123725-86-0

Basic information

• Product Name: ethyl (4S,2E)-4-(N,N-dibenzylamino)pent-2-enoate
• Synonyms: ethyl (4S,2E)-4-(N,N-dibenzylamino)pent-2-enoate
• CAS NO: 123725-86-0
• Molecular Weight: 323.435
• Mol File: 123725-86-0.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: ethyl (4S,2E)-4-(N,N-dibenzylamino)pent-2-enoate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl (4S,2E)-4-(N,N-dibenzylamino)pent-2-enoate(123725-86-0)
• EPA Substance Registry System: ethyl (4S,2E)-4-(N,N-dibenzylamino)pent-2-enoate(123725-86-0)

Safety Data

• Hazardous Substances Data: 123725-86-0(Hazardous Substances Data)

Upstream product

• 617-33-4 ethyl dibromoacetate 
• 120205-96-1 (S)-2-(dibenzylamino)propanal 
• 100-39-0 benzyl bromide 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 87281-16-1 2-dibenzylamino-propionic acid methyl ester 
• 124755-24-4 ethyl [bis(2,2,2-trifluoroethoxy)phosphinyl]acetate 
• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 

Downstream Products

• 136910-59-3 (E)-(S)-2-(N,N-Dibenzyl-aminooxy)-pent-3-enoic acid ethyl ester 
• 123725-89-3 (3R,4S)-4-Dibenzylamino-3-methyl-pentanoic acid ethyl ester 
• 123725-89-3 (3S,4S)-4-Dibenzylamino-3-methyl-pentanoic acid ethyl ester 
• 123725-90-6 (R)-3-((S)-1-Dibenzylamino-ethyl)-heptanoic acid ethyl ester 
• 123725-90-6 (S)-3-((S)-1-Dibenzylamino-ethyl)-heptanoic acid ethyl ester 
• 123725-91-7 (3S,4S)-4-Dibenzylamino-3-phenyl-pentanoic acid ethyl ester 
• 123725-91-7 (3R,4S)-4-Dibenzylamino-3-phenyl-pentanoic acid ethyl ester 
• 123807-64-7 (4R,5S)-1-Benzyl-4,5-dimethyl-2-pyrrolidinone 
• 155626-85-0 S-methyl O-[(4S,2E)-4-(N,N-dibenzylamino)pent-2-en-1-yl] dithiocarbonate 
• 155626-84-9 (4S,2E)-4-(N,N-dibenzylamino)pent-2-en-1-ol 

Relevant articles and documents

Highly selective synthesis of enantiopure (S,E)-α,β-unsaturated γ-amino esters through a sequential reaction of ethyl dibromoacetate with α-amino aldehydes promoted by chromium dichloride

A sequential reaction of ethyl dibromoacetate with various enantiopure N,N-dibenzyl- or N-Boc-α-amino aldehydes (derived from natural α-amino acids), promoted by chromium dichloride, afforded optically active (S,E)-α,β-unsaturated γ-amino esters. The C=C

1,5-Stereocontrol in tin(IV) halide mediated reactions between N- and S-substituted pent-2-enylstannanes and aldehydes or imines

Following transmetalation of (4S)-4-(dibenzylamino)pent-2-enyl(tributyl) stannane with tin(IV) bromide, reactions of the resulting allyltin tribromide with aldehydes gave (3Z)-1,5-syn-5-(dibenzylamino)hex-3-en-1-ols with excellent, ca. 98:2, stereocontrol. (4R)-5-Benzylthio-4-methylpent-2-enyl(tributyl) stannane similarly reacted with aldehydes to give (3Z)-1,5-anti-6-benzylthio-5- methylhex-3-en-1-ols with 87:13 stereocontrol. Although the analogous reaction of (4R)-4-benzylthiopent-2-enyl(tributyl)stannane with benzaldehyde proceeded with some stereoselectivity, 80-90:20-10, in favour of the (3Z)-1,5-syn- diastereoisomer, the yield was low due to a competing Lewis acid catalysed 1,4-elimination. N-Acylamino- and S-acylthio-pent-2-enylstannanes reacted with aldehydes with variable syn/anti-stereoselectivities. Tin(IV) chloride promoted reactions of the 4-(dibenzylamino)pent-2-enylstannane with 1- alkoxycarbonylimines gave (E)-alk-4-enoates with a modest preference for the 2,6-anti-products, 2,6-anti/2,6-syn=75:25.