82105-36-0

Usage

Functional Groups

Ketone, Chloro-phenyl group

Structural Features

3-hydroxy-2-methyl-1-phenyl-propan-1-one backbone
Chloro-phenyl group attached to the third carbon of the propionyl side chain

Common Uses

Organic synthesis
Pharmaceutical research

Role in Organic Synthesis

Building block and intermediate

Potential Medicinal Properties

Studied for anti-inflammatory effects
Studied for analgesic effects

Applications in Pharmaceutical Development

Synthesis of bioactive molecules
Synthesis of pharmaceutical drugs

Therapeutic Potential

Possible treatment for various diseases and conditions

InChI:InChI=1/C16H15ClO2/c1-11(15(18)12-5-3-2-4-6-12)16(19)13-7-9-14(17)10-8-13/h2-11,16,19H,1H3

Upstream product

• 37471-46-8 1-phenyl-1-trimethylsiloxypropene 
• 104-88-1 4-chlorobenzaldehyde 
• 93-55-0 1-phenyl-propan-1-one 
• 66323-99-7 trimethyl[(Z)-(1-phenyl-1-propenyl)oxy]silane 
• 2114-00-3 2-bromo-1-phenyl-1-propanone 
• 4393-06-0 1-Phenyl-2-propen-1-ol 
• 6084-15-7 2-iodo-1-phenylpropan-1-one 

Relevant academic research and scientific papers

Iron-Modified Mesoporous Silica as an Efficient Solid Lewis Acid Catalyst for the Mukaiyama Aldol Reaction

Fe-MCM-41 and Fe-SBA-15, two different iron-containing mesoporous silicas, were successfully synthesized by a straightforward and versatile method using iron acetylacetonate as a metal precursor. pH adjustment with ammonia during the synthesis was found t

Iron(II)-derived lewis acid/surfactant combined catalysis for the enantioselective mukaiyama aldol reaction in pure water

The catalytic asymmetric Mukaiyama aldol reaction in pure water was performed by using a combination of iron(II) dodecyl sulfate, a chiral bipyridine ligand, and benzoic acid. By using the obtained iron(II)-derived Lewis acid/surfactant combined catalyst,

Gallium(III) triflate catalyzed diastereoselective mukaiyama aldol reaction by using low catalyst loadings

A mild method for the diastereoselective Mukaiyama aldol reaction is reported. By using a low loading of the gallium(III) triflate catalyst (down to 0.01 mol-%), the transformation proceeds efficiently to afford the corresponding β-hydroxy ketones in yields up to 92a€‰%. To the best of our knowledge, this is the first report of a metal triflate acting as a safe, bench-stable, and slow-releasing source of triflic acid for the Mukaiyama aldol reaction. A diastereoselective Mukaiyama aldol reaction was performed under mild conditions with a low loading of the gallium(III) triflate catalyst (down to 0.01 mol-%). The transformation proceeded efficiently to afford the corresponding β-hydroxy ketones in yields up to 92a€‰%. Copyright

Study of the lanthanide-catalyzed, aqueous, asymmetric Mukaiyama aldol reaction

The development of efficient methods for the asymmetric Mukaiyama aldol reaction in aqueous solution has received great attention. We have developed a new series of chiral lanthanide-containing complexes that produce Mukaiyama aldol products with outstanding enantioselectivities. In this paper, we describe an optimized ligand synthesis, trends in stereoselectivity that result from changing lanthanide ions, and an exploration of substrate scope that includes aromatic and aliphatic aldehydes and silyl enol ethers derived from aromatic and aliphatic ketones.

Synthesis of β-hydroxy and β-amino ketones from allylic alcohols catalyzed by ru(η5-C5Ph5)(CO)2Cl

An efficient method for the synthesis of β-hydroxy and β-amino ketones from allylic alcohols catalyzed by Ru(η5-C 5Ph5)(CO)2Cl is described. The influence of the stereoelectronic properties of the catalyst on the reaction outcome has been studied. Optimization of the reaction conditions supressed the formation of undesired side products such as saturated ketones, benzyl alcohols, and α,β-unsaturated ketones. Several aromatic and aliphatic allylic alcohols have been reacted with a large variety of aldehydes or imines to produce β-hydroxy ketones or β-amino ketones, respectively, in yields up to 99a%. Based on experimental data, a mechanism via ruthenium alkoxides and ruthenium aldoxides is proposed. In addition, a C-bound ruthenium enolate has been characterized. β-Hydroxy and β-amino ketones are synthesized from allylic alcohols and aldehydes or imines, respectively. The coupling reaction is catalyzed by Ru(η5-C5Ph5)(CO) 2Cl. Mechanistic investigations support a mechanism via ruthenium alkoxide intermediates.

Efficient synthesis of β-hydroxy ketones from allylic alcohols by catalytic formation of ruthenium enolates

A study was conducted to demonstrate the synthesis of β-hydroxy ketones from allylic alcohols by catalytic formation of ruthenium enolates. KOtBu was added to a mixture of complex Ru, containing a cyclopentadienyl ligand bearing five phenyl groups. It was demonstrated that ruthenium chloride reacts with KOtBu, forming a ruthenium tert-butoxide complex. It was also demonstrated that the reaction of the tert-butoxide complex with allylic alcohol produced a new alkoxide, as detected by H NMR spectroscopy.

Iron(II) and zinc(II) complexes with designed pybox ligand for asymmetric aqueous Mukaiyama-aldol reactions

An iron(II) complex with a hindered hydroxyethyl-pybox (he-pybox) ligand shows improved catalytic activity and enantioselectivity for asymmetric Mukaiyama-aldol reactions in aqueous media. This water-stable chiral Lewis acid promotes condensation of aroma

Asymmetric mukaiyama-aldol reaction in aqueous media promoted by zinc-based chiral lewis acids

Asymmetric aldol reactions in aqueous media have been realized by using zinc-based chiral Lewis acids. The aldol products have been obtained with high yield, diastereocontrol and a good level of enantioselectivity. The reactivity of both acetophenone and

Highly diastereoselective reformatsky-type reaction promoted by tin iodide Ate complex

Chemical equation presented An ate type of tin complex, Li+[n-Bu2Snl3]-/HMPA, works as a novel type of reagent to accomplish the highly diastereoselective Reformatsky-type reaction by the halogen-metal exchange method.

Novel chiral gallium Lewis acid catalysts with semi-crown ligands for aqueous asymmetric Mukaiyama aldol reactions

Asymmetric Mukaiyama aldol reactions in aqueous media (water-ethanol = 9:1) were catalyzed by chiral gallium catalysts with semi-crown ligands to give aldol products with good yields, syn-diastereoselectivities and enantioselectivities.