxyphenyl)magnesium bromides (low selectivity but satisfactory yields) and isopropyl- and tert-butylmagnesium chlorides (high selectivity but 33 - 34percent yields) with C-phenylnitrone 4.The relative stereochemistry of hydroxylamine adducts 8a,b (from reaction of 4 with CH3MgBr) and 19a,b (from C-pentylnitrone 7 with MeMgBr) was provenby various correlations and/or by degradation to enantiomerically enriched amines.The other stereochemical assignments are based upon 1H NMR spectral and polarity correlations and/or by analogy to the two proven cases.The configuration of the major product can be rationalized by assuming that the Grignard reagents attack the nitrone face opposite to the pseudoequatorial N-(α-phenyl) group in a six-membered magnesium chelate (27 -> 28). 1H NMR spectral evidence indicates that a 1:1 complex of nitrone 4 and magnesium bromide exists in a chelated structure (29B) in CD2Cl2.Enantioselective syntheses of (S)-α-phenylethylamine (94percent ee) and (S)-2-heptylamine (82percent ee) were accomplished in five steps (33-39percent overall yields) from optically pure (S)-nitrones 4 and 7.