56858-46-9

Upstream product

• 99-81-0 4-Nitrophenacyl bromide 
• 98-59-9 p-toluenesulfonyl chloride 
• 1586031-10-8 C₁₇H₁₇NO₄S 
• 106-45-6 para-thiocresol 
• 296788-00-6 1-(4-nitrophenyl)ethanone O-acetyl oxime 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 100-13-0 4-nitrostyrene 
• 100-19-6 (4-nitrophenyl)ethanone 
• 657-84-1 sodium tosylate 
• 536-57-2 p-toluene sulfinic acid 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 22391-01-1 1-(4-nitrophenyl)-1-(acetyloxy)ethylene 
• 7569-26-8 chloromethyl p-tolylsulfone 
• 555-16-8 4-nitrobenzaldehdye 

Downstream Products

• 61820-99-3 2-diazo-1-(4-nitrophenyl)-2-(toluene-4-sulfonyl)ethanone 
• 1104732-56-0 5-(4-nitrophenyl)-2,2-diphenyl-4-tosyl-2,3-dihydrofuran 
• 1108189-98-5 3-ethoxy-1-(4-nitrophenyl)-2-tosylprop-2-en-1-one 
• 62-23-7 4-nitro-benzoic acid 

Relevant academic research and scientific papers

Reactions of nitrosalicylic aldehydes with chloromethyl tolyl sulfone anion. Synthesis of 2-hydroxydihydrobenzofurans

Vicarious nucleophilic substitution of hydrogen (VNS) with chloromethyl tolyl sulfone carbanion does not occur in 3-, 4- and 5-nitrosalicylaldehydes. Instead, nucleophilic addition to the carbonyl group takes place leading to 2-hydroxydihydrobenzofurans.

Copper-catalyzed aerobic oxidative cross-coupling reactions of vinylarenes with sulfinate salts: A direct approach to β-ketosulfones

A copper-catalyzed aerobic oxidative cross-coupling reactions for the synthesis of β-ketosulfones via formation of a C[sbnd]S bond has been demonstrated. Promoted by the crucial copper catalyst, perfect selectivity and good to excellent yields could be achieved. This method, including inexpensive copper catalyst, wide functional group tolerance, and open air conditions, make it very attractive and practical. More importantly, it also provides a versatile tool for the construction of β-ketosulfones from basic starting materials under mild conditions.

Method for synthesizing beta-ketosulfone derivative under mild condition and obtained beta-ketosulfone derivative

The invention discloses a method for synthesizing a beta-ketosulfone derivative under a mild condition, which comprises the following steps: dissolving aryl olefin and sodium sulfinate in a solvent in a reaction container, adding an acidic additive, sealing the reaction container under the conditions that air exists in the reaction container and no transition metal exists, and purifying after reaction to obtain the beta-ketosulfone derivative. The free radical addition oxidation reaction of olefin and sulfinic acid can be realized under the mild condition without transition metal, the reaction raw materials are cheap and easy to obtain, no organic metal reagent or transition metal is needed, air is used as an oxidizing agent, no dangerous peroxide or persulfide is needed, and the method is compatible with air. The method has the advantages of simple operation and the like, and overcomes the defects of transition metal participation, large catalyst consumption, expensive reagents, high method cost, more reaction steps, more by-products and the like in the prior art.

Dioxygen-Triggered Oxosulfonylation/Sulfonylation of Terminal Olefins toward β-Keto Sulfones/Sulfones

A dioxygen-triggered oxosulfonylation/sulfonylation of unactivated olefins to achieve β-keto sulfones/sulfones has been developed. Interestingly, pluralistic mechanisms were found when different types of compounds were applied as substrates, and different products were achieved. The reaction is carried out with a high atomic efficiency in the absence of a metal and a catalyst at room temperature under an air atmosphere. Importantly, as a proof-of-concept, a bioactive molecule was synthesized on a gram-scale level using this method.

Photosensitizer-free synthesis of β-keto sulfones: Via visible-light-induced oxysulfonylation of alkenes with sulfonic acids

A practical and environment-friendly methodology for the construction of β-keto sulfones through visible-light induced direct oxysulfonylation of alkenes with sulfonic acids at ambient temperature under open-air conditions was developed. Most importantly, the reaction proceeded smoothly without the addition of any photocatalyst or strong oxidant, ultimately minimizing the production of chemical waste.

