24706-50-1

Usage

Chemical Properties

yellow-green fine crystalline powder

InChI:InChI=1/C12H13NO/c14-12-8-4-7-11(9-12)13-10-5-2-1-3-6-10/h1-3,5-6,9,13H,4,7-8H2

Upstream product

• 765-87-7 cyclohexane-1,2-dione 
• 62-53-3 aniline 
• 504-02-9 1,3-cylohexanedione 
• 108-94-1 cyclohexanone 
• 30182-67-3 1,3-Cyclohexanedione 

Downstream Products

• 132600-14-7 1,4-diphenyl-3,4,7,8-tetrahydroquinoline-2,5(1H,6H)-dione 
• 132600-25-0 4-(4-Methoxy-phenyl)-1-phenyl-4,6,7,8-tetrahydro-1H,3H-quinoline-2,5-dione 
• 132600-17-0 4-(4-Nitro-phenyl)-1-phenyl-4,6,7,8-tetrahydro-1H,3H-quinoline-2,5-dione 
• 137959-09-2 3-<(phenyl)amino>-2-(N-ethoxycarbonyl-N'-benzoyl)hydrazinocyclohex-2-en-1-one 
• 504-02-9 1,3-cylohexanedione 
• 62-53-3 aniline 
• 915295-24-8 10-(4-chlorophenyl)-7,8-dihydro-5-phenyl-5H-indeno[1,2-b]quinoline-9,11(6H,10H)-dione 
• 915295-33-9 C₂₂H₁₈N₄O₃ 
• 1158819-85-2 4b,9b-dihydroxy-5-phenyl-4b,5,6,7,8,9b-hexahydroindeno[1,2-b]indole-9,10-dione 

Relevant academic research and scientific papers

Tailoring of spectral response and intramolecular charge transfer in β-enaminones through band gap tuning: Synthesis, spectroscopy and quantum chemical studies

In this paper, we investigate the synthetic tailoring of the spectral response and intramolecular charge transfer (ICT) of β-enaminones through bandgap modulation. Two donor/acceptor substituted β-enaminones, namely, 3-(4-methoxyphenylamino)-2-cyclohexen-1-one (OACO) and 3-(4-nitrophenylamino)-2-cyclohexen-1-one (NACO) have been synthesized along with their unsubstituted counterpart, 3-(phenylamino)-2-cyclohexen-1-one (PACO). Steady state as well as time resolved spectroscopic techniques with picosecond resolution are used to record their spectral responses. Substitution of the donor group (-OCH3) mildly enhances the charge transfer from the phenyl ring to the enaminone moiety, while substitution of the acceptor group (-NO2) jeopardizes the charge transfer through mutual electron withdrawing effects of PNA and enaminone moieties. Combined experimental and quantum chemical investigations reveal that the ground state photophysics of OACO and NACO in water are controlled by both microscopic and macroscopic solvation with dominant contribution from the former. Time dependent density functional theory (TDDFT) calculations predict that the HOMO to [LUMO+1] transition gives rise to the absorption spectra of OACO in water, while the absorption by the enaminone moiety of NACO arises as a result of a HOMO to LUMO transition. A crossing between the first (S1) and the second excited (S2) states takes place in the microclusters of PACO, OACO and NACO with water. The intersystem crossing (ISC) has been found to be the major reason for low quantum yields in these molecules. The band gap modulation through waxing and waning of the conjugation strength is expected to throw light on many ICT-driven processes and provides means of tuning the properties depending on it.

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

Intermolecular Multiple Dehydrogenative Cross-Couplings of Ketones with Boronic Acids and Amines via Copper Catalysis

An efficient and versatile oxidative coupling reaction was developed for the synthesis of valuable β-functionalized unsaturated ketones and meta-substituted phenols. In the case of intramolecular reactions, achieving rapid molecular complexity through multiple dehydrogenative couplings is already a well-established strategy. Herein, we report an intermolecular multiple dehydrogenative coupling between ketones and nucleophilic amines or boronic acids using inexpensive copper(I) oxide as a catalyst. This method provides a facile access to highly desirable chemical products such as α,β-unsaturated ketones, enaminones, and synthetically relevant meta-substituted phenols. (Figure presented.).

Fe-Catalyzed enaminone synthesis from ketones and amines

We have developed an iron-catalyzed direct olefination for enaminone synthesis, with saturated ketones as a source of olefins. This direct ketone β-functionalization reaction has readily available starting materials and a wide range of substrates and requires mild reaction conditions.

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.

Photocyclization to cis-Hexahydrocarbazol-4-ones: Substrate Modification, Mechanism, and Scope

Upon irradiation at = 366 nm, tertiary N-alkoxycarbonyl-N-aryl-β-enaminones furnished exclusively the trans-hexahydrocarbazol-4-ones by a conrotatory [6π] photocyclization but epimerized on silica to cis-hexahydrocarbazol-4-ones (14 examples, 44-98% yield). The acceptor substitution on the nitrogen atom enhanced the stability of the cyclized products compared to N-alkyl-N-aryl-β-enaminones reported previously. The mechanism of the [6π] photocyclization was investigated by quenching experiments, deuterium-labeling experiments, and DFT calculations, suggesting a triplet pathway for the conrotatory ring closure followed by a suprafacial [1,4] hydrogen migration.

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.

Redox Property of Enamines

Enamines are electron-rich compounds bearing intriguing redox properties. Herein, a series of secondary enamines condensed from primary amine and β-ketocarbonyls were synthesized and their electrochemical oxidation properties were systematically studied by cyclic voltammetry. Furthermore, theoretical calculation of oxidation potentials of enamines, particularly those catalytic intermediates, was also conducted to further broaden the scope investigated. Possible structural factors on oxidation and the nature of the resulted radical cation intermediates were revealed and discussed. Correlation of redox potentials with molecular properties such as highest occupied molecular orbital energies and natural population analysis charge were explored, and there appears no simple linear correlation. On the other hand, a good correlation with Mayr's nucleophilicity parameter N was noted among a range of catalytically relevant enamines. Spin population analysis disclosed that enamine radical cations mainly exhibit the carbon-center free radical feature. Taking experimental and computation data together, a comprehensive picture about the redox property of enamines is presented, which would provide guidance in the development of oxidative enamine catalysis and transformations.

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