766-42-7

Basic information

• Product Name: (2R)-2α,6α-Dimethylcyclohexanone
• Synonyms: (2R)-2α,6α-Dimethylcyclohexanone;(2S)-2β,6β-Dimethylcyclohexanone;(2α,6α)-2,6-Dimethylcyclohexanone;cis-2,6-Dimethylcyclohexanone
• CAS NO: 766-42-7
• Molecular Formula: C₈H₁₄O
• Molecular Weight: 126.19616
• Mol File: 766-42-7.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2R)-2α,6α-Dimethylcyclohexanone(CAS DataBase Reference)
• NIST Chemistry Reference: (2R)-2α,6α-Dimethylcyclohexanone(766-42-7)
• EPA Substance Registry System: (2R)-2α,6α-Dimethylcyclohexanone(766-42-7)

Safety Data

• Hazardous Substances Data: 766-42-7(Hazardous Substances Data)

Usage

Description

(2R)-2α,6α-Dimethylcyclohexanone is a cyclic ketone with the molecular formula C8H14O. It belongs to the cyclohexanone family and is a colorless liquid with a pleasant odor. This chemical compound is an important intermediate in the synthesis of various organic compounds.

Uses

Used in Food Industry:
(2R)-2α,6α-Dimethylcyclohexanone is used as a flavoring agent for its pleasant odor, enhancing the taste and aroma of food products.
Used in Perfume and Fragrance Industry:
(2R)-2α,6α-Dimethylcyclohexanone is used as a key ingredient in the production of perfumes and other fragrance products, contributing to their unique scents.
Used in Pharmaceutical Industry:
(2R)-2α,6α-Dimethylcyclohexanone has potential applications in the pharmaceutical industry due to its unique chemical properties, which can be utilized in the development of new drugs and medicinal compounds.
Used in Cosmetic Industry:
(2R)-2α,6α-Dimethylcyclohexanone also has potential applications in the cosmetic industry, where its unique chemical properties can be harnessed for the creation of innovative cosmetic products.

Upstream product

• 109785-14-0 (6S)-(-)-2,6-dimethylcyclohex-2-en-1-one 
• 42846-29-7 (1r*,2R*,6S*)-2,6-dimethylcyclohexanol 
• 2816-57-1 2,6-dimethylcyclohexanone 
• 5183-63-1 2-Ethinyl-1,3-dimethyl-cyclohexanol-⁽²⁾-carbonsaeure-⁽¹⁾-ethylester 
• 5183-62-0 1,3-dimethyl-2-oxo-cyclohexanecarboxylic acid ethyl ester 
• 5183-61-9 3-methyl-2-oxo-cyclohexanecarboxylic acid ethyl ester 
• 576-26-1 2.6-dimethylphenol 
• 101558-68-3 6-(2-methoxy-4-nitrophenoxy)hexanoylhydrazine 
• 101558-67-2 methyl 6-(2-methoxy-4-nitrophenoxy)hexanoate 
• 100200-99-5 potassium 2-methoxy-4-nitrophenolate monohydrate 
• 39170-84-8 cis,cis-2,6-dimethylcyclohexanol 
• 64-17-5 ethanol 
• 7664-93-9 sulfuric acid 
• 19187-65-6 (+/-)-cis-1.3-dimethyl-cyclohexanone-⁽²⁾-oxime 

