481660-32-6

Basic information

• Product Name: Spiro[bicyclo[2.2.1]heptane-2,2-oxirane], 3,3-dimethyl-, (1R,2S,4S)- (9CI)
• Synonyms: Spiro[bicyclo[2.2.1]heptane-2,2-oxirane], 3,3-dimethyl-, (1R,2S,4S)- (9CI)
• CAS NO: 481660-32-6
• Molecular Formula: C10H16O
• Molecular Weight: 152.23344
• Product Categories: CYCLOPENTANE
• Mol File: 481660-32-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Spiro[bicyclo[2.2.1]heptane-2,2-oxirane], 3,3-dimethyl-, (1R,2S,4S)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Spiro[bicyclo[2.2.1]heptane-2,2-oxirane], 3,3-dimethyl-, (1R,2S,4S)- (9CI)(481660-32-6)
• EPA Substance Registry System: Spiro[bicyclo[2.2.1]heptane-2,2-oxirane], 3,3-dimethyl-, (1R,2S,4S)- (9CI)(481660-32-6)

Safety Data

• Hazardous Substances Data: 481660-32-6(Hazardous Substances Data)

Upstream product

• 565-00-4 dl-camphene 
• 5794-04-7 camphene 
• 79-92-5 (+)-camphene 
• 93-59-4 Perbenzoic acid 
• 67-66-3 chloroform 
• 79-92-5 camphene 

Relevant articles and documents

Oxidation studies on some natural monoterpenes: Citral, pulegone, and camphene

Citral extracted from Cymbopogon citratus (Gramineae) was subjected to photochemical epoxidation with hydrogen peroxide to obtain a mixture of epoxy derivatives at the C2=C3 and C6=C7 double bonds. The thermal oxidation of citral with m-chloroperoxybenzoic acid at room temperature gave only the corresponding 6,7-epoxy derivative as a mixture of E and Z isomers with respect to the C2=C3 double bond. Photosensitized oxygenation of citral in the presence of tetraphenylporphyrin, Rose Bengal, or chlorophyll lead to a mixture of two isomeric hydroperoxides, (2E)-6-hydroperoxy-3,7-dimethylocta-2,7-dienal and (2E,5E)-7-hydroperoxy-3,7- dimethylocta-2,5-dienal. Epoxidation of pulegone isolated from Penny royal oil (Mentha pulegium, Lamiaceae) with hydrogen peroxide under irradiation with a sodium lamp lead to a mixture of cis- and trans-isomeric 2,2,6-trimethyl-1- oxaspiro[2.5]octan-4-ones, whereas under conditions of photosensitized oxygenation two hydroperoxide derivatives, 2-(1-hydroperoxy-1-methylethyl)-5- methylcyclohex-2-en-1-one and 2-hydroperoxy-5-methyl-2-(1-methylethenyl) cyclohexan-1-one, were also formed. Camphene reacted with hydrogen peroxide under irradiation to give a mixture of the corresponding endo- and exo-epoxy derivatives and camphor, while its thermal oxidation with m-chloroperoxybenzoic produced only the two former.

Catalytic epoxidation of camphene using methyltrioxorhenium(VII) as catalyst

This work presents the epoxidation of camphene employing methyltrioxorhenium(VII) (MTO) as catalyst. The effect of different factors on the formation of camphene oxide with respect to high yield and selectivity was investigated. First, the ratio camphene:MTO:pyrazole:H2O2 was studied in dichloromethane as solvent in order to determine the optimal condition. Moreover, the influence of the Lewis base adduct (tert-butylpyridine, 4,4′-dimethyl-2,2′-bypridine, imidazole or pyrazole) was investigated. The effect of an aqueous oxidant, namely H2O 2 and a solid oxidant, namely urea hydrogen peroxide (UHP) was also examined. Finally, the solvent was varied from dichloromethane to chloroform, toluene and nitromethane. Based on the results the optimal conditions for the epoxidation of camphene using MTO as catalyst were determined. The molar ratio camphene:MTO:pyrazole:H2O2 of 100:0.5:10:110 in dichloromethane at room temperature leads after 3 h to 97% yield and 98% selectivity toward camphene oxide at 99% conversion.

