22114-45-0

Upstream product

• 108-94-1 cyclohexanone 
• 555-16-8 4-nitrobenzaldehdye 
• 71444-29-6 2-[hydroxy(4-nitrophenyl)methyl]cyclohexan-1-one 
• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 
• 88284-48-4 2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 2981-10-4 1-(cyclohex-1-en-1-yl)piperidine 
• 4471-09-4 N-benzylcyclohexylimine 
• 670-80-4 4-cyclohexen-1-ylmorpholine 

Downstream Products

• 116897-69-9 2-Amino-4-(4-nitrophenyl)-5,6,7,8-tetrahydro-4H-3,1-benzothiazin 
• 849669-34-7 2-(4-nitrobenzylidene)-6-(4-hydroxybenzylidene) cyclohexanone 
• 66661-37-8 2-[1-(4-Nitro-phenyl)-meth-(E)-ylidene]-cyclohexanone O-(2-dimethylamino-ethyl)-oxime 
• 1369791-55-8 C₂₀H₁₆ClNO₃ 

Relevant academic research and scientific papers

Cooperative Effects Between Arginine and Glutamic Acid in the Amino Acid-Catalyzed Aldol Reaction

Catalysis of the aldol reaction between cyclohexanone and 4-nitrobenzaldehyde by mixtures of L-Arg and of L-Glu in wet dimethyl sulfoxide (DMSO) takes place with higher enantioselectivity (up to a 7-fold enhancement in the anti-aldol for the 1:1 mixture)

Redox-Neutral Cobalt(III)-Catalyzed C-H Activation/Annulation of α,β-Unsaturated Oxime Ether with Alkyne: One-Step Access to Multisubstituted Pyridine

A redox neutral Co(III)-catalyzed annulation of α,β-unsaturated oxime ether with alkyne has been reported. Multisubstituted pyridines were synthesized in good yields without the use of any heavy metal oxidants. The developed methodology tolerates a variety of functional groups. Notably, this transformation has been applied to the late-stage modification of the bioactive molecule dehydropregnenolone.

Synthesis of hexahydrophenanthridines via the tandem reaction of benzynes

A tandem insertion-cyclization reaction between carbocyclic β–amino ketones and benzynes has been described, producing hexahydrophenanthridines in moderate to high yields.

Bovine serum albumin-catalysed cross aldol condensation: Influence of ketone structure

Bovine serum albumin (BSA) catalyses the cross aldol condensation and proved to be catalytically active at mild temperature and in ethanol, a cheap and green solvent, contrasting with the strong or expensive reaction media usually employed for this reaction. We herein report the reaction of a set of ketones (butanone, 3-pentanone, cyclopentanone and cyclohexanone) with benzaldehyde and p-nitrobenzaldehyde which provided high conversions (77–95%) of the corresponding enones (isolated in a range of yields from 19% to 74%). Parameters assayed to achieve these conversion values were solvent, ketone/aldehyde molar ratio and temperature. In this procedure only cyclohexanone gave the bis-enone, by-product of the conventional aldol condensation, in low amount even at high benzaldehyde/cyclohexanone molar excess. Under the assayed conditions null or low ketol amounts were observed, except for the reaction of cyclopentanone and p-nitrobenzaldehyde. Moreover, kinetic data of BSA-catalysed aldol condensation of cyclohexanone and p-nitrobenzaldehyde suggest an ordered bi bi mechanism for enone formation; an enamine mechanism involving residues of the catalytic cavity exhibiting abnormal pKa values is also proposed.

Synthesis and Cytotoxic Evaluation of Novel 1,2,3-Triazole-4-Linked (2E,6E)-2-Benzylidene-6-(4-nitrobenzylidene)cyclohexanones

This work describes the synthesis of novel 1,2,3-triazole-4-linked (2E,6E)-2-benzylidene-6-(4-nitrobenzylidene)cyclo-hexanones starting from cyclohexanone. 1-(Cyclohex-1-en-1-yl)piperidine, the enamine from cyclohexanone and piperidine, reacted with 4-nitrobenzaldehyde to obtain 2-(4-nitrobenzylidene)cyclohexanone. Condensation of the latter compound with (prop-2-yn-1-yloxy)benzaldehyde derivatives under acidic conditions gave (4-nitrobenzylidene)-[(prop-2-yn-1-yloxy)-benzylidene]cyclohexanones. Finally, 'click reaction' of these derivatives and various organic azides led to the title compounds. All compounds were examined by MTT assay for cytotoxic activity in one human breast cancer cell line, MDA-MB-231.

Phosphoric acid mediated tautomerism of imines: Addition of a secondary enamine intermediate to aldehydes

A phosphoric acid derivative has been shown to promote the addition between an imine and several aldehyde substrates through an enamine intermediate to give cross-aldol condensation products. The reaction scope and preliminary mechanistic investigations will be presented.

Pyrrolidine-Mediated Direct Preparation of (E)-Monoarylidene Derivatives of Homo- and Heterocyclic Ketones with Various Aldehydes

An efficient method for the facile synthesis of (E)-monoarylidene derivatives of homo-And heterocyclic ketones with various aldehydes in the presence of a pyrrolidine organocatalyst has been achieved. A range of a,β-unsaturated ketones were obtained in mo

Microwave-assisted organocatalytic cross-aldol condensation of aldehydes

An environmentally benign organocatalytic cross-aldol condensation of aldehydes under microwave irradiation in the absence of solvent is described. Using pyrrolidine as a catalyst, an efficient and sustainable atom economic method was developed for the cross-aldol condensation of various aldehydes with excellent results. Among the products, jasmine aldehyde, α-hexyl cinnamaldehyde and cyclamen aldehyde, three compounds of great industrial demand, were synthesised.

Fe3O4 nanoparticles as an efficient and magnetically recoverable catalyst for the synthesis of α β-unsaturated heterocyclic and cyclic ketones under solvent-free conditions

An efficient and green procedure has been developed for the synthesis of monoarylidenes of cyclic and heterocyclic ketones. The reaction was carried out under solvent-free conditions in the presence of a catalytic amount of nanosized magnetite (Fe3O4). The catalyst was easily removed by using an external magnet. The structures of the products were deduced from their 1H NMR, 13C NMR, and infrared spectroscopy and mass spectrometry. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.]

Aldol condensations of aldehydes and ketones catalyzed by primary amine on water

Potassium glycinate-catalyzed aldol condensation reactions of aromatic aldehydes and ketones on water at room temperature have been developed. Under optimal conditions, various condensation adducts are furnished in up to 63 % yield. By simple separation of the oil phase, potassium glycinate-containing water is reused to catalyze aldol condensation for six runs without loss of catalytic activity. Theoretical investigation reveals correlation between the yields and dehydroxylation energy barriers of aldol products, reasonably low activation energy of 11.9 kcal/mol for transition state formation in condensation of benzaldehyde and acetone, vibrations between aldol donor and acceptor, which correspond to the only imaginary frequency (-179.8i).