57344-86-2

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
(S)-3-Phenylcyclohexanone is utilized as an intermediate in the synthesis of various pharmaceuticals and agrochemicals. Its unique structure allows for the development of new and effective compounds with potential therapeutic and pesticidal properties.
Used in Fragrance and Flavoring Agent Production:
(S)-3-PHENYLCYCLOHEXANONE is employed as a key ingredient in the production of fragrances and flavoring agents. Its aromatic nature contributes to the creation of diverse scents and tastes in various consumer products.
Used as a Chiral Auxiliary in Asymmetric Synthesis:
(S)-3-Phenylcyclohexanone serves as a chiral auxiliary in asymmetric synthesis, a technique used to produce enantiomerically pure compounds. Its chiral center plays a crucial role in the selective formation of desired enantiomers, which is essential in the synthesis of biologically active molecules.
Used in Anti-Inflammatory and Antimicrobial Applications:
(S)-3-Phenylcyclohexanone has been studied for its biological activities, including potential anti-inflammatory and antimicrobial properties. Its ability to modulate inflammatory responses and inhibit microbial growth makes it a promising candidate for the development of new therapeutic agents and antimicrobial products.

InChI:InChI=1/C12H14O/c13-12-8-4-7-11(9-12)10-5-2-1-3-6-10/h1-3,5-6,11H,4,7-9H2/t11-/m0/s1

Upstream product

• 930-68-7 cyclohexenone 
• 134880-11-8 (4S)-1-methyl-4,5,6,7-tetrahydro-4-phenyl-2,1-benzisoxazolin-3-one 
• 591-51-5 phenyllithium 
• 1728-18-3 dimethylacetal of cyclohexenone 
• 100-58-3 phenylmagnesium bromide 
• 396718-95-9 [(R)-3-Phenyl-cyclohex-(E)-ylidene]-acetaldehyde 
• 3262-89-3 triphenylboroxine 
• 16419-60-6 2-Methylphenylboronic acid 
• 28557-00-8 phenylzinc chloride 
• 780-69-8 triethoxyphenylsilane 
• 873223-22-4 diphenylindium hydroxide 
• 98-80-6 phenylboronic acid 
• 934-56-5 trimethyl(phenyl)stannane 
• 10345-87-6 3-phenylcyclohex-2-enone 

Downstream Products

• 1489231-21-1 (S)-3-phenylcyclohexanone-2,2,6,6-d 
• 1232059-79-8 C₁₃H₁₉N 
• 1232059-70-9 (1S,3R)-3-phenyl-cyclohexanecarboxylic acid amide 
• 1232059-56-1 C₁₃H₁₅N 
• 1232059-68-5 (1R,3R)-3-phenyl-cyclohexanecarboxylic acid amide 
• 1232059-66-3 C₁₃H₁₆O₂ 
• 76936-85-1 (+)-(R)-3-phenyl-1-(2-tolyl)cyclohexene 

Relevant academic research and scientific papers

Asymmetric Synthesis of Chiral Bicyclo[2.2.1]hepta-2,5-diene Ligands through Rhodium-Catalyzed Asymmetric Arylative Bis-cyclization of a 1,6-Enyne

A series of novel chiral diene ligands (1R,4S)-L1, which are based on the bicyclo[2.2.1]heptadiene skeleton and are substituted with methyl and an ester group at the bridgehead carbons, were synthesized through rhodium-catalyzed asymmetric arylative bis-c

Chiral N-aryl tert-butanesulfinamide-olefin ligands for rhodium-catalyzed asymmetric 1,4-addition of aryl boronic acids to cyclic enones

Chiral N-aryl sulfinamide-olefins which are readily synthesized via C-N coupling and nucleophilic substitution have been used as chiral ligands, which demonstrate moderate to excellent asymmetric catalytic performance in the rhodium-catalyzed asymmetric 1

Synthesis of Silicon-Stereogenic Silanols Involving Iridium-Catalyzed Enantioselective C-H Silylation Leading to a New Ligand Scaffold

Despite a growing focus on the construction of highly enantioenriched silicon-stereogenic organosilicon compounds, the enantioselective synthesis of silicon-stereogenic silanols through asymmetric catalysis remains a considerable challenge. Herein, we realized enantioselective construction of silicon-stereogenic diarylsilanols via an Ir-catalyzed C-H silylation of diarylsilanols along with stereospecific substitution or Tamao-Fleming oxidation. This strategy gives rise to a class of chiral diol catalyst cores (PSiOLs). Transformation of PSiOLs led to the ligand possessing both Si and P-stereocenters, which is capable of inducing excellent enantioselectivity in the rhodium(I)-catalyzed conjugate 1,4-addition of aryl boronic acids to cyclohexenone.

Enantioselective Hydrogenation of Endocyclic Enones: the Solution to a Historical Problem?

The enantioselective hydrogenation of endocyclic enones has been a historical problem for homogeneous catalysis. We herein report an efficient method to reduce endocyclic enones with molecular hydrogen. Catalyzed by a rhodium/Zhaophos complex, a variety of enones with five-, six- or seven-member ring were hydrogenated with high enantioselectivity (92%—99% ee). Excellent chemo- and enantioselectivity demonstrated this method was successfully applied in the enantioselective hydrogenation of citral to produce enantio-enriched citronellal.

