75408-89-8

Usage

Uses

Used in Pharmaceutical Synthesis:
4-Acetylbiphenyl oxime is used as a synthetic intermediate for the production of bis-oximinoalkanoic acids, which are potent PPARα agonists. These agonists play a crucial role in the regulation of lipid metabolism and energy homeostasis, making them valuable in the development of treatments for metabolic disorders and related conditions.

Upstream product

• 92-91-1 biphenyl-4-acetaldehyde 
• 110-86-1 pyridine 
• 64-17-5 ethanol 

Downstream Products

• 92-91-1 biphenyl-4-acetaldehyde 
• 1195946-10-1 1-phenylaminocarbonyloxyimino-1-(4-biphenyl)ethane 
• 1195946-37-2 1-(1-naphthylaminocarbonyloxyimino)-1-(4-biphenyl)ethane 
• 86217-82-5 1-(biphenyl-4-yl)ethanamine 
• 1447004-20-7 1-[5-(1,1-biphenyl)-4-yl]-1H-pyrrol-2-yl-2,2,2-trifluoro-1-ethanone 
• 1447004-26-3 1-(5-[1,1-biphenyl]-4-yl-1H-pyrrol-2-yl)-2,2,2-trifluoro-1-ethanol 
• 1447031-59-5 2-[1,1-biphenyl]-4-yl-5-[2,2,2-trifluoro-1-(5-phenyl-1H-pyrrol-2-yl)-ethyl]-1H-pyrrole 
• 1447031-60-8 2-[1,1-biphenyl]-4-yl-5-{2,2,2-trifluoro-1-[5-(2-thienyl)-1H-pyrrol-2-yl]ethyl}-1H-pyrrole 
• 1447031-66-4 2-[1,1-biphenyl]-4-yl-5-{1-[5-(1,1-biphenyl)-4-yl-1H-pyrrol-2-yl]-2,2,2-trifluoroethyl}-1H-pyrrole 
• 1447031-71-1 4,4-difluoro-3-[(1,1-biphenyl)-4-yl]-5-phenyl-8-trifluoromethyl-4-bora-3a,4a-diaza-s-indacene 
• 1447031-72-2 4,4-difluoro-3-[(1,1-biphenyl)-4-yl]-5-(2-thienyl)-8-trifluoromethyl-4-bora-3a,4a-diaza-s-indacene 
• 1447031-78-8 4,4-difluoro-3,5-bis[(1,1-biphenyl)-4-yl]-8-trifluoromethyl-4-bora-3a,4a-diaza-s-indacene 
• 129993-18-6 1-vinyl-2-(1,1-biphenyl-4-yl)pyrrole 
• 24864-19-5 4-([1,1'-biphenyl]-4-yl)-2-methylthiazole 

Relevant academic research and scientific papers

Identification of histone deacetylase inhibitors with (arylidene)aminoxy scaffold active in uveal melanoma cell lines

Uveal melanoma (UM) represents an aggressive type of cancer and currently, there is no effective treatment for this metastatic disease. In the last years, histone deacetylase inhibitors (HDACIs) have been studied as a possible therapeutic treatment for UM, alone or in association with other chemotherapeutic agents. Here we synthesised a series of new HDACIs based on the SAHA scaffold bearing an (arylidene)aminoxy moiety. Their HDAC inhibitory activity was evaluated on isolated human HDAC1, 3, 6, and 8 by fluorometric assay and their binding mode in the catalytic site of HDACs was studied by molecular docking. The most promising hit was the quinoline derivative VS13, a nanomolar inhibitor of HDAC6, which exhibited a good antiproliferative effect on UM cell lines at micromolar concentration and a capability to modify the mRNA levels of HDAC target genes similar to that of SAHA.

Dehydrative Beckmann rearrangement and the following cascade reactions

The Beckmann rearrangement has been predominantly studied for the synthesis of amide and lactam. By strategically using the in situ generated Appel's salt or Mitsunobu's zwitterionic adduct as the dehydrating agent, a series of Beckmann rearrangement and following cascade reactions have been developed herein. The protocol allows the conversion of various ketoximes into amide, thioamide, tetrazole and imide products in modular procedures. The generality and tolerance of functionalities of this method have been demonstrated.

C3-Arylation of indoles with aryl ketonesviaC-C/C-H activations

C3-Arylation of indoles with aryl ketones is accomplishedviapalladium-catalyzed ligand-promoted Ar-C(O) cleavage and subsequent C-H arylation of indole. Various (hetero)aryl ketones are compatible in this reaction, affording the corresponding 3-arylindoles in moderate to good yields. Further introduction of an indole moiety into the natural products desoxyestrone and evodiamine demonstrate the synthetic utility of this protocol.

