20795-53-3

Basic information

• Product Name: 3-PHENYL-CYCLOHEXANONE
• Synonyms: 3-PHENYL-CYCLOHEXANONE;Cyclohexanone, 3-phenyl-;3-phenylcyclohexan-1-one
• CAS NO: 20795-53-3
• Molecular Formula: C₁₂H₁₄O
• Molecular Weight: 174.24
• Mol File: 20795-53-3.mol
• Article Data: 359

Chemical Properties

• Melting Point: 64 °C
• Boiling Point: 294 °C at 760 mmHg
• Flash Point: 123.7 °C
• Appearance: /
• Density: 1.042 g/cm³
• Vapor Pressure: 0.00167mmHg at 25°C
• Refractive Index: 1.537
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Sparingly), Methanol (Slightly)
• CAS DataBase Reference: 3-PHENYL-CYCLOHEXANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-PHENYL-CYCLOHEXANONE(20795-53-3)
• EPA Substance Registry System: 3-PHENYL-CYCLOHEXANONE(20795-53-3)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 20795-53-3(Hazardous Substances Data)

Usage

Description

3-Phenylcyclohexanone is an organic compound that features a cyclohexanone ring with a phenyl group attached to the third carbon. It is known for its unique chemical properties and reactivity, particularly in organic synthesis.

Uses

Used in Organic Synthesis:
3-Phenylcyclohexanone is used as a key intermediate in the synthesis of various cyclic ketone derivatives. Its ability to undergo ring expansion reactions with beta-selenyl cyclic ketone derivatives makes it a valuable component in the preparation of complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-Phenylcyclohexanone is utilized as a building block for the development of novel drug candidates. Its reactivity and structural features allow for the creation of diverse chemical entities with potential therapeutic applications.
Used in Fragrance Industry:
3-Phenylcyclohexanone is also used in the fragrance industry as a component in the creation of various scent compounds. Its unique aroma profile contributes to the development of new and innovative fragrances for a variety of applications, including perfumes, cosmetics, and air fresheners.

Synthesis Reference(s)

The Journal of Organic Chemistry, 51, p. 4953, 1986 DOI: 10.1021/jo00375a037Tetrahedron Letters, 42, p. 781, 2001 DOI: 10.1016/S0040-4039(00)02176-6

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

Upstream product

• 24760-26-7 phenyl-4 bicyclo<3.1.0>hexen-3 one-2 
• 55815-00-4 3-methoxy-5-phenylcyclohex-2-ene-1-one 
• 930-68-7 cyclohexenone 
• 108-90-7 chlorobenzene 
• 14922-16-8 phenylazo phenyl sulfone 
• 603-36-1 triphenylantimony 
• 100-59-4 phenylmagnesium chloride 
• 934-56-5 trimethyl(phenyl)stannane 
• 3958-47-2 triphenylindium 
• 595-90-4 tetraphenyltin(IV) 
• 603-33-8 triphenylbismuthane 
• 7486-35-3 tri-n-butyl(vinyl)tin 
• 19040-53-0 Trimethylphenyllead 
• 780-69-8 triethoxyphenylsilane 

Downstream Products

• 10345-87-6 3-phenylcyclohex-2-enone 
• 14580-54-2 1-Acetyl-4-phenyl-cyclohexan-2-on 
• 14580-55-3 2-acetyl-3-phenylcyclohexanone 
• 54928-82-4 Cyano-(3-phenyl-cyclohex-1-enyl)-acetic acid methyl ester 
• 54928-83-5 Cyano-[3-phenyl-cyclohex-(E)-ylidene]-acetic acid methyl ester 
• 49673-74-7 3-phenyl-1-cyclohexanol 
• 68670-31-5 (3-Phenyl-cyclohexyl)-acetic acid methyl ester 
• 108062-26-6 (3-phenyl-cyclohexyl)-acetic acid 
• 111945-94-9 [3-Phenyl-cyclohex-(E)-ylidene]-acetic acid 
• 1187537-61-6 C₁₆H₁₈O₄ 
• 1235445-19-8 C₂₇H₂₄FNO₂S 
• 35376-41-1 5-phenylcyclohex-2-en-1-one 
• 20795-53-3 (R)-3-phenylcyclohexanone 
• 57344-86-2 (S)-3-phenylcyclohexanone 

