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805580

Sigma-Aldrich

3-(2-phenylethynyl)-2-oxazolidinone

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Empirical Formula (Hill Notation):
C11H9NO2
CAS Number:
Molecular Weight:
187.19
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

form

solid

storage temp.

2-8°C

SMILES string

O=C1OCCN1C#CC2=CC=CC=C2

InChI

1S/C11H9NO2/c13-11-12(8-9-14-11)7-6-10-4-2-1-3-5-10/h1-5H,8-9H2

InChI key

GBUSLWYYBBBMGC-UHFFFAOYSA-N

Application

Nitrogen-substituted alkynes are strongly polarized alkynes and highly reactive building blocks which have been used for the design of a wide number of transformations. Precursor of highly reactive keteniminium ions and useful reagent for asymmetric synthesis.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Research in the Evano group focuses on three areas: natural product synthesis, copper catalysis, and the chemistry of hetero-substituted alkynes. In particular, they developed a set of efficient and robust procedures, mostly based on copper catalysis, for the synthesis of ynamides starting from readily available starting materials. They have also explored the synthetic potential of these bench-stable reagents which were shown to be remarkable substrates and building blocks, notably in anionic and cationic chemistry. By exploiting and rationalizing the singular and remarkable reactivity of ynamides, reaction pathways that could not be accessed with regular alkynes could be exploited to access various nitrogen-containing molecules, including complex and otherwise hardly accessible nitrogen heterocycles, with high levels of efficiency. The Evano group is currently continuing its work on the chemistry of ynamides, with an emphasis in asymmetric synthesis, and its extension to other classes of hetero-substituted acetylenes.

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