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Usage

Uses

Used in Pharmaceutical Industry:
(S)-1,2-Diphenylethylamine is used as a chiral building block for the synthesis of various pharmaceutical drugs. Its unique structure allows for the creation of a wide range of compounds with potential therapeutic applications.
Used in Organic Chemistry:
(S)-1,2-Diphenylethylamine is used as a reagent for the enantioselective synthesis of chiral compounds. Its ability to selectively produce one enantiomer over the other makes it a valuable tool in the development of enantiomerically pure substances, which are often crucial for the desired biological activity of a compound.
Used in Asymmetric Catalysis:
(S)-1,2-Diphenylethylamine has been studied for its potential use as a ligand in asymmetric catalysis. Its unique properties may enable the development of more efficient and selective catalytic processes, leading to improved synthetic routes for various chemical products.
Used in Biological Research:
(S)-1,2-Diphenylethylamine has been investigated for its biological activity and potential pharmacological properties. Understanding its interactions with biological systems can lead to the discovery of new therapeutic targets and the development of novel drugs with specific applications in medicine.

Upstream product

• 49855-40-5 D_g-threo-α'-chloro-bibenzyl-α-ylamine 
• 128013-82-1 (1S,4R)-2-[(E)-(R)-1,2-Diphenyl-ethylimino]-7,7-dimethyl-bicyclo[2.2.1]heptane-1-carboxylic acid (2-hydroxy-phenyl)-amide 
• 126003-99-4 (1R,2R,5R)-3-[(E)-(S)-1,2-Diphenyl-ethylimino]-2,6,6-trimethyl-bicyclo[3.1.1]heptan-2-ol 
• 100-44-7 benzyl chloride 
• 158109-78-5 (R,E)-N-benzylidene-4-methylbenzenesulfinamide 
• 6921-34-2 benzylmagnesium chloride 
• 25611-78-3 (R,S)-1,2-diphenylethylamine 
• 100-46-9 benzylamine 
• 3938-96-3 ethyl 2-methoxyacetate 
• 451-40-1 phenyl benzyl ketone 
• 100-39-0 benzyl bromide 
• 127498-25-3 10-(N-o-hydroxyphenylamide)-N-benzyl-7,7-dimethyl-dicyclo-<2,2,1>-heptane-2-imine 
• 126003-96-1 C₁₇H₂₃NO 
• 126003-97-2 (1R,2R,5R)-3-(benzylimino)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ol 

Downstream Products

• 87691-40-5 Boc-Phe-His-Sta-Leu-(+)-1,2-dipehnylethylamine 
• 350678-30-7 ((S)-1,2-Diphenyl-ethyl)-(2-phenylsulfanyl-ethyl)-amine 
• 127529-18-4 (S)-(+)-1-(1,2-diphenylethyl)piperidine 
• 74619-81-1 N-benzylidene-(-)-1,2-diphenylethylamine 
• 66730-28-7 N-benzoyl-(-)-1,2-diphenylethylamine 
• 1567834-63-2 C₁₇H₁₆N₂O 
• 134540-84-4 (5R)-5-(4-imidazolylmethyl)-3-<(S)-1,2-diphenylethyl>-2,4-imidazolidinedione 
• 84984-08-7 (1S,1'S)-(+)-N-(2'-hydroxy-1'-isopropylethyl)-1,2-diphenylethylamine hydrochloride 
• 103-29-7 1,1'-(1,2-ethanediyl)bisbenzene 
• 14149-00-9 (S)-1,2-diphenylethylamine hydrochloride 
• 350678-46-5 (S)-1-Benzyl-4-phenylsulfanyl-3,4-dihydro-1H-isoquinoline-2-carbaldehyde 
• 350678-38-5 N-(2-Benzenesulfinyl-ethyl)-N-((S)-1,2-diphenyl-ethyl)-formamide 
• 350678-34-1 N-((S)-1,2-Diphenyl-ethyl)-N-(2-phenylsulfanyl-ethyl)-formamide 
• 350678-51-2 (S)-1-Benzyl-3,4-dihydro-1H-isoquinoline-2-carbaldehyde 

Relevant academic research and scientific papers

Highly efficient enantioselective liquid-liquid extraction of 1,2-amino-alcohols using SPINOL based phosphoric acid hosts

Access to enantiopure compounds on large scale in an environmentally friendly and cost-efficient manner remains one of the greatest challenges in chemistry. Resolution of racemates using enantioselective liquid-liquid extraction has great potential to meet that challenge. However, a relatively feeble understanding of the chemical principles and physical properties behind this technique has hampered the development of hosts possessing sufficient resolving power for their application to large scale processes. Herein we present, employing the previously untested SPINOL based phosphoric acids host family, an in depths study of the parameters affecting the efficiency of the resolution of amino-alcohols in the optic of further understanding the core principles behind ELLE. We have systematically investigated the dependencies of the enantioselection by parameters such as the choice of solvent, the temperature, as well as the pH and bring to light many previously unsuspected and highly intriguing interactions. Furthermore, utilizing these new insights to our advantage, we developed novel, highly efficient, extraction and resolving protocols which provide remarkable levels of enantioselectivity. It was shown that the extraction is catalytic in host by demonstrating transport in a U-tube and finally it was demonstrated how the solvent dependency could be exploited in an unprecedented triphasic resolution system.

