405752
2-Allylcyclohexanone
97%
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About This Item
Linear Formula:
H2C=CHCH2C6H9(=O)
CAS Number:
Molecular Weight:
138.21
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
EC Number:
202-352-2
MDL number:
Assay:
97%
Form:
liquid
Quality Level
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.)
functional group
allyl, ketone
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
signalword
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
10 - Combustible liquids
wgk
WGK 3
flash_point_f
235.4 °F - closed cup
flash_point_c
113 °C - closed cup
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Regulatory Information
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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)
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
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 405752-5G | 04061836685195 |
| 405752-1G | 04061836685188 |