17040-65-2

Basic information

• Product Name: 1-cyclohexenyl-phenyl-methanone
• Synonyms: 1-cyclohexenyl-phenyl-methanone;Methanone,1-cyclohexen-1-ylphenyl-;Cyclohex-1-enyl-phenyl-methanone
• CAS NO: 17040-65-2
• Molecular Formula: C₁₃H₁₄O
• Molecular Weight: 186.25
• Mol File: 17040-65-2.mol

Chemical Properties

• Melting Point: 31-32 °C
• Boiling Point: 300.9°Cat760mmHg
• Flash Point: 126.6°C
• Appearance: /
• Density: 1.065g/cm³
• Vapor Pressure: 0.00109mmHg at 25°C
• Refractive Index: 1.564
• CAS DataBase Reference: 1-cyclohexenyl-phenyl-methanone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-cyclohexenyl-phenyl-methanone(17040-65-2)
• EPA Substance Registry System: 1-cyclohexenyl-phenyl-methanone(17040-65-2)

Safety Data

• Hazardous Substances Data: 17040-65-2(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
1-Cyclohexenyl-phenyl-methanone is used as a key reactant for the synthesis of cyclopentanone enol ethers. Its unique structure allows for the creation of a variety of complex organic molecules, which can be further utilized in different industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1-cyclohexenyl-phenyl-methanone can be used as a building block for the development of novel drugs. Its ability to form enol ethers makes it a promising candidate for the synthesis of bioactive compounds with potential therapeutic applications.
Used in Material Science:
1-Cyclohexenyl-phenyl-methanone may also find applications in material science, particularly in the development of new polymers and composites. Its chemical structure can be exploited to create materials with specific properties, such as enhanced strength, flexibility, or thermal stability.
Used in Flavor and Fragrance Industry:
Due to its aromatic nature, 1-cyclohexenyl-phenyl-methanone could be used in the flavor and fragrance industry as a component in the creation of unique scents and flavors for various products, such as perfumes, cosmetics, and the food industry.

Synthesis Reference(s)

Journal of the American Chemical Society, 106, p. 6417, 1984 DOI: 10.1021/ja00333a054Synthetic Communications, 19, p. 1405, 1989 DOI: 10.1080/00397918908054550

InChI:InChI=1/C13H14O/c14-13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1,3-4,7-9H,2,5-6,10H2

Upstream product

• 36306-47-5 α-1-cyclohexen-1-yl-benzenemethanol 
• 66448-73-5 (+/-)-(cis-2-chloro-cyclohexyl)-phenyl ketone 
• 1855-63-6 cyclohex-1-enecarbonitrile 
• 98-88-4 benzoyl chloride 
• 110-83-8 cyclohexene 
• 107774-09-4 (2-chloro-cyclohexyl)-phenyl ketone 
• 17497-53-9 1-iodo-1-cyclohexene 
• 201230-82-2 carbon monoxide 
• 960-16-7 tributylphenylstannane 
• 71364-51-7 1-<(N,N-dimethylamino)carbonyl>-1-cyclohexene 
• 591-51-5 phenyllithium 
• 947-19-3 1-hydroxycyclohexyl phenyl ketone 
• 108201-51-0 phenyl-1-(2-methoxydiazene-1-oxide-1-yl)cyclohexyl ketone 
• 75-15-0 carbon disulfide 

Downstream Products

• 63808-88-8 (3-benzylidene-cyclohex-1-enyl)-phenyl ketone 
• 1071563-37-5 trans-2-Dimethylamino-1-benzoyl-cyclohexan 
• 37414-09-8 1-Brom-1-benzoyl-2-phenyl-cyclohexan 
• 5554-78-9 1-Phenyl-2-<α-acetoxy-benzyliden>-cyclohexan 
• 54766-46-0 cyclohex-1-enyl-diphenylcarbinol 
• 86328-94-1 4,5,6,7-tetrahydro-2,3-diphenyl-2H-indazole 
• 16492-56-1 1,3-diphenyl-3a,4,5,6,7,7a-hexahydro-1H-indazole 
• 58413-22-2 2,3-diphenyl-4,5,6,7-tetrahydro-2H-indazole 
• 94377-89-6 4,5,6,7-tetrahydro-1,3-diphenyl-1H-indazole 
• 344562-45-4 3a,4,5,6,7,7a-hexahydro-1-methyl-3-phenyl-1H-indazole 
• 1141935-55-8 4,5,6,7-tetrahydro-2-(4-methoxyphenyl)-3-phenyl-2H-indazole 
• 1141935-56-9 4,5,6,7-tetrahydro-1-(4-methoxyphenyl)-3-phenyl-1H-indazole 
• 1352617-37-8 tert-butyl(cyclohexylidene(phenyl)methoxy)dimethylsilane 

Relevant articles and documents

Mechanistic implications in the Morita-Baylis-Hillman alkylation: Isolation and characterization of an intermediate

An intermediate phosphonium salt has never been isolated from the Morita-Baylis-Hillman (MBH) reaction. Due to the weakly basic counterion produced in the MBH alkylation and allylation reactions, the reaction can be stopped after electrophilic attack on t

Diastereoselective Additions of Allylmagnesium Reagents to α-Substituted Ketones When Stereochemical Models Cannot Be Used

The stereoselectivities of reactions of allylmagnesium reagents with chiral ketones cannot be easily explained by stereochemical models. Competition experiments indicate that the complexation step is not reversible, so nucleophiles cannot access the widest range of possible encounter complexes and therefore cannot be analyzed easily using available models. Nevertheless, additions of allylmagnesium reagents to a ketone can still be stereoselective provided that the carbonyl group adopts a conformation that leads to one face being completely blocked from the approach of the allylmagnesium reagent.