Relevant articles and documents

Novel σ1 antagonists designed for tumor therapy: Structure – activity relationships of aminoethyl substituted cyclohexanes

Depending on the substitution pattern and stereochemistry, 1,3-dioxanes 1 with an aminoethyl moiety in 4-position represent potent σ1 receptor antagonists. In order to increase the stability, a cyclohexane ring first replaced the acetalic 1, 3-dioxane ring of 1. A large set of aminoethyl substituted cyclohexane derivatives was prepared in a six-step synthesis. All enantiomers and diastereomers were separated by chiral HPLC at the stage of the primary alcohol 7, and their absolute configuration was determined by CD spectroscopy. Neither the relative nor the absolute configuration had a large impact on the σ1 affinity. The highest σ1 affinity was found for cis-configured benzylamines (1R,3S)-11 (Ki = 0.61 nM) and (1S,3R)-11 (Ki = 1.3 nM). Molecular dynamics simulations showed that binding of (1R,3S)-11 at the σ1 receptor is stabilized by the typical polar interaction of the protonated amino moiety with the carboxy group of E172 which is optimally oriented by an H-bond interaction with Y103. The lipophilic interaction of I124 with the N-substituent also contributes to the high σ1 affinity of the benzylamines. The antagonistic activity was determined in a Ca2+ influx assay in retinal ganglion cells. The enantiomeric cis-configured benzylamines (1R,3S)-11 and (1S,3R)-11 were able to inhibit the growth of DU145 cells, a highly aggressive human prostate tumor cell line. Moreover, cis-11 could also inhibit the growth of further human tumor cells expressing σ1 receptors. The experimentally determined logD7.4 value of 3.13 for (1R,3S)-11 is in a promising range regarding membrane penetration. After incubation with mouse liver microsomes and NADPH for 90 min, 43% of the parent (1R,3S)-11 remained unchanged, indicating intermediate metabolic stability. Altogether, nine metabolites including one glutathione adduct were detected by means of LC-MS analysis.

Phosphine-olefin ligands: A facile dehydrogenative route to catalytically active rhodium complexes

Facile, metal-mediated, (acceptorless) dehydrogenation of tricyclopentyl phosphine directly affords rhodium chelating phosphine-olefin complexes, some of which are catalytically active for 1,4-additions. The Royal Society of Chemistry 2006.

Synthesis of β-Selenylated Cyclopentanones via Photoredox-Catalyzed Selenylation/Ring-Expansion Cascades of Alkenyl Cyclobutanols

A photoredox strategy to access β-selenated cyclic ketone derivatives through the coupling reaction of 1-(1-arylvinyl)cyclobutanols with diselenides under blue LED irradiation and an air atmosphere was developed. This reaction employs the easily accessibl

MORE HIGHLY MIXED, HIGHER ORDER CYANOCUPRATES "rt(2-thienyl)Cu(CN)Li2". EFFICIENT REAGENTS WHICH PROMOTE SELECTIVE LIGAND TRANSFER

The combination of an organolithium (RTLi) and 2-lithiothiophene (2-thienyl) with CuCN forms a new reagents, "RT(2-thienyl)Cu(CN)Li2".This species selectively transfers the RT ligand in substitution reactions with epoxides and halides.In conjugate addition processes, the cuprate reacts with unhindered substrates, while β,β-disubstituted cases unexpectedly afford products resulting from 1,2-addition of the thiophene group.The prospects for use of these reagents in the synthesis of polyene macrolide antibiotics are discussed.

Detailed Structural Analysis of a Self-Assembled Vesicular Amphiphilic NCN-Pincer Palladium Complex by Using Wide-Angle X-Ray Scattering and Molecular Dynamics Calculations

Wide-angle X-ray scattering experiments and all-atomistic molecular dynamics calculations were performed to elucidate the detailed structure of bilayer vesicles constructed by self-assembly of an amphiphilic palladium NCN-pincer complex. We found an excel

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.

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.