2-Adamantanone

Base Information

• Chemical Name: 2-Adamantanone
• CAS No.: 700-58-3
• Molecular Formula: C10H14O
• Molecular Weight: 150.221
• Hs Code.: 29142900
• European Community (EC) Number: 211-847-2
• NSC Number: 126345
• UNII: UI7W503L08
• DSSTox Substance ID: DTXSID9022108
• Nikkaji Number: J55.146E
• Wikipedia: Adamantanone
• Wikidata: Q27093191
• Metabolomics Workbench ID: 52256
• ChEMBL ID: CHEMBL2041316
• Mol file: 700-58-3.mol

Synonyms:Tricyclo[3.3.1.13,7]decanone;2-Oxoadamantane;tricyclo[3.3.1.1(3,7)]decan-2-one;2-Adamantantanone;Tricyclo(3,3,1,13,7)decanone;adamantan-2-one;Adamantanone;Tricyclo(3.3.1.13,7)decanone (9CI);Tricyclo(3.3.1.1(sup 3,7))decanone;Tricyclo(3.3.1.13,7)decan-2-one;

Chemical Property of 2-Adamantanone

Chemical Property:

• Appearance/Colour: white to off-white crystalline powder
• Vapor Pressure: 0.0267mmHg at 25°C
• Melting Point: 256-258 °C (subl.)(lit.)
• Refractive Index: 1.535
• Boiling Point: 246.7 °C at 760 mmHg
• Flash Point: 95.7 °C
• PSA: 17.07000
• Density: 1.105 g/cm³
• LogP: 2.01160
• Storage Temp.: Store below +30°C.
• Solubility.: methanol: 0.1 g/mL, clear
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 150.104465066
• Heavy Atom Count: 11
• Complexity: 177

Purity/Quality:

99%, ^*data from raw suppliers

2-?Adamantanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 52-36/37/38
• Safety Statements: 22-24/25-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C2CC3CC1CC(C2)C3=O
• Uses: 2-Adamantanone has been used as a probe for the dimensions and characteristics for the substrate binding pocket of alcohol dehydrogenases. 2-Adamantanone was used in the synthesis of dispiro N-Boc-protected 1,2,4-trioxane and (+/-)-1-(adamantan-2-yl)-2-propanamine.

Technology Process of 2-Adamantanone

There total 435 articles about 2-Adamantanone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.5%

adamantane (281-23-2) + 3,3-dimethyldioxirane (74087-85-7) → 2-Adamantanone (700-58-3) + 1-adamanthanol (768-95-6) + 1-adamantanol (700-57-2) + 1,3-adamantandiol (5001-18-3) + 1-acetyloxyadamantane (22635-62-7)

Guidance literature:

In acetone; at 20 ℃; for 7.6h; Rate constant; Product distribution; Kinetics;

DOI:10.1016/0040-4039(95)02140-X

Reference yield: 86.0%

adamantane (281-23-2) → 2-Adamantanone (700-58-3) + 1-adamanthanol (768-95-6) + 1,3-adamantandiol (5001-18-3)

Guidance literature:

With methyltrifluoromethyldioxirane; In dichloromethane; at -22 ℃; for 0.0166667h;

DOI:10.1021/ja00199a039

Reference yield: 70.0%

adamantane (281-23-2) → 2-Adamantanone (700-58-3) + 1-adamanthanol (768-95-6) + 1,3-adamantandiol (5001-18-3) + 1-chloro-3-hydroxyadamantane (772-26-9)

Guidance literature:

With tetrachloromethane; water; molybdenum hexacarbonyl; at 140 ℃; for 13h; Inert atmosphere;

DOI:10.1134/S1070428009080041

upstream raw materials:

pyridine

adamantane

3-Methyl-3-buten-2-one

adamantane-2-thione

Downstream raw materials:

homoadamantan-4-one

2,2-bis(phenylselenenyl)adamantane

2-(3-methylphenyl)-2-adamantanol

2-(4-Methylphenyl)-2-adamantanol

Refernces

Quinazolines. XXIII. The synthesis of 3,5 Diazatetracyclo [7,3,1,1,^7,11,0^1,6]tetradecanes (Adamantano [2,1-d]pyrimidines)

10.1071/CH9781769

The research focuses on the synthesis of various polycyclic quinazoline compounds, which are structural analogues of tetrodotoxin, a potent neurotoxin found in certain marine animals. The key intermediate used in the synthesis is 2-oxoadamantane-1-carboxamide (12), which is prepared from adamantan-2-one (7) through a series of reactions involving diazomethane, selenium dioxide, and thionyl chloride. The resulting intermediate (12) is then subjected to reductive amination to produce 2-amino-adamantane-1-carboxamide (14), which can be further transformed into various target compounds such as 3,5-diazatetracyclo[7,3,1,17~11,01~6]tetradecane-4-iminium sulfate (3), 3,5-diazatetracyclo[7,3,1,17~11,01~6]tetradecan-4-one (4), and 3,5-diazatetracyclo[7,3,1,17~11,01~6]tetradecane (5) dipicrate. Other related compounds like 3-oxa-4-azatetracyclo[6,3,1,16~10,O115]tridec-4-en-2-one (15) and 3,4-diazatetracyclo[6,3,1,16~10,O115]tridec-4-en-2-one (16) are also synthesized. The study aims to explore the stability and potential biological activities of these compounds, which are expected to be more stable than the toxin due to their cage-like structure.

6-(4′-Aryloxy-phenyl)vinyl-1,2,4-trioxanes: A new series of orally active peroxides effective against multidrug-resistant Plasmodium yoelii in Swiss mice

10.1016/j.bmcl.2010.06.045

The research focuses on the development of a new series of 6-(40-aryloxy-phenyl)vinyl-1,2,4-trioxanes, specifically compounds 10a–d, 11a–d, and 12a–d, which were synthesized and evaluated for their antimalarial activity against multidrug-resistant Plasmodium yoelii in Swiss mice via the oral route. The purpose of this study was to find structurally simpler, more affordable, and effective synthetic trioxanes that could combat multidrug-resistant malaria. The most active compounds in the series, trioxanes 10b and 10c, demonstrated 100% protection at a dose of 48 mg/kg over four days, comparable to the clinically useful drug β-arteether. The chemicals used in the synthesis process included various aryl alkoxyphenyl vinyl compounds, cyclopentanone, cyclohexanone, 2-adamantanone, and other reagents involved in the photooxygenation and acid-catalyzed condensation steps. The study concluded that cyclopentane-based trioxanes 10b and 10c showed promising activity profiles similar to that of β-arteether, indicating their potential as effective antimalarial agents.