17336-66-2

Usage

Uses

Used in Organic Synthesis:
1-Propiophenone tosylhydrazone 97 is used as a reagent for converting ketones into the corresponding hydrazones. This conversion is crucial in the synthesis of various organic compounds, facilitating the creation of new chemical entities with potential applications in pharmaceuticals, materials science, and other fields.
Used in Coordination Chemistry:
In the realm of coordination chemistry, 1-Propiophenone tosylhydrazone 97 serves as a chelating agent. Its ability to form stable complexes with metal ions is valuable for the development of new coordination compounds, which can be applied in areas such as catalysis, sensing, and medicinal chemistry.
Used as a Ligand in Coordination Compounds Synthesis:
Furthermore, 1-Propiophenone tosylhydrazone 97 is utilized as a ligand in the synthesis of coordination compounds. Its coordination properties allow it to bind to metal centers, contributing to the formation of complexes with unique structures and functionalities. These complexes can be explored for their potential applications in various chemical and technological processes.

Upstream product

• 93-55-0 1-phenyl-propan-1-one 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 

Downstream Products

• 52686-70-1 triethylamine-1-(2-naphthylethyl)borane 
• 59588-12-4 (1-methoxypropyl)benzene 
• 16282-16-9 1,2-diphenyl-butan-1-one 
• 38384-58-6 (E)-1-benzoyl-1-phenylprop-1-ene 
• 54444-14-3 (Z)-1,2-diphenylbut-2-en-1-one 
• 1237535-22-6 3-methyl-2-phenyl-1-tosyl-1H-indole 
• 36146-78-8 N-tert-butyl-2-phenylbutanamide 
• 1393683-53-8 C₁₇H₁₈ 
• 78943-81-4 (+/-)-1ξ,3-diphenyl-pent-1-ene 
• 109155-94-4 1,3-diphenyl-2-pentene 
• 1402934-36-4 1-phenylpropyl 3-phenoxybenzoate 
• 1402745-92-9 (E)-5-phenyl-5-hepten-2-one 
• 1402745-93-0 (E)-6-phenyloct-6-en-3-one 
• 21310-05-4 diphenyl-(1-phenyl-propyl)-phosphine oxide 

Relevant academic research and scientific papers

TRICYCLIC COMPOUNDS AS GLYCOGEN SYNTHASE KINASE 3 (GSK3) INHIBITORS AND USES THEREOF

The present disclosure provides compounds of Formula (I), and salts, solvates, hydrates, polymorphs, co-crystals, tautomers, stereoisomers, isotopically labeled derivatives, and prodrugs thereof. The provided compounds may be useful for inhibiting kinases

Umpolung Difunctionalization of Carbonyls via Visible-Light Photoredox Catalytic Radical-Carbanion Relay

The combination of photoredox catalysis with the Wolff-Kishner (WK) reaction allows the difunctionalization of carbonyl groups by a radical-carbanion relay sequence (photo-Wolff-Kishner reaction). Photoredox initiated radical addition to N-sulfonylhydrazones yields α-functionalized carbanions following the WK-type mechanism. With sulfur-centered radicals, the carbanions are further functionalized by reaction with electrophiles including CO2 and aldehydes, whereas CF3 radical addition furnishes a wide range of gem-difluoroalkenes through β-fluoride elimination of the generated α-CF3 carbanions. More than 80 substrate examples demonstrate the broad applicability of this reaction sequence. A series of investigations including radical inhibition, deuterium labeling, fluorescence quenching, cyclic voltammetry, and control experiments support the proposed radical-carbanion relay mechanism.

Pd-Catalyzed Alkenyl Thioether Synthesis from Thioesters and N-Tosylhydrazones

A Pd-catalyzed alkenyl thioether synthesis was achieved using thioesters and N-tosylhydrazones as starting materials. The thioester acted as an efficient "sulfur source" for catalytic C-S bond formation using N-tosylhydrazone. This method gave Z-alkenyl thioethers with high diastereoselectivity (up to 99:1 diastereomeric ratio). This transformation displayed a wide functional group tolerance and was successfully applied to the late-stage derivatization of a pharmaceutical molecule to the corresponding alkenyl thioether.

Asymmetric Copper-Catalyzed C(sp)-H Bond Insertion of Carbenoids Derived from N-Tosylhydrazones

A chiral copper(I)-phosphoramidite complex efficiently catalyzed the asymmetric insertion of the carbenoids derived from N-tosyl hydrazones into alkyne C-H bonds to give the corresponding chiral alkynylated products in up to 77% yield and with up to 74% e

Cooperative Iodide Pd(0)-Catalysed Coupling of Alkoxyallenes and N-Tosylhydrazones: A Selective Synthesis of Conjugated and Skipped Dienes

Palladium(0)-catalysed hydro-alkylation or -alkenylation of alkoxyallenes with N-tosylhydrazones gives direct access to conjugated and skipped 1-alkoxydienes with high efficiency and excellent functional-group compatibility. The reaction is proposed to in

N-Tosylhydrazone directed annulation via C-H/N-N bond activation in Ru(ii)/PEG-400 as homogeneous recyclable catalytic system: a green synthesis of isoquinolines

A green and sustainable methodology for the synthesis of isoquinolines using Ru(ii)/PEG-400 as a homogeneous recyclable catalytic system has been demonstrated. N-Tosylhydrazone, a rarely explored directing group, has been successfully employed for an annu

Rhodium-Catalyzed B-H Bond Insertion Reactions of Unstabilized Diazo Compounds Generated in Situ from Tosylhydrazones

Although transition-metal-catalyzed B-H bond insertion of carbenes into stable borane adducts has emerged as a promising method for organoborane synthesis, all the diazo compounds used to date as carbene precursors have had an electron-withdrawing group to stabilize them. Herein, we report a protocol for rhodium-catalyzed B-H bond insertion reactions of unstabilized diazo compounds generated in situ from tosylhydrazones. In addition, by using chiral dirhodium catalysts, we also achieved an asymmetric version of the reaction with good to excellent enantioselectivities (up to 98:2 e.r.). This is the first enantioselective heteroatom-hydrogen bond insertion reaction to use unstabilized diazo compounds as carbene precursors. The protocol exhibited good functional group tolerance and could be carried out on a gram scale. It also enabled one-pot transformation of a carbonyl group to a boryl group enantioselectively. The B-H bond insertion products could be easily transformed into chiral alcohols and other widely used organoboron reagents with enantiomeric fidelity.

Palladium-catalyzed heck-type cascade cyclization of (Z)-1-iodo-1,6-dienes with N-tosyl hydrazones

A palladium-catalyzed heck-type cascade cyclization of (Z)-1-iodo-1,6-dienes with N-tosyl hydrazones is reported. The alkylpalladium intermediate coupled with the diazo compound, generating the second alkylpalladium species bearing two β-H, which generate

Copper-Catalyzed Cyanation of N-Tosylhydrazones with Thiocyanate Salt as the "cN" Source

A novel protocol for the synthesis of α-aryl nitriles has been successfully achieved via a copper-catalyzed cyanation of N-tosylhydrazones employing thiocyanate as the source of cyanide. The features of this method include a convenient operation, readily available substrates, low-toxicity thiocyanate salts, and a broad substrate scope.

Directed C-C bond cleavage of a cyclopropane intermediate generated from: N -tosylhydrazones and stable enaminones: Expedient synthesis of functionalized 1,4-ketoaldehydes

An efficient method to construct functionalized 1,4-ketoaldehydes bearing all-carbon α-quaternary centers via regioselective C-C bond activation has been described. The cyclopropanation of bench-stable enaminones with in situ generated diazo reagents from