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CHEMISTRY OF 2,5-BIS(TRIMETHYLSILOXY)FURANS. I: PREPARATION AND DIELS-ALDER REACTIONS

A number of substituted 2,5-bis(trimethylsiloxy)furans were prepared from the corresponding succinic anhydrides, and were found to be reactive dienes from the Diels-Alder reaction with electron-withdrawing dienophiles, giving p-quinones and hydroquinones.

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Tetrahydrofuran – Wikipedia,
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Quantification of furandiones in ambient aerosol

Furandiones are products of the photooxidation of anthropogenic volatile organic compounds (VOC), like toluene, and contribute to secondary organic aerosol (SOA). Because few molecular tracers of anthropogenic SOA are used to assess this source in ambient aerosol, developing a quantification method for furandiones holds a great importance. In this study, we developed a direct and highly sensitive gas chromatography-mass spectrometry method for the quantitative analysis of furandiones in fine particulate matter that is mainly free from interference by structurally-related dicarboxylic acids. Our application of this method in Iowa City, IA provides the first ambient measurements of four furandiones: 2,5-furandione, 3-methyl-2,5-furandione, dihydro-2,5-furandione, and dihydro-3-methyl-2,5-furandione. Furandiones were detected in all collected samples with a daily average concentration of 9.1?¡À?3.8?ng?m?3. The developed method allows for the accurate measurement of the furandiones concentrations in ambient aerosol, which will support future evaluation of these compounds as tracers for anthropogenic SOA and assessment of their potential health impacts.

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Tetrahydrofuran – Wikipedia,
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An optimisation-based framework for the conceptual design of reaction-separation processes

Prior to detailed process design, it is vital to first generate a good flowsheet that meets particular objective. This is particularly the case in bio-based materials and products, where, given a range of chemistries, the synthesis problem is not about the best way to make a particular product but rather the best way to convert a specific feedstock. In order to do so, an optimisation-based framework, which can be used to identify the optimal configuration of a process network that consists of both reactions and separation systems to achieve maximum economic potential, is presented in this paper. A process superstructure, which includes the concept of master reaction stages and subsidiary separation stages, is introduced to facilitate the theory. The problem is formulated as a generalised mixed integer linear programming (MILP) model which accounts for the simultaneous selection of products and identification of the process configuration. The solution of the optimisation problem includes the best possible economic performance, identification of active reactions, reaction ordering and separation sequences along with the corresponding flowsheet of the optimal process. The economic criterion takes account of raw materials costs, product values and separation related costs. Two bio-based chemical case studies are presented to illustrate the applicability of the proposed methodology.

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Tetrahydrofuran – Wikipedia,
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Synthesis of N4-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-L-asparagine analogues. L-2-chloro-, L-2-bromo-, and D,L-2-methylsuccinamic acid analogues

L-Chlorosuccinic anhydride, L-bromosuccinic anhydride, and D,L-methylsuccinic anhydride react with 2-acetamido-2-deoxy-beta-D-glucopyranosylamine to give varying mixtures of N4-(beta-GlcNAc)-2-substituted- and N4-(beta-GlcNAc)-3-substituted-succinamic acid isomers. The two regioisomers are separated by anion exchange chromatography. The N4-(beta-GlcNAc)-2-substituted-succinamic acid isomers are characterized as analogues of N4-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-L-asparagine.

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Tetrahydrofuran – Wikipedia,
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Construction of perhydro indol-2-ones by a methoxide catalyzed deacetylation-Michael-aldol cascade

An efficient, stereoselective Michael-aldol cascade for the one-pot construction of the perhydro indol-2-one bicyclic ring system using an acetate protected doubly-activated pyrrole-2-one pro-nucleophile and alpha,beta-unsaturated carbonyl compounds has been developed. Initiated by a methoxide deacetylation in methanol at room temperature, the cascade is easy to perform, stereoselective, efficient and broad in scope to this synthetically relevant structure.

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Balanced chemical reaction does not necessarily reveal either the individual elementary reactions by which a reaction occurs or its rate law.Electric Literature of 4100-80-5. In my other articles, you can also check out more blogs about 4100-80-5

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Fenbufen, a new anti inflammatory analgesic: synthesis and structure activity relationships of analogs

100 analogs of fenbufen were prepared and tested using the carrageenan, polyarthritis, and UV erythema anti inflammatory tests and the 2 phenyl 1,4 benzoquinone writhing and inflamed paw pressure analgesic tests. Only 3 retained the same full spectrum of activity as fenbufen: dl 4 (4 biphenylyl) 4 hydroxybutyric acid, dl 4 (4 biphenylyl) 1,4 butanediol, and 4 biphenylacetic acid. Fenbufen had the same spectrum of activity as aspirin, phenylbutazone, and indomethacin in the 5 tests. In addition, dose response derived potencies show fenbufen more potent than aspirin and at least as potent as phenylbutazone in all 5 tests. Two related compounds were generally similar.

