7787-20-4

Usage

Uses

Used in Pharmaceutical Industry:
(-)-Fenchone is used as a research compound for studying its inhibitory effects on human TRPA1, a receptor that plays a crucial role in the sensation of pain, temperature, and taste. This application aims to explore the potential of (-)-Fenchone in developing new therapeutic agents for treating various conditions related to these sensations.
Used in Malaria Vector Control:
(-)-Fenchone is also used in research focused on the odorant receptor of the malaria vector Anopheles gambiae. By understanding its interaction with the receptor, scientists hope to develop novel strategies for controlling the spread of malaria, a deadly disease affecting millions of people worldwide.

Preparation

By isolation from cedar leaf oil (Thuja oil) or by various synthetic methods (Arctander, 1969).

Flammability and Explosibility

Notclassified

Pharmacology

In mice, fenchone injected sc in sesame oil produced clonic convulsions at non-lethal doses, with a median convulsive dose (CD50) of 1133 mg/kg, and a dose of 500 mg/kg given sc was an effective arousal agent, reducing the hexobarbitone sleep time (Wenzel & Ross, 1957). In rats, an ip dose of 500 mg/kg had no effect on pentobarbitone-depressed respiration, while ip doses of 50-400 mg/kg increased running activity but did not affect total activity (Wenzel & Ross, 1957). Fenchone showed some antispasmodic action on excised mouse intestine (Haginiwa, Harada & Morishita, 1963), and at 260 mmol/kg showed good choleretic properties of moderately long duration when given orally in olive oil to rats (M?rsdorf, 1966). Thomas (1958) reported that it acted as a central nervous system stimulant. Fenchone has been used medically as a counter-irritant (Merck Index, 1968).

Metabolism

Rimini (1901 & 1909) showed that, in the dog, fenchone was probably oxidized to 4-hydroxyfenchone. Reinartz & Zanke (1936) showed that there were other products. They separated, as lead salts, the glucuronides from the urine of dogs receiving d-fenchone. The lead was removed with sulphuric acid and the resulting solution was hydrolysed. In the resulting mixture of hydroxyfen chones, the presence of 4- and 5-hydroxyfenchones and 7r-apofenchone-3-carboxylic acid was demon strated (Williams, 1959).

Purification Methods

Purification is as for the (+)-enantiomer above and should have the same physical properties except for opposite optical rotations. UV has max 285nm ( 12.29). [Braun & Jacob Chem Ber 66 1461 1933, UV: Ohloff et al. Chem Ber 90 106 1957.] [Beilstein 7 III 392, 7 IV 212.]

InChI:InChI=1/C10H16O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7H,4-6H2,1-3H3/t7-,10+/m0/s1

Upstream product

• 73509-03-2 (1R)-(-)-Fenchone hydrazone 
• 74163-80-7 (1R,4S)-1,3,3-trimethylbicyclo[2.2.1]heptane-2-one oxime 
• 470-08-6 α-fenchyl alcohol 
• 53402-11-2 thiofenchone 
• 89050-88-4 (1R)-2-diazo-1,3,3-trimethylbicyclo[2.2.1]heptane 
• 18084-01-0 (1R,4S)-2-Ethynyl-1,3,3-trimethyl-bicyclo[2.2.1]heptan-2-ol 
• 2217-02-9 (1R)-endo-(+)-fenchol 

Downstream Products

• 2217-02-9 (1R)-endo-(+)-fenchol 
• 131348-06-6 (+)-endo-Fenchylamine 
• 137255-07-3 (1R)-endo-2-ethylfenchol 
• 161276-73-9 (1R,2R)-2-endo-hydroxy-2-exo-phenyl-1,3,3-trimethylbicyclo[2.2.1]heptane 
• 64439-31-2 (1R)-endo-(+)-fenchylalcohol 
• 470-08-6 α-fenchyl alcohol 
• 740817-73-6 (1R,2R)-2-endo-hydroxy-2-exo-allyl-1,3,3-trimethylbicyclo<2.2.1>heptane 
• 240117-99-1 (1R,2R,4S)-2-endo-hydroxy-2-exo-(o-methoxybenzene)-1,3,3-trimethylbicyclo[2.2.1]heptane 
• 740817-73-6 (1R)-1,3,3-trimethyl-2-(prop-2-enyl)bicyclo[2.2.1]heptan-2-ol 
• 366013-96-9 2-((1R,2R,4S)-2-hydroxy-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl)acetonitrile 

