Acetone Derivatives Research Articles

Acoustical studies of some 1,3,4-thiadiazole derivatives in acetone at 303.15 k

Some new 1, 3, 4-thiadiazole have been synthesized and characterized by IR and NMR spectra. Densities, viscosities and ultrasonic velocities of these compounds have been measured over the wide composition range at 303.15 K in acetone. From these data, various acoustical parameters were evaluated. Some these parameters are adiabatic compressibility, intermolecular free length, relaxation strength, relative association, Raos molar constant, salvation number etc. The behaviour of solutions of these compounds in acetone is explained from the evaluated parameters. Keywords: 1, 3, 4-Thiadiazole, density, velocity, Acetone, acoustical properties.

Acoustical Studies on Binary Liquid Mixtures of Some 1,3,4-Oxadiazole Derivatives with Acetone at 303.15 K

The wide spread use of 1,3,4-oxadiazoles as a scaffold in medicinal chemistry establishes this moiety as an important bioactive class of heterocycles. In the present study ultrasonic velocity (u), density (ρ) and viscosity (η) have been measured at frequency 2 MHz in the binary mixtures of 1,3,4-oxadiazole derivatives in acetone at 303.15 K using ultrasonic interferometer technique. The measured value of ultrasonic velocity, density and viscosity have been used to estimate the acoustical parameters namely adiabatic compressibility (βad), relaxation time (τ), acoustic impedance (Zi), free length (Lf), free volume (Vf) and internal pressure (πi), with a view to investigate the nature and strength of molecular interactions. The obtained result support the occurrence of molecular association through hydrogen bonding in the binary liquid mixtures.

Acoustical Studies on Binary Liquid Mixtures of Some 1,3,4-Oxadiazole Derivatives with Acetone at 303.15 K

The wide spread use of 1,3,4-oxadiazoles as a scaffold in medicinal chemistry establishes this moiety as an important bioactive class of heterocycles. In the present study ultrasonic velocity (u), density (ρ) and viscosity (η) have been measured at frequency 2 MHz in the binary mixtures of 1,3,4-oxadiazole derivatives in acetone at 303.15 K using ultrasonic interferometer technique. The measured value of ultrasonic velocity, density and viscosity have been used to estimate the acoustical parameters namely adiabatic compressibility (βad), relaxation time (τ), acoustic impedance (Zi), free length (Lf), free volume (Vf) and internal pressure (πi), with a view to investigate the nature and strength of molecular interactions. The obtained result support the occurrence of molecular association through hydrogen bonding in the binary liquid mixtures.

Antioxidant Activity of <i>Acanthopanax senticosus</i> Extract and Derivatives

Antioxidant activities of acetone and methanol extracts from leaves of Acanthopanax senticosus, one of traditional Chinese medicine consumed in the eastnorth region of China, were examined by a DPPH (1,1-Diphenyl-2-picrylhydrazyl) radical-scavenging assay and a β-carotene-linoleic acid test. In DPPH, the antioxidant activity of the acetone extracts, methanol extracts and derivative were superior to that of control with IC50 were 298.58, 360.16 and 142.21μg/mL, respectively. In the β-carotene-linoleic acid test, IC50 were 305.37, 400.39 and 156.69μg/mL. It was concluded that Acanthopanax senticosus and its derivatives might be a potential natural source of antioxidants.

Consecutive Michael-Claisen Process for Cyclohexane-1,3-dione Derivative (CDD) Synthesis from Unsubstituted and Substituted Acetone

A long-existing problem of cyclohexane-1,3-dione derivatives (CDD) synthesis from unreactive acetone through consecutive Michael–Claisen process was solved under this study. The practical applicability of this process was tested for a novel compound ethyl 3-(2,4-dioxocyclohexyl)propanoate for up to 20-gram scale. Furthermore, the scope of different acetone derivatives was investigated and resulted with similar consecutive Michael–Claisen process for CDD synthesis. The reaction exhibited remarkable regioselectivity in Michael addition followed by Claisen cyclization. In this process high substrate selectivity was observed for CDD ­synthesis following consecutive double-Michael–Claisen and ­Michael–Claisen cyclization.

Synthesis and Antimalarial Activity of Dihydroperoxides and Tetraoxanes Conjugated with Bis(benzyl)acetone Derivatives

Dihydroperoxides and tetraoxanes derived from symmetrically substituted bis(arylmethyl)acetones were synthesized in modest to good yields using several methods. Three of these compounds exhibit an important in vitro antimalarial activity (1.0 μm ≤ IC(50) ≤ 5.0 μm) against blood forms of the human malaria parasite Plasmodium falciparum.

Identification and determination of ephedrine and its congeners in urine by gas chromatography

Abstract A sensitive and specific assay for ephedrine-type compounds in urine is described. The procedure involves the removal of neutral and acidic compounds, then extraction of the bases with ether. This extract, after concentration, is injected into a flame ionisation gas chromatograph equipped with a 2% polyethylene glycol 6000, alkaline treated, column at 165°. Linear detector response between 5 and 100 μg base/ml urine was observed (peak height with respect to an internal marker) and replicate analyses indicated good reproducibility. No interfering compounds have been encountered nor any “on column” decomposition. The amines were further identified by chromatography of their acetone derivatives.

Synthesis and antimicrobial activities of novel 1,4-benzothiazine derivatives

A series of 2H,4H-2-[3,5-dimethyl-4-(substituted) phenyl azo pyrazol-1-yl] carbonyl methyl-3-oxo-1,4-benzothiazine derivatives have been synthesized by the reaction of 2H,4H-2-hydrazino carbonyl methyl-3-oxo-1,4-benzothiazine with acetyl acetone derivatives using ultrasound in lesser time with higher yields. All the synthesized compounds were investigated for their antibacterial activities. The result indicated that the compounds show convincing activities against Gram-positive bacteria (Bacillus subtilis and Streptococcus lactis) when compared with standard drug (ampicillin trihydrate). These compounds were also synthesized by conventional method and their structures have been elucidated on the basis of spectral analyses and chemical reactions.

Application of reactive solvents of melamine for synthesis of polyetherols with perhydro-1,3,5-triazine rings

The application of reactive solvents (RSs), namely hydroxymethyl derivatives of acetone for digestion of isocyanuric acid, which is insoluble in most organic solvents except for DMSO, makes the substrate available for further conversions. At this step, the incorporation of perhydro-1,3,5-triazine ring into RS takes place. The obtained solutions were used for synthesis of polyetherols containing perhydro-1,3,5-triazine rings in reaction with oxiranes: ethylene and propylene oxides. The polyetherols were then used to obtain foamed polyurethanes with enhanced thermal stability. © 2010 Wiley Periodicals, Inc. J Appl Polym Sci, 2011

KSRP/FUBP2 Is a Binding Protein of GO-Y086, a Cytotoxic Curcumin Analogue.

Bis(arylmethylidene)acetone derivatives are an important class of curcumin analogues that exhibit various biological and pharmacological activities. We herein report that GO-Y086, a biotinylated bis(arylmethylidene)acetone, inhibits cancer cell growth. We also show that GO-Y086 specifically interacts with the nuclear protein KSRP/FUBP2 by covalent modification. GO-Y086 markedly suppresses the expression of the c-Myc protein, which plays an important role in cellular proliferation and whose expression is regulated by KSRP/FUBP2.

Synthesis, characterization and studies on the nonlinear optical parameters of hydrazones

Three hydrazones, 2-(4-methylphenoxy)- N′-[(1E)-(4-nitrophenyl)methylene]acetohydrazide (compound-1), 2-(4-methylphenoxy)- N′-[(1E)-(4-methylphenyl)methylene]acetohydrazide ((compound-2) and N′-{(1E)-[4-(dimethylamino)phenyl]methylene}-2-(4-ethylphenoxy) acetohydrazide(compound-3) were synthesized and their third order nonlinear optical properties were investigated using a single beam z-scan technique with nanosecond laser pulses at 532 nm. Open aperture data obtained from the three compounds indicates two photon absorption at this wavelength. The nonlinear refractive index n 2, the nonlinear absorption coefficient β, the magnitude of the effective third order susceptibility χ (3), the second order hyperpolarizability γ h and the coupling factor ρ have been estimated. The values obtained are comparable with the values obtained for 4-methoxy chalcone derivatives and dibenzylidene acetone derivatives. Among the compounds studied, compounds-1 and 3 exhibited the better optical power limiting behaviour at 532 nm. Our studies suggest that compounds-1, 2 and 3 are potential candidates for optical device applications such as optical limiters and optical switches.