Candida antarctica lipase A and Pseudomonas stutzeri lipase as a pair of stereocomplementary enzymes for the resolution of 1,2-diarylethanols and 1,2-diarylethanamines

Candida antarctica lipase A (CALA) and Pseudomonas stutzeri lipase (PSL) displayed opposite enantioselectivities in the acylation of 1,2-diphenylethanol and 1,2-diphenylethanamine. CALA was (S)-selective while PSL was (R)-selective. In addition, fourteen different 1,2-diarylethanols were tested as the substrates of CALA. It was found that most of them were accepted by CALA with high enantioselectivity. The DKR of five representative substrates by the combination of CALA and a ruthenium-based racemization catalyst provided good yields (82-91%) and acceptable enantiopurities (87-94% ee).

COMPOSITIONS AND METHODS FOR CYCLOFRUCTANS AS SEPARATION AGENTS

The present invention relates to derivatized cyclofructan compounds, compositions comprising derivatized cyclofructan compounds, and methods of using compositions comprising derivatized cyclofructan compounds for chromatographic separations of chemical species, including enantiomers. Said compositions may comprise a solid support and/or polymers comprising derivatized cyclofructan compounds.

NMDA receptor affinities of 1,2-diphenylethylamine and 1-(1,2-diphenylethyl)piperidine enantiomers and of related compounds

We resolved 1,2-diphenylethylamine (DPEA) into its (S)- and (R)-enantiomer and used them as precursors for synthesis of (S)- and (R)-1-(1,2-diphenylethyl)piperidine, flexible homeomorphs of the NMDA channel blocker MK-801. We also describe the synthesis o

Monoalkylation of primary amines and N-sulfinylamides

An efficient monoalkylation of primary amines with primary or secondary alcohols catalyzed by Ra-Ni under mild conditions is described. The Royal Society of Chemistry.

Synthesis of highly enantiomerically enriched amines by the diastereoselective addition of triorganozincates to N-(tert-butanesulfinyl)imines

The reaction of triorganozincates with (R)-N-(tert-butanesulfinyl) imines gives the expected α-branched sulfinamides in good to excellent yields with diastereomeric ratios of up to 98:2. The N-sulfinyl group of the products can be easily removed by acidic treatment, affording the corresponding chiral primary amines in enantiomeric excesses of up to 96%. The reactivity and the selectivity shown by the triorganozincates are different from the ones observed with the corresponding Grignard reagents, which allows, in several cases, the preparation of both enantiomers of an amine from the same imine substrate. When mixed triorganozincates are used, one can take advantage of the slow transfer rate of the methyl group to use it as a non-transferable one. Both aromatic and aliphatic aldimines, as well as activated ketimines, are good substrates for these addition reactions.

π-π Stacking versus steric effects in stereoselectivity control: Highly diastereoselective synthesis of syn-1,2-diarpropylamines

N-Arylarylideneamines react with sulfinylbenzyl carbanions derived from 2-(p-tolylsulfinyl)toluenes (S)-1 and (S)-2, affording epimeric mixtures at C1 of 1,2-diarylethyl- and 1,2-diarylpropylamine derivatives. The sulfinyl group completely controls the configuration at C2 in the reactions of (S)-2. The configuration at Cl depends on the electron density of the ring adjacent to the iminic carbon atom which is modulated by π-π stacking interactions with the ring joined to the carbanionic centre. The stereoselectivity was controlled by modifying the acceptor character of the arylideneamine ring with appropriate substituents, the formation of the highly selective (R) configuration at C1 being made possible by electron-donating groups. N-(2,4,6-Trimethoxyphenyl) arylideneamines have been shown to be suitable starting materials for the preparation of (R)-1,2-diarylethyl- and (1R,2S)-1,2-diarylpropylamines (syn epimers) in a highly stereoselective manner.

Base-dependent regio- and diastereoselective alkylation of chiral perhydro 1,3,2-oxazabenzophosphorinane-2-oxides derived from (-)-8-benzylamino menthol

The regioselectivity in the alkylation of chiral perhydro 1,3,2-benzoxazaphosphorinane-2-oxides is dependent on the base used for deprotonation. The ethyl oxazaphosphorinanes are benzylated at the nitrogen substituent after deprotonation with n-BuLi, but

Facile synthesis of optically pure 1,2-diaryl (and 1-alkyl-2-aryl) ethyl and propylamines

(Figure presented) A concise high-yielding route to synthetically useful 1,2-diaryl (and 1-alkyl-2-aryl) ethyl and propylamines in high enantiomeric purity is described. The key step of this route is the completely stereoselective addition of lithium (R)-ortho-(p-toluenesulfinyl)benzylic carbanions to (S).N.p-toluenesulfinylimines, which takes place in very high or quantitative yields. N-Desulfinyiation and C-desulfinylation of the resulting adducts can be achieved with no loss of optical purity employing conventional methods (TFA and Raney-Ni, respectively).

Determination of ring conformation in 1-benzyl-1,2,3,4- tetrahydroisoquinolines and a new synthesis of the chiral compounds

The conformation of the piperideine ring in 1-benzyl-1,2,3,4- tetrahydroisoquinolines was determined as 2H3 form with a pseudoaxial position of the 1-benzyl group by circular dichroism (CD) spectral comparison with 1-methyl-1,2,3,4-tetrahydroisoquinolines. The chiral center at C-1 of 1,2,3,4-tetrahydroisoquinoline (TIQ) was constructed in an unambiguous manner by applying a new method of TIQ synthesis utilizing the Pummerer reaction as a key step. Enantiomerically pure (R)- and (S)-1-methyl- and 1- benzyltetrahydroisoquinolines (1) were prepared starting from readily available chiral amines (2) in good overall yields.