Development of a lipase-mediated epoxidation process for monoterpenes in choline chloride-based deep eutectic solvents

Chemical syntheses in contemporary process industries today are predominantly conducted using organic solvents, which are potentially hazardous to humans and the environment alike. Green chemistry was developed as a means to overcome this hazard and it also holds enormous potential for designing clean, safe and sustainable processes. The present work incorporates the concepts of green chemistry in its design of a lipase-mediated epoxidation process for monoterpenes; the process uses alternative reaction media, namely deep eutectic solvents (DESs), which have not been reported for such an application before. Choline chloride (ChCl), in combination with a variety of hydrogen bond donors (HBD) at certain molar ratios, was screened and tested for this purpose. The process was optimized through the design of experiments (DoE) using the Taguchi method for four controllable parameters (temperature, enzyme amount, peroxide amount and type of substrate) and one uncontrollable parameter (DES reaction media) in a crossed-array design. Two distinct DESs, namely glycerol:choline chloride (GlCh) and sorbitol:choline chloride (SoCh), were found to be the best systems and they resulted in a complete conversion of the substrates within 8 h. Impurities (esters) were found to form in both the DESs, which was a concern; as such, we developed a novel minimal DES system that incorporated a co-substrate into the DES so that this issue could be overcome. The minimal DES consisted of urea·H2O2 (U·H2O2) and ChCl and exhibited better results than both the GlCh and SoCh systems; complete conversions were achieved within 2 h for 3-carene and within 3 h for both limonene and α-pinene. Product isolation with a simple water/ethyl acetate based procedure gave isolated yields of 87.2 ± 2.4%, 77.0 ± 5.0% and 84.6 ± 3.7% for 3-carene, limonene and α-pinene respectively.

"kick-Starting" oxetane photopolymerizations

In the presence of small amounts of 2,2-dialkyl-, 2,2,3-trialkyl-, or 2,2,3,3-tetraalkyl substituted epoxides such as isobutylene oxide, 1,2-limonene oxide, and 2,2,3,3,-tetramethyl oxirane, the photoinitiated cationic ring-opening polymerizations of 3,3-disubstituted oxetanes are dramatically accelerated. The acceleration affect was attributed to an increase in the rate of the initiation step of these latter monomers. Both mono- and disubstituted oxetane monomers are similarly accelerated by the above-mentioned epoxides to give crosslinked network polymers. The potential for the use of such "kick-started" systems in applications such as coatings, adhesives, printing inks, dental composites and in three-dimensional imaging is discussed.

Organocatalyzed epoxidation of alkenes in continuous flow using a multi-jet oscillating disk reactor

The times are changing: A batch process, the Minisci epoxidation, is transformed into a continuous-flow protocol for the selective aerobic radical epoxidation of alkenes. The use of a novel reactor type allows to considerably shorten reactor residence times. Experimental results suggest that two different reaction mechanisms exist for the oxidation: one for the batch conditions and a different one for flow synthesis protocol. Copyright

METHOD FOR MANUFACTURING AN EPOXY COMPOUND AND METHOD FOR EPOXIDIZING A CARBON-CARBON DOUBLE BOND

The present invention provides a method for producing an epoxy compound, comprising oxidizing a carbon-carbon double bond of an organic compound by hydrogen peroxide in the presence of a neutral inorganic salt and a mixed catalyst of a tungsten compound (a), at least one phosphorus compound selected from the group consisting of phosphoric acids, phosphonic acids, and salts thereof (b) and a surfactant (c), and an epoxidizing method comprising oxidizing a carbon-carbon double bond by hydrogen peroxide in the presence of the catalyst and the neutral inorganic salt.

Acid-catalyzed reactions of camphene and α-fenchene epoxides

Isomerization of camphene and α-fenchene epoxides under homogeneous and heterogeneous conditions in media of various acidity was studied. The intermolecular reactions of these epoxy compounds with unsaturated aldehydes, allyl alcohol and methanol on askanite-bentonite clay yielded spiroacetals, and open-chain hydroxyethers and acetals. The results obtained are compared to those for reactions with the initial monoterpenes.

Mn (Br8TPPS) supported on Amberlite IRA-400 as a robust and efficient catalyst for alkene epoxidation and alkane hydroxylation

Manganese (III) meso-tetrakis(p-sulfonatophenyl)-β-octabromoporphyrin (supported on Amberlite IRA-400 [Mn(Br8TPPS)-Ad-400] is a robust and efficient catalyst for epoxidation of alkenes and hydroxylation of alkanes with sodium periodate at room temperature.

Manganese(III) porphyrin supported on polystyrene as a heterogeneous alkene epoxidation and alkane hydroxylation catalyst

Carboxymethylated crosslinked polystyrene resin [poly(4-styrylmethylacylchloride) (PSA)] support have been used to covalently attach manganese(III) tetrakis(4-aminophenyl)-porphyrin. This catalyst was found to be efficient for alkene epoxidation and alkane hydroxylation by sodium periodate. This new hydrogenised catalyst is of high stability and reusability.

NaY zeolite as host for the selective heterogeneous oxidation of silanes and olefins with hydrogen peroxide catalyzed by methyltrioxorhenium

The methyltrioxorhenium(MTO)-catalyzed oxidation of silanes to silanols and the epoxidation of various olefins by aqueous 85% H2O2 proceed in high yields and excellent product selectivities (no disiloxanes, diols) in the presence of the zeolite NaY. The oxidative species is located inside the 12- A supercages. This prevents the bimolecular condensation of the silanol to disiloxane by steric means and the Lewis-acid assisted hydrolysis of the epoxide to the diol.