Fine-Tuning the Bicyclo[3.3.1]nona-2,6-diene Ligands: Second Generation 4,8-Substituted Dienes for Rh-Catalyzed Asymmetric 1,4-Addition Reactions

Design and synthesis of the second generation C2-symmetric 4,8-endo,endo-bis(alkoxy) bicyclo[3.3.1]nona-2,6-diene ligands possessing additional 4,8-exo,exo substituents is reported. The 4,8-exo,exo groups provide a further element for fine-tuning of the ligand structure by enforcing conformational rigidity of the 4,8-endo,endo side chains. Such tetrasubstituted bicyclo[3.3.1]nona-2,6-dienes were employed as steering ligands in the rhodium-catalyzed arylation of cyclic enones with arylboronic acids, providing the corresponding 1,4-addition products in good to excellent yields (69–99 %) and enantioselectivities up to 99 % ee.

C1-Symmetric Binap Derivative Featuring Single Diferrocenylphosphino-Donor Moiety

A C1-symmetric chiral bisphosphine, FcPh-Binap (1), which possesses a single diferrocenylphosphino moiety together with a conventional Ph2P-substituent, was prepared in enantiomerically pure forms. Ligand 1 is sterically less demanding than Fc-Segphos (A)

Enantioselective Reductive Homocoupling of Allylic Acetates Enabled by Dual Photoredox/Palladium Catalysis: Access to C2-Symmetrical 1,5-Dienes

Transition-metal-catalyzed reductive coupling reactions have emerged as powerful protocols to construct C-C bonds. However, the development of enantioselective C(sp3)-C(sp3) reductive coupling remains challenging. Herein, we report a highly regio-, diastereo-, and enantioselective reductive homocoupling of allylic acetates through cooperative palladium and photoredox catalysis using diisopropylethylamine or Hantzsch ester as a homogeneous organic reductant. This straightforward protocol enables the stereoselective construction of C(sp3)-C(sp3) bonds under mild reaction conditions. A series of C2-symmetrical chiral 1,5-dienes were easily prepared with excellent enantioselectivities (up to >99% ee), diastereoselectivities (up to >95:5 dr), and regioselectivities (up to >95:5 rr). The resultant chiral 1,5-dienes can be directly used as chiral ligands in asymmetric synthesis, and they can be also transformed into other valuable chiral ligands.

Enantioselective Conjugate Addition of Stabilized Arylzinc Iodide to Enones: an Improved Protocol of the Hayashi Reaction

Stabilised arylzinc iodide, prepared by direct insertion of zinc into aryl iodides, were used as nucleophiles in the Hayashi Rh-catalysed enantioselective conjugate addition to enones. The reaction conditions were optimized in the addition of phenylzinc i

Counterion Enhanced Organocatalysis: A Novel Approach for the Asymmetric Transfer Hydrogenation of Enones

We present a novel strategy for organocatalytic transfer hydrogenations relying on an ion-paired catalyst of natural l-amino acids as main source of chirality in combination with racemic, atropisomeric phosphoric acids as counteranion. The combination of a chiral cation with a structurally flexible anion resulted in a novel chiral framework for asymmetric transfer hydrogenations with enhanced selectivity through synergistic effects. The optimized catalytic system, in combination with a Hantzsch ester as hydrogen source for biomimetic transfer hydrogenation, enabled high enantioselectivity and excellent yields for a series of α,β-unsaturated cyclohexenones under mild conditions. Moreover, owing to the use of readily available and chiral pool-derived building blocks, it could be prepared in a straightforward and significantly cheaper way compared to the current state of the art.

Tricyclic Sulfoxide-Alkene Hybrid Ligands for Chiral Rh(I) Complexes: The "Matched" Diastereomer Catalyzes Asymmetric C-C Bond Formations

Deprotonation of phenyldibenzo[b,f]tropylidene (8) with LDA/t-BuOK followed by quenching with either diastereomer of inexpensive glucose-based t-Bu-sulfinate (R)- or (S)-11 affords a sulfoxide-alkene hybrid ligand as the diastereomeric pairs (SS,SC)-9/(SS,RC)-10 and (RS,RC)-9/(RS,SC)-10, respectively, which via chromatographic/recrystallization may be separated into the four isomers. The optically pure diastereomeric ligands (SS,SC)-9 and (SS,RC)-10 react with [RhCl(coe)2]2 to form the dinuclear complexes (RS,SC)-11 and (RS,RC)-12, respectively, in which the bidentate ligands coordinate the metal centers through the sulfur and alkene donor functions. These complexes catalyze the conjugate addition of arylboronic acids to cyclic Michael acceptors with enantioselectivities of up to 99% ee. DFT calculations show the preponderant influence of planar chirality of the ligand alkene function. The enantioselectivity switch observed between (RS,SC)-11 and (RS,RC)-12 is explained by the inverted cis-trans coordinations of the substrate molecules in catalytic steps.