364782-99-0

Basic information

• Product Name: 2-Propenamide, N,N-bis[(1R)-1-phenylethyl]-
• CAS NO: 364782-99-0
• Molecular Formula: C19H21NO
• Molecular Weight: 279.382
• Mol File: 364782-99-0.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 2-Propenamide, N,N-bis[(1R)-1-phenylethyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propenamide, N,N-bis[(1R)-1-phenylethyl]-(364782-99-0)
• EPA Substance Registry System: 2-Propenamide, N,N-bis[(1R)-1-phenylethyl]-(364782-99-0)

Safety Data

• Hazardous Substances Data: 364782-99-0(Hazardous Substances Data)

Upstream product

• 10024-74-5 (R,R)-N,N-bis-(1-phenylethyl)amine 
• 814-68-6 acryloyl chloride 

Downstream Products

• 364783-05-1 N,N-bis[(1R)-1-phenylethyl]-3-{[(1S)-1-phenylehtyl]amino}propanamide 
• 364783-06-2 (S)-N-(1'-phenylethyl)-N-benzyl-(R,R)-N',N'-bis(1'-phenylethyl)propionamide 
• 364782-98-9 (R)-N-(1'-phenylethyl)-N-benzyl-(R,R)-N',N'-bis(1'-phenylethyl)propionamide 
• 537041-92-2 (2S)-N,N-bis[(1R)-1-phenylethyl]-3-{[(1S)-1-phenylethyl]amino}-2-(phenylmethyl)propanamide 
• 537041-94-4 (2S)-N,N-bis[(1R)-1-phenylethyl]-3-{[(1S)-1-phenylethyl]amino}-2-propylpropanamide 
• 537041-93-3 (2S)-N,N-bis[(1R)-1-phenylethyl]-2-ethyl-3-{[(1S)-1-phenylethyl]amino}propanamide 
• 537041-91-1 (2S)-N,N-bis[(1R)-1-phenylethyl]-2-methyl-3-{[(1S)-1-phenylethyl]amino}propanamide 
• 537041-97-7 2-aminomethyl-3-phenyl-N,N-bis-(1-phenyl-ethyl)-propionamide 
• 537041-99-9 (S)-2-Aminomethyl-pentanoic acid bis-((R)-1-phenyl-ethyl)-amide 
• 537041-98-8 2-aminomethyl-N,N-bis-(1-phenyl-ethyl)-butyramide 
• 382180-28-1 3-amino-2-methyl-N,N-bis-(1-phenyl-ethyl)-propionamide 
• 623158-18-9 (S,S,S,R,R)-ethyl 5-phenyl-4-{[bis(1'-phenyl-ethyl)]carbamoyl}-pyrrolidine-2-carboxylate 
• 623158-03-2 (R,R,R,R,R)-ethyl 5-phenyl-4-{[bis(1'-phenyl-ethyl)]carbamoyl}-pyrrolidine-2-carboxylate 

Relevant articles and documents

Enantioselective synthesis of β-amino acids Part 13. Diastereoselective alkylation of dianions derived from chiral analogs of β-aminopropanoic acid containing the α-phenylethyl group

Inexpensive acryloyl chloride was converted in 91% overall yield to two derivatives of β-alanine, (R,R,R)-and (R,R,S)-6, containing two chiral auxiliaries. C-Alkylation of (R,R,R)- and (R,R,S)-6 via a dianion derivative, was performed by direct metallation with 2.2 equiv. of lithium hexamethyldisilazane (LHMDS) in THF at - 78°. C-Alkylation of (R,R,S)-6-Li2 ('matched' pair of chiral auxiliaries) afforded the mono-alkylated products 8-11 in 29-96% yield and 54-95% stereoselectivity. Employment of LiCl as an additive generally increased stereoselectivities, whereas the effect of HMPA as a cosolvent was erratic. Chemical correlation of the major diastereoisomer from the alkylation reactions with (S)-α-alkyl-β-alanine (12-15) showed that addition of the electrophile preferentially takes place on the enolate's Si-face. This conclusion is also supported by molecular-modeling studies (ab initio HF/3-21G), which indicate that the lowest-energy conformation for (R,R,S)-6-Li2 presents the more sterically hindered Re-face of the enolate. The theoretical studies also predict a determining role for N-Li-O chelation in (R,R,S)-6-Li2, giving rise to an interesting 'ion-triplet' configuration for the dilithium dianion.