Acylation of Alkenes with the Aid of AlCl3 and 2,6-Dibromopyridine

Friedel-Crafts-type acylation of alkenes with acyl chlorides has been successfully conducted with a wide substrate scope by the combined use of AlCl3 and 2,6-dibromopyridine. Trisubstituted alkenes afford allylketones or vinylketones depending on the presence or absence of hydrogen atom(s) at the β-position to the acylation site, while monosubstituted alkenes exclusively afford vinylketones.

Pd-catalyzed synthesis of α,β-unsaturated ketones by carbonylation of vinyl triflates and nonaflates

A general and highly chemoselective Pd-catalyzed protocol for the synthesis of α,β-unsaturated ketones by carbonylation of vinyl triflates and nonaflates is presented. Applying the specific monophosphine ligand cataCXium A, the synthesis of various vinyl ketones as well as carbonylated natural product derivatives proceeds in good yields.

Enones from Acid Fluorides and Vinyl Triflates by Reductive Nickel Catalysis

A nickel-catalyzed reductive coupling between acid fluorides and vinyl triflates has been described. This method provides an efficient access to various enones and avoids the requirement for acyl or vinyl metallic reagents in the conventional approaches.

Products of reaction of 1-phenyltricyclo[4.1.0.02,7]heptane with N-iodosuccinimide in aqueous THF

Iodohydroxylation of 1-phenyltricyclo[4.1.0.02,7]heptane in aqueous THF at 20°C with N-iodosuccinimide proceeds at the central bicyclobutane bond C1–C7 and results in the formation of two-component mixture of diastereomeric 7-iodo-6-phenyl-6-norpinanols in the ratio 1 : 1.8 in favor of the product of the anti-addition. Treating of iodonorpinanols with trimethylamine in aqueous THF affords 1-benzoylcyclohex-1-ene as a result of 1,4-dehydroiodination accompanied with the Grob fragmentation of the carbon scaffold.

Identification, synthesis and pharmacological evaluation of novel anti-EV71 agents via cyclophilin A inhibition

In this work, the relationship between cyclophilin A (CypA) and EV71 prompted us to screen a series of small molecular CypA inhibitors which were previously reported by our group. Among them, compounds 1 and 2 were discovered as non-immunosuppressive anti-EV71 agents with an EC50 values of 1.07 ± 0.17 μM and 3.36 ± 0.45 μM in virus assay, respectively, which were desirably for the further study. The subsequent chemical modifications derived a novel class of molecules, among which compound 11 demonstrated the most potent anti-EV71 activity in virus assay (EC50 = 0.37 ± 0.17 μM), and low cytotoxicity (CC50 > 25 μM). The following CypA enzyme inhibition studies indicated that there was not only the enzyme inhibition activity, undoubtedly important, functioning in the antiviral process, but also some unknown mechanisms worked in combination, and the further study is underway in our laboratory. Nevertheless, to the best of our knowledge, compound 11 was probably the most potent small molecular anti-EV71 agent via CypA inhibitory mechanism to date. Consequently, our study provided a new potential small molecule for curing EV71 infection.

Oxidative conversion of silyl enol ethers to α,β-unsaturated ketones employing oxoammonium salts

The oxidative conversion of silyl enol ethers to α,β-unsaturated ketones using a less-hindered class of oxoammonium salts (AZADO +BF4-) is described. The reaction proceeds via the ene-like addition of oxoammonium salts to silyl enol ethers.

The intramolecular Morita-Baylis-Hillman-type alkylation reaction

From the initial development of a homologous Morita-Baylis-Hillman reaction utilizing epoxides as electrophiles, the method was expanded to enable the exclusively organocatalyzed intramolecular allylation of enones and to develop the intramolecular MBH-type alkylation of activated alkenes. We successfully utilized both enones and unsaturated thioesters as the activated alkene component. This work, carried out using stoichiometric amounts of the trialkylphosphine, gave an array of functionalized five- and six-membered carbocycles in high yields. With the cycloalkylation of enones and thioesters, conditions that allowed the use of substoichometric amounts of the phosphine catalyst were developed. As a result both five- and six-membered rings can be formed efficiently with little to no loss in yield upon comparison to yields obtained when stoichiometric amounts of trialkylphosphines were employed. We isolated, for the first time, an MBH-type intermediate exhibiting unprecedented trans geometry of the phosphonium salt and acyl group.

Indium(III)-catalyzed coupling between alkynes and aldehydes to α,β-unsaturated ketones

The combined use of a catalytic amount of InX3 (X = OTf and NTf2) and 1-butanol was found to be effective in formal alkynealdehyde metathesis. With this catalytic system, aromatic alkynes reacted with aromatic aldehydes to give chalcones in moderate to good yields. Alkynals were efficiently converted into 5- to 7-membered cyclic compounds by intramolecular alkyne-aldehyde coupling.