Relevant academic research and scientific papers

A Structural View on the Stereospecificity of Plant Borneol-Type Dehydrogenases

The development of sustainable processes for the valorization of byproducts and other waste streams remains an ongoing challenge in the field of catalysis. Racemic borneol, isoborneol and camphor are currently produced from α-pinene, a side product from the production of cellulose. The pure enantiomers of these monoterpenoids have numerous applications in cosmetics and act as reagents for asymmetric synthesis, making an enzymatic route for their separation into optically pure enantiomers a desirable goal. Known short-chain borneol-type dehydrogenases (BDHs) from plants and bacteria lack the required specificity, stability or activity for industrial utilization. Prompted by reports on the presence of pure (?)-borneol and (?)-camphor in essential oils from rosemary, we set out to investigate dehydrogenases from the genus Salvia and discovered a dehydrogenase with high specificity (E>120) and high specific activity (>0.02 U mg?1) for borneol and isoborneol. Compared to other specific dehydrogenases, the one reported here shows remarkably higher stability, which was exploited to obtain the first three-dimensional structure of an enantiospecific borneol-type short-chain dehydrogenase. This, together with docking studies, led to the identification of a hydrophobic pocket in the enzyme that plays a crucial role in the stereo discrimination of bornane-type monoterpenoids. The kinetic resolution of borneol and isoborneol can be easily integrated into the existing synthetic route from α-pinene to camphor thereby allowing the facile synthesis of optically pure monoterpenols from an abundant renewable source.

Photochemical Transformations with Iodine Azide after Release from an Ion-Exchange Resin

This report discloses the photochemical homolytic cleavage of iodine azide after its formation following release from polymer-bound bisazido iodate(I) anions. A series of radical reactions are reported including the 1,2-functionlization of alkenes and the unprecedented chemoselective oxidation of secondary alcohols in the presence of primary alcohols.

Photochemical Oxidation of Thioketones by Singlet Molecular Oxygen Revisited: Insights into Photoproducts, Kinetics, and Reaction Mechanism

Photosensitized oxidation of trimethyl[2.2.1]bicycloheptane thioketones by 1O2 can yield more photoproducts than exclusively ketones and sulfines. Moreover, the ketone/sulfine ratio can be reversed when protic conditions and high thioketone concentrations are used, conversely to earlier results reporting ketones as the main photoproducts. A new mechanistic proposal for sulfine formation is suggested following intermolecular oxygen transfer from a peroxythiocarbonyl intermediate to a second thioketone molecule. Reaction quantum yields (10-5-10-2) depend on the reaction conditions and time. Sulfine production reaches a maximum at short irradiation times, whereas decomposition to the corresponding ketone is observed at long reaction times. When the thioketone substrate has a hydrogen atom at the α position a peroxyvinylsulfenic acid intermediate can be formed by proton transfer. Reaction of this intermediate with another thioketone molecule can yield more sulfine and its tautomeric vinylsulfenic acid, which dimerizes in situ to the thiosulfinate. The hydroperoxyl group of the peroxyvinylsulfenic acid can also rearrange to the α position, and by reaction with the starting thioketone, α-hydroxy thioketone and additional sulfine can be formed, while dehydration yields the α-oxo thioketone. In situ [2 + 2] and [4 + 2] self-cycloaddition of the α-oxo thioketone yields significant amounts of the corresponding adducts at prolonged irradiation times.

4-Benzamido-TEMPO catalyzed oxidation of a broad range of alcohols to the carbonyl compounds with NaBrO3 under mild conditions

4-Benzamido-TEMPO catalyzed oxidation system for conversion of a wide range of alcohols to the aldehydes or ketones with NaBrO3 under room temperature conditions has been developed. The credible, operationally convenient and economical, and condition mild oxidation protocol is particularly of interest in laboratory and in fine chemicals manufacture. 4-Benzamido-TEMPO catalyzed oxidation system for conversion of a wide range of alcohols to the aldehydes or ketones with NaBrO3 as oxidant under room temperature conditions has been developed. Copyright

Direct amination of bio-alcohols using ammonia

A slightly adapted catalyst system has been successfully applied in the direct amination of primary and secondary alcohols. Moreover, the applicability to diols has been shown, giving high selectivity towards the primary diamines. It was found that the Ru/P ratio as well as the amount of ammonia used are highly important in this system, especially for higher substrate loadings. The catalyst was employed on a larger batch scale for the conversion of isomannide to the corresponding diamine. Additionally, it was shown that the catalyst is stable for at least six consecutive runs. No significant loss of activity and selectivity was observed.

9-azanoradamantane N-Oxyl (Nor-AZADO): A highly active organocatalyst for alcohol oxidation

A highly active organocatalyst for alcohol oxidation has been developed. 9-Azanoradamantane N-oxyl (Nor-AZADO 4), constituting an unhindered, stable nitroxyl radical, exhibits superior catalytic activity to 2,2,6,6- tetramethylpiperidine-1-oxyl (TEMPO) and AZADOs in the oxidation of alcohols to their corresponding carbonyl compounds.

Fenchyl substituted 1,2-dioxetanes as an alternative to adamantyl derivatives for bioanalytical applications

The synthesis and study of the chemiluminescence parameters and thermal stability of 1,2-dioxetanes containing a spirofenchyl substituent are reported. Three fenchyl-substituted 1,2-dioxetanes were synthesized by photooxygenation of the corresponding alkenes, obtained by Barton-Kellogg olefination of the readily available (-)-fenchone. The fenchyl-substituted 1,2-dioxetanes showed thermal stabilities similar to those of the corresponding spiroadamantyl- substituted derivatives, although being slightly more labile with respect to unimolecular decomposition than the latter derivatives, which are widely utilized as labels in a great variety of chemiluminescent immunoassays. Fluoride induced decomposition of one triggerable fenchyl 1,2-dioxetane derivative showed kinetic parameters similar to those of the corresponding adamantyl-substituted derivative. The chemiluminescence quantum yields in the one percent range are also similar to that of other widely utilized chemiluminescence systems as the luminol reaction. These results indicate that fenchyl-substituted 1,2-dioxetanes can potentially be utilized as a cheaper alternative to substitute the corresponding spiroadamantyl derivatives in bioanalytical applications.

N,N′-Dichlorobis(2,4,6-trichlorophenyl)urea (CC-2): An efficient reagent for conversion of oximes to ketones

A method for the rapid conversion of oximes into the corresponding carbonyl compounds using N,N′-dichlorobis (2,4,6-trichlorophenyl)urea (CC-2) at room temperature is described. The method is economical as the solid by-product bis(2,4,6-trichlorophenyl)urea could be removed by filtration and recycled after re-chlorination.

First isolation of cis- and trans-1,3,4-selenadiazolines from pivarophenone hydrazones

Sterically congested cis- and trans-1,3,4-selenadiazolines were isolated by one-pot reaction of pivalophenone hydrazones with diselenium dibromide, which suggested in situ formation of selenoketone and diazoalkane intermediates. Thermolysis of these compounds gave symmetrical olefins, whereas oxidation afforded the corresponding azines.

A very mild and chemoselective oxidation of alcohols to carbonyl compounds

matrixpresented Efficient oxidation of primary alcohols and β-amino alcohols to the corresponding aldehydes and α-amino aldehydes can be carried out at room temperature and in methylene chloride, using trichloroisocyanuric acid in the presence of catalytic TEMPO: aliphatic, benzylic, and allylic alcohols, and β-amino alcohols are rapidly oxidized without no overoxidation to carboxylic acids. Secondary carbinols are slowly oxidized so that the reaction is highly chemoselective.