Useful Compound (useful + compound)

Distribution by Scientific Domains

Selected Abstracts

Tetraalkylammonium Salts of Weakly Coordinating Aluminates: Ionic Liquids, Materials for Electrochemical Applications and Useful Compounds for Anion Investigation

Ines Raabe Dr.
Abstract Weak and robust? Tetraalkylammonium salts of weakly coordinating fluorinated alkoxyaluminates are easily accessible, chemically robust materials that show interesting physico-chemical properties like low melting points, high electrochemical stability and electric conductivity in weakly polar solvents such as CH2Cl2, Ph-F and toluene. In this study, we investigated the tetraalkylammonium salts of the weakly coordinating fluorinated alkoxyaluminates [pftb], ([Al(O(C(CF3)3)4],), [hfip], ([Al(OC(H)(CF3)2)4],) and [hftb], ([Al(OC(CH3)(CF3)2)4],) in order to obtain information on their undisturbed spectral and structural properties, as well as to study their electrochemical behavior (i.e., conductivities in non-polar solvents and electrochemical windows). Several of the compounds qualify as ionic liquids with melting points as low as 42,C for [NBu4]+[hfip],. Simple and almost quantitative metathesis reactions yielding these materials in high purity were developed. These [NR4]+ salts serve as model compounds for undisturbed anions and their vibrational spectra,together with simulated spectra based on quantum chemical DFT calculations,were used for the clear assignment of the anion bands. Besides, the ion volumes of the anions (Vion([pftb],)=0.736,nm3, Vion([hftb],)=0.658,nm3, Vion([hfip],)=0.577,nm3) and their decomposition pathways in the mass spectrometric measurements have been established. The salts are highly soluble in non-polar solvents (up to 1.09,mol,L,1 are possible for [NBu4]+[hftb], in CH2Cl2 and 0.41,mol,L,1 for [NBu4]+[hfip], in CHCl3) and show higher molar conductivities if compared to [NBu4]+[PF6],. The electrochemical windows of CH2Cl2, CH3CN and 1,2-F2C6H4 using the [NBu4]+ aluminate electrolytes are up to +0.5,V/,0.7,V larger than those using the standard [NBu4]+[PF6],. [source]

Microwave-Assisted Oxidation of Side Chain Arenes by MagtrieveTM

Marcin Lukasiewicz
Abstract A commercial tetravalent chromium dioxide (MagtrieveTM) as a magnetically retrievable oxidant is shown to be a very useful compound for microwave-assisted and conventional transformation of aromatic and alkyl aromatic molecules into the corresponding aryl ketones, quinones or lactones. [source]

A convenient preparation of 3-acetyl-5-methylisoxazole

Ronald R. Sauers
Starting from 2,5-hexanedione (4), a one-pot preparation of 3-acetyl-5-methylisoxazole (1) is described. 3-Acetyl-5-methylisoxazole (1) is a useful compound for the preparation of 3-oxobutyronitrile (10) and for 3-vinyl-(5-methyl isoxazolyl) ketone (2). [source]

Improved synthesis of [18F]fluoromethyl tosylate, a convenient reagent for radiofluoromethylations

Timothy R. Neal
Abstract The utility of [18F]fluoromethyl tosylate as an [18F]fluoromethylation reagent has been reexamined. The preparation of this potentially useful compound from the reaction of bis(tosyloxy) methane with 18F- was reported several years ago, but it had not found use as a labeling reagent. When the reported reaction of bis(tosyloxy) methane with 18F- was carried out, [18F]fluoromethyl tosylate was formed along with [18F]tosyl fluoride. The product ratio depended upon reaction conditions, with the yield of [18F]fluoromethyl tosylate usually in the range of 25,40%. Addition of a small amount of water to the reaction mixture resulted in a significant increase in the yield of [18F]fluoromethyl tosylate. Reaction conditions were defined that produced a yield of 716% of [18F]fluoromethyl tosylate (decay corrected). The product was conveniently purified by alumina chromatography. Reaction of [18F]fluoromethyl tosylate with the (des-fluoromethyl) fluticasone propionate thioacid precursor produced [18F]fluticasone propionate in improved yield (16%, from fluoride in production-scale runs) over other synthesis methods. Similarly, formation of [18F]choline, [18F]fluoromethionine and N- ([18F]fluoromethyl)spiperone from the reaction of [18F]fluoromethyl tosylate with corresponding precursors was examined. Copyright 2005 John Wiley & Sons, Ltd. [source]

Crystallization and preliminary X-ray analysis of the NADPH-dependent 3-quinuclidinone reductase from Rhodotorula rubra

Daijiro Takeshita
(R)-3-Quinuclidinol is a useful compound that is applicable to the synthesis of various pharmaceuticals. The NADPH-dependent carbonyl reductase 3-quinuclidinone reductase from Rhodotorula rubra catalyzes the stereospecific reduction of 3-quinuclidinone to (R)-3-quinuclidinol and is expected to be utilized in industrial production of this alcohol. 3-Quinuclidinone reductase from R. rubra was expressed in Escherichia coli and purified using Ni-affinity and ion-exchange column chromatography. Crystals of the protein were obtained by the sitting-drop vapour-diffusion method using PEG 8000 as the precipitant. The crystals belonged to space group P41212, with unit-cell parameters a = b = 91.3, c = 265.4,, and diffracted X-rays to 2.2, resolution. The asymmetric unit contained four molecules of the protein and the solvent content was 48.4%. [source]

Development of Pharmaceutical Drugs, Drug Intermediates and Ingredients by Using Direct Organo-Click Reactions

