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Merck
CN

803928

4-(三氟甲基磺酰氧基)-3-(三甲基甲硅烷基)-5,6-二氢吡啶-1(2H)-羧酸苄酯

别名:

Garg Azacyclohexyne Precursor

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关于此项目

经验公式（希尔记法）:
C17H22F3NO5SSi
分子量:
437.51
UNSPSC Code:
12352100
PubChem Substance ID:
329768833
NACRES:
NA.22
Form:
liquid

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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

FP: >230°F

form

liquid

refractive index

n20/D 1.4902

density

1.2625 g/mL at 25 °C

functional group

fluoro, phenyl, triflate

storage temp.

2-8°C

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

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

存储类别

10 - Combustible liquids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

历史批次信息供参考:

分析证书(COA)

Lot/Batch Number
MKCM9738
MKCK2705
MKBW9951V

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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

相关内容

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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