1444-65-1

Usage

Uses

Used in Pharmaceutical Industry:
2-Phenylcyclohexanone is used as a substrate for steroid monooxygenase (STMO) in the pharmaceutical industry. This application is due to its ability to interact with the enzyme, which plays a crucial role in the synthesis and modification of steroids. The compound's involvement in this process makes it a valuable component in the development of drugs targeting hormonal imbalances and other steroid-related conditions.
Used in Chemical Synthesis:
2-Phenylcyclohexanone is also used as a key intermediate in the synthesis of various organic compounds. Its unique structure allows it to be a versatile building block for creating a wide range of molecules with different properties and applications. This makes it an essential component in the chemical synthesis industry, where it contributes to the development of new materials and products.
Used in Research and Development:
In addition to its practical applications, 2-Phenylcyclohexanone is utilized in research and development for its potential to contribute to the understanding of various chemical reactions and processes. Its unique properties and reactivity make it an interesting subject for scientific study, which can lead to the discovery of new compounds and applications in various fields.

Synthesis Reference(s)

Chemistry Letters, 11, p. 325, 1982Journal of the American Chemical Society, 97, p. 7372, 1975 DOI: 10.1021/ja00858a027The Journal of Organic Chemistry, 52, p. 3697, 1987

InChI:InChI=1/C12H14O/c13-12-9-5-4-8-11(12)10-6-2-1-3-7-10/h1-3,6-7,11H,4-5,8-9H2/t11-/m1/s1

Upstream product

• 908094-04-2 phenyldiazomethane 
• 120-92-3 cyclopentanone 
• 5775-23-5 1-phenylcyclohexene oxide 
• 5435-44-9 (E)-3-Ureido-but-2-enoic acid ethyl ester 
• 60-29-7 diethyl ether 
• 19324-77-7 (+/-)-2t-chloro-1r-phenyl-cyclohexanol-⁽¹⁾ 
• 925-90-6 ethylmagnesium bromide 
• 19324-77-7 (+/-)-2c-chloro-1r-phenyl-cyclohexanol-⁽¹⁾ 
• 771-98-2 1-Phenylcyclohexene 
• 1444-64-0 2-phenylcyclohexanol 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 52305-68-7 1-phenylcyclohexane-1,2-diol 
• 144-62-7 oxalic acid 
• 822-87-7 2-Chlorocyclohexanone 

Downstream Products

• 26974-24-3 6-phenyl-1-pyrrolidinocyclohexene 
• 17206-56-3 2-ethyl-2-phenylcyclohexanone 
• 52955-92-7 2-<(dimethylamino)methyl>-6-phenylcyclohexanone 
• 7079-07-4 2-allyl-2-phenylcyclohexan-1-one 
• 101604-45-9 3-(2-oxo-1-phenyl-cyclohexyl)-propionic acid ethyl ester 
• 61875-85-2 (+/-)-1-hydroxy-2t-phenyl-cyclohexane-carbonitrile-(1r) 
• 14996-78-2 2-phenylcycloheptanone 
• 175390-96-2 4-phenyl-1-oxa-spiro[2.5]octane 
• 74395-08-7 3-phenylcycloheptanone 
• 854714-90-2 2-(2-benzyloxy-ethyl)-2-phenyl-cyclohexanone 
• 13128-18-2 4a-Phenyl-Δ⁸-octahydro-chinol-2-on 
• 107772-04-3 1-ethyl-2-phenyl-cyclohexanol 
• 10468-68-5 1,6-diphenyl-cyclohexene 
• 93902-64-8 1,2-diphenylcyclohexanol 

Relevant academic research and scientific papers

An expedient route to heterocycles through α-arylation of ketones and arylamides by microwave induced thermal SRN1 reactions

Microwave irradiation promotes a quick aromatic nucleophilic substitution by a thermally induced electron transfer process to form new C-C bonds by the coupling of aryl radicals and enolate nucleophiles. Diverse 2-aryl-1- phenylethanones can be prepared by the direct α-arylation of acetophenone with different haloarenes. The ketone enolate anion is generated by deprotonation with tBuOK in DMSO and the reaction is carried out in a closed microwave vessel at 70-100°C for 10 min. This simple procedure also allows the synthesis of deoxybenzoin and indole heterocycle derivatives by inter- or intra-molecular ring closure reactions, with moderate to excellent substitution yields. This journal is the Partner Organisations 2014.

