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• 3132-99-8 m-bromobenzoic aldehyde 
• 108-94-1 cyclohexanone 

Relevant academic research and scientific papers

Synthesis, characterization, crystal structure of novel bis-thiomethylcyclohexanone derivatives and their inhibitory properties against some metabolic enzymes

In this study, a series of novel bis-thiomethylcyclohexanone compounds (3a–3j) were synthesized by the addition of thio-Michael to the bis-chalcones under mild reaction conditions. The bis-thiomethylcyclohexanone derivatives (bis-sulfides) were characterized by 1H NMR, 13C NMR, FTIR and elemental analysis techniques. Furthermore, the molecular and crystal structures of 3h, 3i and 3j compounds were determined by single crystal X-ray diffraction studies. In this study, X-ray crystallography provided an alternative and often-complementary means for elucidating functional groups at the enzyme inhibitory site. Acetylcholinesterase (AChE) is a member of the hydrolase protein super family and has a significant role in acetylcholine-mediated neurotransmission. Here, we report the synthesis and determining of novel bis-thiomethylcyclohexanone compounds based hybrid scaffold of AChE inhibitors. The newly synthesized bis-thiomethylcyclohexanone compounds showed Ki values of in range of 39.14–183.23 nM against human carbonic anhydrase I isoenzyme (hCA I), 46.03–194.02 nM against human carbonic anhydrase II isoenzyme (hCA II), 4.55–32.64 nM against AChE and 12.77–37.38 nM against butyrylcholinesterase (BChE). As a result, novel bis-thiomethylcyclohexanone compounds can have promising anti Alzheimer drug potential and record novel hCA I, and hCA II enzymes inhibitor.

Sulfonated PEG-intercalated montmorillonite [(Mt/PEG)-SO3H] as efficient and ecofriendly nanocatalyst for synthesis of α,α′-bis(substituted benzylidene)cycloalkanones

(Montmorillonite/PEG)-SO3H nanocomposite was successfully prepared for the first time and introduced as a solid acid nanocatalyst. Initially, polyethylene glycol (PEG) polymeric chains were intercalated into interlayer spaces of montmorillonite. The resulting Mt/PEG nanocomposite with good mechanical and thermal stability was chosen as a useful clay mineral/polymer support for further modification with chlorosulfonic acid. Structural characterization of (Mt/PEG)-SO3H was carried out using X-ray diffraction (XRD) analysis, Brunauer–Emmett–Teller (BET) measurements, Barrett–Joyner–Halenda (BJH) analysis, scanning electron microscopy (SEM), thermogravimetric analysis (TGA), and Fourier-transform infrared (FT-IR) spectroscopy. The results showed that PEG chains were intercalated into the clay mineral layers and that the Mt/PEG nanocomposite was successfully sulfonated. (Mt/PEG)-SO3H nanocomposite exhibited high specific surface area and good stability up to around 150?°C, showing excellent potential for application as a recyclable nanocatalyst. (Mt/PEG)-SO3H was used as an efficient and ecofriendly solid acid nanocatalyst for preparation of α,α′-bis(substituted benzylidene)cycloalkanones under solvent-free conditions, leading to many interesting findings. The excellent conversion values confirm that the catalyst has strong and sufficient acidic sites, which are responsible for its catalytic performance. The reaction under mild conditions (room temperature) with excellent yield, catalyst recyclability (up to ten times), and simple work-up procedure represent useful advantages of (Mt/PEG)-SO3H for catalysis. Moreover, the reaction could be scaled up to 10 and 15?mmol scales.

Synthesis of air-stable mixed bis-carboxylate titanocene complexes and their catalytic behaviors in cross-aldol and Mannich reactions

