Top Picks: new discover of C9H9BrO2

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Three-Component [1 + 1 + 1] Cyclopropanation with Ruthenium(II)

We report a one-step, Ru(II)-catalyzed cyclopropanation reaction that is conceptually different from the previously reported protocols that include Corey-Chaykovsky, Simmons-Smith, and metal-catalyzed carbene attack on olefins. Under the current protocol, various alcohols and esters are transformed into sulfone substituted cyclopropanes with excellent isolated yields and diastereoselectivities. This new reaction forms highly congested cyclopropane products with three new C-C bonds, three or two new chiral centers and one new quaternary carbon center. Twenty-two examples of isolated substrates are given. Previously reported synthetic routes for similar substrates are all multistep, linear routes that proceed with overall low yields and poor control of stereochemistry. Commercially available Ru(II) dehydrogenation catalysts, that were recently developed for the dehydrogenative synthesis of esters and amides from alcohol and amine substrates, were used in the reaction, with the best catalyst showing excellent activity at 0.2-1 mol % catalyst loading. Mechanistic investigation showed that in the case of alcohol substrates, the catalyst is only responsible for the first dehydrogenation step, and that the identity of the base and the countercation is crucial in achieving high yields. The catalyst is also required for the cyclopropanation of esters, although no dehydrogenation can proceed in this case, suggesting that substrates sensitive to H2 may be acylated prior to reaction.

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Reference£º
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

Discovery of C9H9BrO2

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Discovery, characterization and biological evaluation of a novel (R)-4,4-difluoropiperidine scaffold as dopamine receptor 4 (D4R) antagonists

Herein, we report the synthesis and structure?activity relationship of a novel series of (R)-4,4-difluoropiperidine core scaffold as dopamine receptor 4 (D4) antagonists. A series of compounds from this scaffold are highly potent against the D4receptor and selective against the other dopamine receptors. In addition, we were able to confirm the active isomer as the (R)-enantiomer via an X-ray crystal structure.

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Reference£º
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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The mechanism for the rhodium-catalyzed decarbonylation of aldehydes: A combined experimental and theoretical study

The mechanism for the rhodium-catalyzed decarbonylation of aldehydes was investigated by experimental techniques (Hammett studies and kinetic isotope effects) and extended by a computational study (DFT calculations). For both benzaldehyde and phenyl acetaldehyde derivatives, linear Hammett plots were obtained with positive slopes of +0.79 and +0.43, respectively, which indicate a buildup of negative charge in the selectivity-determining step. The kinetic isotope effects were similar for these substrates (1.73 and 1.77 for benzaldehyde and phenyl acetaldehyde, respectively), indicating that similar mechanisms are operating. A DFT (B3LYP) study of the catalytic cycle indicated a rapid oxidative addition into the C(O)-H bond followed by a rate-limiting extrusion of CO and reductive elimination. The theoretical kinetic isotope effects based on this mechanism were in excellent agreement with the experimental values for both substrates, but only when migratory extrusion of CO was selected as the rate-determining step.

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Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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alpha-Amino Diphenyl Phosphonates as Novel Inhibitors of Escherichia coli ClpP Protease

Increased Gram-negative bacteria resistance to antibiotics is becoming a global problem, and new classes of antibiotics with novel mechanisms of action are required. The caseinolytic protease subunit P (ClpP) is a serine protease conserved among bacteria that is considered as an interesting drug target. ClpP function is involved in protein turnover and homeostasis, stress response, and virulence among other processes. The focus of this study was to identify new inhibitors of Escherichia coli ClpP and to understand their mode of action. A focused library of serine protease inhibitors based on diaryl phosphonate warheads was tested for ClpP inhibition, and a chemical exploration around the hit compounds was conducted. Altogether, 14 new potent inhibitors of E. coli ClpP were identified. Compounds 85 and 92 emerged as most interesting compounds from this study due to their potency and, respectively, to its moderate but consistent antibacterial properties as well as the favorable cytotoxicity profile.

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Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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COMPOUNDS

The present invention relates to novel compounds that inhibit Lp-PLA2 activity, processes for their preparation, to compositions containing them and to their use in the treatment of diseases associated with the activity of Lp-PLA2, for example atherosclerosis, Alzheimer’s disease.

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Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

More research is needed about C9H9BrO2

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Biocatalytic Formal Anti-Markovnikov Hydroamination and Hydration of Aryl Alkenes

Biocatalytic anti-Markovnikov alkene hydroamination and hydration were achieved based on two concepts involving enzyme cascades: epoxidation-isomerization-amination for hydroamination and epoxidation-isomerization-reduction for hydration. An Escherichia coli strain coexpressing styrene monooxygenase (SMO), styrene oxide isomerase (SOI), omega-transaminase (CvTA), and alanine dehydrogenase (AlaDH) catalyzed the hydroamination of 12 aryl alkenes to give the corresponding valuable terminal amines in high conversion (many ?86%) and exclusive anti-Markovnikov selectivity (>99:1). Another E. coli strain coexpressing SMO, SOI, and phenylacetaldehyde reductase (PAR) catalyzed the hydration of 12 aryl alkenes to the corresponding useful terminal alcohols in high conversion (many ?80%) and very high anti-Markovnikov selectivity (>99:1). Importantly, SOI was discovered for stereoselective isomerization of a chiral epoxide to a chiral aldehyde, providing some insights on enzymatic epoxide rearrangement. Harnessing this stereoselective rearrangement, highly enantioselective anti-Markovnikov hydroamination and hydration were demonstrated to convert alpha-methylstyrene to the corresponding (S)-amine and (S)-alcohol in 84-81% conversion with 97-92% ee, respectively. The biocatalytic anti-Markovnikov hydroamination and hydration of alkenes, utilizing cheap and nontoxic chemicals (O2, NH3, and glucose) and cells, provide an environmentally friendly, highly selective, and high-yielding synthesis of terminal amines and alcohols.

