803928

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

• Synonym(s): Garg Azacyclohexyne Precursor
• Empirical Formula (Hill Notation): C₁₇H₂₂F₃NO₅SSi
• Molecular Weight: 437.51
• UNSPSC Code: 12352100
• PubChem Substance ID: 329768833
• NACRES: NA.22

Properties

• 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

Description

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

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H315,H319,H335
• Precautionary Statements: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• 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