Facile One-Pot Access to α-Diazo-β-ketosulfones from Sulfonyl Chlorides and α-Haloketones

A convenient one-pot approach to the preparation of α-diazo-β-ketosulfones from sulfonyl chlorides is described. It involves the conversion of the sulfonyl chloride to sodium sulfinate, alkylation of the latter with α-haloketones followed by diazo transfer using the 'sulfonyl-azide-free' ('SAFE') protocol in aqueous medium. The simple and expedient method relies on readily available starting materials and provides facile access to a wide variety of valuable diazo reagents for organic synthesis.

Heterogeneous copper-catalyzed oxidative coupling of oxime acetates with sodium sulfinates: An efficient and practical synthesis of β-keto sulfones

An efficient and practical route to β-keto sulfones has been developed through heterogeneous oxidative coupling of oxime acetates with sodium sulfinates by using an MCM-41-supported Schiff base-pyridine bidentate copper (II) complex [MCM-41-Sb,Py-Cu (OAc)2] as the catalyst and oxime acetates as an internal oxidant, followed by hydrolysis. The reaction generates a variety of β-keto sulfones in good to excellent yields. This new heterogeneous copper (II) catalyst can be easily prepared via a simple procedure from readily available and inexpensive reagents and exhibits the same catalytic activity as Cu (OAc)2. MCM-41-Sb,Py-Cu (OAc)2 is also easy to recover and is recyclable up to eight times with almost consistent activity.

Method for synthesizing beta-carbonyl sulfone compound

The invention discloses a method for synthesizing a beta-carbonyl sulfone compound. The method comprises the steps that sulfinate and a carbonyl compound containing alpha-position active hydrogen areused as raw materials, in a solvent, under the oxidation of alkali, sodium iodide, nanomicelle and 1,2-dibromoethane, the reaction is carried out at 60-80 DEG C for 10-12 hours, separation and purification are performed, and the beta-carbonyl sulfone compound is obtained. The method is simple in synthesis process, convenient in operation, mild in reaction condition, low in cost and high in yield,does not use transition metal catalysis, and is green and safe.

Dual-tail arylsulfone-based benzenesulfonamides differently match the hydrophobic and hydrophilic halves of human carbonic anhydrases active sites: Selective inhibitors for the tumor-associated hCA IX isoform

The synthesis and characterization of two new sets of arylsulfonehydrazone benzenesulfonamides (4a-4i with phenyl tail and 4j-4q with tolyl tail) are reported. The compounds were designed according to a dual-tails approach to modulate the interactions of the ligands portions at the outer rim of both hydrophobic and hydrophilic active site halves of human isoforms of carbonic anhydrase (CA, EC 4.2.1.1). The synthesized sulfonamides were evaluated in vitro for their inhibitory activity against the following human (h) isoforms, hCA I, II, IV and IX. With the latter being a validated anticancer drug target and a marker of tumor hypoxia, attractive results arose from the Compounds’ inhibitory screening in terms of potency and selectivity. Indeed, whereas the first subset of compounds 4a-4i exhibited great efficacy in inhibiting both the ubiquitous, off-target hCA II (KIs 9.5–172.0 nM) and hCA IX (KIs 7.5–131.5 nM), the second subset of tolyl-bearing derivatives 4j-4q were shown to possess a selective hCA IX inhibitory action over isoforms I, II and IV. The most selective compounds 4l and 4n were further screened for their in vitro cytotoxic activity against MCF-7 and MDA-MB-231 cancer cell lines under hypoxic conditions. The selective IX/II inhibitory trend of 4j-4q compared to those of compounds 4a-4i was unveiled by docking studies. Further exploration of these molecules could be useful for the development of novel antitumor agents with a selective CA inhibitory mechanism.

Efficient sulfonylation of ketones with sodium sulfinates for the synthesis of β-keto sulfones

The oxidative sulfonylation of ketones with sodium sulfinates as the sulfone source and DMSO as the oxidant is reported. A series of β-keto sulfones were obtained in good to excellent yields. The advantages of this efficient protocol include the low cost of DMSO and HBr, and a broad scope.