164660-17-7

Basic information

• Product Name: 4-Hexenoic acid, 3-[[(1S)-1-phenylethyl]-2-propenylamino]-, 1,1-dimethylethyl ester, (3R,4E)-
• CAS NO: 164660-17-7
• Molecular Formula: C21H31NO2
• Molecular Weight: 329.483
• Mol File: 164660-17-7.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 4-Hexenoic acid, 3-[[(1S)-1-phenylethyl]-2-propenylamino]-, 1,1-dimethylethyl ester, (3R,4E)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Hexenoic acid, 3-[[(1S)-1-phenylethyl]-2-propenylamino]-, 1,1-dimethylethyl ester, (3R,4E)-(164660-17-7)
• EPA Substance Registry System: 4-Hexenoic acid, 3-[[(1S)-1-phenylethyl]-2-propenylamino]-, 1,1-dimethylethyl ester, (3R,4E)-(164660-17-7)

Safety Data

• Hazardous Substances Data: 164660-17-7(Hazardous Substances Data)

Upstream product

• 110-44-1 sorbic Acid 
• 81838-85-9 tert-butyl (2E,4E)-2,4-hexadienoate 
• 115914-08-4 (S)-N-(1-phenylethyl)prop-2-en-1-amine 

Downstream Products

• 198543-52-1 (E)-(R)-3-[Benzoyl-((S)-1-phenyl-ethyl)-amino]-hex-4-enoic acid tert-butyl ester 
• 198543-53-2 (E)-(R)-3-(Benzoyl-tert-butoxycarbonyl-amino)-hex-4-enoic acid methyl ester 
• 198769-42-5 (E)-(R)-3-Benzoylamino-hex-4-enoic acid methyl ester 
• 468071-50-3 (2S,αS)-tert-butyl 1-(N-α-methylbenzylamino)-pyrrolidin-2-yl-acetate 
• 104553-43-7 (2S,αS)-tert-butyl pyrrolidin-2-yl-acetate 
• 56633-75-1 (S)-2-(pyrrolidin-2-yl)acetic acid 
• 468071-45-6 (2R,αS)-tert-butyl 1-(N-α-methylbenzyl)-2,5-dihydro-1H-2-pyrrolyl-acetate 
• 164660-21-3 (E)-(R)-3-((S)-1-Phenyl-ethylamino)-hex-4-enoic acid tert-butyl ester 

Relevant articles and documents

Asymmetric synthesis of cyclic β-amino acids and cyclic amines via sequential diastereoselective conjugate addition and ring closing metathesis

Diastereoselective conjugate addition of lithium (S)-N-allyl-N-α-methylbenzylamide to a range of α,β-unsaturated esters followed by ring closing metathesis is used to afford efficiently a range of substituted cyclic β-amino esters in high d.e. Alternatively, conjugate addition to α,β-unsaturated Weinreb amides, functional group conversion and ring closing metathesis affords cyclic amines in high d.e. The further application of this methodology to the synthesis of a range of carbocyclic β-amino esters via conjugate addition, enolate alkylation and ring closing metathesis is also described. Application of this methodology affords, after deprotection, (S)-homoproline, (S)-homopipecolic acid, (S)-coniine and (1S,2S)-trans-pentacin.

The use of lithium (α-methylbenzyl)allylamide for the asymmetric synthesis of unsaturated β-amino acid derivatives

The unsaturated β-amino acid derivatives (3R)-(E)-3-(N-tert- butoxycarbonyl)aminohex-4-enoate and methyl (2S,3S)-3-(N-tert- butoxycarbonyl)-amino-2-bydroxyhex-4-enoate have been synthesised from lithium (s)-(α-methylbenzyl)allylamide and (E,E)-tert-butyl hex-2,4- dienoate. After a highly stereoselective conjugate addition of the lithium amide to the α,β-unsaturated ester, or a highly stereoselective conjugate addition-electrophilic hydroxylation, the adducts are deallylated and the resulting secondary amines converted to either a benzoyl amide or oxazolidinone. The N-α-methylbenzyl group is then removed with either formic acid or using a dissolving metal reduction. These deprotection procedures leave unsaturation in the molecules intact.