52798-47-7

Upstream product

• 67-56-1 methanol 
• 3032-92-6 4-cyanophenylacetylene 

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• 1224699-70-0 (S)-methyl 2-(4-cyanophenyl)-2-hydroxy-4-oxopentanoate 

Relevant academic research and scientific papers

Preparation method of alpha-ketoester compound

The invention discloses a preparation method of an alpha-ketone ester compound. The method specifically comprises the following operation steps: adding raw materials alpha-diazo ester and an organic photocatalyst into a reaction flask, then adding an organic solvent, and reacting for 2-12 hours in air at room temperature under the irradiation of a visible light lamp; after the reaction is monitored by thin-layer chromatography (TLC), stopping the reaction, and extracting a reaction solution by using ethyl acetate; concentrating the extracting solution under reduced pressure to obtain a crude product, and performing column chromatography separation on the crude product to obtain the alpha-diazonium ester compound. According to the preparation method, clean visible light is used as reaction energy, cheap organic dye is used as a photocatalyst, air is used as a green oxidizing agent and an oxygen source, and the preparation method has the advantages of simplicity and convenience in operation, no metal residue and mild reaction conditions.

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.

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.

PHOTOINDUCED ALCOHOLYSIS OF alpha , alpha , alpha -TRIBROMACETOPHENONE TO BENZOYLFORMATE.

Irradiation of p-substituted alpha , alpha , alpha -tribromoacetophenones (1) in O//2-saturated alcohols (MeOH, prim. and sec. alcohols) afforded a new alcoholysis product, benzoylformate (2), in good yield (75-85%) along with benzoate and radical (reduction) products. Sensitization experiments showed that 2 was derived from the triplet excited 1. Formation of 2 as well as the decomposition rate of 1 were greatly accelerated by oxygen, presumably as a result of the involvement of the normally forbidden S//o yields T//1 transition of 1 due to the oxygen-1 charge transfer complex. Independent synthesis and reaction of possible intermediates in the photoalcoholysis of 1 leading to 2 suggested that 2 was formed from spontaneous (dark) reactions of initial photoalcoholysis product, alpha alpha -dibromo- alpha -alkoxyacetophenone.