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Merck
CN

683973

Sigma-Aldrich

(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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About This Item

经验公式(希尔记法):
C21H22ClN3O · H2O
分子量:
385.89
MDL编号:
UNSPSC代码:
12352005
PubChem化学物质编号:
NACRES:
NA.22

质量水平

方案

93%

表单

solid

旋光性

[α]20/D +158°, c = 1 in chloroform

mp

226-230 °C

官能团

ether

SMILES字符串

[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

一般描述

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.

应用

(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.

法律信息

与 BioBlocks, Inc. 联合销售

象形图

Exclamation mark

警示用语:

Warning

危险声明

危险分类

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

靶器官

Respiratory system

储存分类代码

11 - Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

dust mask type N95 (US), Eyeshields, Gloves

法规信息

新产品

从最新的版本中选择一种:

分析证书(COA)

Lot/Batch Number

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访问文档库

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)
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

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

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