16851-72-2

Basic information

• Product Name: N-(P-TOLUENESULFONYL)-3-PYRROLINE
• Synonyms: N-(P-TOLUENESULFONYL)-3-PYRROLINE;N-TOSYL-3-PYRROLINE;1-tosyl-2,5-dihydro-1H-pyrrole;1-(4-Methylphenylsulfonyl)-2,5-dihydropyrrole;1-(p-Tolylsulfonyl)-3-pyrroline;1-(Toluene-4-sulfonyl)-2,5-dihydro-1H-pyrrole;2,5-Dihydro-1-[(4-methylphenyl)sulfonyl]-1H-pyrrole;1-(4-methylbenzenesulfonyl)-2,5-dihydro-1H-pyrrole
• CAS NO: 16851-72-2
• Molecular Formula: C₁₁H₁₃NO₂S
• Molecular Weight: 223.29
• Mol File: 16851-72-2.mol
• Article Data: 160

Chemical Properties

• Melting Point: 127°C
• Boiling Point: 354℃
• Flash Point: 168℃
• Appearance: /
• Density: 1.264
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.601
• PKA: -7.20±0.20(Predicted)
• CAS DataBase Reference: N-(P-TOLUENESULFONYL)-3-PYRROLINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(P-TOLUENESULFONYL)-3-PYRROLINE(16851-72-2)
• EPA Substance Registry System: N-(P-TOLUENESULFONYL)-3-PYRROLINE(16851-72-2)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 16851-72-2(Hazardous Substances Data)

Usage

General Description

N-(p-toluenesulfonyl)-3-pyrroline is a chemical compound that belongs to the class of tosyl compounds, which are often used as protecting groups in organic synthesis. It is a derivative of 3-pyrroline, a heterocyclic compound containing a five-membered ring with an unsaturated nitrogen atom. The tosyl group, consisting of a toluene ring linked to a sulfonyl group, is often used to protect amine and alcohol functional groups in organic synthesis reactions, and it can be easily removed under mild conditions to reveal the original functional group. N-(p-toluenesulfonyl)-3-pyrroline may be used in various organic reactions and as a building block in the synthesis of pharmaceuticals and other organic compounds. Additionally, it may have applications in materials science and chemical research.

InChI:InChI=1/C11H13NO2S/c1-10-4-6-11(7-5-10)15(13,14)12-8-2-3-9-12/h2-7H,8-9H2,1H3

Upstream product

• 50487-72-4 N,N-Diallyltosylamide 
• 109-96-6 3-Pyrroline 
• 98-59-9 p-toluenesulfonyl chloride 
• 135979-17-8 N-allyl-4-methyl-N-(3-methylbut-2-en-1-yl)benzenesulfonamide 
• 918871-59-7 C₁₄H₁₈O₂S 
• 17639-64-4 N-p-toluenesulfonylpyrrole 
• 1440956-52-4 1-tosylpyrrolidin-3-ylboronic acid 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 1440956-22-8 C₁₇H₂₆BNO₄S 
• 25630-24-4 N,N-diallylbenzenesulfonamide 
• 67-56-1 methanol 
• 50-00-0 formaldehyd 
• 55022-46-3 4-methyl-N-prop-2-ynylbenzenesulfonamide 
• 101-83-7 N-cyclohexyl-cyclohexanamine 

Downstream Products

• 16851-78-8 3,4-dibromo-1-[(4-methylphenyl)sulfonyl]pyrrolidine 
• 170456-84-5 4-bromo-1-(toluene-4-sulfonyl)pyrrolidin-3-ol 
• 1004764-08-2 2-[4-(3-chloropropoxy)phenyl]-5-[(4-methylphenyl)sulfonyl]-4,5,6,6a-tetrahydro-3aH-pyrrolo[3,4-d][1,3]thiazol-3a-ol 
• 1004764-09-3 2-[4-(3-chloropropoxy)phenyl]-5-[(4-methylphenyl)sulfonyl]-5,6-dihydro-4H-pyrrolo[3,4-d][1,3]thiazole 
• 17639-64-4 N-p-toluenesulfonylpyrrole 
• 165883-19-2 (+)-(R)-3-phenyl-N-(p-toluenesulfonyl)pyrrolidine 
• 1018476-72-6 ((CH₃)4C₅H)Co(NO)2C₄H₆NSO₂C₆H₄CH₃ 

Relevant articles and documents

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The reaction of electron-rich carbene-precursor olefins containing two imidazolinylidene moieties [(2,4,6- Me3C6H2CH2)NCH2 CH2N(R)C=]2 (2a: R = CH2CH2OMe, 2

Organic-inorganic hybrid silica material derived from a monosilylated Grubbs-Hoveyda ruthenium carbene as a recyclable metathesis catalyst

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Immobilization of grubbs catalyst as supported ionic liquid catalyst (Ru-SILC)

Grubbs olefin metathesis catalyst was immobilized as a ruthenium-supported ionic liquid catalyst (Ru-SILC) in pores of amorphous alumina with the aid of ionic liquid [hmim]PF6. This Ru-SILC was effective for various olefin metathesis reactions

Olefin metathesis catalyst bearing a chelating phosphine ligand

An improved synthetic procedure for the complex (SPY-5-34)-dichloro- (κ2(C,P)-diphenyl-(2-benzylidene)-phosphine)-(1,3-bis(2,4, 6-trimethylphenyl)-4,5-dihydro-imidazol-2-ylidene)-ruthenium (2) was elaborated and the title compound was tested as

Mixed N-heterocyclic carbene/phosphite ruthenium complexes: Towards a new generation of olefin metathesis catalysts

The synthesis, characterisation and catalytic behaviour of ruthenium indenylidene complexes bearing an N-heterocyclic carbene and triisopropylphosphite are described.

