117974-11-5

Basic information

• Product Name: 1-amino-4-phenylbutan-2-ol
• Synonyms: 1-amino-4-phenylbutan-2-ol
• CAS NO: 117974-11-5
• Molecular Weight: 165.235
• Mol File: 117974-11-5.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: 1-amino-4-phenylbutan-2-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-amino-4-phenylbutan-2-ol(117974-11-5)
• EPA Substance Registry System: 1-amino-4-phenylbutan-2-ol(117974-11-5)

Safety Data

• Hazardous Substances Data: 117974-11-5(Hazardous Substances Data)

Usage

Molecular structure

A butanol molecule with an amino group and a phenyl group attached to the second carbon.

Usage

Chiral auxiliary for asymmetric synthesis of various compounds (e.g. pharmaceuticals, agrochemicals), potential treatment for neurological disorders, precursor for synthesis of biologically active compounds, building block for new synthetic drugs, and development of new materials with specific chemical and biological properties.

Importance

Versatile applications in organic chemistry and pharmaceutical research.

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 75-52-5 nitromethane 
• 103264-16-0 1-nitro-4-phenyl-but-3-en-2-one 
• 123933-98-2 Benzyl-(2-hydroxy-4-phenyl-butyl)-carbamic acid benzyl ester 
• 1126-76-7 1,2-Epoxy-4-phenylbutane 
• 141377-53-9 1-nitro-4-phenylbutan-2-ol 
• 121054-03-3 2-hydroxy-4-phenylbutanenitrile 
• 244140-55-4 t-4,t-5-epoxy-r-6-ethoxy-3-phenyl-5,6-dihydro-4H-1,2-oxazine 
• 768-56-9 4-Phenylbut-1-ene 

Downstream Products

• 21176-65-8 5-phenethyl-oxazolidine-2-thione 
• 22820-50-4 1-(isopropylamino)-4-phenylbutan-2-ol 
• 913642-44-1 N-tert-butoxycarbonyl-1-amino-4-phenyl-2-butanol 
• 681284-73-1 4-Chloro-1-(2-phenylethyl)imidazo[1,2-a]quinoxaline 
• 681285-28-9 1-[(3-chloroquinoxalin-2-yl)amino]-4-phenylbutan-2-one 
• 681285-32-5 t-butyl 4-(1-(2-phenylethyl)imidazo[1,2-a]quinoxalin-4-yl)piperazine-1-carboxylate 
• 71813-55-3 5-(2-phenylethyl)oxazolidin-2-one 
• 1243250-51-2 1-acetamido-4-phenylbutan-2-yl acetate 

Relevant articles and documents

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Easy kinetic resolution of some β-amino alcohols by Candida antarctica lipase B catalyzed hydrolysis in organic media

Herein, we present an easy and eco-friendly pathway to obtain some enantiomerically enriched β-amino alcohols using essentially as β-blockers. The enzymatic hydrolysis is conducted in hydrophobic organic media, assisted by sodium carbonate and CAL-B. We describe a new and effective procedure in terms of the chemo- and enantioselectivity, which allows for the formation of both enantiomers: the 2-acetamido-1-arylacetates and 2-acetamido-1-arylethanols were obtained with high ee values (up to >99%), while the selectivities reached E >200. The obtained results show a high CAL-B affinity toward the deacylation of the 2-acetamido-1-arylacetates compared to the acylation one. The structure of the 2-acetamido-1-arylacetates had a significant influence on both reactivity and selectivity of the CAL-B catalyzed deacylation. A multigram scale O-deacylation of racemic 2-acetamido-1-phenylacetate has been carried out, giving access both enantiomers with high enantiomeric purity and good isolated chemical yields.

1,2-oxazines as building blocks for stereoselective synthesis: Preparation of oxygen-substituted 1,2-oxazines, either by alcohol addition or by epoxidation, and subsequent hydrogenation leading to 1,2-amino alcohols and pyrrolidines

Stereodefined oxygen-substituted 1, 2-oxazines were prepared by three different routes. The cycloaddition of enol ethers such as 1 with a-nitrosoalkenes generated in situ gave the heterocycles 3 and 4. Acid-catalysed additions of alcohols to the 6H-1, 2-oxazines 5 led to mixtures of the adducts 6 and the substitution products 7 with moderate chemoselectivity. Epoxidation of the 6H-1, 2-oxazines 5 proceeded more efficiently and furnished the corresponding epoxides 25 and 32 in reasonable to excellent yields. It was demonstrated that the resulting oxygen-substituted 1, 2-oxazines were suitable precursors for the preparation of cyclic or acyclic primary and secondary amines in racemic or enantiopure form. Hydrogenation of the 3-phenyl-substituted 1, 2-oxazines 3 and 25a and of (6S)- and (6R)-32 preferentially furnished the 1, 2amino alcohols 15, rac-29 and (2S)- and (2R)-29. On the other hand, reduction of the 3-ethoxycarbonyl-substituted 1, 2-oxazines 4, 6d and 20 led to the formation of the N-protected proline esters 21-24 in moderate yields. It was also found that the 5-methyl-6H-1, 2-oxazine 10 was a good precursor for the propargylic ether 11, which allowed a Pauson-Khand reaction leading to the tricyclic compounds 13 and 14. Hydrogen peroxide converted 10 into a hydroperoxide intermediate, which was further transformed into the l, 2-oxazin-6-one 28b. Overall, the results demonstrate the remarkable potential of suitably substituted 1, 2-oxazine derivatives for the stereoselective synthesis of amines.