56246-58-3

Usage

Uses

Used in Pharmaceutical Industry:
[1R-(1alpha,2alpha,5alpha)]-6,6-dimethylspiro[bicyclo[3.1.1]heptane-2,2'-oxirane] is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique structure and reactivity make it a valuable building block for the development of new drugs with potential therapeutic applications.
Used in Fragrance Industry:
In the fragrance industry, [1R-(1alpha,2alpha,5alpha)]-6,6-dimethylspiro[bicyclo[3.1.1]heptane-2,2'-oxirane] is used as a key component in the creation of unique and complex scents. Its distinct chemical properties contribute to the development of novel fragrances with appealing olfactory profiles.
Used in Chemical Synthesis:
[1R-(1alpha,2alpha,5alpha)]-6,6-dimethylspiro[bicyclo[3.1.1]heptane-2,2'-oxirane] is utilized as a versatile building block in organic synthesis, allowing for the development of a wide range of chemical products. Its unique structure and reactivity enable the synthesis of various compounds with potential applications in different industries, such as materials science, agrochemicals, and specialty chemicals.
Used in Research and Development:
Due to its unique structure and potential applications, [1R-(1alpha,2alpha,5alpha)]-6,6-dimethylspiro[bicyclo[3.1.1]heptane-2,2'-oxirane] is also used in research and development settings. Scientists and researchers can explore its properties and reactivity to develop new methodologies, synthetic routes, and applications in various fields.

Upstream product

• 18172-67-3 beta-pinene 
• 177698-19-0 Beta-pinene 

Downstream Products

• 19894-91-8 (S)-4-(1-hydroxy-1-methylethyl)-1-cyclohexene-1-methanol 
• 536-59-4 (-)-perillyl alcohol 
• 1116113-12-2 (1R,2S,5S)-6,6-dimethyl-2-(phenylselanylmethyl)bicyclo[3.1.1]heptan-2-ol 
• 100692-55-5 dihydroperilla alcohol 
• 83921-02-2 7-hydroxy-α-terpineol 
• 23963-70-4 (S)-4-Isopropyl-cyclohex-1-enecarbaldehyde 
• 4764-14-1 cis-myrtanal 
• 51152-12-6 (-)-cis-myrtanol 
• 128301-02-0 (1S,2S,5S)-(+)-6,6-dimethylbicyclo[3.1.1]heptane-2-carboxaldehyde 
• 19894-97-4 (1R)-Myrtenol 
• 15111-96-3 (S)-(4-(prop-1-en-2-yl)cyclohex-1-en-1-yl)methyl acetate 
• 100053-22-3 (S)-7-formyloxy-p-menth-1-en-8-ol 
• 65221-01-4 7-acetoxy-p-menth-1-en-8-ol 
• 57717-97-2 (R)-Perillyl alcohol 

Relevant academic research and scientific papers

7,7-Dimethyl-2,10-epoxybicyclo[3.1.1]heptane. Synthesis, structure, and products of epoxide ring cleavage

7,7-Dimethyl-2,10-epoxybicyclo[3.1.1]heptane obtained by treatment of (-)-β-pinene with peroxybenzimidic acid has α configuration.

Synthesis of sulfur-containing bis-terpenoids based on monoterpene oxides

Ethanedithiol and di(mercaptoethyl)sulfide react regio- and stereoselectively with (+)-3-carene and α-hydroxy(-)-β-pinene β-oxides in the presence of sodium ethoxide to give the corresponding bis- and tris-sulfides with two terpene fragments.

