51089-06-6

Upstream product

• 62-53-3 aniline 
• 1655-07-8 ethyl 2-oxocyclohexane carboxylate 
• 132723-22-9 2-Oxocyclohexylidenemethanone 
• 28637-56-1 2,2-dimethyl-5,6,7,8-tetrahydro-4H-benzo[d][1,3]dioxin-4-one 
• 41302-34-5 2-(methoxycarbonyl)cyclohexanone 
• 108-94-1 cyclohexanone 

Downstream Products

• 59846-79-6 2-Aminocyclohexen-1-carboxanilid 
• 127603-96-7 Methanesulfonic acid (1R,2S)-2-phenylcarbamoyl-cyclohexyl ester 
• 127603-96-7 Methanesulfonic acid (1S,2S)-2-phenylcarbamoyl-cyclohexyl ester 
• 127604-08-4 (1S,2R)-2-Bromo-cyclohexanecarboxylic acid phenylamide 
• 127604-03-9 (1S,6R)-7-Phenyl-7-aza-bicyclo[4.2.0]octan-8-one 
• 32119-42-9 N-phenylcyclohex-1-enecarboxamide 
• 28870-35-1 3-amino-1-oxo-2-phenyl-1,2,5,6,7,8-hexahydroisoquinoline-4-carbonitrile 
• 855428-14-7 2-Hydroxy-cyclohexanecarboxylic acid phenylamide 

Relevant academic research and scientific papers

Identification of new biologically active synthetic molecules: comparative experimental and theoretical studies on the structure-antioxidant activity relationship of cyclic 1,3-ketoamides

Antioxidant agent is a chemical that prevents the oxidation of other chemical substances. Its use is the most effective means of protecting the organism by neutralizing the harmful effects of free radicals caused by oxidative stress. In the present work, a series of β-ketoamides containing a variety of monosubstituted amide groups were synthesized and tested as antioxidant agents. In order to establish a possible structure-antioxidant activity relationship, we are presenting a systematic theoretical study of these molecules with the aim of clarifying the active sites. In particular, we discuss the selectivity resulting from the choice of a free radical/antioxidant system. The theoretical study of these molecules was carried out using density functional theory (DFT) calculations at the B3LYP/6-311G (d,p) level of theory. In order to shed light on the antioxidant properties of β-ketoamides, O–H bond dissociation enthalpies (BDEs), ionization potentials (IPs), electron affinities (EAs), proton affinities (PAs), and electron transfer enthalpies (ETEs) are performed in the gas phase and in ethanol. The results obtained show that the HAT mechanism is thermodynamically more favored in the gas phase, while the SPLET is preferred in the polar solvent.

Highly Selective Difluoromethylations of β-Keto Amides with -TMSCF 2Br under Mild Conditions

Without employing any transition metal and other additives, efficient methods for selective difluoromethylations of β-keto amides with TMSCF 2 Br reagent have been developed under mild conditions. This protocol allows a convenient access to various α-difluoromethyl β-keto amides with excellent yields (up to 93%) and high carbon/oxygen (C/O) regioselectivities (up to 99:1). The C/O selectivity of β-keto amides could be easily reversed and controlled by simply changing the base. This protocol can be easily scaled-up and the C-difluoromethylation product could be reduced into CF 2 H-containing amino alcohol derivatives. Moreover, the first enantioselective electrophilic difluoromethylation of β-keto amides has been achieved by phase-transfer catalysis.

A Chiral Phenanthroline Ligand with a Hydrogen-Bonding Site: Application to the Enantioselective Amination of Methylene Groups

A silver-catalyzed amination is reported that occurs at the aliphatic C3-substituent of various quinolones and pyridones. The C-H amination reaction proceeded with high site-and enantioselectivity (14 examples, 83-97% ee). The key to its success is the use of a chiral phenanthroline ligand that is attached via an ethynyl linker to the 8-position of octahydro-1H-4,7-methanoisoindol-1-one. AgPF6 (10 mol %) served as the silver source, PhI.NNs as the nitrene precursor, and 1,10-phenanthroline as the coligand. The reaction outcome can be understood by assuming a nitrene C-H insertion within a hydrogen-bonded silver complex in which a single C-H bond is exposed to the catalytic reaction center.

An efficient and rapid synthesis of β-carboxamide derivatives using 2,2-dimethyl-2H,4H-1,3-dioxin-4-ones by microwave irradiation

A general, efficient and rapid method for the synthesis of various β-carboxamide derivatives using microwave irradiation is described. Excellent isolated yields were obtained in very short reaction times when conventional heating was replaced by microwave irradiation.

4-Alkyl- and 3,4-dialkyl-1,2,3,4-tetrahydro-8-pyridono[5,6- g]quinolines: Potent, nonsteroidal androgen receptor agonists

A series of human androgen receptor (hAR) agonists based on 4-alkyl-; 4,4-dialkyl-; and 3,4-dialkyl-1,2,3,4-tetrahydro-8-pyridono[5,6-g]quinoline was synthesized and evaluated in competitive receptor binding assays and an androgen receptor cotransfection assay in a mammalian cell background. A number of compounds in this series demonstrated activity equal to or better than dihydrotestosterone in both assays and represent a novel class of compounds for use in androgen replacement therapy.

Synthesis of β-Ketocarboxamide Derivatives Using 2,2-Dimethyl-2H,4H-1,3-dioxin-4-ones

Thermal reaction of 2,2-dimethyl-2H,4H-1,3-dioxin-4-ones (1) with amines was studied.Acylketenes 2, generated by heating of 1, reacted with anilines and benzylamine to give the corresponding β-ketocarboxamides (3,4, and 5) in good yields.The reaction of 1 with ammonia gave 3-amino-2-alkenamides (7), which were hydrolyzed to β-ketocarboxamides (6).The former products 7 were readily transformed to the 6-substituted 2-methyl-3H-pyrimidin-4-ones (9) via the 3-acetamido-2-alkenamides (8).Acylation of O-benzylhydroxylamine with 1 gave the β-ketohydroxamic acids 10.Debenzylation of 10 followed by cyclization gave rise to 5-alkyl-3-hydroxyisoxazoles (12).The reaction of 1 with amides gave the corresponding N-acetylated amides (13). Keywords --- 2H,4H-1,3-dioxin-4-one; thermal fragmentation; acylketene; acylation; carboxamide; hydroxamic acid; 3-hydroxyisoxazole; 3H-pyrimidin-4-one