547-60-4

Usage

Uses

Used in Chemical Synthesis:
(1alpha,2alpha,5alpha)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one is used as a key intermediate in the synthesis of various chemical compounds, particularly in the field of organic chemistry. Its unique structure and functional groups make it a valuable building block for creating new molecules with potential applications in various industries.
Used in Pharmaceutical Industry:
(1alpha,2alpha,5alpha)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one is used as a potential pharmaceutical candidate for the development of new drugs. Its complex structure and functional groups may offer unique interactions with biological targets, leading to the discovery of novel therapeutic agents.
Used in Fragrance Industry:
(1alpha,2alpha,5alpha)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one is used as a fragrance ingredient in the perfumery industry. Its unique scent profile and stability make it a valuable component in the creation of new fragrances and perfumes.
Used in Material Science:
(1alpha,2alpha,5alpha)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one is used as a component in the development of new materials with specific properties, such as improved thermal stability or enhanced chemical resistance. Its incorporation into polymers or other materials can lead to the creation of innovative products with unique characteristics.

InChI:InChI=1S/C10H16O/c1-6-8-4-7(5-9(6)11)10(8,2)3/h6-8H,4-5H2,1-3H3

Upstream product

• 80-56-8 Pinene 
• 473-55-2 2,6,6-trimethylbicyclo[3.1.1]heptane 
• 1686-14-2 α-pinene epoxide 
• 217320-94-0 2-Pinene oxide 
• 1686-14-2 2α,3α-epoxypinane 
• 51152-11-5 (1R*,2R*,3R*,5S*)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ol 
• 473-61-0 (1RS:2SR:3RS)-Pinanol-⁽³⁾ 
• 64-19-7 acetic acid 
• 80-56-8 rac-α-pinene 
• 473-61-0 (1S*,2R*,3R*)-2,6,6-Trimethylbicyclo<3.1.1>heptan-3-ol 

Downstream Products

• 1845-25-6 (-)-(2R,3R,5R)-2-hydroxy-3-pinanone 
• 141243-74-5 (+)-(1R,2R)-2,7,7-Trimethyl-3-oxabicyclo<4.1.1>octan-4-one 

Relevant academic research and scientific papers

Synthesis of bimetallic Zr(Ti)-naphthalendicarboxylate MOFs and their properties as Lewis acid catalysis

Bimetallic Zr(Ti)-NDC based metal-organic frameworks (MOFs) have been prepared by incorporation of titanium(iv) into zirconium(iv)-NDC-MOFs (UiO family). The resulting materials maintain thermal (up to 500 °C), chemical and structural stability with respect to parent Zr-MOFs as can be deduced from XRD, N2 adsorption, FTIR and thermal analysis. The materials have been studied in Lewis acid catalyzed reactions, such as, domino Meerwein-Ponndorf-Verley (MPV) reduction-etherification of p-methoxybenzaldehyde with butanol, isomerization of α-pinene oxide and cyclization of citronellal.

Ring-opening of epoxides promoted by organomolybdenum complexes of the type [(η5-C5H4R)Mo(CO)2(η3-C3H5)] and [(η5-C5H5)Mo(CO)3(CH2R)]

The cyclopentadienyl molybdenum carbonyl complexes [(η5-C5H4R)Mo(CO)2(η3-C3H5)] and [(η5-C5H5)Mo(CO)3(CH2R)] (R = H, COOH) have been shown to promote acid-catalysed reactions in liquid phase, under moderate conditions. The catalytic alcoholysis of styrene oxide with ethanol at 35 °C gave 2-ethoxy-2-phenylethanol in 100% yield within 30 min for the dicarbonyl complexes and 3-6 h for the tricarbonyl complexes. Steady catalytic performances were observed in consecutive runs with the same catalytic solution, suggesting fairly good catalytic stability. In the second acid-catalysed reaction studied, the isomerization of α-pinene oxide at 55 °C gave campholenic aldehyde and trans-carveol in a total yield of up to 86% at 100% conversion. Chemoselectivity is shown to be solvent dependent.

Aminium Salts Catalyzed Rearrangement of α-Pinene and β-Ionone Oxides

β-ionone and α-pinene oxides 1,3 isomerize rapidly and selectively to 1-(1,2,2-trimethylcyclopent-1-yl)-pent-2-en-1,4-dione 2 and the industrially important 2,2,3-trimethyl-3-cyclopentene acetaldehyde 4, under the influence of catalytic amounts of aminium salts A, B.In order to find insights into the mechanism of our procedure, protic and Lewis acids-catalyzed rearrangements have also been reconsidered.

Studies on the Oxidation of cis- and trans-Pinane with Molecular Oxygen

The pinanes are preferably attacked at the tertiary C-H bond in 2-position, but products of the oxidative attack at the secondary C-H-bonds in 3- and 4-position are also found.At 100 deg C cis-pinane is attacked more easily than trans-pinane (kcis : ktrans = 6.4), the relative rates of attack at the secondary C-H bonds in positions 3 and 4 with respect to the tertiary C-H bond in 2-position were also determined (in cis-pinane ksec : ktert = 0.027; in trans-pinane ksec : ktert = 0.20).After the attack at the 2-C-H bond the radical formed can either react with oxygen to form the corresponding cis- and trans-peroxy radicals and further to give cis- and trans-2-hydroperoxy pinane or fragmentate to the monocyclic radical derived from α-terpinene, giving as a final products α-terpinene hydroperoxide and the bicyclic 8-hydroperoxy 4,4,8-trimethyl 2,3-dioxabicyclononane.The corresponding alcohols were found after reduction with sodium sulphite.The oxidation at position 2 of the pinanes delivers not only the cis- and trans-hydroperoxide but also, as short-lived intermediates, the corresponding 2-pinanyloxy radicals.These radicals fragmentate forming a carbon radical with cyclobutane structure whose oxidation products were identified.Besides fragmentation of the 2-pinanyloxy radical also an intramolecular H-transfer from the methyl group in 9-position to the oxygen of the trans-pinanyloxy radical takes place leading to 9-hydroperoxy trans-pinane-2-ol.

ORGANOBORANES FOR SYNTHESIS. 3. OXIDATION OF ORGANOBORANES WITH AQUEOUS CHROMIC ACID. A CONVENIENT SYNTHESIS OF KETONES FROM ALKENES VIA HYDROBORATION

Organoboranes react with alkaline hydrogen peroxide to provide a wide variety of alcohols.These alcohols can be taken up in ether solvent and converted without isolation into the corresponding ketones by treatment with chromic acid.Organoboranes can also be oxidized directly with chromic acid to the corresponding ketones.The chromic acid oxidation of organoboranes provides a new, convenient procedure for the synthesis of α-substituted cycloalkanones via hydroboration.The conversion of organoboranes into ketones proceeds through the intermediate alcohol.Representative cycloalkanones and α-methylcycloalkanones have been prepared from the corresponding alkenes via hydroboration, followed by chromic acid oxidation.