7086-80-8

Basic information

• Product Name: 2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohexanone
• CAS NO: 7086-80-8
• Molecular Formula: C₁₀H₁₆O₂
• Molecular Weight: 168.2328
• Mol File: 7086-80-8.mol

Chemical Properties

• Boiling Point: 269.3°C at 760 mmHg
• Flash Point: 112.2°C
• Density: 1.026g/cm³
• Vapor Pressure: 0.000975mmHg at 25°C
• Refractive Index: 1.489
• CAS DataBase Reference: 2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohexanone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohexanone(7086-80-8)
• EPA Substance Registry System: 2-hydroxy-2-methyl-5-(prop-1-en-2-yl)cyclohexanone(7086-80-8)

Safety Data

• Hazardous Substances Data: 7086-80-8(Hazardous Substances Data)

Upstream product

• 6485-40-1 (R)-Carvone 
• 59121-82-3 (1R,2R,4S)-1-methyl-4-(prop-1-en-2-yl)cyclohexane-1,2-diol 
• 203719-53-3 (-)-limonene oxide 
• 39904-04-6 (1S,2S,4S)-limonene glycol 
• 1946-00-5 (1S,2S,4R)-limonene-1,2-diol 
• 5989-27-5 D-limonene 
• 1195-92-2 Limonene oxide 
• 13833-08-4 1-methyl-4-(1-methylethenyl)-cyclohexane-1,2-diol 
• 506422-90-8 2-bromo-1-hydroxy-p-menth-8-ene 
• 185329-56-0 1-methyl-4-(1-methylethenyl)-1,2-cyclohexanediol 
• 124-41-4 sodium methylate 
• 39904-09-1 (1R,2R,4R)-1-methyl-4-(prop-1-en-2-yl)cyclohexane-1,2-diol 

Downstream Products

• 7105-59-1 methyl (3R)-3-isopropenyl-6-oxoheptanoate 

Relevant articles and documents

Microwave assisted bi-functional activation of β-bromo-tert-alcohols

Microwave-assisted dehydration-oxidation of β-bromo-tert-alcohols to afford 2,3-unsaturated ketones in good yield is reported. The reaction of substrates with DMSO in 1:1 ratio (w/v) is promoted by ZnS in a solvent-free condition. A concurrent bi-functional activation of trans-vicinal bromo- and hydroxyl groups with ZnS is elucidated. This is a new observation under microwave and applies to β-bromo-tert-alcohols derived from 1,4-disubstitued-1-cyclohexenes. It is very useful in the synthesis of 2,3-unsaturated ketones derived from monoterpenes which are valuable flavour compounds. [Figure not available: see fulltext.]

Enantioselective total syntheses of the proposed structures of prevezol B and evaluation of anti-cancer activity

The first enantioselective total syntheses of the proposed structures of the natural product prevezol B are reported. The reported syntheses complement the previously-reported syntheses of the proposed structures of prevezol C, a stereoisomer of prevezol B. It was previously shown that the structure of the naturally occurring prevezol C had been incorrectly assigned. This work has led us to conclude that the proposed structures of prevezol B are also incorrect and major revision of both of the structures of the prevezols B and C is required. Cytotoxicity studies on the human cervical cancer cell line HeLa revealed that the synthesized prevezol B and C compounds were not active even at the highest concentration used (100 μM). However, one of the synthetic precursors was shown to have modest potency against HeLa cells (IC50 = 23.5 ± 1.8 μM). This journal is

Synthesis of the proposed structures of Prevezol C

The first enantioselective synthesis of the proposed relative structures of Prevezol C is reported in 11 linear steps from readily available materials. The unusual syn bromohydrin was installed via a multistep sequence culminating in a diastereoselective

Total synthesis of (+)-omphadiol

A smooth transition from (R)-carvone to a β-lactone and then to (+)-omphadiol characterizes the first total synthesis of this sesquiterpene, which was achieved in ten steps and 18 overall yield. All six contiguous stereogenic centers were introduced in a

A new diastereoselective entry to the (1S,4R)- and (1S,4S)-isomers of 4-isopropyl-1-methyl-2-cyclohexen-1-ol, aggregation pheromones of the ambrosia beetle Platypus quercivorus

A concise diastereoselective and enantiopure route to the (1S,4R)- and (1S, 4S)-isomers of 4-isopropyl-1-methyl-2-cyclohexen-1-ol via a palladium-catalysed deoxygenation of the enol triflate derived from limonene glycol. Crown Copyright

Direct conversion of tert-β-bromo alcohols to ketones with zinc sulfide and DMSO

tert-β-Bromo alcohols, derived from simple monoterpene hydrocarbons, react with zinc sulfide in dimethyl sulfoxide to afford saturated ketones as the major and hydroxy ketones as the minor products. The reaction involves initial nucleophilic attack by DMSO on the carbon attached to the halogen, which is assisted by electrophilic zinc sulfide. Subsequent Kornblum type oxidation yields the α-hydroxy ketone. On the other hand, abstraction of proton β to the hydroxyl group followed by an attack of the neighboring hydroxyl moiety on the sulfur of the dimethylsulfoxonium intermediate and its subsequent collapse yields an enol, which tautomerizes to a saturated ketone. The latter pathway is predominantly followed.

Conversion of α,β-unsaturated ketones into α-hydroxy ketones using an Mn(III) catalyst, phenylsilane and dioxygen: Acceleration of conjugate hydride reduction by dioxygen

Treatment of a variety of α,β-unsaturated ketones with Mn(dpm)3 (3 mol%)/PhSiH3 (1.3 equiv.)/isopropyl alcohol/O2, followed by reductive work-up with P(OEt)3 resulted in the formation of α-hydroxy-ketones. (C) 2000 Elsevier Science Ltd.

Carbocyclic Construction by the Sigmatropic Rearrangement of Cyclic Sulfonium Ylides. A New Entry for the Stereoselective Synthesis of Substituted Cyclohexanones

The rhodium(II)-catalyzed cyclization of acyclic α-diazo-β-keto esters 1c,d provided stereoselectively the highly substituted cyclohexanones 3c,d respectively, by the sigmatropic rearrangement via stereocontrolled nine-membered allylsulfonium ylides 2c,d.Further elaboration of 3d toward the cyclohexanone 36 accomplished asymmetric formal syntheses of the representative elemanoids, 37 and 38.The compound 3c was transformed into the cyclohexanone 34a and cyclohexene 43, which could serve as the key intermediates for the synthesis of natural products possessing contigously cis-arranged trimethylcyclohexanone and its related moieties, respectively.

Stereoselective Favorskii Rearrangement of Carvone Chlorohydrin; Expedient Synthesis of (+)-Dihydronepetalactone and (+)-Iridomyrmecin

(+)-Dihydronepetalactone and (+)-iridomyrmecin were synthesized from the stereoselective Favorskii rearrangement product of (+)-carvone chlorohydrin.