36646-74-9

Basic information

• Product Name: 2-cyclohexen-1-one, 3-[(4-methylphenyl)amino]-
• Synonyms: 2-cyclohexen-1-one, 3-[(4-methylphenyl)amino]-;3-[(4-methylphenyl)amino]cyclohex-2-en-1-one;3-[(4-methylphenyl)amino]-1-cyclohex-2-enone;ZINC04235204;3-(4-methylanilino)cyclohex-2-en-1-one
• CAS NO: 36646-74-9
• Molecular Formula: C₁₃H₁₅NO
• Molecular Weight: 201.2643
• Mol File: 36646-74-9.mol

Chemical Properties

• Melting Point: 138-139 °C
• Boiling Point: 339.6±42.0 °C(Predicted)
• Appearance: /
• Density: 1.147±0.06 g/cm3(Predicted)
• PKA: 0.94±0.20(Predicted)
• CAS DataBase Reference: 2-cyclohexen-1-one, 3-[(4-methylphenyl)amino]-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-cyclohexen-1-one, 3-[(4-methylphenyl)amino]-(36646-74-9)
• EPA Substance Registry System: 2-cyclohexen-1-one, 3-[(4-methylphenyl)amino]-(36646-74-9)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 36646-74-9(Hazardous Substances Data)

Upstream product

• 504-02-9 1,3-cylohexanedione 
• 106-49-0 p-toluidine 
• 765-87-7 cyclohexane-1,2-dione 

Relevant articles and documents

Formation of 3-Aminophenols from Cyclohexane-1,3-diones

meta-Aminophenols are formed by the action of DBU on 3-amino-2-chlorocyclohex-2-en-1-ones at room temperature in MeCN. The chloro compounds are generated by treating 3-aminocyclohex-2-en-1-ones with the easily prepared halogenating agent BnNMe3·ICl2 in Me

Expeditious and eco-friendly synthesis of new multifunctionalized pyrrole derivatives and evaluation of their antioxidant property

Diminution of oxidative stress-mediated diseases is an essential pharmaceutical objective in modern biomedical research. The present work stresses upon the efficient and eco-friendly synthesis of an array of novel diversely functionalized pyrrole derivatives which are found to be antioxidants with reactive oxygen species (ROS) shielding competency against the deleterious consequence of oxidative stress. The results of the investigation displayed the effect of structural modification of the pyrrole derivatives on their respective antioxidant properties to various ROS. Noteworthy, the pyrrole moiety bearing 4-hydroxycoumarin or 2-hydroxy-1,4-naphthoquinone as substituent showed outstanding defensive potency towards [rad]OH and O2 [rad] ? while, nitrogen atom linked with aliphatic side-chain in the pyrrole scaffold made a strong affirmative impression in DPPH[rad] scavenging assay. More interestingly, an influencing reducing power was observed in pyrrole derivatives carrying cyclohexane 1,3-dione as one of the substituents. To have a comprehensive acuteness into the antioxidant capacity of the synthesized pyrrole derivatives against Trolox as a standard antioxidant, a crucial approach was taken into account by calculating TEAC (Trolox Equivalent Antioxidant Capacity) in case of [rad]OH and DPPH[rad] scavenging activity.

Hypervalent Iodine(III)-Mediated Counteranion Controlled Intramolecular Annulation of Exocyclic β-Enaminone to Carbazolone and Imidazo[1,2-a]pyridine Synthesis

A highly efficient and flexible protocol for intramolecular annulation of exocyclic β-enaminones has been disclosed for the synthesis of carbazolones and imidazo[1,2-a]pyridines through a counter-anion-controlled free-radical mechanism promoted by hypervalent iodine(III). The cooperative behavior of HTIB and AgSbF6 plays a crucial role in the intramolecular annulation process through C?C and C?N bond formation to give the desired products. The mechanistic insights suggest that the two competitive reactions involved in the system are guided by the nature of the counteranion, which determines the formation of the final products. A wide variety of carbazolones and imidazo[1,2-a]pyridine molecules have been prepared and isolated in good to excellent yields.

A novel and reusable magnetic nanocatalyst developed based on graphene oxide incorporated strontium nanoparticles for the facial synthesis of β-enamino ketones under solvent-free conditions

A novel magnetic SrFeGO nanocatalyst (NC) was synthesized through a simple sol–gel technique by introducing strontium and iron oxide nanoparticles onto graphene. The synthesized NC was characterized using FT-IR and FE-SEM. Subsequently, the catalytic activity of SrFeGO was tested in a reaction between β-dicarbonyl compounds and aniline derivatives to gain β-enamino ketone derivatives under solvent-free conditions. It was found that SrFeGO NC is a potential catalyst for the synthesis of β-enamino ketones. The β-enamino ketone produced by such reactions could be isolated in high purity without the need for chromatographic purifications. The newly prepared magnetic graphene oxide nanocomposite could be recovered and reused for numerous times with no significant decrease in efficiency. Moreover, the protocol has the advantages of excellent yielding (up to 98%) in short a reaction time, benefitting an easy workup procedure and being environmentally friendly.

