30339-32-3

Usage

Uses

Used in Pharmaceutical Industry:
α-Phenyl-2-p-tolylethylamine is used as a resolving base for Ibuprofen (I140000), a nonsteroidal anti-inflammatory drug (NSAID). It is employed for its ability to selectively inhibit both PGH synthase-1 and PGH synthase-2 enzymes with comparable potency, making it an effective treatment for inflammation, pain, and fever.
As a Selective Cyclooxygenase Inhibitor:
α-Phenyl-2-p-tolylethylamine is used as a selective cyclooxygenase inhibitor with an IC50 value of 14.9 μM. Its selectivity towards cyclooxygenase enzymes contributes to its potential therapeutic applications in managing inflammation and pain while minimizing side effects associated with non-selective NSAIDs.

Upstream product

• 30275-30-0 1-phenyl-2-(p-tolyl)ethylamine 
• 492-41-1 (1R,2S)-norephedrine 
• 111630-13-8 phenyl p-tolylmethyl ketone O-methyloxime 

Relevant academic research and scientific papers

Peptide-catalyzed stereoselective conjugate addition reactions generating all-carbon quaternary stereogenic Centers

A powerful catalyst: Quaternary stereogenic centers adjacent to tertiary stereocenters were formed with high diastereoselectivities and enantioselectivities in conjugate addition reactions between aldehydes and β,β-disubstituted nitroolefins by using a peptidic catalyst (see scheme). γ-Amino acids and heterocyclic compounds bearing quaternary stereogenic centers are easily accessible from the products. Copyright

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.

Practical resolution of 1-phenyl-2-(4-methylphenyl)ethylamine using a single resolving agent controlled by the dielectric constant of the solvent

A practical resolution of 1-phenyl-2-(4-methylphenyl)ethylamine 1 for obtaining (R)- and (S)-enantiomers by a dielectrically controlled resolution (DCR) method using a single resolving agent, (S)-mandelic acid 2, has been studied. The configuration of the excess enantiomer 1 in the less-soluble diastereomeric salt was found to vary depending on the solvent controlled by adjusting the solvent dielectric constant ε and the water content of the alcohol solvent. It was found that the presence of water molecules and the solvent molecular structures was key to controlling the configurational change phenomenon in the chiral discrimination between molecules 1 and 2. Moreover, the reaction environment controlled by the solvent dielectric constant plays a very distinct role in utilizing water molecules for crystallizing the less-soluble diastereomeric salt during the resolution. Based on the results, a practical resolution process for (R)-1 and (S)-1 production has been developed involving a simple solvent switch method; the (S)-1?(S)-2?H2O salt (33% yield, 96% de, E 64%) was obtained by the crystallization from 74% (w/w) aqueous ethanol in the first resolution, while the (R)-1?(S)-2 salt (23% yield, 98% de, E 46%) was crystallized from 100% ethanol of the condensate of the mother liquor after the first resolution.

Resolution of 1-phenyl-2-(p-tolyl)ethylamine via diastereomeric salt formation

(S)-1-Phenyl-2-(p-tolyl)ethylamine (S)-1, used for the industrial scale resolution of chrysanthemic acids, was obtained via resolution of the racemate with the hemiphthalate of (S)-isopropylidene glycerol (R)-2. The maximum experimental efficiency [69% yield and >99% e.e. of (S)-1] was achieved by a simple precipitation of (S)-1·(R)-2 from the solution of the 1:1 diastereomeric salt mixture in 93/7 isopropanol/water at saturation of the more soluble (R)-1·(R)-2 salt. Such an experimental efficiency was consistent with 0.79 maximum theoretical resolvability, derived from the solubilities of the two diastereomeric salts, and with DSC data, which indicated that the (S)-1·(R)-2/(R)-1·(R)-2 system is a binary mixture exhibiting an eutectic with composition approximately corresponding to a 0.2 molar ratio of (S)-1·(R)-2.

ASYMMETRIC REDUCTION OF OXIME ETHERS. DISTINCTION OF ANTI AND SYN ISOMERS LEADING TO ENANTIOMERIC AMINES.

Anti and syn ketoxime ethers were reduced with a chiral reducing agent prepared from (-)-norephedrine and 2 eq of BH3 to give S and R amines respectively in up to 92percentee.The preferred absolute configuration of the amine was dependent on the geometry of the oxime ether.