4345-46-4

Basic information

• Product Name: Isoxazole, 3,5-dimethyl-4-phenyl-
• CAS NO: 4345-46-4
• Molecular Formula: C11H11NO
• Molecular Weight: 173.214
• Mol File: 4345-46-4.mol

Chemical Properties

• CAS DataBase Reference: Isoxazole, 3,5-dimethyl-4-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Isoxazole, 3,5-dimethyl-4-phenyl-(4345-46-4)
• EPA Substance Registry System: Isoxazole, 3,5-dimethyl-4-phenyl-(4345-46-4)

Safety Data

• Hazardous Substances Data: 4345-46-4(Hazardous Substances Data)

Upstream product

• 79-24-3 Nitroethane 
• 100-51-6 benzyl alcohol 
• 1160169-35-6 1-(3-methyl-2-phenyl-2H-azirin-2-yl)ethanone 
• 10558-25-5 4-bromo-3,5-dimethyl-1,2-oxazole 
• 591-50-4 iodobenzene 
• 832114-00-8 3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoxazole 
• 17958-94-0 Perfluoroctansulfonsaeure-phenylester 
• 108-86-1 bromobenzene 
• 16114-47-9 3,5-dimethylisoxazole-4-boronic acid 
• 300-87-8 3,5-dimethyl-1,2-oxazole 
• 98-80-6 phenylboronic acid 
• 98-13-5 Phenyltrichlorosilane 
• 2633-57-0 triallyl(phenyl)silane 
• 100-52-7 benzaldehyde 

Relevant articles and documents

The direct C(sp2)-H functionalization and coupling of aromatic N-heterocycles with (hetero)aryl bromides by [PdX2(imidazolidin-2-ylidene)(Py)] catalysts

In this study, a series of air- and moisture-stable imidazolidin-2-ylidene-based new palladium complexes with the general formula [PdX2(NHC)(Py)] were synthesized (NHC = N-heterocyclic carbene, Py = pyridine, X = Cl or I). The structures of the

The direct C4-arylation of 3,5-dimethylisoxazole with aryl bromides catalyzed by imidazolidin-2-ylidene based palladium-PEPPSI complexes

In this study, the synthesis and characterization of four new imidazolinium salts as carbene precursors and their corresponding four new PEPPSI-type (PEPPSI = .Pyridine Enhanced Precatalyst Preparation Stabilization and Initiation) palladium complexes wer

A Monophosphine Ligand Derived from Anthracene Photodimer: Synthetic Applications for Palladium-Catalyzed Coupling Reactions

Herein, we present an air-stable dianthracenyl monophosphine ligand (diAnthPhos) which can be prepared in two steps from commercially available anthracene derivatives. The ligand exhibits excellent efficiency for palladium-catalyzed coupling reactions. In particular, Miyaura borylation of heterocycle-containing electrophiles can be facilitated employing the diAnthPhos ligand with a broad substrate scope and low catalyst loading. The valuable synthetic utility of the new ligand is further demonstrated by a one-pot Miyaura borylation/Suzuki coupling protocol for heteroaryl-containing substrates.

Ferrocenyl palladacycles derived from unsymmetrical pincer-type ligands: Evidence of Pd(0) nanoparticle generation during the Suzuki-Miyaura reaction and applications in the direct arylation of thiazoles and isoxazoles

A new family of ferrocenyl-palladacycle complexes Pd(L1)Cl (Pd1) and Pd(L2)Cl (Pd2) were synthesized and characterized by UV-visible, IR, ESI-MS, and NMR spectral studies. The molecular structures of Pd1 and Pd2 were determined by X-ray crystallographic studies. Palladacycle catalyzed Suzuki-Miyaura cross-coupling reactions were investigated utilizing the derivatives of phenylboronic acids and substituted chlorobenzenes. Mechanistic investigation authenticated the generation of Pd(0) nanoparticles during the catalytic cycle and the nanoparticles were characterized by XPS, SEM and TEM analysis. Direct C-H arylation of thiazole and isoxazole derivatives employing these ferrocenyl-palladacycle complexes was examined. The reaction model for the arylation reaction implicating the in situ generation of Pd(0) nanoparticles was proposed.

