Brief introduction of 1,5-Diphenylpenta-1,4-dien-3-one

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A novel synthesis of thienopyridine, pyrroloquinolinothiophene, pyrazolopyridin-3-yl-phenylthiourea and thiazolylpyrazolopyridine derivatives

Dibenzalacetones 1a-c reacted with cyanothioacetamide (2) to give the new styrylpyridinethione derivatives 3a-c which were used as the starting materials for the synthesis of other several heterocyclic compounds. Reactions with chloroacetone (4), N-arylmaleimides 7a,b, and ethyl iodide gave 2-S-acetonyl pyridines 5a-c, pyrrolo[3,4-f]quinolines 9a-f, and 2-S-ethylpyridines 11a-c, respectively. Several cycloaddition reactions were carried out on 3a-c, 5a-c, and 6a-c with dienophiles 7a,b, to afford the corresponding cycloadducts 9a-f, 10a-f, and 8a-f, respectively. Structures were established based on elemental analyses and spectral data. The antimicrobial activity of the newly synthesized compounds was tested.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

Extracurricular laboratory:new discovery of (S)-Butane-1,3-diol

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Cloning and expression in Escherichia coli of a gene coding for a secondary alcohol dehydrogenase from Candida parapsilosis

A gene encoding a stereo-specific secondary alcohol dehydrogenase (CpSADH) that catalyzed the oxidation of (S)-1,3-BDO to 4-hydroxy-2-butanone was cloned from Candida parapsilosis. This CpSADH-gene consisted of 1,009 nucleotides coding for a protein with M, 35,964. A recombinant Escherichia coli JM109 strain harboring the expression plasmid, pKK-CPA1, produced (R)-1,3-BDO (93.5% ee, 94.7% yield) from the racemate without any additive to regenerate NAD+ from NADH.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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Microwave-assisted stereoselective 1,3-dipolar cycloaddition of C,N-diarylnitrone (i.e., N-(arylmethylidene)benzenamine N-oxide) and bis(arylmethylidene)acetone (=1,5-diarylpenta-1,4-dien-3-one): NMR and crystal analysis of diastereoisomeric bis(isoxazolidines)

Microwave-assisted stereoselective 1,3-dipolar cycloaddition of C,N-diarylnitrones (i.e., N-(arylmethylidene)benzenamine N-oxides) 2 to substituted bis(arylmethylidene)acetones (=1,5-diarylpenta-1,4-dien-3-ones) 1 leading to diastereoisomer pairs of bis-isoxazolidines 3 and 4 in good to excellent yield is described (Scheme2 and Table2). The configuration outcome of the reaction is discussed based on the NMR and X-ray data of the products. Copyright

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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Synthesis and absolute configuration of two defensive alkaloids from the Mexican bean beetle, Epilachna varivestis

Syntheses of (2S,12’R)-2-(12′-aminotridecyl)-pyrrolidine (1) and (28,12’R)-1-(2′-hydroxyethyl)-2-(12′-aminotridecyl)-pyrrolidine (2), two defensive alkaloids recently isolated from the Mexican bean beetle, Epilachna varivestis, are described. By a comparison of 1H NMR data of MTPA derivatives of natural alkaloid 2 with those of the synthetic standard, we confirm the (2S,12’R) configuration previously suggested for this alkaloid. Further support of these assignments was provided by the synthesis and 1H NMR investigation of(2S,12’S)-1, (2S,12’S)-2, and their MTPA derivatives.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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The dibenzylideneacetone adducts of uranyl bis(beta-diketonates). The low temperature NMR behaviour and molecular structure of [UO2(TTA)2·DBA]

Uranyl complexes of the type [UO2(OO)2·DBA] (OO = TTA, DBM and BA) have been prepared and characterized by 1H, 19F and 13C{1H} NMR, IR spectroscopic techniques and elemental analyses. The low temperature behaviour of the complex [UO2 (TTA)2·DBA] was studied by the 19F NMR technique and its structure solved by single-crystal X-ray diffraction. The structure determination shows that the uranium atom has pentagonal-bipyramidal geometry with the four oxygen atoms of TTA and one oxygen atom of DBA lying on the basal plane and two uranyl oxygen atoms occupy the apices.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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PYRANDERIVATE DURCH <4+2>-CYCLOADDITION ZWISCHEN alpha,beta-UNGESAETTIGTEN CARBONYLVERBINDUNGEN UND PHOSPHACUMULENYLIDEN

alpha,beta-Unsaturated carbonyl compounds 1 and phosphacumulene ylides 2 undergo a <4+2>-cycloaddition with formation of pyran-substituted phosphoranes 3.Benzoic acid catalyzed Hofmann degradation of 3 yields the deeply coloured pyran derivatives 5.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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Synthesis of monodisperse oligo(1,4-phenyleneethynylene-alt-1,4- triptycyleneethynylene)s

