7332-98-1

Upstream product

• 16537-09-0 t-butyl phenylacetate 
• 2902-69-4 2,2,2-trichloroacetophenone 
• 75-65-0 tert-butyl alcohol 
• 774-40-3 hydroxy-phenyl-acetic acid ethyl ester 
• 75-91-2 tert.-butylhydroperoxide 
• 102-13-6 2-methylpropyl phenylacetate 
• 556-91-2 aluminum tri-tert-butoxide 
• 72410-67-4 tert-butyl 2-diazo-2-phenylacetate 
• 75716-83-5 tert-butyl α-oxo-1H-imidazole-1-acetate 
• 100-58-3 phenylmagnesium bromide 
• 117356-18-0 β-hydroxy β-phenyl acetate de t-butyle 
• 108-86-1 bromobenzene 
• 691-64-5 di-tert-butyl oxalate 
• 1603-79-8 phenylglyoxylic acid ethyl ester 

Downstream Products

• 4768-43-8 (R)-α-hydroxyphenylacetic acid tert-butyl ester 
• 4768-43-8 tert-butyl (S)-2-hydroxy-2-phenylacetate 
• 100-52-7 benzaldehyde 
• 611-73-4 Benzoylformic acid 
• 107-46-0 Hexamethyldisiloxane 
• 122889-19-4 Phenyl-[(Z)-trimethylsilanyl-imino]-acetic acid tert-butyl ester 
• 4412-08-2 3-methyl-2-phenylbut-2-enoic acid 
• 33131-54-3 4-Bromo-3-bromomethyl-2-phenyl-but-2-enoic acid 
• 1070237-13-6 tert-butyl 2-hydroxy-3-nitro-2-phenylpropanoate 
• 117356-18-0 β-hydroxy β-phenyl acetate de t-butyle 
• 1224978-67-9 (R)-tert-butyl 2-cyano-2-phenyl-2-trimethylsiloxyacetate 
• 1310929-07-7 C₁₇H₂₃NO₄ 

Relevant academic research and scientific papers

Visible-Light-Enabled Paternò-Büchi Reaction via Triplet Energy Transfer for the Synthesis of Oxetanes

One of the most efficient ways to synthesize oxetanes is the light-enabled [2 + 2] cycloaddition reaction of carbonyls and alkenes, referred to as the Paternò-Büchi reaction. The reaction conditions for this transformation typically require the use of hig

Structure-Activity Relationship Studies of α-Ketoamides as Inhibitors of the Phospholipase A and Acyltransferase Enzyme Family

The phospholipase A and acyltransferase (PLAAT) family of cysteine hydrolases consists of five members, which are involved in the Ca2+-independent production of N-acylphosphatidylethanolamines (NAPEs). NAPEs are lipid precursors for bioactive N-acylethanolamines (NAEs) that are involved in various physiological processes such as food intake, pain, inflammation, stress, and anxiety. Recently, we identified α-ketoamides as the first pan-active PLAAT inhibitor scaffold that reduced arachidonic acid levels in PLAAT3-overexpressing U2OS cells and in HepG2 cells. Here, we report the structure-activity relationships of the α-ketoamide series using activity-based protein profiling. This led to the identification of LEI-301, a nanomolar potent inhibitor for the PLAAT family members. LEI-301 reduced the NAE levels, including anandamide, in cells overexpressing PLAAT2 or PLAAT5. Collectively, LEI-301 may help to dissect the physiological role of the PLAATs.

Iron-Catalyzed Cleavage Reaction of Keto Acids with Aliphatic Aldehydes for the Synthesis of Ketones and Ketone Esters

The radical–radical coupling reaction is an important synthetic strategy. In this study, the iron-catalyzed radical–radical cross-coupling reaction based on the decarboxylation of keto acids and decarbonylation of aliphatic aldehydes to obtain valuable aryl ketones is reported for the first time. Remarkably, when tertiary aldehydes were used as carbonyl sources, ketone esters were selectively obtained instead of ketones. The gram-scale preparation of aryl ketone through this strategy was easily achieved by using only 3 mol % of the iron catalyst. As a proof-of-concept, the bioactive molecule flurprimidol was synthesized in two steps by using this strategy.

