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393274

Sigma-Aldrich

3-Methoxy-2-cyclopenten-1-one

99%

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About This Item

Fórmula lineal:
CH3OC5H5(=O)
Número de CAS:
4683-50-5
Peso molecular:
112.13
MDL number:
MFCD00192267
UNSPSC Code:
12352100
PubChem Substance ID:
24864510
NACRES:
NA.22

assay

99%

form

solid

mp

49-53 °C (lit.)

SMILES string

COC1=CC(=O)CC1

InChI

1S/C6H8O2/c1-8-6-3-2-5(7)4-6/h4H,2-3H2,1H3

InChI key

DTWCFCILAJVNPE-UHFFFAOYSA-N

Categorías relacionadas

General description

3-Methoxy-2-cyclopenten-1-one (3-methoxycyclopent-2-enone) is a 3-methoxycycloalk-2- enone.

Application

3-Methoxy-2-cyclopenten-1-one (3-methoxycyclopent-2-enone) may be used in the following studies:
  • Synthesis of 3-cyclopentyl-2-cyclopenten-1-one.
  • As a starting material in the synthesis of 3-alkyl-2-aryl-2-cyclopenten-1-one oxime derivatives and kjellmanianone, an antibiotic.
  • As one of the reagent in the synthesis of 3-aryl enones.
  • Preparation of 1:1 diastereomeric mixture of TBS (tert-butyldimethylsilyl)-protected enones.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Sigma-Aldrich

C102814

2-Cyclohexen-1-one

Tetrahedron, 47, 173-173 (1991)
Patrick Y Toullec et al.
Proceedings of the National Academy of Sciences of the United States of America, 101(16), 5810-5814 (2004-04-09)
The enantioselective formation of a quaternary stereogenic center coinciding with a hydroxylation process is a very rare reaction from a homogeneous catalysis point of view. Indeed, to our knowledge, no asymmetric transition-metal-catalyzed direct hydroxylation has been reported before. We describe
Yeonjoon Kim et al.
Bioorganic & medicinal chemistry letters, 24(13), 2807-2810 (2014-05-24)
3-Alkyl-2-aryl-2-cyclopenten-1-one oxime derivatives (1) were studied as a novel class of inhibitors of tumor necrosis factor α (TNF-α) with regard to synthesis and in vitro SAR inhibition of TNF-α. The in vitro IC50 values of these compounds in rat and
Gamal A I Moustafa et al.
The Journal of organic chemistry, 77(2), 1202-1207 (2012-01-03)
The alkylation of dienolates generated from 3-methoxycycloalk-2-enones having a 3'-hydroxyl alkenyl chain provides the corresponding quaternized cycloalkenones in a highly diastereoselective manner. The high degree of stereocontrol in the α-quaternization possibly implies intervention of a rigid chelating transition state that
Discovery of orally efficacious melanin-concentrating hormone receptor-1 antagonists as antiobesity agents. Synthesis, SAR, and biological evaluation of bicyclo [3.1. 0] hexyl ureas.
McBriar MD, et al.
Journal of Medicinal Chemistry, 49(7), 1202-1207 (2012)

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