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Reference£º
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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1-(Arylalkyl)quinolizidine Derivatives and Thio-Isosteric Analogues as Ligands for Sigma Receptors

A set of 1-(arylalkyl)quinolizidines, isosteric thioanalogues, and variously functionalized congeners were synthesized (see 1-25) and tested for affinity to sigma 1 and sigma 2 receptor subtypes, by displacing [ 3H]- (+)-pentazocine and [3H]DTG from guinea pig brain and rat brain preparations, respectively. All compounds exhibited a good affinity for the sigma1 subtype, with subnanomolar Ki values for the best of them, while only modest or poor affinity for the sigma2 subtype was observed (Tables 1 and 2). Some structure-activity relationships were put forward.

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Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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Related Products of 214894-89-0, In homogeneous catalysis, catalysts are in the same phase as the reactants. Enzymes are biological catalysts that produce large increases in reaction rates and tend to be specific for certain reactants and products. In a document type is Article, and a compound is mentioned, CAS :214894-89-0, Name is 5-(Bromomethyl)-2,3-dihydro-1,4-benzodioxine, introducing its new discovery.

Iron-Catalyzed Borrowing Hydrogen beta- C(sp3)-Methylation of Alcohols

Herein we report the iron-catalyzed beta-C(sp3)-methylation of primary alcohols using methanol as a C1 building block. This borrowing hydrogen approach employs a well-defined bench-stable (cyclopentadienone)iron(0) carbonyl complex as precatalyst (5 mol %) and enables a diverse selection of substituted 2-arylethanols to undergo beta-C(sp3)-methylation in good isolated yields (24 examples, 65% average yield).

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Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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Electric Literature of 214894-89-0, Chemistry can be defined as the study of matter and the changes it undergoes. You¡¯ll sometimes hear it called the central science because it is the connection between physics and all the other sciences, starting with biology. In a document type is Article, and a compound is mentioned, 214894-89-0, Name is 5-(Bromomethyl)-2,3-dihydro-1,4-benzodioxine, molecular weight is 229.0706, introducing its new discovery.

Catechol-based inhibitors of bacterial urease

Targeted covalent inhibitors of urease were developed on the basis of the catechol structure. Forty amide and ester derivatives of 3,4-dihydroxyphenylacetic acid, caffeic acid, ferulic acid and gallic acid were obtained and screened against Sporosarcinia pasteurii urease. The most active compound, namely propargyl ester of 3,4-dihydroxyphenylacetic acid exhibited IC50 = 518 nM andkinact/Ki = 1379 M?1 s?1. Inhibitory activity of this compound was better and toxicity lower than those obtained for the starting compound ? catechol. The molecular modelling studies revealed a mode of binding consistent with structure-activity relationships.

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Reference£º
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem

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Kinetics and Mechanism of the Arase-Hoshi R2BH-Catalyzed Alkyne Hydroboration: Alkenylboronate Generation via B-H/C-B Metathesis

The mechanism of R2BH-catalyzed hydroboration of alkynes by 1,3,2-dioxaborolanes has been investigated by in situ 19F NMR spectroscopy, kinetic simulation, isotope entrainment, single-turnover labeling (10B/2H), and density functional theory (DFT) calculations. For the Cy2BH-catalyzed hydroboration 4-fluorophenylacetylene by pinacolborane, the resting state is the anti-Markovnikov addition product ArCH = CHBCy2. Irreversible and turnover-rate limiting reaction with pinacolborane (k ? 7 ¡Á 10-3 M-1 s-1) regenerates Cy2BH and releases E-Ar-CH?CHBpin. Two irreversible events proceed in concert with turnover. The first is a Markovnikov hydroboration leading to regioisomeric Ar-C(Bpin)?CH2. This is unreactive to pinacolborane at ambient temperature, resulting in catalyst inhibition every ?102 turnovers. The second is hydroboration of the alkenylboronate to give ArCH2CH(BCy2)Bpin, again leading to catalyst inhibition. 9-BBN behaves analogously to Cy2BH, but with higher anti-Markovnikov selectivity, a lower barrier to secondary hydroboration, and overall lower efficiency. The key process for turnover is B-H/C-B metathesis, proceeding by stereospecific transfer of the E-alkenyl group within a transient, mu-B-H-B bridged, 2-electron-3-center bonded B-C-B intermediate.

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Reference£º
Benzodioxan,
1,4-Benzodioxane | C8H8O2 – PubChem