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Merck
CN

754706

Sigma-Aldrich

8-Isopropylquinoline N-oxide

97%

别名:

8-Isopropylquinoline 1-oxide

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About This Item

经验公式(希尔记法):
C12H13NO
分子量:
187.24
MDL编号:
UNSPSC代码:
12352005
PubChem化学物质编号:
NACRES:
NA.22

检测方案

97%

形式

liquid

折射率

n20/D 1.644

密度

1.134 g/mL at 25 °C

储存温度

2-8°C

SMILES字符串

CC(C)c1cccc2ccc[n+]([O-])c12

InChI

1S/C12H13NO/c1-9(2)11-7-3-5-10-6-4-8-13(14)12(10)11/h3-9H,1-2H3

InChI key

LYLSTLGFFOQSKE-UHFFFAOYSA-N

应用

8-Isopropylquinoline N-oxide can be used as a reagent:
  • In the oxidative cyclization of diynes in the presence of gold catalyst.
  • For the preparation of pyrrolo[3,4-c]quinolin-1-ones by asymmetric alkyne oxidation of chiral N-propargyl ynamides in the presence of a copper catalyst.
  • In the synthesis of 8-(1-methylethyl)-2-[(4-methylphenyl)sulfonyl]- quinoline by deoxygenative and selective sulfonylation with sodium p-toluenesulfinate using iodine/TBHP as a catalyst.

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable


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Iodine/TBHP-Promoted One-Pot Deoxygenation and Direct 2-Sulfonylation of Quinoline N-Oxides with Sodium Sulfinates: Facile and Regioselective Synthesis of 2-Sulfonylquinolines
Sumunnee L, et al.
European Journal of Organic Chemistry, 2017(5), 1025-1032 (2017)
Recent advances in catalytic asymmetric intermolecular oxidation of alkynes
Shen W-B and Tang X-T
Organic & Biomolecular Chemistry, 17(30), 7106-7113 (2019)
Pascal Nösel et al.
Journal of the American Chemical Society, 135(41), 15662-15666 (2013-09-21)
In the presence of a gold catalyst an unprecedented oxidative cyclization of diynes takes place. The reaction cascade is initiated by an oxygen transfer from a N-oxide onto a gold-activated alkyne. The formed α-oxo carbene is transferred across the second

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