Ruthenium-catalyzed olefin metathesis in ionic liquids

Figure presented Ionic liquid 1-butyl-3-methylimidazoliumhexafluorophosphate ([bmim]PF6) is described as an effective medium for ring-closing metathesis (RCM) using Grubbs catalysts. When [bmim]PF6 was used as solvent, the RCM showed

Allenyl esters as quenching agents for ruthenium olefin metathesis catalysts

In the attempt to synthesize substituted allenyl esters through a metathesis coupling of unsubstituted allenyl esters and alkenes using a variety of ruthenium catalysts, it was discovered that allenyl esters themselves cleanly arrested the activity of the catalysts. Further studies suggests possible utility of allene esters as general quenching agents for metathesis reactions. To explore this idea, several representative olefin metathesis reactions, including ring closing, were successfully terminated by the addition of simple allenyl esters for more convenient purification.

Ruthenium catalysts bearing chelating carboxylate ligands: application to metathesis reactions in water

The novel catalytic system, composed of a ruthenium alkylidene containing a surfactant fragment in the catalysts molecule, is reported. Ring closing metathesis and cross metathesis reactions proceed efficiently in neat water at room temperature, in air, without need of adding an external surfactant.

Non covalent immobilization of pyrene-tagged ruthenium complexes onto graphene surfaces for recycling in olefin metathesis reactions

Synthesis of Hoveyda-type ruthenium complexes, modified by pyrene tags on the NHC ligand and/or the benzylidene moiety, is described. Thanks to non-covalent π-π interactions these new complexes were immobilized on carbon supports [reduced graphene oxide (rGO) or graphene] and their activity and recoverability for metatheses reactions have been studied. A SIPr-based complex possessing the pyrene function on the benzylidene ligand (C2) delivered the best results for the ring closing metathesis of diethyldiallyl malonate as benchmark reaction. The presence of additional pyrene-functionalized styrenyl-ether as ligand to the rGO-supported catalyst (C2/L@rGO) noticeably improved the recycling procedure allowing supplementary efficient catalytic runs. This may be due either to a facilitated boomerang effect or to a gradual release of the active species in solution. Finally, catalyst C2/L@rGO was proven to be successfully used to promote metathesis reactions in a multisubstrate procedure, the same supported-catalyst batch being successively engaged to transform three different substrates, in diene and ene-yne RCM reactions.

A dormant ruthenium catalyst bearing a chelating carboxylate ligand: In situ activation and application in metathesis reactions

(Chemical Equation Presented) Sleeping beauty: A dormant catalyst, 1, can be activated in situ by various acids (HA) to form complexes 2 of high activity in olefin metathesis. After the reaction and when subjected to silica gel chromatography, these catalysts are readily transformed back into 1. This system shows a high degree of tunability and excellent applicability in model metathesis reactions.

Nucleophile dependent formation of 6- and 7-membered: N -heterocycles by platinum-catalysed cyclisation of 1,5-bisallenes

An unprecedented Pt-catalysed cyclisation of N-tethered 1,5-bisallenes in the presence of oxygen nucleophiles is reported, where formation of 6- or 7-membered rings is driven by the choice of nucleophile and the mechanism dictated by the nucleophile and the electronic properties of the bisallene. The reaction in the presence of alcohols gives preferentially vinyltetrahydropyridines with an extra alkoxy group and Pt-H as the active species in the catalytic cycle, while formation of di- and tetrahydroazepines with an extra hydroxyl group is favoured when water is used as nucleophile, via nucleophilic attack/carbocyclization as the favoured pathway. The products obtained are frequently found in the core of natural products with important biological activities, so understanding this complex mechanistic behaviour and exploiting this new methodology will have a big impact in organic synthesis and organometallic chemistry.

Fluorous phase-transfer activation of catalysts: Application of a new rate-enhancement strategy to alkene metathesis

Reactions of the bis(pyridine) complex (H2IMes)(Py) 2(Cl)2Ru(=CHPh) and fluorous phosphines P(CH 2CH2Rfn)3 (n = a, 6; b, 8; c, 10; Rfn = (CF2)n-1

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A novel photochemical approach to the kainoid ring system is presented alongside model studies to demonstrate its feasibility.

Ring-Closing Olefin Metathesis Catalyzed by Well-Defined Vanadium Alkylidene Complexes

Vanadium-based catalysts have shown activity and selectivity in ring-opening metathesis polymerization of strained cyclic olefins comparable to those of Ru, Mo, and W catalysts. However, the application of V alkylidenes in routine organic synthesis is limited. Here, we present the first example of ring-closing olefin metathesis catalyzed by well-defined V chloride alkylidene phosphine complexes. The developed catalysts exhibit tolerance to various functional groups, such as an ether, an ester, a tertiary amide, a tertiary amine, and a sulfonamide. The size and electron-donating properties of the imido group and the phosphine play a crucial role in the stability of active intermediates. Reactions with ethylene and olefins suggest that both β-hydride elimination of the metallacyclobutene and bimolecular decomposition are responsible for catalyst degradation.

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.).

One-pot chemoenzymatic reactions in water enabled by micellar encapsulation

The use of micellar conditions to enable one-pot reactions involving both transition metal and enzymatic catalysts is reported. Representative enzymatic transformations under micellar conditions are unaffected by the presence of non-ionic surfactants, including designer surfactants such as TPGS-750-M. Furthermore, the presence of enzymes has a negligible effect on transition metal catalysis under micellar conditions in water. Finally, three one-pot chemoenzymatic reactions in water are reported in which the micelle-forming surfactant TPGS-750-M is a crucial factor for reaction efficiency.