6267-39-6

Basic information

• Product Name: 3-Ethoxy-5,5-dimethyl-2-cyclohexen-1-one
• Synonyms: 3-Ethoxy-5,5-dimethyl-2-cyclohexen-1-one
• CAS NO: 6267-39-6
• Molecular Formula: C₁₀H₁₆O₂
• Molecular Weight: 168.2328
• Mol File: 6267-39-6.mol
• Article Data: 26

Chemical Properties

• Boiling Point: 257.7°Cat760mmHg
• Flash Point: 104.5°C
• Appearance: /
• Density: 0.97g/cm³
• Vapor Pressure: 0.0143mmHg at 25°C
• Refractive Index: 1.467
• CAS DataBase Reference: 3-Ethoxy-5,5-dimethyl-2-cyclohexen-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Ethoxy-5,5-dimethyl-2-cyclohexen-1-one(6267-39-6)
• EPA Substance Registry System: 3-Ethoxy-5,5-dimethyl-2-cyclohexen-1-one(6267-39-6)

Safety Data

• Hazardous Substances Data: 6267-39-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C10H16O2/c1-4-12-9-5-8(11)6-10(2,3)7-9/h5H,4,6-7H2,1-3H3

Upstream product

• 17530-69-7 3-chloro-5,5-dimethylcyclohex-2-en-1-one 
• 141-52-6 sodium ethanolate 
• 64-17-5 ethanol 
• 126-81-8 dimedone 
• 35024-12-5 (4,4-dimethyl-2,6-dioxo-cyclohexyl)-phenyl-iodonium betaine 
• 74-96-4 ethyl bromide 
• 75-03-6 ethyl iodide 
• 51238-67-6 1,3-dichloro-5,5-dimethyl-cyclohexa-1,3-diene 

Downstream Products

• 64265-27-6 5,5-dimethyl-3-(2-phenylethyl)cyclohex-2-enone 
• 4694-17-1 5,5-dimethlycyclohex-2-en-1-one 
• 78-59-1 3,5,5-Trimethylcyclohex-2-en-1-one 
• 29339-44-4 4'-methoxy-5,5-dimethyl-5,6-dihydro-[1,1'-biphenyl]-3(4H)-one 
• 31952-20-2 3-Ethoxy-5,5-dimethyl-2-cyclohexen-1-ol 
• 65253-29-4 [3-Ethoxy-5,5-dimethyl-cyclohex-2-en-(E)-ylidene]-acetic acid ethyl ester 
• 130660-07-0 3-(3,3-dimethylbut-1-yn-1-yl)-5,5-dimethylcyclohex-2-enone 
• 65253-27-2 (E)-3-ethoxy-5,5-dimethyl-2-cyclohexenylidene acetonitrile 
• 65253-28-3 (Z)-3-ethoxy-5,5-dimethyl-2-cyclohexenylidene acetonitrile 
• 99706-74-8 3--5,5-dimethylcyclohex-2-en-1-one 
• 28017-80-3 3-tert-butyl-5,5-dimethylcyclohex-2-en-1-one 
• 97345-29-4 (E,Z)-3-butylidene-1-ethoxy-5,5-dimethylcyclohex-1-ene 
• 28017-78-9 3-Aethyl-5,5-dimethyl-2-cyclohexen-1-on 
• 36047-17-3 5,5-dimethyl-3-phenyl-2-cyclohexen-1-one 

Relevant articles and documents

Visible Light-Mediated Photochemical Reactions of 2-(2′-Alkenyloxy)cycloalk-2-enones

The title compounds were prepared, and their reactivity was studied upon sensitized irradiation at λ = 420 nm. Thioxanthen-9-one was employed as the sensitizer at a loading of 10 mol % in small-scale reactions and of 2.5 mol % on a larger scale. Cyclohex-

Intramolecular [2+2] Photocycloaddition of Cyclic Enones: Selectivity Control by Lewis Acids and Mechanistic Implications

The intramolecular [2+2] photocycloaddition of 3-alkenyl-2-cycloalkenones was performed in an enantioselective fashion (nine representative examples, 54–86 % yield, 76–96 % ee) upon irradiation at λ=366 nm in the presence of an AlBr3-activated oxazaborolidine as the Lewis acid. An extensive screening of proline-derived oxazaborolidines showed that the enantioface differentiation depends strongly on the nature of the aryl group at the 3-position of the heterocycle. DFT calculations of the Lewis acid–substrate complex indicate that attractive dispersion forces may be responsible for a change of the binding mode. The catalytic [2+2] photocycloaddition was shown to proceed on the triplet hypersurface with a quantum yield of 0.05. The positive effect of Lewis acids on the outcome of a given intramolecular [2+2] photocycloaddition was illustrated by optimizing the key step in a concise total synthesis of the sesquiterpene (±)-italicene.

Br?nsted Acid Catalysis in Visible-Light-Induced [2+2] Photocycloaddition Reactions of Enone Dithianes

1,3-Dithiane-protected enones (enone dithianes) were found to undergo an intramolecular [2+2] photocycloaddition under visible-light irradiation (λ=405 nm) in the presence of a Br?nsted acid (7.5–10 mol %). Key to the success of the reaction is presumably the formation of colored thionium ions, which are intermediates of the catalytic cycle. Cyclobutanes were thus obtained in very good yields (78–90 %). It is also shown that the dithiane moiety can be reductively or oxidatively removed without affecting the photochemically constructed ring skeleton.