Rhodium(III)-Catalyzed Direct C-H Arylation of Various Acyclic Enamides with Arylsilanes

The stereoselective β-C(sp2)-H arylation of various acyclic enamides with arylsilanes via Rh(III)-catalyzed cross-coupling reaction was illustrated. The methodology was characterized by extraordinary efficacy and stereoselectivity, a wide scope of substrates, good functional group tolerance, and the adoption of environmentally friendly arylsilanes. The utility of this present method was evidenced by the gram-scale synthesis and further elaboration of the product. In addition, Rh(III)-catalyzed C-H activation is considered to be the critical step in the reaction mechanism.

Rhodium-Catalyzed C?H Activation/Annulation Cascade of Aryl Oximes and Propargyl Alcohols to Isoquinoline N-Oxides

A β-hydroxy elimination instead of common oxidization to carbonyl group in secondary propargyl alcohols was successfully developed to form 2-benzyl substituted isoquinoline N-oxides by a Rhodium-catalyzed C?H activation and annulation cascade, in which moderate to excellent yields (up to 92%) could be obtained under mild reaction conditions, along with good regioselectivity, broad generality and applicability. (Figure presented.).

Synthesis of 5-Vinyl-2-isoxazolines by Palladium-Catalyzed Intramolecular O-Allylation of Ketoximes

An efficient method for the synthesis of 5-vinyl-2-isoxazolines by Pd-catalyzed intramolecular O-allylation of ketoximes has been developed. The reaction involves Pd(0)-catalyzed π-allyl formation via leaving group ionization or Pd(II)-catalyzed allylic C-H activation followed by intramolecular nucleophilic oxime oxygen attack. This methodology has been elaborated to various value-added products by epoxidation, Wacker oxidation, cross-metathesis, hydroboration-oxidation, dihydroxylation, and catalytic hydrogenation.

Rhodium(iii)-catalyzed asymmetric [4+1] spiroannulations of: O -pivaloyl oximes with α-diazo compounds

Chiral RhIII catalysts can catalyze the asymmetric [4+1] spiroannulation of O-pivaloyl oximes with α-diazo homophthalimides under redox-neutral and acid/base-neutral conditions, leading to formation of chiral spirocyclic imines as a result of C-H activation and N-O cleavage. The reaction proceeded with high efficiency and features broad substrate scope, mild reaction conditions, and high to excellent enantioselectivities. This journal is

Access to pyrrolo[2,1-: A] isoindolediones from oxime acetates and ninhydrin via Cu(i)-mediated domino annulations

A copper-mediated domino condensation reaction of readily accessible oxime acetates with ninhydrin is reported to afford pyrrolo[2,1-a]isoindolediones via new C-C & C-N bond formations. A wide range of oxime acetates were shown to generally participate in the reaction to produce the condensed products in excellent yields. The necessary control experiments were performed and the mechanism is proposed to involve sequentially the formation of iminium radical via Cu-mediated N-O bond cleavage of oxime acetates, addition of the radical to ninhydrin and rearrangement via ring expansion.

Direct Enamido C(sp2)?H Diphosphorylation Enabled by a PCET-Triggered Double Radical Relay: Access to gem-Bisphosphonates

Herein we report a novel and straightforward protocol for the construction of valuable gem-BPs by means of proton-coupled electron-transfer (PCET)-triggered enamido C(sp2)?H diphosphorylation. This reaction represents a rare example of realizing the challenging double C?P bond formation at a single carbon atom, thus providing facile access to a broad variety of structurally diverse bisphosphonates from simple enamides under silver-mediated conditions. Initial mechanistic studies demonstrated that the diphosphorylation involves two rounds of PCET-initiated radical relay process.

Copper(0)/PPh3-Mediated Bisheteroannulations of o-Nitroalkynes with Methylketoximes Accessing Pyrazo-Fused Pseudoindoxyls

A copper(0)/PPh3-mediated cascade bisheteroannulation reaction of o-nitroalkynes with methylketoximes has been developed that provides viable access to a diverse range of pyrazo-fused pseudoindoxyl compounds. Synthetically useful functional groups including sensitive C-I bonds are compatible with this system. Mechanistic studies suggest a reaction cascade involving sequential PPh3-mediated deoxygenative cycloisomerization and copper-catalyzed [3 + 2] pyrazo-annulation.