873-95-0

Usage

Uses

Used in Organic Synthesis:
3-AMINO-5,5-DIMETHYL-2-CYCLOHEXEN-1-ONE is utilized as a key intermediate in organic synthesis for the creation of various complex organic molecules. Its unique structure allows for multiple points of reactivity, facilitating the formation of a wide array of chemical products.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 3-AMINO-5,5-DIMETHYL-2-CYCLOHEXEN-1-ONE is employed as a building block for the development of new drugs. Its presence in chemical reactions can lead to the synthesis of compounds with potential medicinal properties, contributing to the discovery of novel therapeutic agents.
Used in Biological Activity Studies:
3-AMINO-5,5-DIMETHYL-2-CYCLOHEXEN-1-ONE is also used in biological research to study its inherent biological activity. Scientists are investigating its potential as a therapeutic agent, exploring how it interacts with biological systems and its effects on various diseases or conditions.

InChI:InChI=1/C8H13NO/c1-8(2)4-6(9)3-7(10)5-8/h3H,4-5,9H2,1-2H3

Upstream product

• 126-81-8 dimedone 
• 106-49-0 p-toluidine 
• 762-21-0 acetylenedicarboxylic acid diethyl ester 
• 75-31-0 isopropylamine 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 108-91-8 cyclohexylamine 
• 104-86-9 4-chlorobenzylamine 
• 10269-01-9 3-bromobenzylamine 
• 889-31-6 5,5-dimethyl-3-benzylamino-2-cyclohexen-1-one 
• 99-09-2 3-nitro-aniline 
• 100-46-9 benzylamine 
• 104-84-7 para-methylbenzylamine 
• 5763-61-1 3,4-dimethoxybenzylamine 
• 108-44-1 1-amino-3-methylbenzene 

Downstream Products

• 23645-83-2 N-(5,5-dimethyl-3-oxocyclohex-1-en-1-yl)acetamide 
• 23008-45-9 3-amino-5,5-dimethyl-cyclohex-2-enone-imine 
• 37456-53-4 6,6-dimethyl-3-morpholin-4-yl-2-phenyl-1,5,6,7-tetrahydro-indol-4-one 
• 119022-19-4 4-hydroxy-7,7-dimethyl-3-phenyl-7,8-dihydrochinolin-2,5(1H,6H)-dion 
• 72431-33-5 3-Amino-5,5-dimethyl-2-piperidinomethyl-2-cyclohexen-1-on 
• 33365-81-0 2,2'-methylene-bis-(5,5-dimethyl-3-aminocyclohex-2-en-1-one) 
• 76159-33-6 3-Amino-2-hydroxymethyl-5,5-dimethyl-2-cyclohexen-1-on 
• 90043-96-2 3-crotonoylamino-5,5-dimethylcyclohex-2-enone 
• 90043-95-1 1,3-bis(5,5-dimethyl-3-oxocyclohex-1-enylamino)-3-methylpropan-1-one 
• 113859-91-9 5,5-Dimethyl-3-(1-methyl-2-oxo-2-phenyl-ethylamino)-cyclohex-2-enone 
• 96797-03-4 5,6,7,8-tetrafluoro-2,2-dimethylbenzo<2,1-b>quinoline-4-one 
• 96797-04-5 3-Amino-2-(hydroxy-pentafluorophenyl-methyl)-5,5-dimethyl-cyclohex-2-enone 
• 113859-94-2 3,6,6-Trimethyl-2-phenyl-1,5,6,7-tetrahydro-indol-4-one 
• 113859-88-4 5,5-Dimethyl-3-(2-oxo-1-phenyl-propylamino)-cyclohex-2-enone 

Relevant academic research and scientific papers

Efficient synthesis of decahydroacridine-1,8-diones and polyhydroquinolines using the step-wise method

Various symmetrical and unsymmetrical decahydroacridine-1,8-dione and polyhydroquinoline derivatives were synthesized via two-step cyclocondensation reactions. The advantages of this step-wise addition of reactants in comparison with other one-pot reactions are avoiding the formation of 2 or 3 undesired by-products, therefore allowing cleaner work up of reaction. The important factor of this effective cyclocondensation method is that the prepared β-enaminone component was added dropwise to the solution, in which the Knoevenagel condensation product is slowly being formed by reaction of aldehyde molecule and 1,3-dicarbonyl compounds. The results of the proposed step-wise method are compared and discussed with those obtained in the one-pot reactions.

On the enantioselective phosphoric-acid-catalyzed hantzsch synthesis of polyhydroquinolines

A reinvestigation of a chiral phosphoric-acid-catalyzed four-component Hantzsch enantioselective synthesis of polyhydroquinolines reported in 2009 is presented. In our hands, when the reaction was performed with fidelity to the original report using a chiral enantiopure phosphoric acid catalyst, no enantioselectivity was observed. Unlike in the original report, enantioselectivity results are backed by baseline separation of the enantiomers by HPLC analyses on chiral stationary phase with UV and chiroptical detection.