(Chemical Equation Presented) The synthesis of monodisperse oligo(p-phenyleneethynylene)s 8an with alternating 2,5-dihexyl-1,4-phenylene and 6,14-di-tert-butyl-1,4-triptycylene units and orthogonally protected alkyne end groups is reported. Starting from 6,14-di-tert-butyl-1-(2-triisopropylsilylethynyl)-4-(2-trimethylsilylethynyl) -triptycene (5a), 1,4-dihexyl-2,5-diiodobenzene (10), and 1,4-dihexyl-2-iodo-5- (3-hydroxyprop-1-ynyl)-benzene (9), oligomers with up to four repeating units, i.e., eight phenyleneethynylene units, were prepared through a partially divergent-convergent route with the alkynyl-aryl (Sonogashira-Hagihara) coupling as the key reaction. The starting compound 5a was prepared from triptycenequinone through a sequence of addition of 2- trialkylsilylethynyllithium, reduction and concomitant elimination of water, conversion of the phenol into a triflate, and finally Pd/Cu-catalyzed coupling with trialkylsilylethyne. A similar access to the key compound for a stringent divergent-convergent route, 6,14-di-tert-butyl-1-(3-hydroxybut-1-ynyl)-4-(2- triisopropylsilylethynyl)triptycene (6), is reported. The optical properties of the oligomers 8an and the corresponding oligo(2,5-dihexyl-1,4- phenyleneethynylene) s in dilute solution are almost identical, whereas they differ significantly for the solid, undiluted compounds.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

Extracurricular laboratory:new discovery of (S)-Propane-1,2-diol

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Preparation and Chiroptical Properties of Optically Active Vinyl Ether-Iron and Olefin-Iron Complexes. A CD Quadrant Rule Correlating Absolute Configurations.

Exchange etherification of dicarbonylcyclopentadienyl(eta2-ethyl vinyl ether)iron tetrafluoroborate (4) with optically active primary and secondary alcohols yields a mixture of diastereomeric cations.These isomers are in rapid equilibrium at room temperature.The most favorable equilibrium ratio of such diastereomers (4:1) is achieved with (+)- or (-)-menthol, and the absolute configuration of the predominant diastereomer, formed with (-)-menthol, has been determined.Optically active dicarbonylcyclopentadienyl (eta2-olefin)iron tetrafluoroborate may also be prepared from optically active epoxides.A study of the circular dichroism of these optically active complexes, together with those prepared earlier from the dioxene-iron complex (1), has been carried out and a mechanism by which asymmetry is induced at the achiral metal center is proposed.These observations provide the basis for a quadrant rule relating the sign of the Cotton effect near 450 nm and the absolute configuration of the olefin-iron complex.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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1,4-THIAZINE DIOXIDE AND 1,2,4-THIADIAZINE DIOXIDE DERIVATIVES AS BETA-SECRETASE INHIBITORS AND METHODS OF USE

The present disclosure provides a class of compounds useful for the modulation of beta-secretase enzyme (BACE) activity. The compounds have a general Formula I: wherein variables A, X, R2, R2′, R3, R4, R5, R6, and R7 of Formula I are defined herein. This disclosure also provides pharmaceutical compositions comprising the compounds, and uses of the compounds and compositions for treatment of disorders and/or conditions related to Abeta plaque formation and deposition, resulting from the biological activity of BACE. Such BACE mediated disorders include, for example, Alzheimer’s Disease, cognitive deficits, cognitive impairments, and other central nervous system conditions.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate

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Stereo- and regioselective photocycloaddition of extended alkenes using gamma-cyclodextrin

Photoexcitation of dibenzalacetones (1a-d) in homogeneous media and solid state yields a mixture of products with poor conversions. Irradiation of the reactants complexed to gamma-cyclodextrin predominantly affords a single dimer (syn adduct 6) despite the possibility for several monomeric and dimeric products. High selectivity in the cavitand-mediated reaction along with the structural characterization of the inclusion complex provides insight into the supramolecular interactions that drive the self-assembly of the host-guest system.

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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate