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393274

3-Methoxy-2-cyclopenten-1-one

Name: 3-Methoxy-2-cyclopenten-1-one
Brand: ALDRICH

99%

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About This Item

Linear Formula:

CH₃OC₅H₅(=O)

CAS Number:

4683-50-5

Molecular Weight:

112.13

NACRES:

NA.22

PubChem Substance ID:

24864510

UNSPSC Code:

12352100

MDL number:

MFCD00192267

Assay:

99%

Form:

solid

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Properties

Quality Level

100

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

Description

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Stereoselective α-quaternization of 3-methoxycycloalk-2-enones via 1,4-diastereoinduction of alkoxy dienolates.

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

Synthesis and structure-activity relationship of cyclopentenone oximes as novel inhibitors of the production of tumor necrosis factor-α.

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

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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Global Trade Item Number

SKU	GTIN
393274-5G	04061832619156