16738-11-7

Usage

Uses

Used in Pharmaceutical Industry:
[1,1'-Biphenyl]-4-acetic acid, α-oxo-, methyl ester is used as an intermediate for the synthesis of various pharmaceutical compounds. Its unique chemical structure allows it to be a versatile building block in the development of new drugs.
Used in Fragrance Industry:
In the fragrance industry, [1,1'-Biphenyl]-4-acetic acid, α-oxo-, methyl ester is used as a key ingredient in perfumes and cosmetics. Its aromatic nature and pleasant scent make it a valuable addition to a wide range of fragrance products.
Used in Cosmetics Industry:
[1,1'-Biphenyl]-4-acetic acid, a-oxo-, methyl ester is also used as a fragrance ingredient in the cosmetics industry, where its appealing scent and chemical properties contribute to the overall sensory experience of various cosmetic products.
Used as a Solvent:
[1,1'-Biphenyl]-4-acetic acid, α-oxo-, methyl ester is utilized as a solvent in various chemical processes due to its ability to dissolve a wide range of substances, making it a useful tool in organic synthesis.
Used in Organic Synthesis:
As an intermediate in organic synthesis, [1,1'-Biphenyl]-4-acetic acid, α-oxo-, methyl ester plays a crucial role in the production of various chemical compounds, further expanding its applications across different industries.

Upstream product

• 67-56-1 methanol 
• 6244-53-7 ethyl (4-phenylphenyl)glyoxylate 
• 13158-04-8 -methoxy-essigsaeure-methylester 
• 29079-00-3 4-ethynyl-1,1'-biphenyl 
• 4974-58-7 4-biphenylglyoxal 
• 5449-21-8 2-([1,1’-biphenyl]-4-yl)-2-oxoacetic acid 
• 74-88-4 methyl iodide 
• 92-91-1 biphenyl-4-acetaldehyde 
• 14002-51-8 4-biphenyl-carboxylic acid chloride 
• 18166-02-4 N-trimethylsilylmethylamine 
• 124-38-9 carbon dioxide 
• 648428-46-0 (1,1'-biphenyl)-4-yl(trimethylsilyl)methanone 

Downstream Products

• 1616777-66-2 methyl 2-([1,1'-biphenyl]-4-yl)-2-hydroxy-3-(2-phenyloxazol-5-yl)propanoate 
• 37974-77-9 1-[(1,1′-biphenyl)-4-yl]-3-phenylpropane-1,3-dione 

Relevant academic research and scientific papers

Tandem Photoredox-Chiral Phosphoric Acid Catalyzed Radical-Radical Cross-Coupling for Enantioselective Synthesis of 3-Hydroxyoxindoles

A photochemical protocol that couples diarylamines and α-ketoesters to afford the chiral 3-hydroxyoxindoles through tandem photoredox and chiral phosphoric acid catalysis is developed. The reaction involves an enantioselective photochemical radical-radical cross-coupling process. The chiral phosphoric acid is discovered to play crucial roles by decreasing the reductive potentials of α-ketoesters and stereocontrolling the downstream asymmetric radical-radical cross-coupling via the formation of pentacoordinate complex.

Visible-Light-Induced Catalyst-Free Carboxylation of Acylsilanes with Carbon Dioxide

Intermolecular carbon-carbon bond formation between acylsilanes and carbon dioxide (CO2) was achieved by photoirradiation under catalyst-free conditions. In this reaction, siloxycarbenes generated by photoisomerization of the acylsilanes added to the C═O bond of CO2 to give α-ketocarboxylates, which underwent hydrolysis to afford α-ketocarboxylic derivatives in good yields. Control experiments suggest that the generated siloxycarbene is likely to be from the singlet state (S1) of the acylsilane and the addition to CO2 is not in a concerted manner.

Preparation method for rapidly generating alpha-ketone ester through iodine-mediated alpha-diazonium ester oxidation

The invention relates to the field of research of ketone ester compounds, in particular to a preparation method for rapidly generating alpha-ketone ester through iodine-mediated alpha-diazo ester oxidation, the preparation method comprises the following steps: in an organic solvent, stirring alpha-diazo ester and iodine elementary substance as raw materials at room temperature for about half an hour to obtain the alpha-ketone ester compound. According to the method, transition metal does not need to be used as a catalyst, a strong oxidant does not need to be used, only under the room temperature condition, the low-toxicity and cheap iodine elementary substance is used as the oxidant, and the alpha-keto ester is generated through efficient oxidation of the alpha-diazonic acid ester. The method has the advantages that the reaction time is short (about 0.5 hour), the universality is high, the alpha-diazonic acid ester with electron donating groups or electron withdrawing groups can achieve medium to excellent yield (80%-99%), a greener alternative approach is represented, and a new general synthesis route is provided for efficient preparation of alpha-ketoester.

