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Enzymatic Resolution of 3-oxodicyclopentadiene on a Decagram Scale

2018

The chiral building block 3-oxodicyclopentadiene (1) can be readily resolved on a decagram scale by a short sequence consisting of (1) reduction to the corresponding endo-alcohol, (2) enzymatic oxidative resolution with a ketoreductase enzyme to give (+)-1 and the (+)-form of the endo-alcohol, and (3) reoxidation of the (+)-endo-alcohol with another ketoreductase to give (–)-1. With a selectivity factor of 310, the enantiomeric ratios of the resolved (+)-endo-alcohol and (+)-ketone are both >99:1. Both enzymatic oxidations could be performed with a at least 300:1 substrate/catalyst ratio (w/w).

chemistry.chemical_classificationentsyymithapetustetrahydromethanoindenoneResolution (mass spectrometry)alkoholit (yhdisteet)ChemistryStereochemistryoxidationOrganic ChemistrySubstrate (chemistry)resolutionAlcoholCatalysisalcoholsgram-scale synthesischemistry.chemical_compoundEnzymeEnantiomerSelectivity
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Photocrosslinkable dextran hydrogel films as substrates for osteoblast and endothelial cell growth

2012

Functional hydrogel films on solid supports are versatile materials with large potential for cell growth and tissue engineering. Here, we report on a modular approach to generate functional hydrogel composite films for endothelial and osteoblast cell co-culture. The polymer network of the parent hydrogel was formed by a dextran derivative (BP-CMD), which contained carboxymethyl (CM) groups for further chemical functionalization and benzophenone (BP) moieties as a photocrosslinkable unit. BP-CMD could be synthesized by three different routes, first with the benzophenone unit attached via an amide bond, or second by an ether bond, or third as an ion pair between the benzophenone ammonium salt…

chemistry.chemical_classificationfood.ingredientMaterials scienceComposite numberGeneral ChemistryPolymerGelatinchemistry.chemical_compoundDextranfoodchemistryTissue engineeringCovalent bondPolymer chemistryMaterials ChemistryBenzophenoneSurface plasmon resonanceJournal of Materials Chemistry
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Studien zum Vorgang der Wasserstoffübertragung, 47.Elektroreduktion von 1,4-Benzoldicarbonitril, 1,4-Diacetylbenzol und Terephthalaldehyd

1978

Die Elektroreduktion von 1,4-Benzoldicarbonitril in Gegenwart von Essigsaure fuhrt bei einem Stromdurchgang von 4.5 Faraday-aquivalenten/mol in 80proz. Ausbeute zu 4-Amino-methylbenzonitril (1). Bei Anwendung von 6 Faraday-aquivalenten/mol konnen geringe Mengen an 4-Methylbenzonitril (2) nachgewiesen werden. Bei der praparativen Elektroreduktion von 1,4-Diacetylbenzol in Gegenwart unterschiedlicher Mengen an Essigsaure entstehen 4-(1-Hydroxyethyl)acetophenon (3), 1,1′-(1,4-Phenylen)diethanol (4) sowie polymere Pinakole 5 in den in Tabelle 1 angegebenen Mengen. Terephthalaldehyd wird in Gegenwart von Essigsaure zu 4-Hydroxymethylbenzaldehyd (6), Terephthalalkohol (7) und einem polymeren Pina…

chemistry.chemical_compoundAcetic acidPolarographychemistryPinacolOrganic ChemistryPolymer chemistryHydrogen transferPhysical and Theoretical ChemistryCyclic voltammetryHigh-performance liquid chromatographyAcetic acid concentrationAcetophenoneJustus Liebigs Annalen der Chemie
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Über die Synthese von o-Acylamino-ß-dimethylamino-propiophenonen 1. Mitt.: Verhalten von o-Nitro- und o-Carbäthoxyamino-acetophenon bei der Mannich-R…

1970

Das bei der Mannich-Reaktion von o-Carbathoxyamino-acetophenon mit Paraformaldehyd und Dimethylamin-hydrochlorid erhaltene Kondensationsprodukt wurde als ein Gemisch von o-Carbathoxyamino-β-dimethylamino-propiophenon und o-Carbathoxyamino-α-dimethylaminomethyl-acrylophenon identifiziert. Durch Variation der Versuchsbedingungen konnte das Acrylophenonderivat als Hauptprodukt erhalten werden. Es war durch Saurekatalyse in 1-N-Carbathoxy-3-dimethylaminomethyl-4-oxo-1,2,3,4-tetrahydrochinolin uberfuhrbar. Synthesis of o-Acylamino-β-dimethylamino-propiophenones The aminomethylation product of o-carbethoxyamino-acetophenone, paraformaldehyde and dimethylamine-hydrochloride was identified as a mix…

chemistry.chemical_compoundAcid catalysisAcrylophenonechemistryDrug DiscoveryPharmaceutical ScienceParaformaldehydeMedicinal chemistryArchiv der Pharmazie
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Proton Acid-induced Rearrangements of α-Alkynylestradiol Methyl Ethers