Dhevalapally B. Ramachary
Abstract Here we report on our studies of the use of combinations of amino acids, amines, K2CO3 or Cs2CO3 and CuSO4/Cu for catalysing green cascade reactions. We aimed to prepare the highly reactive and substituted olefin species 7 and 8, under very mild and environmentally friendly conditions, thus giving the hydrogenated products 10 and 12 through the action of Hantzsch ester (4) by self-catalysis through decreasing the HOMO,LUMO energy gaps between olefins 7/8 and Hantzsch ester (4) through biomimetic reductions. Highly useful compounds 10 to 14 were assembled from simple substrates such as aldehydes 1, ketones 2, CH acids 3, Hantzsch ester (4) and alkyl halides 5 by diversity-oriented green synthesis involving cascade olefination/hydrogenation (O/H), olefination/hydrogenation/alkylation (O/H/A) and hydrogenation/olefination/hydrogenation (H/O/H) reaction sequences in one-pot fashion with stereospecific organo- and organo-/metal-carbonate catalysis. Highly functionalized diverse compounds such as 10 to 14 are biologically active products and have found wide applications as pharmaceutical drugs, drug intermediates and drug ingredients. For the first time in organocatalysis, we report the O/H/A/TE reaction to furnish high yields of transesterification products 11 by simply mixing the reactants under proline/K2CO3 catalysis conditions. Additionally, a novel organocatalytic H/O/H reaction sequence for the synthesis of alkyl-substituted aromatics has been developed. Furthermore, for the first time we have developed organocatalysed cascade olefination/hydrogenation/hydrolysis (O/H/H) reactions to furnish highly useful materials such as 2-oxochroman-3-carboxylic acid (14kc) and 2-amino-4H -chromene-3-carbonitrile (14kj) in good yields. Experimentally simple and environmentally friendly organocatalytic two-carbon homologation through cascade O/H/H reactions of aldehydes 1, Meldrum's acid (3c), Hantzsch ester (4) and acetic acid/triethylamine in ethanol has been demonstrated. Additionally, we have developed a green synthesis of the highly substituted 1,2,3-triazole 17 from simple substrates through a two-step combination of olefination/hydrogenation/alkylation and Huisgen cycloaddition reaction sequences under stereospecific organocopper catalysis conditions. In this paper we have found strong support for our hypothesis that, "decreasing the HOMO,LUMO energy gap between olefins 7/8 and Hantzsch ester (4) will drive the biomimetic hydrogenation reaction by self-catalysis". This self-catalysis was further confirmed with many varieties of examples.( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008) [source]

Highly Efficient Asymmetric Epoxidation of Electron-Deficient ,,,-Enones and Related Applications to Organic Synthesis

Changwu Zheng
Abstract The asymmetric epoxidation of electron-deficient olefins has been achieved using inexpensive and readily available prolinols as catalysts with good to excellent yields and enantioselectivities. The utility of the resulting chiral epoxides was illustrated by elaboration to several synthetically useful compounds featuring a concise synthesis of (,)-(5R,6S)-balasubramide. [source]

Review of flavonoids and other phenolics from fruits of different tomato (Lycopersicon esculentum Mill.) cultivars

Rune Slimestad
Abstract BACKGROUND: Tomato, one of the most important vegetables worldwide, contains a range of flavonoids and phenolic acids in addition to lycopene, which are regarded as potentially useful compounds with respect to health benefits. Composition data in fresh tomatoes vary due to genetic and environmental factors and cultural practices. Breeding programs aim to produce tomatoes with enhanced levels of flavonoids and other phenolics. RESULTS: The present paper gives an overview of flavonoids, stilbenoids and other phenolics reported to occur in tomato fruits. Contents are reported for a wide range of cultivars and types. Metabolism of phenolics during fruit maturation and tissue location are described, and an overview of measured contents is given. Effects of environmental conditions and cultural practices are estimated using available literature. Recent literature on transgenic tomatoes is included, and possibilities for regulating phenolic contents in tomatoes are discussed. CONCLUSION: The literature review clearly discloses a rapidly growing interest in flavonoids and other phenolics in tomato fruits and products made thereof. This is particularly connected to the antioxidant properties of these compounds as well as other possible health effects. Choice of cultivar and effects of environment and agronomic practices are important factors with respect to phenolic qualities and quantities of tomatoes. Copyright 2009 Society of Chemical Industry [source]

Subtype-selective targeting of voltage-gated sodium channels

Steve England
Voltage-gated sodium channels are key to the initiation and propagation of action potentials in electrically excitable cells. Molecular characterization has shown there to be nine functional members of the family, with a high degree of sequence homology between the channels. This homology translates into similar biophysical and pharmacological properties. Confidence in some of the channels as drug targets has been boosted by the discovery of human mutations in the genes encoding a number of them, which give rise to clinical conditions commensurate with the changes predicted from the altered channel biophysics. As a result, they have received much attention for their therapeutic potential. Sodium channels represent well-precedented drug targets as antidysrhythmics, anticonvulsants and local anaesthetics provide good clinical efficacy, driven through pharmacology at these channels. However, electrophysiological characterization of clinically useful compounds in recombinant expression systems shows them to be weak, with poor selectivity between channel types. This has led to the search for subtype-selective modulators, which offer the promise of treatments with improved clinical efficacy and better toleration. Despite developments in high-throughput electrophysiology platforms, this has proven very challenging. Structural biology is beginning to offer us a greater understanding of the three-dimensional structure of voltage-gated ion channels, bringing with it the opportunity to do real structure-based drug design in the future. This discipline is still in its infancy, but developments with the expression and purification of prokaryotic sodium channels offer the promise of structure-based drug design in the not too distant future. [source]