SHP2 INHIBITORS, COMPOSITIONS AND USES THEREOF

Provided are compounds of Formula (I), methods of using the compounds as SHP2 inhibitors, and pharmaceutical compositions comprising such compounds. The compounds are useful in treating SHP2-mediated diseases.

Copper-Catalyzed Thiolation of Terminal Alkynes Employing Thiocyanate as the Sulfur Source Leading to Enaminone-Based Alkynyl Sulfides under Ambient Conditions

A highly efficient protocol for copper-catalyzed thio-alkynylation of enaminone-based thiocyanates with terminal alkynes under mild conditions has been developed. This scalable amino group-directed thio-alkynylation proceeds in the open air with a broad substrate scope and an excellent yield. The demonstrated synthetic transformation creates the opportunity for a wide variety of sulfur-containing useful materials. Gram-scale synthesis and further synthetic transformations of alkynyl sulfides highlight the potential utility of the method.

Cu catalyzed cross-dehydrogenative coupling reaction for the synthesis of 3-hydroxy-2-pyrrolidinones

A new convenient strategy for the synthesis of 3-hydroxy-2-pyrrolidinone derivatives featuring regioselective C–C coupling has been developed. This is a Cu (II) catalyzed cross dehydrogenative coupling (CDC) involving enamino-ketones of benzyl amines and di-alkyl acetylenedicarboxylate, followed by cyclization by primary amines. TBHP (tert-butyl hydroperoxide) has been used as the oxidant to promote the coupling protocol. This synthetic route principally demonstrates the scope of CDC reaction and also applicable to gram-scale synthesis.

6 Hz active anticonvulsant fluorinated n-benzamide enaminones and their inhibitory neuronal activity

A small library of novel fluorinated N-benzamide enaminones were synthesized and evaluated in a battery of acute preclinical seizure models. Three compounds (GSA 62, TTA 35, and WWB 67) were found to have good anticonvulsant activity in the 6-Hz ‘psychomotor’ 44-mA rodent model. The focus of this study was to elucidate the active analogs’ mode of action on seizure-related molecular targets. Electrophysiology studies were employed to evaluate the compounds’ ability to inhibit neuronal activity in central olfactory neurons, mitral cells, and sensory-like ND7/23 cells, which express an assortment of voltage and ligand-gated ion channels. We did not find any significant effects of the three compounds on action potential generation in mitral cells. The treatment of ND7/23 cells with 50 μM of GSA 62, TTA 35, and WWB 67 generated a significant reduction in the amplitude of whole-cell sodium currents. Similar treatment of ND7/23 cells with these compounds had no effect on T-type calcium currents, indicating that fluorinated N-benzamide enaminone analogs may have a selective effect on voltage-gated sodium channels, but not calcium channels.

Efficient synthesis of acridinediones in aqueous media

An efficient synthesis of acridinediones in two steps have been achieved using water as a reaction media without chromatographic purification. First step involves the reaction of dimedone with ammonium acetate to yield enaminone in water which on further

Synthesis and biological activity of 2′, 3′-iso-aryl-abscisic acid analogs

2′, 3′-iso-Benzoabscisic acid (iso-PhABA), an excellent selective abscisic acid (ABA) analog, was developed in our previous work. In order to find its more structure-activity information, some structural modifications were completed in this paper, includi

Ammonium acetate as a catalyst and/or reactant in the reaction of dimedone, aromatic aldehyde, and malononitrile: synthesis of tetrahydrobenzo[b]pyrans and hexahydroquinolines

Abstract: The reaction of aromatic aldehydes, dimedone, and malononitrile in the presence of ammonium acetate has afforded tetrahydrobenzo[b]pyrans instead of polyhydroquinolines under both grinding and reflux conditions; thus ammonium acetate acts as a c

Evaluation of magnetically recyclable nano-Fe3O4 as a green catalyst for the synthesis of mono- and bis-tetrahydro-4H-chromene and mono and bis 1,4-dihydropyridine derivatives

Magnetically separable Fe3O4 nanoparticles were used as an environmental friendly catalyst for the synthesis of mono- and bis-tetrahydro-4H-chromene and mono- and bis-1,4-dihydropyridine derivatives via three-component reactions of aromatic aldehydes and malononitrile with cyclic β-dicarbonyls or cyclic β-enaminoketones respectively. These reactions were carried out in EtOH and at reflux. Fe3O4 nanoparticles can be magnetically separated from the reaction mixture by a magnet and recycled without significant loss of catalytic activity.