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Merck
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文件

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%

同義詞:

Bode 催化剂 2

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About This Item

經驗公式（希爾表示法）:
C21H22ClN3O · H2O
CAS號碼:
903571-02-8
分子量：:
385.89
分類程式碼代碼:
12352005
PubChem物質ID:
329760886
NACRES:
NA.22

化驗

93%

形狀

solid

光學活性

[α]20/D +158°, c = 1 in chloroform

mp

226-230 °C

SMILES 字串

[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 密鑰

GUECWMLEUCWYOS-WKOQGQMTSA-M

相關類別

一般說明

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.

應用

(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.

法律資訊

与 BioBlocks, Inc. 联合销售

象形圖

Exclamation mark
GHS07

訊號詞

Warning

危險聲明

H315,H319,H335

危險分類

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

標靶器官

Respiratory system

儲存類別代碼

11 - Combustible Solids

水污染物質分類（WGK）

WGK 3

閃點（°F）

Not applicable

閃點（°C）

Not applicable

個人防護裝備

dust mask type N95 (US), Eyeshields, Gloves

分析證明 (COA)

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存取文件庫

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)
Carbene-catalyzed enantioselective oxidative coupling of enals and di (hetero) arylmethanes
Chen Q, et al.
Chemical Science, 9(46), 8711-8715 (2018)

文章

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.

N-Heterocyclic Carbene (NHC) 化合物

Rovis 已證明三唑鎓鹽在鹽基存在下可在高對映選擇性的分子內 Stetter 反應中作為 N-heterocyclic carbene 的有機催化劑1。

相關內容

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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