N-(p-Toluenesulfonyl)-3-pyrroline

Base Information

• Chemical Name: N-(p-Toluenesulfonyl)-3-pyrroline
• CAS No.: 16851-72-2
• Molecular Formula: C11H13NO2S
• Molecular Weight: 223.296
• Hs Code.: 2933990090
• European Community (EC) Number: 924-758-5,677-555-6
• DSSTox Substance ID: DTXSID00456644
• Nikkaji Number: J978.939A
• Wikidata: Q72509249
• Mol file: 16851-72-2.mol

Synonyms:16851-72-2;N-(p-Toluenesulfonyl)-3-pyrroline;1-Tosyl-2,5-dihydro-1H-pyrrole;1-(4-methylphenyl)sulfonyl-2,5-dihydropyrrole;N-Tosyl-3-pyrroline;1H-Pyrrole, 2,5-dihydro-1-[(4-methylphenyl)sulfonyl]-;1-(4-methylbenzenesulfonyl)-2,5-dihydro-1H-pyrrole;1-Tosyl-3-pyrroline;n-tosyl-2,5-dihydropyrrole;1-(toluene-4-sulfonyl)-2,5-dihydro-1H-pyrrole;SCHEMBL258778;AMY6802;DTXSID00456644;UNYMIBRUQCUASP-UHFFFAOYSA-N;MFCD01321189;AKOS015912387;AS-36577;CS-0052873;FT-0600684;T1665;2,5-Dihydro-1-(4-methyl-phenyl-sulphonyl)-pyrrole;J-010463

Chemical Property of N-(p-Toluenesulfonyl)-3-pyrroline

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 127 °C
• Refractive Index: 1.601
• Boiling Point: 354.167 °C at 760 mmHg
• PKA: -7.20±0.20(Predicted)
• Flash Point: 167.994 °C
• PSA: 45.76000
• Density: 1.264 g/cm³
• LogP: 2.57420
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 223.06669983
• Heavy Atom Count: 15
• Complexity: 326

Purity/Quality:

98%,99%, ^*data from raw suppliers

1-Tosyl-2,5-dihydro-1H-pyrrole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R36/37/38:
• Hazard Codes: R36/37/38:
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)S(=O)(=O)N2CC=CC2

Technology Process of N-(p-Toluenesulfonyl)-3-pyrroline

There total 56 articles about N-(p-Toluenesulfonyl)-3-pyrroline which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

N,N-Diallyltosylamide (50487-72-4) → ethene (74-85-1) + 1-[(4-methylphenyl)sulfonyl]-2,5-dihydro-1H-pyrrole (16851-72-2)

Guidance literature:

With Hoveyda-Grubbs catalyst second generation; In dichloromethane; at 40 ℃; for 1h; Concentration; Solvent; Temperature; Flow reactor;

DOI:10.1021/op500223e

Reference yield: 100.0%

N,N-Diallyltosylamide (50487-72-4) → 1-[(4-methylphenyl)sulfonyl]-2,5-dihydro-1H-pyrrole (16851-72-2)

Guidance literature:

With N,N-bis-(mesityl)imidazolium chloride; caesium carbonate; acetylene; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; In toluene; at 80 ℃; for 2.5h;

DOI:10.1002/1522-2675(20011114)84:11<3335::AID-HLCA3335>3.0.CO;2-4

Reference yield: 99.0%

N-allyl-N-(2-butenyl)-p-toluenesulfonamide → 1-[(4-methylphenyl)sulfonyl]-2,5-dihydro-1H-pyrrole (16851-72-2)

Guidance literature:

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In water; at 20 ℃; for 3h; Microwave irradiation;

DOI:10.1002/adsc.200800114

upstream raw materials:

Z-1,4-dichlorobutene

toluene-4-sulfonamide

N,N-Diallyltosylamide

formaldehyd

Downstream raw materials:

(+)-(R)-3-phenyl-N-(p-toluenesulfonyl)pyrrolidine

Refernces

• 1、 Hacon, Jonathon,Morris, Amanda,Johnston, Michael J.,Shanahan, Stephen E.,Barker, Mike D.,Inglis, Graham G. A.,Macdonald, Simon J. F.. "Carbon-carbon bond forming reactions with substrates absorbed non-covalently on a cellulose chromatography paper support". . p. 625 - 627. Retrieved 2007.
• 2、 Fuerstner,Ackermann,Beck,Hori,Koch,Langemann,Liebl,Six,Leitner. "Olefin metathesis in supercritical carbon dioxide". . p. 9000 - 9006. Retrieved 2001.
• 3、 Mwangi, Martin T.,Runge, M. Brett,Bowden, Ned B.. "Occlusion of Grubbs' catalysts in active membranes of polydimethylsiloxane: Catalysis in water and new functional group selectivities". . p. 14434 - 14435. Retrieved 2006.
• 4、 Brendgen, Thomas,Fahlbusch, Tilmann,Frank, Markus,Schuehle, Daniel T.,Sessler, Miriam,Schatz, Juergen. "Metathesis in pure water mediated by supramolecular additives". . p. 303 - 307. Retrieved 2009.
• 5、 Songis, Olivier,Slawin, Alexandra M. Z.,Cazin, Catherine S. J.. "An unusual cationic Ru(ii) indenylidene complex and its Ru(iii) derivative - Efficient catalysts for high temperature olefin metathesis reactions". . p. 1266 - 1268. Retrieved 2012.
• 6、 Ahn,Yang,Georg. "A convenient method for the efficient removal of ruthenium byproducts generated during olefin metathesis reactions.". . p. 1411 - 1413. Retrieved 2001.
• 7、 Thiel, Vasco,Wannowius, Klaus-Juergen,Wolff, Christiane,Thiele, Christina M.,Plenio, Herbert. "Ring-closing metathesis reactions: Interpretation of conversion-time data". . p. 16403 - 16414. Retrieved 2013.
• 8、 Lee, Sang Ick,Sim, So Hee,Kim, Soo Min,Kim, Kwang,Chung, Young Keun. "GaCl3-catalyzed allenyne cycloisomerizations to allenenes". . p. 7120 - 7123. Retrieved 2006.
• 9、 Mennecke, Klaas,Grela, Karol,Kunz, Ulrich,Kirschning, Andreas. "Immobilisation of the Grubbs III olefin metathesis catalyst with polyvinyl pyridine (PVP)". . p. 2948 - 2952. Retrieved 2005.
• 10、 Sashuk, Volodymyr,Danylyuk, Oksana. "A Thermo- and Photo-Switchable Ruthenium Initiator for Olefin Metathesis". . p. 6528 - 6531. Retrieved 2016.