Ni: Vs. Pd in Suzuki-Miyaura sp2-sp2 cross-coupling: A head-to-head study in a comparable precatalyst/ligand system

The Suzuki-Miyaura reaction is a cornerstone method for sp2-sp2 cross-coupling in industry. There has been a concerted effort to enable the use of Ni catalysis as an alternative to Pd in order to mitigate cost and improve sustainability. Despite significant advances, ligand development for Ni-catalyzed Suzuki-Miyaura cross-coupling remains underdeveloped when compared to Pd and, as a consequence, ligands for Ni-catalyzed processes are typically taken from the Pd arena. In this study we evaluate the effect of using a similar Ni and Pd precatalyst based on a common bidentate ligand (dppf) in a head-to-head format for the most common type of biaryl couplings, establishing the practical implications of direct replacement of Pd with Ni, and identifying the potential origins of these observations in a mechanistic context.

Highly Site Selective Formal [5+2] and [4+2] Annulations of Isoxazoles with Heterosubstituted Alkynes by Platinum Catalysis: Rapid Access to Functionalized 1,3-Oxazepines and 2,5-Dihydropyridines

Platinum-catalyzed formal [5+2] and [4+2] annulations of isoxazoles with heterosubstituted alkynes enabled the atom-economical synthesis of valuable 1,3-oxazepines and 2,5-dihydropyridines, respectively. Importantly, this Pt catalysis not only led to unique reactivity dramatically divergent from that observed under Au catalysis, but also proceeded via unprecedented α-imino platinum carbene intermediates.

Atom-Economic Synthesis of Fully Substituted 2-Aminopyrroles via Gold-Catalyzed Formal [3+2] Cycloaddition between Ynamides and Isoxazoles

A concise and flexible synthesis of fully substituted 2-aminopyrroles via gold-catalyzed formal [3+2] cycloaddition between ynamides and isoxazoles has been developed. Under mild reaction conditions, various 2-aminopyrrole derivatives were obtained in good to excellent yields, thus providing an efficient and atom-economic way for the construction of fully substituted 2-aminopyrroles. It was all very formal: A novel gold-catalyzed formal [3+2] cycloaddition between ynamides and isoxazoles has been developed, allowing the concise and flexible synthesis of fully substituted 2-aminopyrroles. Importantly, this strategy provides new mechanistic insights and offers an atom-economic way for the construction of fully substituted 2-aminopyrroles.

INHIBITORS OF TRANSCRIPTION FACTORS AND USES THEREOF

The present invention provides novel compounds of any one of Formulae (I) to (IV), and pharmaceutically compositions thereof. Compounds of any one of Formulae (I) to (IV) are believed to be inhibitors of bromodomain-containing proteins (e.g., bromo and ex

Biased multicomponent reactions to develop novel bromodomain inhibitors

BET bromodomain inhibition has contributed new insights into gene regulation and emerged as a promising therapeutic strategy in cancer. Structural analogy of early methyl-triazolo BET inhibitors has prompted a need for structurally dissimilar ligands as probes of bromodomain function. Using fluorous-tagged multicomponent reactions, we developed a focused chemical library of bromodomain inhibitors around a 3,5-dimethylisoxazole biasing element with micromolar biochemical IC50. Iterative synthesis and biochemical assessment allowed optimization of novel BET bromodomain inhibitors based on an imidazo[1,2-a]pyrazine scaffold. Lead compound 32 (UMB-32) binds BRD4 with a Kd of 550 nM and 724 nM cellular potency in BRD4-dependent lines. Additionally, compound 32 shows potency against TAF1, a bromodomain-containing transcription factor previously unapproached by discovery chemistry. Compound 32 was cocrystallized with BRD4, yielding a 1.56 ? resolution crystal structure. This research showcases new applications of fluorous and multicomponent chemical synthesis for the development of novel epigenetic inhibitors.

One-pot synthesis of isoxazoles from enaminones: An application of Fe(II) as the catalyst for ring expansion of 2H-azirine intermediates

We report an application of FeCl2 as an inexpensive, nontoxic, and efficient catalyst in a clean ring expansion reaction of 2H-azirine derivatives, an intermediate formed through the PhI(OAc)2-mediated azirination of readily availabl