17596-79-1

Usage

Uses

Used in Pharmaceutical Industry:
(S)-2-Phenyl-1-propylamine is used as a key intermediate in the synthesis of pyrazolyl-containing tricyclic derivatives, which are known for their potential as anticancer agents. These derivatives target specific cellular pathways, exhibiting inhibitory effects on tumor growth and progression.
Used in Enantioselective Synthesis:
In the field of organic chemistry, (S)-2-Phenyl-1-propylamine is utilized as a building block for the enantioselective synthesis of pyrizinostatin. Pyrizinostatin is a pyroglutamyl peptidase inhibitor, which has potential applications in the development of novel therapeutics for various diseases.

InChI:InChI=1/C9H13N/c1-8(7-10)9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3/t8-/m1/s1

Upstream product

• 173216-42-7 (S)-1-azido-2-phenylpropane 
• 34713-70-7 2-Phenylpropanal 
• 582-22-9 2-phenylpropylamine 
• 1823-91-2 (R)-α-methylbenzyl cyanide 
• 914080-21-0 N-(4-methoxyphenyl)-N-((2R)-2-phenylpropyl)amine 
• 100-42-5 styrene 
• 72171-09-6 ((S)-2-Methoxymethyl-pyrrolidin-1-yl)-[2-phenyl-prop-(E)-ylidene]-amine 
• 74669-73-1 2-phenylpropyl 4-methylbenzenesulfonate 
• 37778-99-7 (S)-2-phenyl-1-propanol 
• 591-80-0 pent-4-enoic acid 
• 89999-52-0 ((S)-2-Methoxymethyl-pyrrolidin-1-yl)-(2-phenyl-propyl)-amine 
• 109757-73-5 1-nitro-2-phenylpropane 
• 746647-15-4 (S)-1-nitro-2-phenylpropane 
• 98-86-2 acetophenone 

Downstream Products

• 4663-89-2 ((S)-2-phenyl-propyl)-carbamic acid-(2-hydroxy-ethyl ester) 
• 617-94-7 1-methyl-1-phenylethyl alcohol 
• 93-54-9 1-Phenyl-1-propanol 
• 1123-85-9 (RS)-2-phenyl-1-propanol 
• 1517-68-6 (S)-1-phenylpropan-2-ol 
• 1572-95-8 (R)-1-phenyl-propan-2-ol 
• 97826-55-6 (+)-6-(S-2-phenyl-1-propylamino)-9-(β-D-ribofuranosyl)-9H-purine 
• 21260-36-6 [S]-(-)-N-methyl-2-phenylpropylamine 
• 943912-87-6 (2S)-(3-benzoylphenyl)propanoyloxy-N-[(2S)-phenylpropyl]acetamide 
• 609772-13-6 {[2-chloro-3-(trifluoromethyl)phenyl]methyl}[(2S)-2-phenylpropyl]amine 
• 791068-46-7 (S)-1-methyl-3-[(2-phenyl-propylamino)methyl]-1H-quinoxalin-2-one 
• 880347-50-2 (S)-E-3-(2-phenyl-propylcarbamoyl)-acrylic acid 
• 1228108-64-2 (S,S)-1,1',6,6',7,7'-hexamethoxy-3,3'-dimethyl-N₅,N₅'-bis(2-phenylpropyl)-2,2'-binaphthyl-5,5'-dicarboxamide 
• 1312945-83-7 (S)-2-(1-methyl-3-phenyl-4-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-6-yloxy)-N-(2-phenylpropyl)acetamide 

Relevant academic research and scientific papers

2-nitro- and 2,4-dinitrobenzenesulfonamides as protecting groups for primary amines

Procedures for the deprotection of the 2-nitro- and 2,4-dinitrobenzenesulfonamides to give the corresponding primary amines were developed. The 2-Nitrobenzenesulfonyl group was effectively removed by HSCH2CH2OH/DBU or PhSH/Cs2/

Resolution of (±)-β-methylphenylethylamine by a novel chiral stationary phase for Pirkle-type column chromatography

In this study, a new Pirkle-type chiral column stationary phase for resolution of β-methylphenylethyl amine was described by using activated Sepharose 4B as a matrix, L-tyrosine as a spacer arm, and an aromatic amine derivative of L-glutamic acid as a ligand. The binding capacities of the stationary phase were determined at different pH values (pH = 6, 7, and 8) using buffer solutions as mobile phase, and enantiomeric excess (ee) was determined by HPLC equipped with chiral column. The ee was found to be 47%.

CO2-Assisted asymmetric hydrogenation of prochiral allylamines

A new methodology for the asymmetric hydrogenation of allylamines takes advantage of a reversible reaction between amines and carbon dioxide (CO2) to suppress unwanted side reactions. The effects of various parameters (pressure, time, solvent, and base additives) on the enantioselectivity and conversion of the reaction were studied. The homogeneously-catalyzed asymmetric hydrogenation of 2-arylprop- 2-en-1-amine resulted in complete conversion and up to 82% enantiomeric excess (ee). Added base, if chosen carefully, improves the enantioselectivity and chemoselectivity of the overall reaction.

