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393274

Sigma-Aldrich

3-Methoxy-2-cyclopenten-1-one

99%

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About This Item

Linear Formula:
CH3OC5H5(=O)
CAS Number:
4683-50-5
Molecular Weight:
112.13
MDL number:
MFCD00192267
UNSPSC Code:
12352100
PubChem Substance ID:
24864510
NACRES:
NA.22

Quality Level

100

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

Related Categories

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Sigma-Aldrich

C102814

2-Cyclohexen-1-one

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)
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

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