903571-02-8

Basic information

• Product Name: Bode Catalyst 2
• Synonyms: (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;Bode Catalyst 2;[5a-R,10b-S]-2-(2,4,6-Trimethyl-phenyl)-2,5a,6,10b-tetrahydro-4H-5-oxa-2,3-diaza-10c-azonia-cyclopenta[c]fluorene chloride;(+)-(5aR,10bS)-5a,10b-Dihydro-2-(2,4,6-triMethylphenyl)-4H,6H-indeno[2,1-b][1,2,4]triazolo;(+)-(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;(+)-(5aR,10bS)-5a,10b-Dihydro-2-mesityl-4H,6H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazinium Chloride Bode Catalyst 2;(+)-(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 (+)-(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
• CAS NO: 903571-02-8
• Molecular Formula: C21H22ClN3OH2O
• Molecular Weight: 0
• Mol File: 903571-02-8.mol
• Article Data: 3

Chemical Properties

• Melting Point: 226-230 °C
• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: Bode Catalyst 2(CAS DataBase Reference)
• NIST Chemistry Reference: Bode Catalyst 2(903571-02-8)
• EPA Substance Registry System: Bode Catalyst 2(903571-02-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 903571-02-8(Hazardous Substances Data)

Usage

Uses

(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.

General Description

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.

InChI:InChI=1/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

Upstream product

• 862095-80-5 (4aR,9aS)-3-methoxy-2,4a,9,9a-tetrahydroindeno[2,1-b][1,4]oxazine 
• 24006-09-5 mesitylhydrazine hydrochloride 
• 862095-79-2 indeno[2,1-b]-1,4-oxazin-3(2H)-one,4,4a,9,9a-tetrahydro-,(4aR,9aS)- 
• 88-05-1 2,4,6-trimethylaniline 
• 1345817-96-0 (Z)-2-mesityl-1-((4aR,9aS)-4,4a,9,9a-tetrahydroindeno[2,1b][1,4]oxazin-3(2H)-ylidene)hydrazine hydrochloride 
• 122-51-0 orthoformic acid triethyl ester 
• 955378-07-1 C₂₀H₂₃N₃O*ClH 
• 913718-34-0 (4aS,9aR)-4,4a,9,9a-tetrahydroindeno[2,1-b][1,4]oxazin-3(2H)-one 

Downstream Products

• 1283850-69-0 C₃₀H₂₇ClN₃O₂⁽¹⁺⁾ 

Relevant articles and documents

Oxyanion steering and CH-π interactions as key elements in an N-heterocyclic carbene-catalyzed [4 + 2] cycloaddition

The N-heterocyclic carbene catalyzed [4 + 2] cycloaddition has been shown to give γ,δ-unsaturated δ-lactones in excellent enantio- and diastereoselectivity. However, preliminary computational studies of the geometry of the intermediate enolate rendered am

ENANTIOSELECTVE REACTIONS CATALYZED BY CHIRAL TRIAZOLIUM SALTS

This invention provides a convenient method for converting imines and other electrophiles into heterocyclic ring systems. The process does not require the use of metallic reagents, and is catalyzed by an organic heterocyclic carbene catalyst. Accordingly,