Tunable organometallic Lewis acid catalysts were developed by combining salicylic acid (H2-Sal) with benzoic acid (H-Ben), 4-fluorobenzoic acid (H-BenF) and 3-thiophenic acid (H-Th), as coligands for mixed bis-carboxylate titanocene complexes. Three air-stable complexes [Cp2Ti(η1-HSal)(η1-Ben)] (1), [Cp2Ti(η1-HSal)(η1-BenF)] (2) and [Cp2Ti[η1-HSal][(η1-Th)] (3) were prepared in high yields by the reaction of salicylato titanocene chelate with carboxylate ligands. The mixed bis-carboxylate titanocene complexes were fully characterized by physicochemical and spectroscopic methods. Single-crystal X-ray diffraction studies revealed Ti–O(H-Sal) bond distances in 1, 2 and 3 of 1.972(3), 1.9245(18) and 1.912(5)??, respectively, while the bond distances involving the coligands of 1, 2 and 3 are 1.908(3)?? (Ti–OBen), 1.9296(19)?? (Ti–OBenF) and 1.945(5)?? (Ti–OTh), respectively. These bis-carboxylate titanocene complexes showed satisfactory activities and selectivities in Mannich and cross-aldol reactions. Notably, complex 3 bearing the labile thiophene carboxylate ligand gave high yields with a diastereomer ratio (d.r.) as high as 1:99 for the direct Mannich reactions of benzaldehyde, cyclohexanone and aniline. In cross-aldol reaction of benzaldehyde and cyclohexanone, 1 and 2 successfully catalyzed the formation of double-aldol products in up to 99?% yield.

Design, characterization, and use of N,N-diethyl-N-sulfoethanaminium hydrogen sulfate {[Et3N-SO3H]HSO4} as a novel and highly efficient catalyst for preparation of α,α′-bis(arylidene)cycloalkanones

Abstract: The aim of this work is to introduce a novel and attractive protic acidic ionic liquid as catalyst for organic synthesis. To achieve this aim, N,N-diethyl-N-sulfoethanaminium hydrogen sulfate {[Et3N-SO3H]HSO4} was prepared by reaction of NEt3 with ClSO3H and then with H2SO4. The novel acidic ionic liquid was identified by Fourier-transform infrared (FT-IR), 1H nuclear magnetic resonance (NMR), 13C NMR, and mass spectroscopies. Its catalytic activity was then examined in the cross-aldol condensation reaction of arylaldehydes with cycloalkanones under solvent-free conditions, obtaining α,α′-bis(arylidene)cycloalkanones in high yield after short reaction time. Graphical Abstract: [Figure not available: see fulltext.]

Synthesis and fluorescence properties of α,α'-bis(substituted- benzylidene)cycloalkanones catalyzed by 1-methyl-3(2-(sulfooxy)ethyl)-1h- imidazol-3-ium chloride

-Bis(substituted-benzylidene)cycloalkanones were synthesized via a solvent-free cross-aldol condensation of aromatic aldehydes with cycloalkanones in the presence of a catalytic amount 1-methyl-3(2-(sulfooxy)ethyl)-1H-imidazol- 3-ium chloride at room temperature with excellent yields. The screening for optical properties indicated that the size of cycloalkanone has an influence on the fluorescence emission of products. Products coming from cyclohexanone have stronger fluorescence emission than those from cyclopentanone. Copyrigh

Synthesis of β,β′-bis(substituted benzylidene) cycloalkanones catalyzed by amino-functionalized ionic liquid

Condensation of aromatic aldehydes with cyclopentanone and cyclohexanone using amino-functionalized ionic liquid, 1-aminoethyl-3-methyl tetrafluoroborate as solvent and catalyst was successfully performed for preparation of α,α′-bis(substituted benzylidene)cycloalkanones. The catalyst can be recovered and reused for at least three times without apparently lose of activity. The process is simple, environmentally benign and proceeds in excellent yields.

Study of substituent effects in substituted dibenzal acetones

The present work involves a detailed study of the ultra-violet absorption spectra of various substituted dibenzylidene ketones derived from acetone, ethyl methyl ketone, diethyl ketone, cyclopentanone and cyclohexanone by condensing with several meta- and para-substituted benzaldehydes in n-hexane and in ethanol to ascertain the transition dominant in these solvents. These ketones exist as equilibrium mixtures of s-cis, cis and s-cis, trans conformations. The ultraviolet absorption spectra of the ketones exhibit two bands due to π* ← π transition around 250 and 320 nm. The 320 nm band is prominent in all the cases. There is no indication of π* ← n transition in any of the spectra. The 320 nm band is structureless in all the cases except those shown by the dibenzylidene ketones derived from cyclopentanone in hexane. Therefore it can be inferred that the dibenzylide ketones derived from all the ketones except those derived from cyclopentanone are non-planar.