Iron-Catalyzed Diastereoselective Synthesis of Disubstituted Morpholines via C-O or C-N Bond Formation

The diastereoselective synthesis of 2,6- and 3,5-disubstituted morpholines was achieved from 1,2-amino ethers and 1,2-hydroxy amines substituted by an allylic alcohol using an iron(III) catalyst. The morpholines were obtained either by C-O or C-N bond formation. A plausible mechanism is suggested, involving a thermodynamic equilibrium to explain the formation of the cis diastereoisomer as the major product.

Enantioselective Synthesis of β-Methyl Amines via Iridium-Catalyzed Asymmetric Hydrogenation of N-Sulfonyl Allyl Amines

The iridium-catalyzed asymmetric hydrogenation of several N-sulfonyl allyl amines is reported. All substrates can be easily obtained by the Ir-catalyzed isomerization of N-tosylaziridines reported previously. The commercially available threonine-derived phosphinite (UbaPHOX) iridium complex has been found to be the best catalyst for this catalytic application, affording β-methyl amines with good to excellent ee values (up to 94%). The synthetic potential of this novel methodology was demonstrated by the formal synthesis of Lorcaserin and LY-404187. (Figure presented.).

Rhodium-catalyzed asymmetric hydrogenation of β-branched enamides for the synthesis of β-stereogenic amines

Using a rhodium complex of a bisphosphine ligand (R)-SDP, β-branched simple enamides with a (Z)-configuration were hydrogenated to β-stereogenic amines in quantitative yields and with excellent enantioselectivities (88-96% ee).

Biocatalytic Formal Anti-Markovnikov Hydroamination and Hydration of Aryl Alkenes

Biocatalytic anti-Markovnikov alkene hydroamination and hydration were achieved based on two concepts involving enzyme cascades: epoxidation-isomerization-amination for hydroamination and epoxidation-isomerization-reduction for hydration. An Escherichia coli strain coexpressing styrene monooxygenase (SMO), styrene oxide isomerase (SOI), ω-transaminase (CvTA), and alanine dehydrogenase (AlaDH) catalyzed the hydroamination of 12 aryl alkenes to give the corresponding valuable terminal amines in high conversion (many ≥86%) and exclusive anti-Markovnikov selectivity (>99:1). Another E. coli strain coexpressing SMO, SOI, and phenylacetaldehyde reductase (PAR) catalyzed the hydration of 12 aryl alkenes to the corresponding useful terminal alcohols in high conversion (many ≥80%) and very high anti-Markovnikov selectivity (>99:1). Importantly, SOI was discovered for stereoselective isomerization of a chiral epoxide to a chiral aldehyde, providing some insights on enzymatic epoxide rearrangement. Harnessing this stereoselective rearrangement, highly enantioselective anti-Markovnikov hydroamination and hydration were demonstrated to convert α-methylstyrene to the corresponding (S)-amine and (S)-alcohol in 84-81% conversion with 97-92% ee, respectively. The biocatalytic anti-Markovnikov hydroamination and hydration of alkenes, utilizing cheap and nontoxic chemicals (O2, NH3, and glucose) and cells, provide an environmentally friendly, highly selective, and high-yielding synthesis of terminal amines and alcohols.

Enantioselective Hydroaminomethylation of Olefins Enabled by Rh/Br?nsted Acid Relay Catalysis

Herein, by employing a rhodium catalyst with a commercial ligand and a phosphoric acid catalyst, highly chemo-, regio-, and enantioselective hydroaminomethylation of olefins is realized through a relay catalytic hydroformylation/dynamic kinetic reductive amination process. The method features mild conditions (1 bar of syngas, room temperature in most cases), high yields (up to 99%), and high enantioselectivities (up to >99.5:0.5 er). Besides styrenes, acrylamides also provided the products with high yields and enantioselectivities. Aliphatic alkenes and vinyl esters are also applicable for the current method, albeit lower yields and enantioselectivities were obtained.

Iridium-Catalyzed Enantioselective Hydrogenation of β,β-Disubstituted Nitroalkenes

A highly efficient, iridium-catalyzed, enantioselective hydrogenation of β,β-disubstituted nitroalkenes has been developed. Using a complex consisting of iridium and (S,S)-f-spiroPhos as the catalyst, a variety of β,β-disubstituted nitroalkenes were successfully hydrogenated to the corresponding chiral nitroalkanes with excellent enantioselectivities (up to 98% ee) and high turnover numbers (TON=1000).

Dynamic kinetic resolution of 2-phenylpropanal derivatives to yield β-chiral primary amines via bioamination

The amination of racemic α-chiral aldehydes, 2-phenylpropanal derivatives, was investigated employing ω-transaminases. By medium and substrate engineering the optical purity of the resulting β-chiral chiral amine could be enhanced to reach optical purities up to 99% ee. Using enantiocomplementary ω-transaminases allowed us to access the (R)- as well as the (S)-enantiomer in most cases. It is important to note that the stereopreference of the ω-transaminases found for α-chiral aldehydes did not correlate with the stereopreference previously observed for the amination of methyl ketones. In one case the stereopreference switched even upon exchanging a methyl substituent to a methoxy group.