57186-75-1

Basic information

• Product Name: 1-[(4-methylphenyl)sulfonyl]-1,2,3,6-tetrahydropyridine
• Synonyms: 1-[(4-methylphenyl)sulfonyl]-1,2,3,6-tetrahydropyridine;1,2,3,6-Tetrahydro-1-[(4-methylphenyl)sulfonyl]pyridine;1-Tosyl-1,2,3,6-tetrahydropyridine;1-Tosyl-1,2,5,6-tetrahydropyridine
• CAS NO: 57186-75-1
• Molecular Formula: C₁₂H₁₅NO₂S
• Molecular Weight: 237.32
• Mol File: 57186-75-1.mol
• Article Data: 86

Chemical Properties

• Melting Point: 102-103.5 °C
• Boiling Point: 369.1±52.0 °C(Predicted)
• Appearance: /
• Density: 1 +-.0.06 g/cm3(Predicted)
• PKA: -6.28±0.20(Predicted)
• CAS DataBase Reference: 1-[(4-methylphenyl)sulfonyl]-1,2,3,6-tetrahydropyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[(4-methylphenyl)sulfonyl]-1,2,3,6-tetrahydropyridine(57186-75-1)
• EPA Substance Registry System: 1-[(4-methylphenyl)sulfonyl]-1,2,3,6-tetrahydropyridine(57186-75-1)

Safety Data

• Hazardous Substances Data: 57186-75-1(Hazardous Substances Data)

Upstream product

• 211814-64-1 5-[N-(4-methylphenylsulfonyl)amino]penta-1,2-diene 
• 627-32-7 1-iodopropan-3-ol 
• 347885-68-1 4-bromo-1-tosylpiperidine 
• 104144-06-1 N,N-di-3-butenyl-p-toluenesulfonamide 
• 289890-80-8 4-iodo-1-[(4-methylphenyl)sulfonyl]piperidine 
• 1274845-59-8 1-(1-p-toluenesulfonylpiperidin-4-yl)ethan-1-one 
• 54288-70-9 4-bromopiperidine hydrobromide 
• 606926-42-5 N-(4-methylphenylsulfonyl)-4-[(trifluoromethanesulfonyl)oxy]-1,2,3,6-tetrahydropyridine 
• 98-59-9 p-toluenesulfonyl chloride 
• 41979-39-9 4-piperidone hydrochloride 
• 80213-12-3 1-[(4-methylbenzene)-sulfonyl]-4-piperidinol 
• 557-21-1 zinc(II) cyanide 
• 920-39-8 isopropylmagnesium bromide 
• 1066-54-2 trimethylsilylacetylene 

Downstream Products

• 1251537-47-9 (1-tosylpiperidin-4-yl)boronic acid 
• 1624333-45-4 1-tosyl-4-((trifluoromethyl)thio)piperidine 

Relevant articles and documents

Palladium-catalyzed regio- and stereoselective synthesis of N-protected 2,4-dialkylated azacyclobutanes from amino allenes

Palladium-catalyzed reaction of N-arylsulfonyl-1-alkyl-3,4-dienylamines with an aryl iodide in the presence of potassium carbonate in DMF at around 70°C affords most predominantly the 2,4-cis-disubstituted azacyclobutanes bearing an aryl group on the doub

Regiocontrolled Reductive Vinylation of Aliphatic 1,3-Dienes with Vinyl Triflates by Nickel Catalysis

The regiocontrolled functionalization of 1,3-dienes has become a powerful tool for divergent synthesis, yet it remains a long-standing challenge for aliphatic substrates. Herein, we report a reductive approach for a branch-selective 1,2-hydrovinylation of aliphatic 1,3-dienes with R-X electrophiles, which represents a new selectivity pattern for diene functionalization. Simple butadiene, aromatic 1,3-dienes, and highly conjugated polyene were also tolerated. The combination of Ni(0) and the phosphine-nitrile ligand generally resulted in >20:1 regioselectivity with the retention of the geometry of the C3-C4 double bonds. This reaction proceeds with a broad substrate scope, and it allows for the conjugation of two biologically active units to form more complex polyene molecules, such as tetraene and pentaene as well as heptaene.

Activated Hoveyda-Grubbs Olefin Metathesis Catalysts Derived from a Large Scale Produced Pharmaceutical Intermediate – Sildenafil Aldehyde

Two EWG-activated Hoveyda-Grubbs-type ruthenium complexes (Sil-II and Sil-II’) were obtained, characterized, and screened in a set of olefin metathesis reactions. These catalysts were conveniently synthesized from a commercially available pharmaceutical building block – Sildenafil aldehyde – in two steps only. Stability and catalytic activity tests disclosed that the bulkier NHC-ligand bearing catalyst Sil-II’ is visibly more stable and productive than its smaller NHC-analogue Sil-II. Good application profile of catalyst Sil-II’ was confirmed in a set of diverse metathesis reactions including ring-closing metathesis (RCM) and cross-metathesis (CM) of complex polyfunctional substrates of medicinal chemistry interest, including a challenging macrocyclization of the Pacritinib precursor. Compatibility of the new catalyst with various green solvents was checked and metathesis of Sildenafil and Tadalafil-based substrates was successfully conducted in acetone. The mechanism of Sil-II’ initiation has been investigated through kinetic experiments unveiling that the decrease of the steric hindrance of the chelating alkoxy moiety (from iPrO to EtO) favors the interchange initiation pathway over the typical dissociation pathway for other popular 2nd generation Hoveyda-Grubbs catalysts. (Figure presented.).