Awesome Chemistry Experiments For 5-(Bromomethyl)-2,3-dihydro-1,4-benzodioxine

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We report the synthesis and in vitro activity of a series of novel pyrrolidinyl pyridones and pyrazinones as potent inhibitors of prolyl oligopeptidase (POP). Within this series, compound 39 was co-crystallized within the catalytic site of a human chimeric POP protein which provided a more detailed understanding of how these inhibitors interacted with the key residues within the catalytic pocket.

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Reference:
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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A nickel-catalyzed cross coupling of aryl fluorides via C-F bond activation has been developed. The alkylation method allows selective replacement of aryl fluorides by alkyl groups and enables the synthesis of diverse and otherwise difficult to access scaffolds in good yields.

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Reference:
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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Copper complexes generated in situ from CuCl2, alkyl Grignard reagents, and 1,3-dienes play important roles as catalytic active species for the 1,2-hydroalkylation of 1,3-dienes by alkyl fluorides through C-F bond cleavage. The alkyl group is introduced to an internal carbon atom of the 1,3-diene regioselectively, thus giving rise to the branched terminal alkene product. Making the switch: A copper-hydride species, generated by the treatment of a copper salt with alkyl Grignard reagents, catalyzes the 1,2-hydroalkylation of 1,3-dienes by alkyl fluorides and Grignard reagents. The alkyl group of the alkyl fluoride is selectively introduced to an internal carbon atom of the 1,3-diene and the Grignard reagent acts as hydride source to give the branched terminal alkene, even in the presence of alkenes and alkynes.

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Reference:
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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Organic compounds showing the ability to inhibit effector toxin secretion or translocation mediated by bacterial type III secretion systems are disclosed. The disclosed type III secretion system inhibitor compounds are useful for combating infections by Gram-negative bacteria such as Salmonella spp., Shigella flexneri, Pseudomonas spp., Yersinia spp., enteropathogenic and enteroinvasive Escherichia coli, and Chlamydia spp. having such type III secretion systems

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Reference:
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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It was possible to functionalize the three fluorobenzyl alcohols and the three 2-(fluorophenyl)ethanols by metalation and subsequent carboxylation, the prototype electrophilic trapping reaction. Triisopropylsilyl (TIPS) outperformed methoxymethyl (MOM) as an O-protective group making seven new fluorobenzoic acids accessible in 63% average yield. Moreover, the TIPS group tolerates weakly basic and acidic media and, therefore, may facilitate further structural elaboration. The unprotected alcohols reacted more sluggishly and were unable to provide two of the targeted products (acids 1 and 2). The yield averaged only 46% in the five other cases (acids 3-7). The direct metalation of fluorinated benzyl and phenethyl alcohols remains nevertheless an attractive option because of its operational simplicity. All three (trifluoromethyl)benzyl alcohols and two of the three (trifluoromethyl)phenethyl alcohol isomers were successfully submitted to the metalation/functionalization sequence. These five starting materials gave rise to a total of nine new benzoic acids or lactones (compounds 8-14 and 17-18). Despite the poor yields (31% on average), the organometallic methods employed are, in general, extremely selective, economical and easy to perform. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

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Reference:
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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Due to their biological activity and structural analogy to corresponding alpha-amino acids, alpha-aminophosphonates and their fluorinated derivatives provide an important source for drug discovery. Therefore convenient access to this class of compounds is still desirable. Four series of novel phosphonate analogues of fluorinated phenylalanine containing variable number of fluorine atoms in different positions of the phenyl ring were synthesized and subjected to solid state characterization by single-crystal X-ray diffraction analysis, and to studies with the use of NMR, HRMS and DFT methods. Such an approach provided valuable information in regard to preferable conformation, hydrogen bonds and also weak intermolecular interactions present in the crystals investigated. As analogues of naturally occurring compounds, the obtained alpha-aminophosphonates have a big potential for biological activity. Formation of some indolinylphosphonates as minor products arisen from intramolecular SNAr reactions show that aminophosphonates exhibiting an electronically depleted aromatic group, and possessing a fluorine atom in ortho position of the phosphonoalkyl substituent may give an entrance to further derivatives that may exhibit entirely new properties.

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Reference:
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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Vibronically-resolved S1-S0 electronic spectra of 2-(p-fluorophenyl)ethanol have been studied by use of laser-induced fluorescence excitation and dispersed fluorescence spectroscopic methods in a supersonic free jet expansion. Two conformational isomers of the molecule are identified, and with the aid of the predictions of quantum chemistry calculations these are assigned to gauche and anti conformers. The assignments are corroborated by analyzing the vibronic features in the dispersed fluorescence spectra of the two conformers and their TDDFT predicted electronic transition energies. Energetic and spectral features of the conformers are compared with those of the parent molecule 2-phenylethanol.

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Reference:
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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A series of novel, highly potent, achiral factor Xa inhibitors based on a benzoic acid scaffold and containing a chlorophenethyl moiety directed towards the protease S1 pocket is described. A number of structural features, such as the requirements of the P1, P4 and ester-binding pocket ligands were explored with respect to inhibition of factor Xa. Compound 46 was found to be the most potent compound in a series of antithrombotic secondary assays.

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Reference:
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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A novel catalytic system formed from Fe(stearate)2/NH 2CH2CH2NH2 and polymethylhydrosiloxane was directly developed for the hydrosilylation of carboxylic acid esters to alcohols. The catalytic method exhibits broad substrate scope, including 20 aliphatic, aromatic, and heterocyclic esters. The corresponding alcohols are obtained in moderate to very good yields. The first iron-catalyzed hydrosilylation of carboxylic acid esters to alcohols is described. A catalytic system formed by Fe(stearate)2/NH 2CH2CH2NH2 and polymethylhydrosiloxane (PMHS) is used for this transformation, which has a broad substrate scope, including 20 aliphatic, aromatic, and heterocyclic esters. The corresponding alcohols are obtained in moderate to very good yields. Copyright

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Reference:
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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The selective addition of arylmethylmagnesium halides with formaldehyde giving arylethyl alcohols is extremely challenging. To circumvent the difficulties, in the current communication, we have reported on the nucleophilic addition of benzyl zinc reagents derived from inexpensive and abundant benzyl chlorides to paraformaldehyde. The reaction investigated herein is hitherto unknown and was found to be selective, operationally simple, atom- and step-economical and high yielding to deliver phenethyl alcohols utilized as key perfumery ingredients in 60?83% yields. After successful establishment of the reaction condition, the reaction was also scaled up successfully to deliver a large-scale preparation of the phenethyl alcohol.

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Reference:
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem