41780-53-4

Usage

Uses

Used in Organic Synthesis:
N'-(4-tert-butylcyclohexylidene)-4-Methylbenzenesulfonohydrazide is used as a reagent in organic synthesis for its ability to participate in various chemical reactions, facilitating the formation of new compounds and structures.
Used in Pharmaceutical Research:
In pharmaceutical research, N'-(4-tert-butylcyclohexylidene)-4-Methylbenzenesulfonohydrazide is utilized as a reagent to explore its potential in drug development. Its unique chemical properties and reactivity make it a candidate for creating novel pharmaceutical agents.
Used in Material Development:
N'-(4-tert-butylcyclohexylidene)-4-Methylbenzenesulfonohydrazide is also used in the development of new materials, where its capacity to modify and functionalize other molecules can lead to the creation of advanced materials with specific properties for various applications.

Upstream product

• 85814-70-6 C₁₇H₂₅N₃O₄S 
• 98-53-3 4-tercbutyl-cyclohexanone 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 81842-54-8 4-t-Butyl-2-nitrocyclohexanone 

Downstream Products

• 63031-67-4 4-(1,1-dimethylethyl)cyclohexen-1-yltrimethylsilane 
• 49661-11-2 4-tert.-Butylcyclohexanon N,N-Ditosylhydrazon 
• 3178-22-1 tert-butylcyclohexane 
• 19422-34-5 1,1-difluoro-4-t-butylcyclohexane 
• 23525-05-5 1-bromo-4-(tert-butyl)cyclohex-1-ene 
• 76421-27-7 4-tert-butyl-6-n-butylcyclohexene-1-carboxaldehyde 
• 98-53-3 4-tercbutyl-cyclohexanone 
• 54923-65-8 (4-tert-Butylcyclohex-1-enyl)methanol 
• 319457-67-5 4-tert-Butyl-1-[(methoxymethoxy)methyl]cyclohex-1-ene 
• 287944-06-3 2-(4-(tert-butyl)cyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1379610-66-8 2-(4-(tert-butyl)cyclohexyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1379610-64-6 2-(4-(tert-butyl)cyclohexyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 83587-48-8 (2-(4-(tert-butyl)cyclohexylidene)ethyl)benzene 
• 175284-37-4 4-tert-butylcyclohexyl pivalate 

Relevant academic research and scientific papers

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.

Copper-catalyzed tri- or tetrafunctionalization of alkenylboronic acids to prepare tetrahydrocarbazol-1-ones and indolo[2,3-a]carbazoles

We describe a cascade strategy for tri- or tetrafunctionalization of alkenylboronic acids to prepare diverse tetrahydrocarbazol-1-ones and indolo[2,3-a]carbazoles in good yields withN-hydroxybenzotriazin-4-one (HOOBT) and arylhydrazines as oxygen and nitrogen sources, respectively. Mechanistic studies reveal that the domino reaction undergoes the copper-catalyzed Chan-Lam reaction, [2,3]-rearrangement, nucleophilic substitution, oxidation and sequential [3,3]-rearrangement over five steps in a one-pot reaction. The reaction shows a broad substrate scope and tolerates a wide range of functional groups. More importantly, the reaction is easily performed at gram scales and the product is purified by simple extraction, washing, and recrystallization without flash column chromatography. The present protocol features easily available starting materials, high site-marked functionalization, five-step cascade in one pot, multiple C-C/C-O/C-N bond formation, and diversity of indole motifs.

Catalyst-free synthesis of spiropyrazolines from chalcones and cyclic ketone N -tosylhydrazones

Treatment of cyclic ketone N-tosylhydrazones with chalcones in the presence of cesium carbonate at 110 °C affords spiropyrazolines with high selectivity and excellent yields. This protocol possesses many advantages such as readily available and stable sta

Unsymmetrical 1,1-diborated multisubstituted sp3-carbons formed via a metal-free concerted-asynchronous mechanism

We have experimentally proved the unsymmetrical 1,1-diboration of diazo compounds, formed in situ from aldehydes and cyclic and non-cyclic ketones, in the absence of any transition metal complex. The heterolytic cleavage of the mixed diboron reagent, Bpin-Bdan, and the formation of two geminal C-Bpin and C-Bdan bonds has been rationalised based on DFT calculations to occur via a concerted-asynchronous mechanism. Diastereoselection is attained on substituted cyclohexanones and DFT studies provide understanding on the origin of the selectivity. The alkoxide-assisted selective deborylation of Bpin from multisubstituted sp3-carbon and generation of a Bdan stabilized carbanion, easily conducts a selective protodeboronation sequence.

