19822-67-4

Basic information

• Product Name: 2,2,5-trimethyl-4-cyclohepten-1-one
• Synonyms: 2,2,5-trimethyl-4-cyclohepten-1-one;Karahanaenone;Einecs 243-351-7
• CAS NO: 19822-67-4
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.23344
• EINECS: 243-351-7
• Mol File: 19822-67-4.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 213.5°Cat760mmHg
• Flash Point: 77.8°C
• Appearance: /
• Density: 0.893g/cm³
• Vapor Pressure: 0.163mmHg at 25°C
• Refractive Index: 1.452
• CAS DataBase Reference: 2,2,5-trimethyl-4-cyclohepten-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2,5-trimethyl-4-cyclohepten-1-one(19822-67-4)
• EPA Substance Registry System: 2,2,5-trimethyl-4-cyclohepten-1-one(19822-67-4)

Safety Data

• Hazardous Substances Data: 19822-67-4(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 99, p. 4192, 1977 DOI: 10.1021/ja00454a066Tetrahedron Letters, 18, p. 2633, 1977

InChI:InChI=1/C10H16O/c1-8-4-5-9(11)10(2,3)7-6-8/h6H,4-5,7H2,1-3H3

Upstream product

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• 97277-67-3 1-(5-ethynyl-5-methyl-2-tetrahydrofuranyl)-1-methylethanol 
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Downstream Products

• 163188-34-9 N-p-hydroxyphenyl-3,3,6-trimethyl-5-cyclohepten-2-one-1-carboxamide 

Relevant articles and documents

Chemoenzymatic synthesis of homochiral (R)- and (S)-karahanaenol from (R)-limonene

Terpinolene oxide, a monoterpene belonging to the p-menthane group, is easily derived from naturally abundant (R)-limonene. It was isomerized with montmorillonite clay catalyst to karahanaenone (2,2,5-trimethylcyclohept-4- en-1-one) by ring enlargement. The enantiomers of the corresponding alcohol, karahanaenol (2,2,5-trimethylcyclohept-4-en-1-ol), known for their individual organoleptic properties, were resolved through Pseudomonas cepacia lipase mediated enantiospecific alcoholysis of its acetate derivative.

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Olefin metathesis in supercritical carbon dioxide

Liquid or supercritical carbon dioxide (scCO2) is a versatile reaction medium for ring-opening metathesis polymerization (ROMP) and ring-closing olefin metathesis (RCM) reactions using well-defined metal catalysts. The molybdenum alkylidene complex 1 and ruthenium carbenes 2 and 3 bearing PCy3 or N-heterocyclic carbene ligands, respectively, can be used and are found to exhibit efficiency similar to that in chlorinated organic solvents. While compound 1 is readily soluble in scCO2, complexes 2 and 3 behave like heterogeneous catalysts in this reaction medium. Importantly, however, the unique properties of scCO2 provide significant advantages beyond simple solvent replacement. This pertains to highly convenient workup procedures both for polymeric and low molecular weight products, to catalyst immobilization, to reaction tuning by density control (RCM versus acyclic diene metathesis polymerization), and to applications of scCO2 as a protective medium for basic amine functions. The latter phenomenon is explained by the reversible formation of the corresponding carbamic acid as evidenced by 1H NMR data obtained in compressed CO2. Together with its environmentally and toxicologically benign character, these unique physicochemical features sum up to a very attractive solvent profile of carbon dioxide for sustainable synthesis and production.

Olefin metathesis in compressed carbon dioxide

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