94-66-6

Basic information

• Product Name: 2-Allylcyclohexanone
• Synonyms: 2-ALLYLCYCLOHEXANONE;2-(2-PROPENYL)CYCLOHEXANONE;TIMTEC-BB SBB006544;O-ALLYLCYCLOHEXANONE;2-(2-propenyl)-cyclohexanon;Cyclohexanone, 2-allyl-;2-allylcyclohexan-1-one;2-Allylcyclohexanone, 97 %
• CAS NO: 94-66-6
• Molecular Formula: C9H14O
• Molecular Weight: 138.21
• EINECS: 202-352-2
• Product Categories: C9;Carbonyl Compounds;Ketones
• Mol File: 94-66-6.mol
• Article Data: 100

Chemical Properties

• Boiling Point: 94 °C23 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: clear light yellow liquid
• Density: 0.927 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.378mmHg at 25°C
• Refractive Index: n20/D 1.469(lit.)
• Water Solubility: Insoluble
• CAS DataBase Reference: 2-Allylcyclohexanone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Allylcyclohexanone(94-66-6)
• EPA Substance Registry System: 2-Allylcyclohexanone(94-66-6)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 22-26-36/37/39-45-37/39
• RIDADR: UN 3077
• WGK Germany: 3
• Hazardous Substances Data: 94-66-6(Hazardous Substances Data)

Usage

Chemical Properties

clear light yellow liquid

Uses

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

Synthesis Reference(s)

Chemistry Letters, 13, p. 1721, 1984Journal of the American Chemical Society, 85, p. 207, 1963 DOI: 10.1021/ja00885a021The Journal of Organic Chemistry, 51, p. 421, 1986 DOI: 10.1021/jo00354a001

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.

InChI:InChI=1/C9H14O/c1-2-5-8-6-3-4-7-9(8)10/h2,8H,1,3-7H2/t8-/m1/s1

Upstream product

• 1125-99-1 1-(1-Cyclohexen-1-yl)pyrrolidine 
• 591-87-7 Allyl acetate 
• 61771-75-3 ethyl 1-allyl-2-oxocyclohexanecarboxylate 
• 75265-85-9 sodium 2-oxocyclohexane-1-carboxylate 
• 106-95-6 allyl bromide 
• 823-45-0 2-(hydroxymethylene)cyclohexanone 
• 5320-73-0 (2-allyl-cyclohexylidene)-cyano-acetic acid ethyl ester 
• 854447-21-5 (2-allyl-cyclohexylidene)-phenyl-acetonitrile 
• 107-21-1 ethylene glycol 
• 137334-09-9 tert-butyl 2-oxocyclohexanecarboxylate 
• 89100-18-5 1-Allyl-2-oxo-cyclohexanecarboxylic acid tert-butyl ester 
• 28399-89-5 3-Cyclooctenylacetat 
• 91906-66-0 pimelic acid diallyl ester 
• 108-94-1 cyclohexanone 

Downstream Products

• 5277-36-1 2,2-diallylcyclohexanone 
• 36302-35-9 (S)-2-allylcyclohexanone 
• 94-66-6 (R)-2-allylcyclohexanone 
• 183378-27-0 (R)-7-Allyl-oxepan-2-one 
• 58928-67-9 2-allyl-2-propylcyclohexanone 
• 51873-57-5 N-(2-allylcyclohexylidene)(phenyl)methanamine 
• 655233-56-0 C₉H₁₄O₂ 
• 5846-43-5 2-propylcyclohexanol 
• 464919-78-6 (-)-(1R,2R)-2-allyl-1-isopropenylcyclohexanol 

Relevant articles and documents

α-Allylation of aryl- or heteroarylketones via the Claisen rearrangement

A new one-step synthesis of α-allyl or α-(2-haloallyl) aryl- or heteroarylketones from the corresponding ketones via the Claisen rearrangement is described.

A synthetic approach to 5/5/6-polycyclic tetramate macrolactams of the discodermide type

A flexible synthetic route to the 16-membered tetramate-embedding macrocyclic scaffold present in various polycyclic tetramate macrolactams (PTMs) was developed which differs from the seminal synthesis of ikarugamycin by Boeckman Jr. in protecting groups and the order of connections. We also devised a short approach to various stereoisomers of the 5/5/6-tricarbocyclic motif found in discodermide and other PTMs, starting from the Weiss’ diketone.

Atroposelective Synthesis of Axially Chiral N-Arylpyrroles by Chiral-at-Rhodium Catalysis

A transformation of fluxional into configurationally stable axially chiral N-arylpyrroles was achieved with a highly atroposelective electrophilic aromatic substitution catalyzed by a chiral-at-metal rhodium Lewis acid. Specifically, N-arylpyrroles were alkylated with N-acryloyl-1H-pyrazole electrophiles in up to 93 percent yield and with up to >99.5 percent ee, and follow-up conversions reveal the synthetic utility of this new method. DFT calculations elucidate the origins of the observed excellent atroposelectivity.

Reactivity of Lithium β-Ketocarboxylates: The Role of Lithium Salts

Lithium β-ketocarboxylates 1(COOLi), prepared by the reaction of lithium enolates 2(Li+) with carbon dioxide, readily undergo decarboxylative disproportionation in THF solution unless in the presence of lithium salts, in which case they are indefinitely stable at room temperature in inert atmosphere. The availability of stable THF solutions of lithium β-ketocarboxylates 1(COOLi) in the absence of carbon dioxide allowed reactions to take place with nitrogen bases and alkyl halides 3 to give α-alkyl ketones 1(R) after acidic hydrolysis. The sequence thus represents the use of carbon dioxide as a removable directing group for the selective monoalkylation of lithium enolates 2(Li+). The roles of lithium salts in preventing the disproportionation of lithium β-ketocarboxylates 1(COOLi) and in determining the course of the reaction with bases and alkyl halides 3 are discussed.