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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

Assay

99%

form

solid

mp

49-53 °C (lit.)

functional group

ether
ketone

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCB9340
MKBF9701V
MKAA2199
07109DJ
12406JE

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Sigma-Aldrich

C102814

2-Cyclohexen-1-one

Tetrahedron, 47, 173-173 (1991)
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)
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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