1993

When subjected to proton catalysis, the α-alkynylestradiol methyl ethers 1a and 1b furnish the Rupe or Meyer-Schuster rearrangement products 2, 4, and 5a. In the presence of sulfuric acid, α-ethynylestradiol 3-methyl ether (1a) is converted into the D-homosteroid 3a. The use of deuterated acids gives rise to the formation of the corresponding deuterated steroids 2b, 2c, 3b, and 5b. Some mechanistic implications of these results are also discussed.

chemistry.chemical_compoundAcid catalysisReaction mechanismchemistryProtonDeuteriumOrganic ChemistryOrganic chemistrySulfuric acidEtherPhysical and Theoretical ChemistryEnoneCatalysisLiebigs Annalen der Chemie
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Über die Synthese von o-Acylamino-β-dimethylamino-propiophenonen 2. Mitt.: Aminomethylierung von o-Carbäthoxyamino- und o-Nitro-acetophenon1)

1970

Die bei der Mannich-Reaktion mit o-Carbathoxyamino- und o-Nitro-acetophenon zu Acrylophenonderivaten fuhrende Sekundarreaktion zwischen den Aminomethylierungsprodukten und Formaldehyd konnte auf folgende Weise nahezu vollstandig vermieden werden: durch Verhindern des Zerfalls von intermediar entstehendem Dimethylaminomethylol in seine Komponenten wird die Bildung des Carbonium-Imonium-Kations derart beschleunigt, das fur die Nebenreaktion erforderlicher freier Formaldehyd rasch aus dem Reaktionsmedium verschwindet. — Die Synthese von o-Carbathoxyamino-, o-Nitro- und o-Amino-β-dimethylamino-propiophenon sowie seines Formyl- und Acetylderivates wird beschrieben. Synthesis of o-Acylamino-β-dim…

chemistry.chemical_compoundAcrylophenoneChemistryDrug DiscoveryFormaldehydePharmaceutical ScienceMedicinal chemistryArchiv der Pharmazie
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Cyclic esters of aliphatic diacids with pyrocatechol and hydroquinone

1985

Cyclic esters of adipic acid, suberic acid and sebacic acid were prepared by reaction of the acid dichlorides and pyrocatechol or hydroquinone in benzene under high dilution conditions. While only the cyclic dimers could be obtained from hydroquinone, pyrocatechol formed cyclic monomers as well as cyclic dimers (and also a cyclic dimer with succinic acid). The structure of all compounds was confirmed by1H-NMR- and mass spectra. The crystal structures of the pyrocatechol esters were determined by single crystal X-ray analysis.

chemistry.chemical_compoundAdipic acidMonomerchemistrySebacic acidHydroquinoneSuccinic acidDimerPolymer chemistryGeneral ChemistryBenzeneSuberic acidMonatshefte f�r Chemie Chemical Monthly
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Zearalenone presence in wheat field samples from Romania

2016

chemistry.chemical_compoundAgronomyField (physics)Chemistry010401 analytical chemistryGeneral Medicine010402 general chemistryToxicology01 natural sciencesZearalenone0104 chemical sciencesToxicology Letters
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Comparative cytotoxicity effect of zearalenone and its metabolites on the CHO-K1 cells

2009

chemistry.chemical_compoundBiochemistryChemistryGeneral MedicineToxicologyCytotoxicityZearalenoneToxicology Letters
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ChemInform Abstract: Light Induced C-C Coupling of 2-Chlorobenzazoles with Carbamates, Alcohols, and Ethers.

2016

A light induced, transition-metal-free C-C coupling reaction of 2-chlorobenzazoles with aliphatic carbamates, alcohols, and ethers is presented. Inexpensive reagents, namely sodium acetate, benzophenone, water, and acetonitrile, are employed in a simple reaction protocol using a cheap and widely available 25 W energy saving UV-A lamp at ambient temperature.

chemistry.chemical_compoundC c couplingchemistryReagentLight inducedBenzophenoneOrganic chemistryGeneral MedicineAcetonitrileSodium acetateCoupling reactionChemInform
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