Enantioselective Protonation of Silyl Enol Ether Using Excited State Proton Transfer Dyes

Enantiopure excited state proton transfer (ESPT) dyes were used for the asymmetric protonation of silyl enol ether. Under 365 nm irradiation, with 3,3′-dibromo-VANOL as the ESPT dye, up to 49% enantioselectivity with a 68% yield of product was observed at room temperature. The reaction is effective with a range of silyl enol ethers and can also be achieved with visible light upon the addition of triplet sensitizer. The relatively low ee of the protonated product is due to the racemization/decomposition of the ESPT dye in the excited state as indicated by circular dichroism, HPLC, and UV-vis spectroscopy.

GaCl3-catalyzed skeletal rearrangement of α,α, α-trisubstituted aldehydes

(Chemical Equation Presented) GaCl3 is found to be a superior catalyst for the skeletal rearrangement of α,α,α- trisubstituted aldehydes to ketones. The rearrangement can proceed smoothly in the presence of a catalytic amount of GaCl3, and even substrates having no heteroatoms α to the carbonyl group or without steric strains can be used. Double activation of a carbonyl group by two molecules of GaCl 3 was supported on the basis of experimental data and a DFT study.

First Enantioselective Protonation of Prochiral Allyltrimethyltins Using Lewis Acid Assisted Chiral Br?nsted Acids

The LBA which is prepared from tin tetrachloride and optically active binaphthol or its monomethyl ether is a highly effective reagent for the enantioselective protonation of prochiral allyltrimethyltins. The absolute stereochemical selectivity is quite different from that in the protonation of silyl enol ethers which we reported earlier.

SmI2-mediated reductive enolization of α-hetero-substituted ketones and enantioselective protonation

High enantioselectivity (up to 94% ee) has been achieved in the protonation of samarium enolates which were generated by Sml2-mediated reduction of 2-aryl-2-methoxycrclohexanones using a C2-symmetric chiral diol as a proton source.

Synthesis of an enantiopure 2-arylcyclohexanols from prochiral enol acetates by an enantioselective protonation/diastereoselective reduction sequence

The enantioselective protonation with 2-sulfinyl alcohols of lithium enolates of 2-arylcyclohexanones with different substituents on the phenyl group takes place with excellent enantioselectivities (89-99%). Chiral 2-phenylcyclohexanone and 2-arylcyclohexanones carrying electron donor substituents on the aromatic ring are converted into the corresponding trans-2-arylcyclohexanols by diastereoselective reduction with sodium naphthalenide in the presence of acetamide. The stereochemical integrity of the tertiary stereocenter is fully preserved using this reduction procedure. Interestingly, the chiral proton source is not consumed in the synthesis.

Chiral aminoborane as a chiral proton source for asymmetric protonation of lithium enolates derived from 2-arylcycloalkanones

Reaction of lithium enolates of 2-arylcycloalkanones 2 with (R,R)-aminoborane 1, prepared from (1R,2R)-1,2-diaminocyclohexane 4 and PhBCl2, gives the corresponding optically active ketones 3 with up to 93% ee; this is the first example of enantioselective protonation using a metal-containing chiral proton source.

ANOMALOUS STEREOCHEMISTRY OF GASE-PHASE ACID-INDUCED RING OPENING IN 1-PHENYLCYCLOHEXENE OXIDE

The first experimental evidence for an entropy-driven frontside displacement in a gas-phase cationic nucleophilic substitution has been provided by the results concerning the ring opening of 1-phenylcyclohexene oxide catalized by gaseous acids.

Synthesis and cytotoxicity of a novel 1-alkylaminomethyl-2,4-diaryl- butadiene-1,3 fragment integrated within cyclohex(pent)enes

A group of 1-alkylaminomethyl-2-aryl-3-arylidenecyclohex(pent)enes 3a-n with a 1-alkylaminomethyl-2,4-diaryl-1,3-butadiene fragment and a group of their congeners 3-alkylaminomethyl-1,2-diarylcyclohexene 7a-f have been synthesised for the first time. The conjugated system in 1-alkylaminomethyl-2-aryl-3- arylidenecyclohex(pent)enes 3a-n was unambiguously confirmed by X-ray crystallography. Cytotoxicity tests revealed that 3a-n possess inconsistent cytotoxicity against cancer cells, not their congeners 7a-f.

A study of substrate specificity of toluene dioxygenase in processing aromatic compounds containing benzylic and/or remote chiral centers

A series of substituted arenes containing remote chiral centers were screened as substrates for toluene dioxygenase (TDO). The absolute stereochemistry of the new metabolites was determined by chemical and spectroscopic correlation with synthetic standards. There was no evidence for kinetic resolution; enantiomers were indiscriminately processed by the enzyme to diastereomeric pairs, which were separable upon derivatization. Some of these new metabolites are useful as synthons for morphine synthesis. Full experimental details are reported for those new compounds stable to isolation and for derivatives of those that are unstable.