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Sigma-Aldrich

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

Synonym(s):

Garg Azacyclohexyne Precursor

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About This Item

Empirical Formula (Hill Notation):
C17H22F3NO5SSi
Molecular Weight:
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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Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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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

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