Formal carbon insertion of n-tosylhydrazone into B-B and B-Si bonds: Gem-diborylation and gem-silylborylation of sp3 carbon

A convenient method is developed to synthesize 1,1-diboronates from the corresponding N-tosylhydrazones. This method is also applicable to synthesize 1-silyl-1-boron compounds. Meanwhile, derivatization and consecutive Pd-catalyzed cross-coupling reaction

Copper-catalyzed direct ortho-alkylation of N-iminopyridinium ylides with N-tosylhydrazones

Copper-catalyzed cross-coupling of N-tosylhydrazones with N-iminopyridinium ylides leads to the direct C-H alkylation. This direct C-H bond alkylation transformation uses inexpensive CuI as the catalyst without any ligand. The reaction is operationally simple and conducted under mild conditions, giving the corresponding alkylated pyridines in moderate to good yields. DFT calculation provides insights into the reaction mechanism, suggesting that the reaction proceeds through the Cu carbene migratory insertion process.

Transition-metal-free synthesis of pinacol alkylboronates from tosylhydrazones

Highly efficient: Pinacol alkylboronates were synthesized by the reaction of tosylhydrazones with bis(pinacolato)diboron or pinacolborane under transition-metal-free conditions. This reaction represents an expeditious conversion of carbonyl functionality into a boronate group. Copyright

Catalytic enantioselective allyl- and crotylboration of aldehydes using chiral diol·SnCl4 complexes. Optimization, substrate scope and mechanistic investigations

We report a novel class of C2-symmetric chiral diols derived from the hydrobenzoin skeleton. The combination of these diols with SnCl 4 under Yamamoto's concept of Lewis acid assisted Bronsted acidity (LBA catalysis) leads to high levels of asymmetric induction in the allylboration of aldehydes by commercially available allylboronic acid pinacol ester 1a. The corresponding homoallylic alcohol products of synthetically useful aliphatic aldehydes are obtained in excellent yields with up to 98:2 er. This combined acid manifold is also efficient in catalyzing the diastereo- and enantioselective crotylboration of aldehydes, thus providing the propionate units in >95:5 dr and up to 98:2 er. The X-ray crystal structure of the optimal diol·SnCl4 complex, Vivol (4m)·SnCl 4, unambiguously shows the Bronsted acidic character of this LBA catalyst and its highly dissymmetrical environment. Further controls have ruled out a possible boron transesterification mechanism with the chiral diol and point to LBA catalyst-derived activation of the pinacol allylic boronates 1. Due to slow dissociation of the diol·SnCl4 complex, a small excess of diol is required in order to suppress a competing racemic cycle catalyzed by free SnCl4.

Convenient preparation of cycloalkenyl boronic acid pinacol esters

A practical method for the preparation of cycloalkenyl boronic acid pinacol esters is described. These important synthetic intermediates are typically made using more expensive methods like transition metal-catalyzed borylation of alkenyl halides or trifl

Elucidation of the catalytic mechanisms of the non-haem iron-dependent catechol dioxygenases: Synthesis of carba-analogues for hydroperoxide reaction intermediates

The catalytic mechanisms of the non-haem iron-dependent intradiol and extradiol catechol dioxygenases are thought to involve transient hydroperoxide reaction intermediates, formed by reaction of a catechol substrate with dioxygen. The synthesis of carba-analogues of these intermediates is described in which the hydroperoxide functional group (-OOH) is replaced by a hydroxymethyl group (-CH2OH), and the cyclohexadienone skeleton simplified to a cyclohexanone. Analogues of the "proximal" hydroperoxide in which the hydroxymethyl group was positioned axially with respect to the ring were found to act as reversible competitive inhibitors (Ki 0.7-7.6 mM) for the extradiol enzyme 2,3-dihydroxyphenylpropionate 1,2-dioxygenase (MhpB) from Escherichia coli, whereas analogues in which the hydroxymethyl group was positioned equatorially showed no inhibition. In contrast, assays versus the intradiol-cleaving protocatechuate 3,4-dioxygenase from Pseudomonas sp. showed inhibition only by an analogue containing an equatorial hydroxymethyl group (IC50 9.5 mM). These data support the existence of a proximal hydroperoxide intermediate in the extradiol catechol dioxygenase mechanism, and suggest that the conformation adopted by the hydroperoxide reaction intermediate may be an important determinant in the reaction specificity of the extradiol and intradiol dioxygenases. The Royal Society of Chemistry 2000.