56052-53-0

Usage

Uses

Used in Pharmaceutical Research:
3-(2-hydroxyphenyl)-1-phenylpropan-1-one is utilized as a key intermediate in the synthesis of various pharmaceutical compounds due to its reactive functional groups and structural diversity. Its presence in the development of new drugs is attributed to its ability to form a wide range of derivatives, enhancing the exploration of novel therapeutic agents.
Used in Organic Synthesis:
In the field of organic synthesis, 3-(2-hydroxyphenyl)-1-phenylpropan-1-one serves as a building block for the creation of complex molecules. Its versatile reactivity allows for the formation of numerous chemical entities, contributing to the advancement of synthetic chemistry and the discovery of new chemical compounds with potential applications.
Used in Medicinal Chemistry:
3-(2-hydroxyphenyl)-1-phenylpropan-1-one is employed as a crucial component in medicinal chemistry, where its unique structure facilitates the design and synthesis of bioactive molecules. Its potential biological activity and the ease of modification make it an attractive candidate for the development of new pharmaceutical agents targeting various diseases and conditions.
Used in Drug Discovery:
3-(2-hydroxyphenyl)-1-phenylpropan-1-one plays a significant role in drug discovery, where its exploration aids in identifying lead compounds with therapeutic potential. Its presence in this field underscores the importance of structural diversity and reactivity in the quest for innovative and effective treatments.

InChI:InChI=1/C15H14O2/c16-14-9-5-4-8-13(14)10-11-15(17)12-6-2-1-3-7-12/h1-9,16H,10-11H2

Upstream product

• 644-78-0 2-hydroxychalcone 
• 533-58-4 2-Iodophenol 
• 4393-06-0 1-Phenyl-2-propen-1-ol 
• 95-56-7 2-hydroxybromobenzene 
• 90-02-8 salicylaldehyde 
• 768-03-6 Phenyl vinyl ketone 
• 31702-30-4 cis-3-bromoflavan 
• 100-52-7 benzaldehyde 
• 98-86-2 acetophenone 
• 18885-85-3 2-phenyl-4H-benzo-1,3,2-dioxaborine 
• 1214-47-7 1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one 
• 93514-42-2 2-phenylchromene 
• 118-93-4 o-hydroxyacetophenone 
• 88186-87-2 2,3-cis-2-acetoxy-3-bromoflavan 

Downstream Products

• 62019-26-5 (2,3-dihydrobenzofuran-2-yl)(phenyl)methanone 
• 494-12-2 flavan 
• 1132755-87-3 (R)-3,4-dihydro-2-phenyl-2H-1-benzopyran 
• 55539-49-6 3-(2-hydroxyphenyl)-1-phenyl-1-propanol 
• 1309687-09-9 C₁₅H₁₂O₂ 

Relevant academic research and scientific papers

Chemoselective transfer hydrogenation of Α,Β-unsaturated carbonyls catalyzed by a reusable supported Pd nanoparticles on biomass-derived carbon

We herein report highly chemoselective transfer hydrogenation of α,β-unsaturated carbonyl compounds to saturated carbonyls with formic acid as a hydrogen donor over a stable and recyclable heterogeneous Pd nanoparticles (NPs) on N,O-dual doped hierarchical porous biomass-derived carbon. The synergistic effect between Pd NPs and incorporated heteroatoms on carbon plays a critical role on promoting the reaction efficiency. A series of α,β-aromatic and aliphatic unsaturated carbonyl compounds was selectively reduced to their corresponding saturated carbonyls in up to 97% isolated yields with good tolerance of various functional groups. In addition, the catalyst can be successively reused for at least 6 times without significant loss in reaction efficiency.

Chemoselective Hydrogenation of α,β-Unsaturated Carbonyls Catalyzed by Biomass-Derived Cobalt Nanoparticles in Water

Herein, we report highly chemoselective hydrogenation of α,β-unsaturated carbonyls to saturated carbonyls catalyzed by cobalt nanoparticles supported on the biomass-derived carbon from bamboo shoots with molecular hydrogen in water, which is the first prototype using a heterogeneous non-noble metal catalyst for such organic transformation as far as we know. The optimal cobalt nanocatalyst, CoOx@NC-800, manifested remarkable activity and selectivity for hydrogenation of C=C in α,β-unsaturated carbonyls under mild conditions. A broad set of α,β-aromatic and aliphatic unsaturated carbonyls were selectively reduced to their corresponding saturated carbonyls in up to 99 % yields with good tolerance of various functional groups. Meanwhile, a new straightforward one-pot cascade synthesis of saturated carbonyls was realized with high activity and selectivity via the cross-aldol condensation of ketones with aldehydes followed by selective hydrogenation. More importantly, this one-pot strategy is applicable for the expedient synthesis of Loureirin A, a versatile bioactive and medicinal molecule, from readily available starting materials, further highlighting the practical utility of the catalyst. In addition, the catalyst can be easily separated for successive reuses without significant loss in both activity and selectivity.

