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803928

Sigma-Aldrich

Benzyl 4-(trifluoromethylsulfonyloxy)-3-(trimethylsilyl)-5,6-dihydropyridine-1(2H)-carboxylate

Sinónimos:

Garg Azacyclohexyne Precursor

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About This Item

Fórmula empírica (notación de Hill):
C17H22F3NO5SSi
Peso molecular:
437.51
UNSPSC Code:
12352100
PubChem Substance ID:
329768833
NACRES:
NA.22

description

FP: >230°F

form

liquid

refractive index

n20/D 1.4902

density

1.2625 g/mL at 25 °C

storage temp.

2-8°C

SMILES string

C[Si](C)(C)C1=C(OS(=O)(C(F)(F)F)=O)CCN(C(OCC2=CC=CC=C2)=O)C1

InChI

1S/C17H22F3NO5SSi/c1-28(2,3)15-11-21(16(22)25-12-13-7-5-4-6-8-13)10-9-14(15)26-27(23,24)17(18,19)20/h4-8H,9-12H2,1-3H3

InChI key

QGKRRFLQHRMSAL-UHFFFAOYSA-N

General description

Benzyl 4-(trifluoromethylsulfonyloxy)-3-(trimethylsilyl)-5,6-dihydropyridine-1(2H)-carboxylate is a silyl triflate. It can be prepared from 4-methoxypyridine, via a three-step route.

Application

Benzyl 4-(trifluoromethylsulfonyloxy)-3-(trimethylsilyl)-5,6-dihydropyridine-1(2H)-carboxylate may be used as a starting reagent for the synthesis of 3,4-piperidyne. 3,4-Piperidyne is a precursor for the synthesis of various functionalized heterocyclic compounds.
Building block is a precursor for a highly useful azacyclohexyne intermediate, which is generated in the presence of Cesium Fluoride. The azacyclohexyne can be trapped in situ with dipolariphiles and other dienes to form bicyclic carbocycles and heterocycles.

Other Notes

Generation and Regioselective Trapping of a 3,4-Piperidyne for the Synthesis of Functionalized Heterocycles

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Referencia del producto
Descripción
Precios

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Travis C McMahon et al.
Journal of the American Chemical Society, 137(12), 4082-4085 (2015-03-15)
We report the generation of the first 3,4-piperidyne and its use as a building block for the synthesis of annulated piperidines. Experimental and computational studies of this intermediate are disclosed, along with comparisons to the well-known 3,4-pyridyne. The distortion/interaction model

Contenido relacionado

Garg Group – Professor Product Portal

The Garg group develops methods for the synthesis of natural products and pharmaceuticals. One key method pertains to heterocyclic arynes, such as indolynes and pyridynes, which are generated in situ from silyltriflate precursors under mild fluoride based reaction conditions.

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