62085-75-0

Upstream product

• 98-01-1 furfural 
• 108-94-1 cyclohexanone 
• 95164-74-2 optically inactive 2-((Ξ)-furfurylidene)-6-[[2]furyl-(2-oxo-cyclohexyl)-methyl]-cyclohexanone 
• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 
• 108-93-0 cyclohexanol 
• 56-23-5 tetrachloromethane 
• 64-17-5 ethanol 
• 7732-18-5 water 

Downstream Products

• 122388-23-2 2,6-bis-[[2]furyl-(2-oxo-cyclohexyl)-methyl]-cyclohexanone 
• 95164-74-2 optically inactive 2-((Ξ)-furfurylidene)-6-[[2]furyl-(2-oxo-cyclohexyl)-methyl]-cyclohexanone 

Relevant academic research and scientific papers

Reactions Of Ruran Aldehydes 4. Oxidation-Reduction Reactions Of Furfural with Monohydric Alcohols

Furfural oxidizes aliphatic and alicyclic alcohols at 70-100 deg C under the action of sodium alcoholate to aldehydes and ketones, and then participates in a crotonate condensation.At 0-10 deg C the alcohol is not oxidized but the adduct with alkoxide ion is oxidized to form an alkyl furoate.

Potent and Selective Inhibitors of Trypanosoma cruzi Triosephosphate Isomerase with Concomitant Inhibition of Cruzipain: Inhibition of Parasite Growth through Multitarget Activity

Triosephosphate isomerase (TIM) is an essential Trypanosoma cruzi enzyme and one of the few validated drug targets for Chagas disease. The known inhibitors of this enzyme behave poorly or have low activity in the parasite. In this work, we used symmetrical diarylideneketones derived from structures with trypanosomicidal activity. We obtained an enzymatic inhibitor with an IC50value of 86 nm without inhibition effects on the mammalian enzyme. These molecules also affected cruzipain, another essential proteolytic enzyme of the parasite. This dual activity is important to avoid resistance problems. The compounds were studied in vitro against the epimastigote form of the parasite, and nonspecific toxicity to mammalian cells was also evaluated. As a proof of concept, three of the best derivatives were also assayed in vivo. Some of these derivatives showed higher in vitro trypanosomicidal activity than the reference drugs and were effective in protecting infected mice. In addition, these molecules could be obtained by a simple and economic green synthetic route, which is an important feature in the research and development of future drugs for neglected diseases.

Bi-functional modified-phosphate catalyzed the synthesis of α-α′-(EE)-bis(benzylidene)-cycloalkanones: Microwave versus conventional-heating

The impregnation of hydroxyapatite (HAP) by NaNO3 leads to a modified-hydroxyapatite which has a bi-functional acid-base property. Sodium-modified-hydroxyapatite (Na-HAP) efficiently catalyzed the cross-aldol condensation of arylaldehydes and cycloketones to afford α-α′- (EE)-bis(benzylidene)-cycloalkanones in good yields under microwave irradiation. Moreover, the methodology described in this paper provides a very easy and efficient synthesis carried out in water as the greenest available solvent under conventional heating. A comparison study between these two different modes of heating was investigated. The catalyst was easily recovered and efficiently re-used.

An efficient synthesis of E-2-amino-4-aryl-8-(arylmethylene)-5,6,7,8- tetrahydrobenzo[d]pyrimidines and their lower analogues

Base-catalysed cyclocondensation of α,α′- bis(arylmethylene)cyclohexanones with guanidine hydrochloride has been found to generate E-2-amino-4-aryl-8-(arylmethylene)-5,6,7,8-tetrahydrobenzo[d] pyrimidines in high yield, the structures of which have been established from their analytical and spectral data. The corresponding lower analogues, α,α′-bis(arylmethylene)cyclopentanones also were found to produce similar products viz. E-2-amino-4-aryl-7-(arylmethylene)-cyclopenteno[1, 2-d]pyrimidines in comparable yield under the same reaction condition.

A facile synthesis of α,α′-(EE)-bis(benzylidene)-cycloalkanones and their antitubercular evaluations

An economical and facile synthesis of α,α′-(EE)-bis(benzylidene)-cycloalkanones was achieved by the reaction of cycloalkanones with different aromatic aldehydes using ethanolic KOH in good yields. Few of the selected compounds were reduced with NaBH4 to the respective α,α′-(EE)-bis(benzylidene)-cycloalkanols. All these compounds and our earlier synthesized cyclohexyl phenyl methanols were evaluated for their antitubercular, antifungal and antibacterial activities. Several compounds displayed moderate antitubercular activity with MIC = 12.5-1.56 μg/mL. However, none of the compounds displayed any significant antifungal activity.

Facile formation of bis(3-indolyl)methylarenes by iodine-catalyzed reaction of indole with α,α′-bis(arylmethylene)ketones and α-substituted arylmethyleneketones in dry ethanol

Bis(3-indolyl)methylarenes are obtained in good yield by reaction of indole with α,α′-bis(arylmethylene)ketones and α-substituted arylmethyleneketones in dry ethanol using catalytic amount of molecular iodine at room temperature. A plausible mechanism for formation of these products has been suggested.

Synthesis and spectroscopic and structural studies of cross-conjugated dienones derived from cyclic ketones and aromatic aldehydes

Cross-conjugated dienones were synthesized by the reactions of cyclic ketones with two equivalents of aromatic aldehydes under basic conditions. An NMR spectroscopic study and X-ray diffraction analysis demonstrated that all reaction products are formed as E,E isomers. Spontaneous photochemical trans-cis isomerization of cross-conjugated dienones under the scattered light in solution was observed for the first time. The degree of isomerization depends mainly on the nature of the central fragment of the dienone molecule. The previously unknown product of photochemical [2+2]-cycloaddition of 2,5-bis[(E)-(3-pyridyl)methylidene]cyclopentanone was synthesized and characterized by spectroscopic methods and X-ray diffraction. Under the conditions used, only one isomer of the cyclobutane adduct was obtained. Springer Science+Business Media, Inc. 2006.

Solvent-free crossed aldol condensation of cyclic ketones with aromatic aldehydes assisted by microwave irradiation

A fast alumina-promoted crossed aldol-condensation reaction of aldehydes and cyclic ketones under microwave irradiation is described. This process is simple, efficient, and environmentally benign and proceeds in fairly high yield without any self-condensation. Springer-Verlag 2005.

Aldol condensations of aldehydes and ketones catalyzed by rare earth(III) perfluorooctane sulfonates in fluorous solvents

Rare earth(III) perfluorooctane sulfonates (RE(OPf)3) catalyze the efficient aldol condensation of different ketones with various aromatic aldehydes in fluorous solvents without the occurrence of any self-condensations. By simple separation of the fluorous phase containing only catalyst, reaction can be repeated several times.

Copper triflate-catalyzed cross-aldol condensation: A facile synthesis of α,α′-bis(substituted benzylidene) cycloalkanones

A facile, efficient, and clean procedure is described for synthesis of α,α′-bis(substituted benzylidene) cycloalkanones with good yields by the reaction of cycloalkanones with aromatic aldehydes using Cu(OTf)2 as catalyst. The catalyst was easily recovered and reused without loss of activity. Copyright Taylor & Francis, Inc.