Second example for the heterocomplexation of chiral diols and complete disproportionation of enantiomers for non-racemic 2,3- O-cyclohexylidene-1,1,4,4-tetraphenylthreitols

Inclusion complexation of a tricyclic dipeptide derived from ( S)-proline toward several chiral diols was examined, and observed that inclusion complexation behavior depended strongly on the composition of diol. For 2,3- O-alkylidene-1,1,4,4-tetraphenylthreitols, the derivatives of cyclohexanone and acetone reacted with the dipeptide to generate a 1:2 inclusion complex; however, the former is achiroselective, affording the second heterocomplex known to date. Based on the heterocomplexation, complete disproportionation of enantiomers of non-racemic 2,3- O-cyclohexylidene-1,1,4,4-tetraphenylthreitol was successfully realized, leading to highly effective separation of the excess enantiomer from the racemate. On the other hand, inclusion complexation did not occur between the dipeptide and rac-pinanediol or (4 R,5 R)-4-diphenylhydroxymethyl-5-hydroxy-2,6,6-triphenyl-1,3,2-dioxaborolane.

Synthesis of some cyclopentenones and crystal structure of 4-hydroxy-3,4-bis(4-methoxyphenyl)-5,5-dimethyl-2-cyclopenten-1-one

Sodium-hydroxide-catalyzed condensation of di-p-methyl- and di-p-methoxybenzil with acetone derivatives was investigated in methanol. Di- and trisubstituted products were obtained as cyclopentenones, while tetraaryl-substituted systems were isolated as cyclopentadienones. The structures of the products were identified by elemental analysis, infrared (IR), nuclear magnetic resonance (1H NMR), and mass spectroscopy. The solid-state structure of 4-hydroxy-3,4-bis(4-methoxyphenyl)-5,5-dimethyl-2-cyclopenten-1-one was further studied by single-crystal X-ray diffraction analysis. The title compound crystallizes in an orthorhombic space group and intermolecular O–H···O and C–H···O hydrogen bonds stabilize the crystal lattice.

Density Functional Studies on the Complexation and Spectroscopy of Uranyl Ligated with Acetonitrile and Acetone Derivatives

The coordination of nitrile (acetonitrile, propionitrile, and benzonitrile) and carbonyl (formaldehyde, acetaldehyde, and acetone) ligands to the uranyl dication (UO(2)(2+)) has been examined using density functional theory (DFT) utilizing relativistic effective core potentials (RECPs). Complexes containing up to six ligands have been modeled in the gas phase for all ligands except formaldehyde, for which no minimum could be found. A comparison of relative binding energies indicates that 5-coordinate complexes are predominant, while 6-coordinate complexes involving propionitrile and acetone ligands might be possible. Additionally, the relative binding energy and the weakening of the uranyl bond is related to the size of the ligand, and in general, nitriles bind more strongly to uranyl than carbonyls.

Facile Syntheses of Some Thieno[2,3-d] Pyrimidine Derivatives

In one-pot synthesis 2-arylidene-5,6,7,8-tetrahydrothiazolo[3,2-a] cyclopenteno-thieno[2,3-d] pyrimidine-3,5-diones (3) were prepared via the reaction of a ternary mixture of 2-thioxo-1,3,4,5,6,7-hexahydr cyclopentinothieno [2,3-d]-4-one (2), chloroacetic acid and a proper aldehyde. Compound 2 reacted with 3-chloropent-2, 4-dione in ethanolic potassium hydroxide yielding the S-acetyl acetone derivative 5f . The latter compound reacted with hydrazine hydrate and phenyl hydrazine yielded the 2-pyrazolthio derivative 10a, b. Compound 5f also underwent cyclization on heating with acetic acid—pyridine solution to give 11. The 2-methylthio derivative 5a, when treated with hydrogen peroxide gave the corresponding oxidized product 9.