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Tetrahydrofuran – Wikipedia,
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Novel selective PDE4 inhibitors. 1. Synthesis, structure-activity relationships, and molecular modeling of 4-(3,4-dimethoxyphenyl)-2H-phthalazin-1-ones and analogues

A number of 6-(3,4-dimethoxyphenyl)-4,5-dihydro-2H-pyridazin-3-ones and a novel series of 4-(3,4-dimethoxyphenyl)-2H-phthalazin-1-ones were prepared and tested on the cGMP-inhibited phosphodiesterase (PDE3) and cAMP-specific phosphodiesterase (PDE4) enzymes. All tested compounds were found to specifically inhibit PDE4 except for pyridazinone 3b, which showed moderate PDE4 (pIC50 = 6.5) as well as PDE3 (pIC50 = 6.6) inhibitory activity. In both the pyridazinone and phthlazinone series it was found that N-substitution is beneficial for PDE4 inhibition, whereas in the pyridazinone series it also accounts for PDE4 selectivity. In the phthalazinone series, the cis-4a,5,6,7,8,8a-hexahydrophthalazinones and their corresponding 4a,5,8,8a-tetrahydro analogues showed potent PDE4 inhibitory potency (10/11c,d: pIC50 = 7.6-8.4). A molecular modeling study revealed that the cis-fused cyclohexa(e)ne rings occupy a region in space different from that occupied by the other fused (un)saturated hydrocarbon rings applied; we therefore assume that the steric interactions of these rings with the binding site play an important role in enzyme inhibition.

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Tetrahydrofuran – Wikipedia,
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Investigation on the structural features of Zhundong subbituminous coal through ruthenium ion-catalyzed oxidation

The structural features of Zhundong subbituminous coal (ZSBC) were investigated by ruthenium ion-catalyzed oxidation (RICO) and subsequent analyses with a gas chromatograph/mass spectrometer and an atmospheric-pressure solid analysis probe/time of flight-mass spectrometer (ASAP/TOF-MS). The results suggest that condensed aromatic rings linked by short polymethylene bridged linkages, long side chains, and oxygen-containing groups are predominant in ZSBC. Aliphatic bridged linkages connecting 3 aromatic rings also exist in ZSBC. Several heterocyclic carboxylic acids were produced from RICO of ZSBC. The heterocyclic moieties include tetrahydrofuran, pyridine, pyrazole, benzo[b]thiophene, and dithiole rings, suggesting the existence of oxygen-, nitrogen-, and sulfur-containing building blocks in ZSBC. According to analysis with ASAP/TOF-MS, a series of heavier arenecarboxylic acids were detected in the products from RICO of ZSBC and aromatic rings of the heavier arenepolycarboxylic acids include naphthalene, biphenyl, anthracene, phenylnaphthalene, and methyl(phenyl)tetrahydroanthracene, implying that ZSBC contains highly condensed aromatic rings. The existence of chlorine- and bromine-containing moieties was confirmed by the identification of chlorine- and bromine-containing species produced from RICO of ZSBC.

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Tetrahydrofuran – Wikipedia,
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Synthesis and Applications of Hajos-Parrish Ketone Isomers

Numerous natural products possess ring systems and functionality for which Hajos-Parrish ketone isomers with a transposed methyl group (termed “iso-Hajos-Parrish ketones”) would be of value. However, such building blocks have not been exploited to the same degree as the more typical Hajos-Parrish hydrindane. An efficient three-step synthesis of such materials was fueled by a simple method for the rapid preparation of highly functionalized cyclopentenones, several of which are new chemical entities that would be challenging to access through other approaches. Furthermore, one iso-Hajos-Parrish ketone was converted into two distinct natural product analogues and one natural product. As one indication of the value of these new building blocks, that latter target was obtained in 10 steps, having previously been accessed in 18 steps using the Hajos-Parrish ketone. Moving methyl groups: Hajos-Parrish ketone isomers with a transposed methyl group, termed “iso-Hajos-Parrish ketones”, are useful building blocks for diverse targets. A new synthetic method to cyclopentenones is used in a three-step approach to several of these compounds. Furthermore, a natural product that was previously accessed in 18 steps was now synthesized in 10 steps using an iso-Hajos-Parrish ketone.

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Ligands for the common allosteric site of acetylcholine M2-receptors: Development and application

Ligands for the allosteric site of acetylcholine M2 receptors are able to retard the dissociation of simultaneously bound ligands for the orthosteric site. This effect promotes receptor occupation by the orthosteric ligand. The allosteric effect opens various therapeutic perspectives, e.g., in organophosphorus poisoning. The aim of our studies was to optimize the affinity of the modulators for the common allosteric binding site of muscarinic M2 receptors, the orthosteric site of which was liganded with the N-methylscolopamine. The phthalimido substituted hexane-bisammonium compound W84 served as a starting point. Previous molecular modelling studies revealed two positive charges and two aromatic imides in a sandwich-like arrangement to be essential for a high allosteric potency. A three-dimensional quantitative structure activity relationship (3D QSAR) analysis predicted compounds with substituents of increasing size on the lateral imide moieties to enhance the affinity for the allosteric binding site. Thus, we synthesized and pharmacologically evaluated compounds bearing ‘saturated’ phthalimide moieties as well as phthalimidines with substituents of systematically increasing size in position 3 or on the aromatic ring at one or both ends of the molecule. Within each series, QSAR could be derived: 1. ‘Saturation’ of the aromatic ring of the phthalimide moiety results in less potent compounds. 2. Increasing the size of the substituents in position 3 of the phthalimide enhances the potency. 3. Putting substituents on the aromatic part of the phthalimide increases the potency more effectively: the introduction of a methyl group in position 5 gave a compound with a potency in the nanomolar concentration range which was subsequently developed as the first radioligand for the allosteric binding site. Copyright (C) 2000 Elsevier Science B.V.

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