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Merck
CN

683973

(5aR,10bS)-5a,10b-二氢-2-(2,4,6-三甲苯基)-4H,6H-茚并[2,1-b]-1,2,4-三唑并[4,3-d]-1,4-噁嗪鎓氯化物

93%

别名:

Bode 催化剂 2

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关于此项目

经验公式（希尔记法）:
C21H22ClN3O · H2O
化学文摘社编号:
903571-02-8
分子量:
385.89
MDL number:
MFCD20265585
UNSPSC Code:
12352005
PubChem Substance ID:
329760886
NACRES:
NA.22

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产品名称

(5aR,10bS)-5a,10b-二氢-2-(2,4,6-三甲苯基)-4H,6H-茚并[2,1-b]-1,2,4-三唑并[4,3-d]-1,4-噁嗪鎓氯化物, 93%

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

InChI key

GUECWMLEUCWYOS-WKOQGQMTSA-M

assay

93%

form

solid

optical activity

[α]20/D +158°, c = 1 in chloroform

mp

226-230 °C

functional group

ether

Quality Level

100

相关类别

Legal Information

与 BioBlocks, Inc. 联合销售

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.

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.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

存储类别

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

法规信息

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历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
MKCR7041
MKCR3440
MKCQ7238
MKCQ3609
MKCL1724

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Carbene-catalyzed enantioselective oxidative coupling of enals and di (hetero) arylmethanes
Chen Q, et al.
Chemical Science, 9(46), 8711-8715 (2018)
N-Heterocyclic Carbene (NHC) Compounds
Aldrich Chemfiles, 7(9), 21-21 (2007)
Enantioselective synthesis of dihydropyridinones via NHC-catalyzed aza-Claisen reaction
Wanner B, et al.
Organic Letters, 13(19), 5378-5381 (2011)
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)
Synthesis of a N-Mesityl Substituted Aminoindanol-Derived Triazolium Salt.
Struble JR and Bode JW.
Organic Syntheses, 362-376 (2010)

商品

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.

相关内容

Bode Group – Prof. Product Portal

Bode Group creates N-mesityl-NHC catalysts for enantioselective annulations and SnAP reagents for one-pot aldehyde conversion into N-heterocycles.

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