Sustainable catalytic epoxidation of biorenewable terpene feedstocks using H2O2as an oxidant in flow microreactors

Solvent-free continuous flow epoxidation of the alkene bonds of a range of biorenewable terpene substrates have been carried out using a recyclable tungsten-based polyoxometalate phase transfer catalyst and aqueous H2O2 as a benign oxidant. These sustainable flow epoxidation reactions are carried out in commercial microreactors containing static mixing channels that enable common monoterpenes (e.g. untreated crude sulfate turpentine, limonene, etc.) to be safely epoxidized in short reaction times and in good yields. These flow procedures are applicable for the flow epoxidation of trisubstituted and disubstituted alkenes for the safe production of multigram quantities of a wide range of epoxides. This journal is

Sustainable catalytic protocols for the solvent free epoxidation and: Anti -dihydroxylation of the alkene bonds of biorenewable terpene feedstocks using H2O2 as oxidant

A tungsten-based polyoxometalate catalyst employing aqueous H2O2 as a benign oxidant has been used for the solvent free catalytic epoxidation of the trisubstituted alkene bonds of a wide range of biorenewable terpene substrates. This epoxidation protocol has been scaled up to produce limonene oxide, 3-carene oxide and α-pinene oxide on a multigram scale, with the catalyst being recycled three times to produce 3-carene oxide. Epoxidation of the less reactive disubstituted alkene bonds of terpene substrates could be achieved by carrying out catalytic epoxidation reactions at 50 °C. Methods have been developed that enable direct epoxidation of untreated crude sulfate turpentine to afford 3-carene oxide, α-pinene oxide and β-pinene oxide. Treatment of crude epoxide products (no work-up) with a heterogeneous acid catalyst (Amberlyst-15) results in clean epoxide hydrolysis to afford their corresponding terpene-anti-diols in good yields.

Syntheses and reactions of terpene β-hydroxyselenides and β-hydroxydiselenides

A convenient method for the synthesis of optically active trans-hydroxyselenides and trans-hydroxydiselenides from the bicyclic terpene group based on the reactions of sodium selenide or sodium diselenide with cis- and trans-(+)-3-carane, trans-(+)-2-carane and (-)-β-pinane epoxides is described. The corresponding cis-hydroxy and cis-methoxydiselenides were obtained in the reaction of sodium diselenide with β-hydroxy- and β-methoxytosylates. The influence of a hydroxy group at the β-position on the diastereomeric ratio of the products of the asymmetric methoxyselenenylation of styrene has been established by composition of the products, crystal structure analyses, and theoretical calculations using a DFT method on the B3LYP level (6-311G(d)).

Opening of epoxide rings catalyzed by niobium pentachloride

The behavior of several epoxides when treated with NbCl5 was studied. In general, the studied epoxides reacted rapidly with NbCl5, giving, in most cases, more than one product (chlorohydrins, products containing solvent residues, as well as rearrangement products). A detailed study was performed to verify the effects of the temperature (rt, 0°C, or -78°C) and of the NbCl5 molar concentration on the composition of the products, yield, and time required for the reactions. Copyright Taylor & Francis Group, LLC.

Selective epoxidation of monoterpenes with methyltrioxorhenium and H2O2

In the presence of pyridine as a co-catalyst, CH3ReO3 catalyses the epoxidation of terpenes such as α-pinene with H2O2 with minimal rearrangement of the epoxide. Pyridine is also critical to suppress isomerisation of the olefin substrate (in case of nerol, geraniol). The reaction can be directed towards selective single or double epoxidation, or in one step towards the rearranged product (e.g. from linalool to the ring- closure product linalool oxide.

Cyclobutane Ring Opening of Pin-2(10)-ene with Mercury(II) Salts. A New, High-yield Synthesis of p-Mentha-1,8-dien-7-ol

The nucleophilic attack of pin-2(10)-ene-mercury(II) complex systems by water results in the opening of the four-membered ring leading to an allylic organomercury(II) derivative (11) with the p-menthane skeleton.This intermediate can be reduced by hydride to p-menth-1(2)-en-8-ol (6a) or can undergo an in situ SE2' elimination yielding p-menth-1(7)-en-8-ol (9a), in high yields. (-)-2,10-Epoxypinane (15) reacts with mercury(II) salts at room temperature, giving the diol (16) in a quantitative yield.Compound (16) is a suitable intermediate for convenient preparation of p-mentha-1,8-dien-7-ol (17) and its derivatives.