Downstream Products

• 42846-29-7 (1r*,2R*,6S*)-2,6-dimethylcyclohexanol 
• 39170-84-8 cis,cis-2,6-dimethylcyclohexanol 
• 42846-29-7 trans,trans-2,6-dimethylcyclohexanol 
• 766-43-8 trans-2,6-dimethylcyclohexanone 
• 39170-84-8 cis,cis-2,6-dimethylcyclohexanol 
• 1481685-04-4 1-(dibromomethyl)-2,6-dimethylcyclohexanol 
• 51036-70-5 1-(2,6-Dimethyl-cyclohex-1-enyl)-2-(3-methoxy-phenyl)-ethanone 
• 109785-14-0 (6S)-(-)-2,6-dimethylcyclohex-2-en-1-one 
• 128593-70-4 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (S)-1,3-dimethyl-2-oxo-cyclohexyl ester 
• 128593-71-5 (2R,6S)-2-acetyl-2,6-dimethylcyclohexanone 
• 109785-13-9 (R)-1.3-dimethyl-cyclohexen-⁽³⁾-one-⁽²⁾ 
• 123992-60-9 ethyl (ξ-acetoxy-2β,6β-dimethyl-1-cyclohexyl)acetate 
• 123992-74-5 2-(diazoacetonylidene)-1β,3β-dimethylcyclohexane 
• 123992-70-1 ethyl (2β,6β-dimethyl-1-cyclohexylidene)acetate 

Relevant articles and documents

ORGANIC COMPOUND USED AS FRAGRANCE INGREDIENTS

A compound of formula I wherein R1, R2, R3 and R4 can be independently selected from H or Me, n ＝ 0, 1, the dotted lines are indicating single bonds, or in case n ＝ 0 an isolated double bond at position 3', or in case n ＝ 1 an isolated double bond at position 3' or 4', and the wavy bond is indicating an unspecified configuration of the adjacent double bond. Said compounds, as well as precursors capable to generate said compounds, are useful as fragrance ingredients.

5-exo-trig Versus 6-endo-trig cyclization of Alk-5-enoyl radicals: The role of one-carbon ring expansion

Alk-5-enoyl radicals were made to cyclize in exo and endo modes to give the corresponding cycloketone radicals, which are related through one-carbon ring expansion. Relative kinetic data were determined for the ring closure of the 2-methylhept-5-enoyl radical generated by the reaction of the corresponding phenyl-seleno ester with Bu3SnH over the temperature range 233-323 K. The conversion to absolute rates provided Arrhenius expressions for the 5-exo-trig and 6-endo-trig cyclizations. Ab initio and semiempirical (AM1) calculations were performed on the hex-5-enoyl and hept-5-enoyl radicals, respectively, and the outcomes aided in the rationalization of the preexponential factors and activation energies. Both 1,5- and 1,6-ring closure occur via in a lower energy 'chairlike' transition state. The observed high regioselectivity is due to favorable entropic and enthalpic factors associated with the formation of the smaller ring. The stereoselectivity was higher in the 1,6-ring closure (70:30) than in the 1,5-ring closure (55:45), the trans isomer being predominant in both. For the one-carbon ring expansion studies, the radicals of interest were obtained by deoxygenation of suitable alcohols via the O-phenyl thiocarbonates with (TMS)3-SiH. The one-carbon ring expansion in the cyclopentanone series for the secondary alkyl radicals was studied over the temperature range 343-413 K by means of free-radical clock methodology and yielded the Arrhenius expression. The rate constant was 4.2 x 103 s-1 at room temperature and the reverse reaction (ring contraction) was found to be at least 10 times slower. Since the intermediacy of acyl radicals can be excluded, the reaction must occur via 3-membered cyclic intermediate radicals (or transition states).

Inducibility of an Enone Reductase System in the Fungus Beauveria sulfurescens: Application in Enantioselective Organic Synthesis

Microbiological reduction of α,β-unsaturated carbonyl compounds is studied.Inducibility of the enone reductase system of Beauveria sulfurescens is reported.The best inducer is shown to be cyclohex-2-en-1-one.An appropriate procedure using induced resting mycelium is developed to reduce substituted cyclohexenones that are shown to be unable to induce the reducing enzyme.Optically pure trans-(2R,6R)-(-)-2,6-dimethylcyclohexan-1-one and trans-(2R,6R)-(-)-2,6-dimethylcyclohexan-1-ol are obtained from (+/-)-2,6-dimethylcyclohex-2-en-1-one along with optically pure (6S)-(-)-2,6-dimethylcyclohex-2-en-1-one.