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683973

Sigma-Aldrich

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

93%

Synonyme(s) :

Bode Catalyst 2

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About This Item

Formule empirique (notation de Hill):
C21H22ClN3O · H2O
Numéro CAS:
903571-02-8
Poids moléculaire :
385.89
Code UNSPSC :
12352005
ID de substance PubChem :
329760886
Nomenclature NACRES :
NA.22

Pureté

93%

Forme

solid

Activité optique

[α]20/D +158°, c = 1 in chloroform

Pf

226-230 °C

Groupe fonctionnel

ether

Chaîne SMILES 

[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

Clé InChI

GUECWMLEUCWYOS-WKOQGQMTSA-M

Description générale

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.

Application

(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.

Informations légales

Sold in collaboration with BioBlocks, Inc.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H315,H319,H335

Classification des risques

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

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Faites votre choix parmi les versions les plus récentes :

Certificats d'analyse (COA)

Lot/Batch Number
MKCR7041
MKCR3440
MKCQ7238
MKCQ3609
MKCL1724

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

Consulter la Bibliothèque de documents

N-Heterocyclic Carbene (NHC) Compounds
Aldrich Chemfiles, 7(9), 21-21 (2007)
Carbene-catalyzed enantioselective oxidative coupling of enals and di (hetero) arylmethanes
Chen Q, et al.
Chemical Science, 9(46), 8711-8715 (2018)
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)
Synthesis of a N-Mesityl Substituted Aminoindanol-Derived Triazolium Salt.
Struble JR and Bode JW.
Organic Syntheses, 362-376 (2010)

Articles

N-Heterocyclic Carbene (NHC) Compounds

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.

Contenu apparenté

Bode Group – Professor Product Portal

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.

Bode Group – Professor Product Portal

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.

Bode Group – Professor Product Portal

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.

Bode Group – Professor Product Portal

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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