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405752

Sigma-Aldrich

2-Allylcyclohexanone

97%

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About This Item

Linear Formula:
H2C=CHCH2C6H9(=O)
CAS Number:
94-66-6
Molecular Weight:
138.21
EC Number:
202-352-2
MDL number:
MFCD00043548
UNSPSC Code:
12352100
PubChem Substance ID:
24865329
NACRES:
NA.22

Assay

97%

form

liquid

refractive index

n20/D 1.469 (lit.)

bp

94 °C/23 mmHg (lit.)

density

0.927 g/mL at 25 °C (lit.)

SMILES string

C=CCC1CCCCC1=O

InChI

1S/C9H14O/c1-2-5-8-6-3-4-7-9(8)10/h2,8H,1,3-7H2

InChI key

UPGHEUSRLZSXAE-UHFFFAOYSA-N

General description

2-Allylcyclohexanone is a β,γ-unsaturated ketone. Selective oxidation of 2-allylcyclohexanone by benzonitrile-hydrogen peroxide has been reported. Asymmetric synthesis of 2-alkylcyclohexanones by alkylation of cyclohexanone enamines (III) of L-proline ester derivatives has been described. Oxidation of 2-allylcyclohexanone by 90% hydrogen peroxide catalyzed by arsonated polystyrene has been studied.

Application

2-Allylcyclohexanone may be used in the synthesis of the following:
  • bicyclo[3.3.1]non-2-en-9-one
  • R-(-)-epilachnene, an antipode of the defensive droplets from the Mexican bean beetle, Epilachna varivestis

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

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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Stereochemical Studies. IX. Asymmetric Synthesis of 2-Alkylcyclo-hexanones with Enamine Alkylation.
Hiroi K, et al.
Chemical & Pharmaceutical Bulletin, 20, 246-257 (1972)
Bridget McCarthy Cole et al.
The Journal of organic chemistry, 61(22), 7832-7847 (1996-11-01)
Mn(III)-based oxidative free-radical cyclization of unsaturated ketones is a versatile synthetic procedure with broad applicability. For example, oxidation of cyclopentanone 1a with 2 equiv of Mn(OAc)(3).2H(2)O and 1 equiv of Cu(OAc)(2).H(2)O in AcOH at 80 degrees C for 1.5 h
Biphase and triphase catalysis. Arsonated polystyrenes as catalysts in the Baeyer-Villiger oxidation of ketones by aqueous hydrogen peroxide.
Jacobson SE, et al.
Journal of the American Chemical Society, 101(23), 6938-6946 (1979)
A Modified Thermodynamically Controlled Deracemization of 2-Allylcyclohexanone and Its Application to Asymmetric Synthesis of (R)-(-)-Epilachnene.
Kaku H, et al.
Chemistry Letters (Jpn), 33(5), 516-517 (2004)
A simplified procedure for epoxidation by benzonitrile-hydrogen peroxide. Selective oxidation of 2-allylcyclohexanone.
Payne GB.
Tetrahedron, 18(6), 763-765 (1962)

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