547-60-4

Basic information

• Product Name: (1alpha,2alpha,5alpha)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one
• Synonyms: (1alpha,2alpha,5alpha)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one;Bicyclo3.1.1heptan-3-one, 2,6,6-trimethyl-, (1R,2S,5S)-rel-;3-PINANONE;trans-2,6,6-Trimethylbicyclo[3.1.1]heptan-3-one;2,6,6-trimethylnorpinan-3-one;2,7,7-trimethylbicyclo[3.1.1]heptan-3-one
• CAS NO: 547-60-4
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.23344
• EINECS: 208-926-9
• Mol File: 547-60-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 212°Cat760mmHg
• Flash Point: 72.8°C
• Appearance: /
• Density: 0.95g/cm³
• CAS DataBase Reference: (1alpha,2alpha,5alpha)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: (1alpha,2alpha,5alpha)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one(547-60-4)
• EPA Substance Registry System: (1alpha,2alpha,5alpha)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one(547-60-4)

Safety Data

• Hazardous Substances Data: 547-60-4(Hazardous Substances Data)

Usage

General Description

"(1alpha,2alpha,5alpha)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one" is a chemical compound with a complex structure featuring two bridging carbon atoms that form a bicyclic structure. The bicyclic structure consists of a six-membered ring and a three-membered ring. The molecule also contains three alpha-oriented methyl groups on the second and sixth carbon atoms and a ketone group at the third carbon atom. (1alpha,2alpha,5alpha)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-one belongs to the class of organic compounds known as tricyclic compounds, specifically tricyclic monoterpenoids. These are monoterpenes containing exactly three rings, where the parent system is derived from a carbocyclic compound. Detailed study is necessary to determine the physical properties, potential uses and safety parameters of this compound.

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

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

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 articles and documents

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.

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.

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.