138983-03-6

Basic information

• Product Name: (R)-2-(1-hydroxyethyl)-6-phenylpyridine
• Synonyms: (R)-2-(1-hydroxyethyl)-6-phenylpyridine
• CAS NO: 138983-03-6
• Molecular Weight: 199.252
• Mol File: 138983-03-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (R)-2-(1-hydroxyethyl)-6-phenylpyridine(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-(1-hydroxyethyl)-6-phenylpyridine(138983-03-6)
• EPA Substance Registry System: (R)-2-(1-hydroxyethyl)-6-phenylpyridine(138983-03-6)

Safety Data

• Hazardous Substances Data: 138983-03-6(Hazardous Substances Data)

Usage

Description

(R)-2-(1-hydroxyethyl)-6-phenylpyridine, also known as R-phenylpipecolic acid, is a chiral organic compound belonging to the pyridine family. It is the biologically active R enantiomer, known for its potential therapeutic applications, particularly in the treatment of neurological disorders and as an anti-inflammatory agent. (R)-2-(1-hydroxyethyl)-6-phenylpyridine has been studied for its neuroprotective effects and its ability to modulate the immune system, as well as for its potential anti-cancer properties. Its unique structure and promising pharmacological activities make it a subject of ongoing research and development in the field of medicinal chemistry.

Uses

Used in Pharmaceutical Industry:
(R)-2-(1-hydroxyethyl)-6-phenylpyridine is used as a therapeutic agent for neurological disorders due to its neuroprotective effects and ability to modulate the immune system.
Used in Anti-inflammatory Applications:
(R)-2-(1-hydroxyethyl)-6-phenylpyridine is used as an anti-inflammatory agent, leveraging its potential to modulate the immune system and provide relief from inflammation.
Used in Anticancer Applications:
(R)-2-(1-hydroxyethyl)-6-phenylpyridine is used as a potential anti-cancer agent, with ongoing research exploring its properties and efficacy in cancer treatment.
Used in Medicinal Chemistry Research:
(R)-2-(1-hydroxyethyl)-6-phenylpyridine is used as a subject of research and development in the field of medicinal chemistry, focusing on its unique structure and pharmacological activities for the creation of new drugs and therapies.

Upstream product

• 59576-29-3 methyl(2-phenylpyridin-6-yl)-methanone 
• 108-05-4 vinyl acetate 
• 139163-61-4 α-methyl-6-phenyl-2-pyridinemethanol 
• 49669-13-8 1-(6-bromopyridin-2-yl)-ethanone 
• 626-05-1 2,6-Dibromopyridine 
• 204244-63-3 (R)-2-(1-acetoxyethyl)-6-phenylpyridine 
• 138983-04-7 (R)-(+)-2-(1-hydroxyethyl)-6-bromopyridine 
• 98-80-6 phenylboronic acid 

Downstream Products

• 1146666-02-5 (S)-2-(1-azidoethyl)-6-phenylpyridine 
• 428514-88-9 (R)-1-(6-phenylpyridin-2-yl)ethyl methanesulfonate 

Relevant articles and documents

Copper-catalyzed asymmetric reductions of aryl/heteroaryl ketones under mild aqueous micellar conditions

Enantioselective syntheses of nonracemic secondary alcohols have been achieved in an aqueous micellar medium via copper-catalyzed (Cu(OAc)2·H2O/(R)-3,4,5-MeO-MeO-BIPHEP) reduction of aryl/heteroaryl ketones. This methodology serves as a green protocol to access enantio-enriched alcohols under mild conditions (0-22 °C) using a base metal catalyst, together with an inexpensive, innocuous, and convenient stoichiometric hydride source (PMHS). The secondary alcohol products are formed in good to excellent yields with ee values greater than 90%.

Preparation of new chiral pyridine-phosphine ligands and their Pd-catalyzed asymmetric allylic alkylations

Enantiomerically pure 2-(diphenylphosphino)methyl-N-[1-(2-pyridinyl)ethyl] 1 and 2 have been prepared by the stereospecific substitution of enantiomerically pure 1-(2-pyridinyl)ethyl methanesulfonate 6 eith enantiomerically pure 2-(diphenylphosphino)methylpyrrolidine. Asymmetric allylic akylation of 1,3-diphenyl-2-propenyl acatate 11 with dimethyl malonate sodium salt using the (S,S)-ligand 1 affords the (R)-product 12 with up to 86% e.e. in good yield.

Enantioselective Synthesis of Optically Active Pyridine Derivatives and C2-Symmetric 2,2'-Bipyridines

Optically active pyridine derivatives 2, 15, 18, 19, 21, 26, and 27 are obtained by enantioselective reduction of the corresponding ketones 5, 7, 11-13, 24, and 25 using the chiral borane reagent chlorodiisopinocampherylborane .Nickel(0)-mediated coupling of bromopyridines 2, 15, and 31 gives C2-symmetric 2,2'-bipyridines (R,R)-32, (R,R)-33, and (S,S)-38, respectively, which form metal complexex with Co(II), Pd(II), Cu(I), and Ag(I).Aryl-substituted pyridines 26, and 39-41 are synthesized by palladium(0)-catalized cross coupling of 2 and 15 with boronic acids 42-44.Key Words: 2,2-Bipyridines / Pyridines, optically active / Chiral ligands / Asymmetric Synthesis / Catalysis, enantioselective