123559-91-1

Usage

Synonym

R-Phenibut

Chemical compound

Yes

Potential properties

Psychoactive, anxiolytic

Mechanism of action

GABA receptor agonist

Effects

Sedative, anxiolytic, mood-enhancing, stress-reducing

Potential uses

Treatment of anxiety, insomnia, and other neurological conditions

Legal status

Restricted in some countries due to potential for abuse and dependence.

Upstream product

• 22966-19-4 trans-4'-methoxychalcone 
• 557-20-0 diethylzinc 
• 959-23-9 4'-methoxychalcone 
• 100-52-7 benzaldehyde 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 97-93-8 triethylaluminum 
• 1345023-22-4 C₁₈H₁₆O₄ 
• 1345023-39-3 C₂₀H₂₂O₄ 

Relevant academic research and scientific papers

Copper-catalyzed enantioselective 1,4-conjugate addition of dialkylzinc reagents to α,β- and α,β,γ,δ-unsaturated ketones

An enantioselective Cu(II)-catalyzed conjugate addition of dialkylzinc reagents to α,β- or α,β,γ,δ-unsaturated ketones with chiral cyclohexane-based amidophosphine ligands was developed. With 2 mol% of Cu(OAc)2·H2O/L5, the conjugate

Enantiopure sulfoximines-catalyzed 1, 4-additions to 2-en-ketone

An efficient chiral catalyst procedure for the preparation of β-chiral ketone via the 1, 4-additions reaction of 2-en-ketone has been developed using enantiopure sulfoximines modified with functional groups as ligands. The carefully design and synthesized

Enantioselective copper(II)-catalyzed conjugate addition of diethylzinc to β-substituted enones utilizing BINOL-based phosphoramidite ligands

A family of new chiral phosphoramidite ligands based on 3,3′-disubstituted (S)-BINOL have been successfully synthesized. The chiral phosphoramidite ligands were subsequently applied to the copper(II)-catalyzed enantioselective addition of diethylzinc to β

Tree of macromolecule loaded dinaphthol Asia phosphorus amide ligand, its synthetic method and its application

The invention discloses dendrimer polymer loaded binaphthol phosphoramidite ligand and a synthesis method thereof and application of the dendrimer polymer loaded binaphthol phosphoramidite ligand in asymmetric Michael addition reaction of diethyl zinc to

Paracyclophane-derived monodentate phosphoramidite ligands for copper-catalyzed asymmetric conjugate addition of diethylzinc to substituted chalcones

Copper-catalyzed asymmetric conjugate addition of diethylzinc to chalcones could be realized by using [2.2]paracyclophane-derived monodentate phosphoramidite ligands. The excellent yield and enantioselectivity (up to 98% yield and 95% enantiomeric excess) could be realized with low catalyst loading of 1.0 mol % and low ligand loading of 1.2%.

Modulation of multifunctional N,O,P ligands for enantioselective copper-catalyzed conjugate addition of diethylzinc and trapping of the zinc enolate

In this work, we have successfully synthesized a new family of chiral Schiff base-phosphine ligands derived from chiral binaphthol (BINOL) and chiral primary amine. The controllable synthesis of a novel hexadentate and tetradentate N,O,P ligand that contains both axial and sp3-central chirality from axial BINOL and sp3-central primary amine led to the establishment of an efficient multifunctional N,O,P ligand for copper-catalyzed conjugate addition of an organozinc reagent. In the asymmetric conjugate reaction of organozinc reagents to enones, the polymer-like bimetallic multinuclear Cu-Zn complex constructed in situ was found to be substrate-selective and a highly excellent catalyst for diethylzinc reagents in terms of enantioselectivity (up to >99 % ee). More importantly, the chirality matching between different chiral sources, C2-axial binaphthol and sp3-central chiral phosphine, was crucial to the enantioselective induction in this reaction. The experimental results indicated that our chiral ligand (R,S,S)-L1- and (R,S)-L4-based bimetallic complex catalyst system exhibited the highest catalytic performance to date in terms of enantioselectivity and conversion even in the presence of 0.005 mol % of catalyst (S/C=20 000, turnover number (TON)=17 600). We also studied the tandem silylation or acylation of enantiomerically enriched zinc enolates that formed in situ from copper-L4-complex-catalyzed conjugate addition, which resulted in the high-yield synthesis of chiral silyl enol ethers and enoacetates, respectively. Furthermore, the specialized structure of the present multifunctional N,O,P ligand L1 or L4, and the corresponding mechanistic study of the copper catalyst system were investigated by 31P NMR spectroscopy, circular dichroism (CD), and UV/Vis absorption. Match maker: The chiral bimetallic multinuclear Cu-Zn complex that contains a novel phosphine ligand and bears matching axial and sp3-central chirality from binaphthol and chiral amine was found to be a highly efficient catalyst in the enantioselective conjugate addition of an organic zinc reagent. Copyright

Enantioselective conjugate addition of dialkylzincs to α,β- unsaturated enones catalyzed by Ni(acac)2 and (+)-(1S,2R)-7,7- dimethyl-1-morpholinoisonorborneol

A mixture of chiral ligand 4 [(+)-MINBOL] and Ni(acac)2 (12.5 and 0.5 mol % respectively) is able to successfully catalyze the enantioselective conjugate 1,4-addition of dialkylzinc to α,β- unsaturated enones in propionitrile to give the corres

The effects of solvent on switchable stereoselectivity: Copper-catalyzed asymmetric conjugate additions using D2-symmetric biphenyl phosphoramidite ligands

A highly enantioselective copper-catalyzed conjugate addition of diethylzinc to acyclic aromatic enones was developed with phosphoramidite ligands bearing a D2-symmetric biphenyl backbone. This type of reaction demonstrated that toluene and THF solvents can completely reverse the absolute configuration of the products, thus simplifying the process of accessing either enantiomer (S: 92% ee, 94% yield; R: 99% ee, 96% yield).

Switchable stereoselectivity: The effects of substituents on the D 2-symmetric biphenyl backbone of phosphoramidites in copper-catalyzed asymmetric conjugate addition reactions with triethylaluminium

A highly enantioselective copper-catalyzed conjugate addition with triethylaluminium was developed using phosphoramidite ligands bearing a D 2-symmetric biphenyl backbone. For these ligands we demonstrated that the 3,3',5,5'-substituents on the biphenyl backbone can completely reverse the absolute configuration of the products. Copyright

The long-arm effect: Influence of axially chiral phosphoramidite ligands on the diastereo- and enantioselectivity of the tandem 1,4-addition/fluorination

Long arm of the law: The long-armed phosphoramidite 1 was used as a catalyst for the title reaction of acyclic alkylidene β-ketoesters with dialkylzinc and fluorinating reagents. The products, containing adjacent carbon- and fluorine-substituted stereocenters, are obtained in high yield as well as diastereo- and enantioselectivity. NSFI=N-fluorobenzenesulfonimide.