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Merck

683973

Sigma-Aldrich

(5aR,10bS)-5a,10b-Dihydro-2-(2,4,6-trimethylphenyl)-4H,6H-indeno[2,1-b]-1,2,4-triazolo[4,3-d]-1,4-Oxaziniumchlorid Monohydrat

93%

Synonym(e):

Bode Katalysator 2

Anmeldenzur Ansicht organisationsspezifischer und vertraglich vereinbarter Preise


About This Item

Empirische Formel (Hill-System):
C21H22ClN3O · H2O
CAS-Nummer:
Molekulargewicht:
385.89
UNSPSC-Code:
12352005
PubChem Substanz-ID:
NACRES:
NA.22

Qualitätsniveau

Assay

93%

Form

solid

Optische Aktivität

[α]20/D +158°, c = 1 in chloroform

mp (Schmelzpunkt)

226-230 °C

Funktionelle Gruppe

ether

SMILES String

[Cl-].Cc1cc(C)c(c(C)c1)-[n+]2c[n@@H]3[C@@H]4[C@@H](Cc5ccccc45)OCc3n2

InChI

1S/C21H22N3O.ClH/c1-13-8-14(2)20(15(3)9-13)24-12-23-19(22-24)11-25-18-10-16-6-4-5-7-17(16)21(18)23;/h4-9,12,18,21H,10-11H2,1-3H3;1H/q+1;/p-1/t18-,21+;/m1./s1

InChIKey

GUECWMLEUCWYOS-WKOQGQMTSA-M

Allgemeine Beschreibung

It is an N-mesityl-substituted chiral triazolium N-heterocyclic carbene (NHC) compound. It was developed as an organocatalyst by the Bode group, for the catalytic generation of reactive species including activated carboxylates, homoenolates, and enolates.

Anwendung

(5aR,10bS)-5a,10b-Dihydro-2-(2,4,6-trimethylphenyl)-4H,6H-indeno[2,1-b]-1,2,4-triazolo[4,3-d]-1,4-oxazinium chloride monohydrate can be used as a catalyst:
  • In the preparation of dihydropyridinones by reacting enals or α′-hydroxyenones with vinylogous amides via aza-Claisen annulations.
  • In the oxidative coupling reactions of di(hetero)arylmethanes with enals to yield benzimidazole fused lactams.
  • In the synthesis of organosilanes by reacting enals with β-silyl enones.

Rechtliche Hinweise

Sold in collaboration with BioBlocks, Inc.

Piktogramme

Exclamation mark

Signalwort

Warning

Gefahreneinstufungen

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Zielorgane

Respiratory system

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

dust mask type N95 (US), Eyeshields, Gloves


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In der Dokumentenbibliothek finden Sie die Dokumentation zu den Produkten, die Sie kürzlich erworben haben.

Die Dokumentenbibliothek aufrufen

Synthesis of a N-Mesityl Substituted Aminoindanol-Derived Triazolium Salt.
Struble JR and Bode JW.
Organic Syntheses, 362-376 (2010)
Access to Enantioenriched Organosilanes from Enals and β-Silyl Enones: Carbene Organocatalysis
Zhang Y, et al.
Angewandte Chemie (International Edition in English), 130(17), 4684-4688 (2018)
Enantioselective synthesis of dihydropyridinones via NHC-catalyzed aza-Claisen reaction
Wanner B, et al.
Organic Letters, 13(19), 5378-5381 (2011)
N-Heterocyclic Carbene (NHC) Compounds
Aldrich Chemfiles, 7(9), 21-21 (2007)

Artikel

Rovis has demonstrated that triazolium salt in the presence of a base can act as an N-heterocyclic carbene organocatalyst1 in highly enantioselective intramolecular Stetter reactions.

Verwandter Inhalt

The Bode Group aims to develop new reactions and reagents for the synthesis of complex molecules. The Bode Group has developed N-mesityl-substituted NHCs as organocatalysts for the catalytic generation of reactive species including activated carboxylates, homoenolates, and enolates. These novel catalysts and reactions have made possible a new generation of highly enantioselective annulations from simple starting materials under mild reaction conditions, usually at room temperature and without added reagents. Furthering the goal of designing new reagents to enable the assembly of complex molecules, the Bode group has developed SnAP reagents for the facile, one-pot conversion of aldehydes into N-unprotected, saturated N-heterocycles, including bicyclic and spirocyclic structures. These easy to handle reagents provide a simple and robust alternative to the challenging and restrictive cross-coupling methods for the functionalization of saturated N-heterocycles.

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