Anti-Selective Catalytic Asymmetric Nitroaldol Reaction of α-Keto Esters: Intriguing Solvent Effect, Flow Reaction, and Synthesis of Active Pharmaceutical Ingredients

A rare-earth metal/alkali metal bimetallic catalyst proved particularly effective for enantioselectively coupling nitroalkanes and α-keto esters in an anti-selective manner to afford synthetically versatile, densely functionalized, and optically active α-nitro tertiary alcohols. A chiral diamide ligand captured two distinct metal cations, giving rise to a catalytically competent solid-phase heterobimetallic catalyst by simple mixing via self-assembly. The advantage of the solid-phase asymmetric catalyst was realized by successful application to the enantio- and diastereoselective reaction in a continuous-flow platform. The use of closely related solvents in terms of structures and polarity parameters, THF and its methylated congener 2-Me-THF, had an unexpectedly large solvent effect both on the reaction rate and the stereoselectivity. The nitroaldol products share a privileged unit for active pharmaceutical ingredients, as demonstrated by the streamlined enantioselective synthesis of the marketed antifungal agents efinaconazole and albaconazole.

I 2 /TBHP-Promoted Approach to α-Keto Esters from Trifluoromethyl β-Diketones and Alcohols via C-C Bond Cleavage

A metal-free oxidative coupling reaction of trifluoromethyl β-diketones with alcohols for the synthesis of α-keto esters in good to excellent yields has been developed. Preliminary mechanistic studies suggest that an I 2 /TBHP promoted sequential iodination, C-C bond cleavage, C-O bond formation and oxidation pathway is involved in this reaction.

In Situ Generated AgII-Catalyzed Selective Oxo-Esterification of Alkyne with Alcohol to α-Ketoester: Photophysical Study

An expert and easy one-step catalytic method for the multi O-C coupling of alkyne is developed for the synthesis of valuable α-ketoesters and their chiral analogues, in contrast to the generation of esters by a noncatalytic method. The in situ generated powerful AgII catalyst from AgOTf is the workhorse in the oxidative grafting of alkyne with PhIO and alcohol. The radical mechanism is confirmed in our controlled experiments and UV-vis study.

Rh-catalyzed asymmetric hydrogenation of racemic aldimines via dynamic kinetic resolution

Catalyzed by a rhodium complex of P-stereogenic diphosphine ligand trichickenfootphos (TCFP), asymmetric hydrogenation of racemic aldimines via dynamic kinetic resolution has been realized for the preparation of chiral arylglycines with good yields and enantioselectivities.

Electrochemical synthesis of the aryl α-ketoesters from acetophenones mediated by Ki

Two C-O bonds formed in one step: The oxidative coupling reaction of acetophenones with alcohol was developed by a dioxygen activation to afford α-ketoesters under electrochemical conditions. This novel transformation not only provides a simple and efficient approach to synthetize α-ketoester derivatives, but also invents a new strategy to construct a C-O bond by virtue of an anode oxidation (see scheme). Copyright

Optically pure 4-aryl-2-hydroxytetronic acids

The present invention relates to a method for synthesis of optically pure stereogenically labile 4-aryl-2-hydroxytetronic acids from an optically pure aidehyde. The invention further relates to the use of such optically pure compounds as potent inhibitors of platelet aggregation by working at the level of cyclooxygenase, and additionally as inhibitors of cyclooxygenase and 5-lipoxygenase. The invention further relates to the pharmaceutical use of such.compounds in the treatment of coronary artery diseases, especially in the treatment and/or prevention of atherosclerosis, and in the treatment of various inflammatory pathologies, especially arthritis.

Synthesis of optically pure 4-aryl-2-hydroxytetronic acids

The present invention relates to a method for synthesis of optically pure stereogenically labile 4-aryl-2-hydroxytetronic acids from an optically pure aldehyde. The invention further relates to the use of such optically pure compounds as potent inhibitors of platelet aggregation by working at the level of cyclooxygenase. the invention further relates to the pharmaceutical use of such compounds in the treatment of coronary artery diseases, especially in the treatment and/or prevention of atherosclerosis.