Cyclic enaminone as new chemotype for selective cyclooxygenase-2 inhibitory, anti-inflammatory, and analgesic activities

The cyclic enaminone moiety has been identified as a new scaffold for selective inhibition of cyclooxygenase-2 with anti-inflammatory and analgesic activities. The designed cyclic enaminones have been synthesized conveniently through the development of a new catalyst-free methodology and evaluated for cyclooxygenase (COX-1 and COX-2) inhibitory activities. Three compounds 7d, 8, and 9 predominantly inhibited COX-2 with selectivity index of 74.09, 19.45 and 108.68, respectively, and were assessed for in vivo anti-inflammatory activity in carrageenan induced rat paw edema assay. The anti-inflammatory activity of 7d was comparable to that of celecoxib at a dose of 12.5 mg/kg. However, the compounds 8 and 9 were more/equally effective as anti-inflammatory agent compared to celecoxib at the doses of 12.5 mg/kg and 25 mg/kg and also exhibited anti-inflammatory activity comparable to that of diclofenac. The therapeutic potential of the most active compound 9 was further assessed by performing in vivo thermal and mechanical hyperalgesia tests using various models that revealed its analgesic activity. The in vivo non-ulcerogenicity of 9 revealed the gastrointestinal safety as compared to the non-selective COX inhibitor indomethacin. The in vitro antioxidant activity and in vivo experiments on heart rate and blood pressure provided the cardiovascular safety profile of 9. The molecular docking studies rationalize the COX-2 selectivity of the newly found anti-inflammatory compounds 7d, 8, and 9.

Iodine(III)-Promoted Ring Contractive Cyanation of Exocyclic β-Enaminones for the Synthesis of Cyanocyclopentanones

A highly efficient hypervalent iodine-promoted regiocontrolled ring contractive cyanation (RCC) reaction of exocyclic β-enaminones for the synthesis of cyanocyclopentanone (CCP) was demonstrated at ambient temperature with a wide substrate scope. The meth

Hypervalent Iodine-Promoted Aromatization of Exocyclic β-Enaminones for the Synthesis of meta-N,N-Diarylaminophenols

A metal- and additive-free milder cascade approach for the synthesis of meta-N,N-diarylaminophenols (DAAP) starting from exocyclic β-enaminones has been developed. The feasibility of the process is rationalized by the suitable molecular geometry of β-enaminones for tandem N-arylative α-iodination and aromatization under milder basic conditions. Furthermore, the developed strategy has been extended to the synthesis of meta-N-benzyl-N-arylaminophenols (BAAP). 4-Ethylpropionyl-2-cyclohexenone has been explored to give 7-diarylaminochroman-2-one (DAAC) by employing a similar one-pot approach. The plausible mechanistic steps were deduced based upon isolation of a stable intermediate and structural identification through X-ray crystallographic analysis. (Figure presented.).

An Efficient One-Pot Three-Component Synthesis of Some New Polyhydroquinolines via Enaminone Intermediates

For a wide spectrum of pharmacological effects of polyhydroquinolines, this study introduces a developed safe, simple, higher yields and fast method for the synthesis of some new hexahydroquinoline derivatives using one-pot three-component cyclocondensation reaction, via the reaction of 1,3-cyclohexanedione with primary amine and arylidinemalononitrile or salicylaldehyde derivatives. The prepared compounds were reacted with different reagents as N,N-dimethylformamide dimethylacetal, acetic anhydride, sulphuric acid, and hydrazine hydrate forming several polycyclic hexahydroquinoline and acridine derivatives. All these new compounds have been characterized by spectral data and expected to be effective pharmaceutical drugs.

Synthesis, crystal structure and effect of indeno[1,2-b]indole derivatives on prostate cancer in vitro. Potential effect against MMP-9

A highly regiospecific synthesis of a series of indenoindoles is reported, together with X-ray studies and their activity against human prostate cancer cells PC-3 and LNCaP in vitro. The most effective compound 7,7-dimethyl-5-[(3,4-dichlorophenyl)]-(4bRS,9bRS)-dihydroxy-4b,5,6,7,8,9bhexahydro-indeno[1,2-b]indole-9,10-dione 7q reduced the viability in both cell lines in a time and dose-dependent manner. Inhibitory effects were also observed on the adhesion, migration, and invasion of the prostate cancer cells as well as on clonogenic possibly by inhibition of MMP-9 activity. Molecular docking of 7q and 6k into MMP-9 human active site was also performed to determine the probable binding mode.

FeCl3-Catalyzed Combinatorial Synthesis of Functionalized Spiro[Indolo-3,10′-indeno [1,2- b ]quinolin]-trione Derivatives

An efficient, inexpensive, environmentally friendly and high yield one-pot route to new spiro[indolo-3,10′-indeno [1,2-b]quinolin]-trione derivatives has been developed, involving three-component reaction of enaminones, N-substituted isatins and Indane-1,3-dione catalyzed by FeCl3. The approach to this spiro-heterocycle is noteworthy because it results in the formation of three new σ (two C-C and one C-N) bonds in a single operation, leading to the construction of novel spiro skeleton. This method works on a large scale in excellent yields.