Cobalt-Catalyzed Transfer Hydrogenation of α-Ketoesters and N-Cyclicsulfonylimides Using H2O as Hydrogen Source

A Co-catalyzed effective transfer hydrogenation of various α-ketoesters and N-cyclicsulfonylimides by safe and environmentally benign H2O as hydrogen source is described. The reaction used easily available and easy to handle zinc metal as a reductant. Interestingly, the catalytic system does not require ligand for reduction of N-cyclicsulfonylimides. (Figure presented.).

Pd(OAc)2-Catalyzed Asymmetric Hydrogenation of α-Iminoesters

An efficient Pd(OAc)2-catalyzed asymmetric hydrogenation of α-iminoesters was realized for the first time at 1 atm hydrogen pressure and room temperature. Pd(OAc)2, a less expensive Pd salt with low toxicity, was found to be the most suitable catalyst precursor rather than Pd(TFA)2 which is usually the catalyst of choice for homogeneous asymmetric hydrogenation. The chiral α-arylglycine fragments are widely found in many chiral products and bioactive molecules.

Organocatalytic Nitroaldol Reaction Associated with Deuterium-Labeling

A deuterium-labeling reaction of nitroalkanes in deuterium oxide and the subsequent nitroaldol reaction have been accomplished under basic and organocatalytic conditions to provide the deuterium-labeled β-nitroalcohols in high yields and high deuterium contents. β-Deuterated β-nitroalcohols could be smoothly obtained from the reaction of nitroalkanes and various electrophiles using the easily-removal basic resin WA30. Furthermore, the asymmetric nitroaldol reaction using nitromethane and α-keto esters as electrophiles in the presence of a quinine-derived organocatalyst in deuterium oxide could provide the desired β-deuterated nitroalcohol derivatives with high enantioselectivities. (Figure presented.).

Copper catalyzed photoredox synthesis of α-keto esters, quinoxaline, and naphthoquinone: Controlled oxidation of terminal alkynes to glyoxals

Herein, we report a facile visible light induced copper catalyzed controlled oxidation of terminal CC alkynes to α-keto esters and quinoxalines via formation of phenylglyoxals as stable intermediates, under mild conditions by using molecular O2 as a sustainable oxidant. The current copper catalysed photoredox method is simple, highly functional group compatible with a broad range of electron rich and electron poor aromatic alkynes as well as aliphatic alcohols (1°, 2° and 3° alcohols), providing an efficient route for the preparation of α-keto esters (43 examples), quinoxaline and naphthoquinone with higher yields than those in the literature reported thermal processes. Furthermore, the synthetic utility of the products has been demonstrated in the synthesis of two biologically active molecules, an E. coli DHPS inhibitor and CFTR activator, using the current photoredox process. In addition, we applied this methodology to the one-pot synthesis of a heterocyclic compound (quinoxaline, an FLT3 inhibitor) by trapping the intermediate phenylglyoxal with O-phenylenediamine. The intermediate phenylglyoxal can also be isolated and further reacted with an internal alkyne to form naphthoquinone. This process can be readily scaled up to the gram scale.

Novel Synthesis of α-Keto Esters and Amides by an sp3 C-H Oxidation of Nitromethyl Aryl Ketones Promoted by Ion-Supported (Diacetoxyiodo)benzene

A simple and efficient method is described for the preparation of α-keto esters or amides from nitromethyl aryl ketones. In the presence of nucleophiles (alcohols or amines), the ion-supported (di-acetoxyiodo)benzene-promoted sp3 C-H oxidation of nitromethyl aryl ketones proceeded efficiently under mild conditions to give the corresponding α-keto esters and amides in moderate to good yields. This is the first reported use of (diacetoxyiodo)benzene in the synthesis of α-keto esters and amides. The reaction is ecofriendly and has the -advantages of mild conditions, short reaction times, and a recyclable reagent.

2-Oxo-Driven Coupling Reactions of 2-Oxo Aldehydes/2-Oxo Iminium Ions and Hydroperoxides at Room Temperature

An efficient 2-oxo-group-promoted direct coupling reaction between 2-oxo aldehydes and hydroperoxides has been developed. The method has been used successfully for the generation of different 2-oxo esters and acids. This reaction harnesses the hydrogen-bonding-induced self-decomposition tendency of hydroperoxides; the intermediates produced by this process then attack the aldehyde or iminium ion to generate cross-coupled products either by direct coupling or by an amine-catalysed pathway. No external oxidants or metal catalysts are required for our method, and the reaction takes place at room temperature.