68479-99-2

Basic information

• Product Name: alpha,2,2-trimethyl-6-methylenecyclohexylpropyl acetate
• Synonyms: alpha,2,2-trimethyl-6-methylenecyclohexylpropyl acetate;alpha,2,2-trimethyl-6-methylene-cyclohexanepropano acetate;Acetic acid [3-(2,2-dimethyl-6-methylenecyclohexyl)-1-methylpropyl] ester;alpha,2,2-Trimethyl-6-methylene-cyclohexanepropanol, acetate;Cyclohexanepropanol, alpha,2,2-trimethyl-6-methylene-, 1-acetate;Cyclohexanepropanol, alpha,2,2-trimethyl-6-methylene-, acetate;Einecs 270-879-5;trimethyl-6-methylene cyclohexyl propyl acetate
• CAS NO: 68479-99-2
• Molecular Formula: C₁₅H₂₆O₂
• Molecular Weight: 238.36574
• EINECS: 270-879-5
• Mol File: 68479-99-2.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 286°Cat760mmHg
• Flash Point: 84.8°C
• Appearance: /
• Density: 0.92g/cm³
• CAS DataBase Reference: alpha,2,2-trimethyl-6-methylenecyclohexylpropyl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: alpha,2,2-trimethyl-6-methylenecyclohexylpropyl acetate(68479-99-2)
• EPA Substance Registry System: alpha,2,2-trimethyl-6-methylenecyclohexylpropyl acetate(68479-99-2)

Safety Data

• Hazardous Substances Data: 68479-99-2(Hazardous Substances Data)

Upstream product

• 3293-45-6 3-acetoxy-1-(2,6,6-trimethyl-cyclohex-2-enyl)-butane 
• 13720-13-3 4-(6',6'-dimethyl-2'-methylenecyclohexyl)butan-2-ol 
• 108-24-7 acetic anhydride 

Downstream Products

• 74055-26-8 2-Acetoxy-4-(6',6'-dimethyl-2'-trideuteriomethyl-1'-cyclohexen-1'-yl)butan 
• 74055-25-7 2-Acetoxy-4-(2'-hydroxy-6',6'-dimethyl-2'-trideuteriomethyl-1'-cyclohexyl)butan 
• 74055-20-2 4-(6',6'-dimethyl-2'-trideuteriomethyl-1'-cyclohexen-1'-yl)-2-butanon 
• 74055-27-9 4-(6',6'-dimethyl-2'-trideuteriomethyl-1'-cyclohexen-1'-yl)-2-butanol 

Relevant articles and documents

15. Photochemische Reaktionen. Zur Photochemie tetraalkylsubstituierter γ-Keto-olefine

The phtochemistry of 7,8-dihydro-β-ionone (1) in solution is shown to depend on temperature, polarity and viscosity of the solvent.UV irradiation (λ>=245nm) in pentane at +25 deg converts 1 to the isomeric ethers 3 (16percent), 5A (48percent) and 5B (22percent), whereas at -65 deg 7,8-dihydro-γ-ionone (26) is obtained in 12percent yield together with 13percent of 3, 12percent of 5A and 9percent of 5B.The 1n, ?*-excitation of 1 in acetonitrile gives similar results.In the more viscous 1,2,3-triacetoxypropane the photoisomerization 1 - 26 takes place even at +60 deg (10percent yield, cf. 40percent at -15 deg).In alcoholic solvents, however, no formation of 26 is detected, but the hitherto unknown -photocycloaddition 1 - 11 can be observed (4percent at -7 deg, 15percent at -65 deg in 2-propanol).An intermediate e may be involved (Scheme 14).In addition to the photoreactions 1 - 3, 5A, 5B and 11 the isomerization of 1 to the novel spirocyclic ketone 28 takes place in alcoholic solvents only.Photoisomerization 1 - 3 is presumably a photo-ene process involving a stereoselective intramolecular H-transfer.This type of photoisomerization is restricted to cyclic γ-keto-olefines.The tetraalkylated acyclic γ-keto-olefines 14 and 15 photoisomerize exclusively by -cycloaddition, independent of the solvent.On 1n, ?*-excitation the δ, ε-unsaturated bicyclic ketone 44 undergoes Norrish-Type-II photofragmentation to the diene 45 or isomerizes to the γ, δ-unsaturated ketone 17.Competition between these two reactions is strongly temperature dependent: photolysis in pentane at -72 deg yields quantitatively 45, whereas at +35 deg only 30percent of 45 and 68percent of 17 are obtained.UV irradiation of the novel spirocyclic ketone 28 gives as primary photoproduct the isomeric aldehyde 29, and in a secondary photoreaction the isomeric oxetanes 30A and 30B.Experiments with deuteriated substartes show that the isomerization of type 28 - 29 is stereocontrolled.