Domino Double Michael−Claisen Cyclizations: A Powerful General Tool for Introducing Quaternary Stereocenters at C(4) of Cyclohexane-1,3-diones and Total Synthesis of Diverse Families of Sterically Congested Alkaloids

Reactions of substituted acetone derivatives with acrylic acid esters (>200 mol %) in the presence of t-BuOK (200 mol %) in t-BuOH-THF (1:1 by volume) turned out to proceed as a cascade process consisting of the first Michael addition, the second Michael addition, and the last Claisen reaction to afford 4,4-disubstituted cyclohexane-1,3-diones. Only more substituted enolates play the role of a Michael donor in this cascade process, and therefore the ketone took up two alkoxycarbonylethyl groups on the same carbon bearing more substituents. Such intermediates were followed by intramolecular Claisen reactions leading to cyclohexane-1,3-diones bearing quaternary stereogenic centers at C(4), which bears an alkoxycarbonylethyl group and the substituent of the starting acetone derivatives. Thus-obtained 4,4-disubstituted cyclohexane-1,3-diones were successfully employed for total syntheses of intricate alkaloids of biological interest such as (+)-aspidospermidine, (+/-)-galanthamine, (+/-)-lycoramine, and (+/-)-mesembrine, all featuring quaternary stereogenic centers. DFT calculations provided us with clear-cut explanations for the observed chemoselectivity of the cascade process involving ketone-based enolates under thermodynamically controlled conditions.

Solubility of Diamantane, Trimantane, Tetramantane, and Their Derivatives in Organic Solvents

The solubility of diamantane, trimantane, tetramantane, and their derivatives in acetone, cyclohexane, ethyl acetate, toluene, heptane, and 1-pentanol was measured using the solid disappearance method for temperatures ranging from (273.15 to 348.15) K. The experimental solubility data have been correlated with different thermodynamic models to obtain engineering parameters for use in process design.

Synthesis of Novel Cyclopentenone Derivatives and Crystal Structure Determination of 3,4-bis(4-chlorophenyl)-5,5- dimethyl-4-hydroxy-2-cyclopenten-1-one

New cyclopentenone derivatives were prepared via aldol condensation of substituted benzils with acetone derivatives in alkaline media. The structures of products were confirmed by elemental analysis, IR, 1H NMR, 13C NMR and mass spectroscopy and supported by a single crystal X-ray diffraction analysis of 3,4- bis(4-chlorophenyl)-5,5- dimethyl-4-hydroxy-2-cyclopenten-1-one. The crystal structure of title compound in the solid state is stabilised by O–H…O and C-H…O hydrogen bonds, as well as by Cl…Cl close contacts.

π-Acidic alkene ligand effects in Pd-catalysed cross-coupling processes: exploiting the interaction of dibenzylidene acetone (dba) and related ligands with Pd(0) and Pd(ii)

pi-Acidic alkene (olefin) ligands positively influence Pd-catalysed cross-coupling processes, interacting with both palladium(0) and palladium(ii) species, in some cases stabilising key catalytic intermediates. Rates of oxidative addition and reductive elimination are both affected. In certain cases, beta-hydrogen elimination can be slowed down by pi-acidic alkenes, which opens up new reaction pathways (e.g. interception of sigma-alkylpalladium(ii) species by appropriate nucleophiles). pi-Acidic alkene ligands can act independently or in a synergistic fashion with another two-electron donor ligand (e.g. amine, phosphine or N-heterocyclic carbene). The purpose of this perspective article is to highlight the impressive results that can be obtained using pi-acidic alkene ligands, with a particular focus on dibenzylidene acetone (dba) derivatives. Other types of alkene ligands, e.g. macrocyclic alkenes, are also discussed.

Synthesis and Reactions of Novel Thienopyrimidine and Thiazolothienopyrimidine Derivatives

In a one-pot reaction, 2-arylidine-6,7,8,9-tetrahydrohexenothieno[2,3-d]pyrimi-dine-3(3H),5(5H)-diones 2a, b were prepared by the reaction of a ternary mixture of 2-thioxo-5,6,7,8-tetrahydrohexenothieno[2,3-d]pyrimidin-4(4H)-one 1 (1), chloroacetic acid, and a proper aldehyde. Compound 2a react with hydroxyl amine hydrochloride to give corresponding oxime derivative 4. Reaction of 1 with 3-chloropent-2, 4-dione in ethanolic sodium hydroxide solution yielded S-acetyl acetone derivative 5b. The latter compound reacted with hydrazines affording the 2-pyrazolthio 6. Compound 5b reacted with urea and thiourea to give 7a, b. Also, compound 5b underwent cyclization on boiling with acetic anhydride/pyridine mixture to yield thiazolopyrimidine derivative 8. Ketone compound 8 formed an oxime 9. Moreover, condensation of 8 with aromatic aldehyde furnished the derivative 11.