One-Pot Synthesis of O-Heterocycles or Aryl Ketones Using an InCl3/Et3SiH System by Switching the Solvent

An efficient one-pot synthesis of O-heterocycles or aryl ketones has been achieved using Et3SiH in the presence of InCl3 via a sequential ionic hydrogenation reaction by switching the solvent. This methodology can be used to construct C-O bonds and to prepare conjugate reduction products, including chromans, tetrahydrofurans, tetrahydropyrans, dihydroisobenzofurans, dihydrochalcones, and 1,4-diones in a facile manner. In addition, a novel plausible mechanism involving a conjugate reduction and a tandem reductive cyclization was verified by experimental investigations.

Rh-Catalyzed Decarbonylative Addition of Salicylaldehydes with Vinyl Ketones: Synthesis of Taccabulins A–E

A rhodium-catalyzed decarbonylative addition of salicylaldehydes with vinyl ketones was developed to synthesize o-hydroxydihydrochalcones (2-hydroxyphenethyl ketones). These decarbonylative addition reactions afforded various functionalized o-hydroxydihydrochalcones in moderate to good yields with broad functional group tolerance and selectivity. This method was also applied further in the divergent synthesis of dihydrochalcone derived taccabulins A–E.

Nanopalladium on polyethylenimine–grafted starch: An efficient and ecofriendly heterogeneous catalyst for Suzuki–Miyaura coupling and transfer hydrogenation reactions

Functionalized natural polysaccharides are attractive supports for colloidal metal nanocatalysts due to their abundance, cheapness, biocompatibility and biodegradability. In this study, isocyanate–functionalized starch was prepared by treating with diisocyanate. Polyethylenimine grafted onto starch via the formation of urea linker. The palladium nanoparticles deposited starch PEIS@Pd(0) was obtained through a chelating–in situ reduction procedure. Characterization of these materials was done using Fourier transform infrared spectroscopy, scanning electron microscopy, transmission electron microscopy, X–ray diffraction, and inductive coupled plasma atomic emission spectrometry. The catalytic activity of PEIS@Pd(0) was then tested in two series of model reactions: Suzuki–Miyaura coupling and transfer hydrogenation. The catalyst could be recovered by simple filtration and was reused for five times without significant loss of catalytic activity, which confirmed the good stability of the catalyst.

A Modular Synthesis of 2-Alkyl- and 2-Arylchromans via a Three-Step Sequence

A convergent three-step method for the synthesis of 2-substituted chromans is described. These results have been accomplished via the Heck coupling of readily accessible allylic alcohols and 2-iodophenols, followed by reduction and Mitsunobu cyclization. The utility and generality of this method is demonstrated through the synthesis of a series of 2-aryl-, 2-heteroaryl- and 2-alkylchromans, as well as an azachroman derivative. The asymmetric version of this approach via a Noyori-catalyzed ketone reduction and subsequent cyclization is likewise highlighted.

Michael additions of highly basic enolates to ortho -quinone methides

A protocol by which ketone or ester enolates and ortho-quinone methides (o-QMs) are generated in situ in a single reaction flask from silylated precursors under the action of anhydrous fluoride is reported. The reaction partners are joined to give a variety of β-(2-hydroxyphenyl)-carbonyl compounds in 32-94% yield in a single laboratory operation. The intermediacy of o-QMs is supported by control experiments utilizing enolate precursors and conventional alkyl halides as competitive alkylating agents and the isolation of 1,5-dicarbonyl products resulting from conjugate additions that do not restore the aromatic system.

Tosylhydrazine mediated conjugate reduction and sequential reductive coupling cyclization: Synthesis of 2-arylchromans

Tosylhydrazine mediated conjugate reduction of 2-hydroxyl chalcones and sequential reductive coupling cyclization is described. This is an unprecedented protocol and an extremely efficient method for a one-pot domino synthesis of 2-arylchromans in good to excellent yields from commercially available, cheap starting materials. More importantly, the two-step reactions can be easily controlled to afford dihydrochalcones or 2-arylchromans by the mole amounts of tosylhydrazine. Furthermore, the operational simplicity of the process and the high functional group tolerance are remarkable.

A novel transition metal-free conjugate reduction of α,β-unsaturated ketones with tosylhydrazine as a hydrogen source

A novel and efficient method has been developed for the chemoselective conjugate reduction of α,β-unsaturated ketones with tosylhydrazine as a hydrogen source to the corresponding saturated ketones in moderate to good yields. The present protocol does not require the use of transition metal, and is efficient being applicable to a wide range of substrates (25 examples).

CYCLIC PEROXIDE OXIDATION OF AROMATIC COMPOUND PRODUCTION AND USE THEREOF

The present invention provides a method for converting an aromatic hydrocarbon to a phenol by providing an aromatic hydrocarbon comprising one or more aromatic C-H bonds and one or more activated C-H bonds in a solvent; adding a phthaloyl peroxide to the solvent; converting the phthaloyl peroxide to a di-radical; contacting the di-radical with the one or more aromatic C-H bonds; oxidizing selectively one of the one or more aromatic C-H bonds in preference to the one or more activated C-H bonds; adding a hydroxyl group to the one of the one or more aromatic C-H bonds to form one or more phenols; and purifying the one or more phenols.