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:

adamantan-2-ylideneacetonitrile

N-(2-Adamantyl)-2-pyrrolidone

Benzyloxy-(2-hydroxy-adamantan-2-yl)-acetic acid

N-(Adamantylidentosylmethyl)-formamid

Refernces

• 1、 Bailey, William F.,Bartelson, Ashley L.,Wiberg, Kenneth B.. "Contrasting reactions of ketones and thioketones with alkyllithiums: A coordinated experimental and computational investigation". . p. 3199 - 3207. Retrieved 2012.
• 2、 Cao, Jian,Campbell, James,Liu, Li,Mason, Ralph P.,Lippert, Alexander R.. "In Vivo Chemiluminescent Imaging Agents for Nitroreductase and Tissue Oxygenation". . p. 4995 - 5002. Retrieved 2016.
• 3、 Bietti, Massimo,Dilabio, Gino A.,Galeotti, Marco,Groff, Benjamin D.,Mayer, James M.,Romero-Montalvo, Eduardo,Salamone, Michela,Van Santen, Jeffrey A.. "Bimodal Evans-Polanyi Relationships in Hydrogen Atom Transfer from C(sp3)-H Bonds to the Cumyloxyl Radical. A Combined Time-Resolved Kinetic and Computational Study". . p. 11759 - 11776. Retrieved 2021.
• 4、 Voloshin, A. I.,Sharipov, G. L.,Kazakov, V. P.,Tolstikov, G. A.. "MECHANISM OF ACTIVATION AND CATALYSIS OF CHEMILUMINESCENCE BY Eu(fod)3 CHELATE IN THERMAL DECOMPOSITION OF ADAMANTYLIDENEADAMANTANE-1,2-DIOXETANE". . p. 828 - 834. Retrieved 1992.
• 5、 Kazakov,Voloshin,Ostakhov,Zharinova. "Chemiluminescence and catalysis of decomposition of dispiro(diadamantane-1,2-dioxetane) in the presence of EuIII and TbIII tris(benzoyltrifluoroacetonate) complexes". . p. 386 - 393. Retrieved 1998.
• 6、 Meyer, Matthew M.,Kass, Steven R.. "Enolates in 3-D: An experimental and computational study of deprotonated 2-adamantanone". . p. 4274 - 4279. Retrieved 2010.
• 7、 Kazakov,Voloshin,Ostakhov,Khusainova,Zharinova. "Photocatalytic decomposition of dispiro(diadamantane-1,2-dioxetane) initiated by Ce(ClO4)3 in the excited state". . p. 693 - 698. Retrieved 1997.
• 8、 Ivleva, E. A.,Klimochkin, Yu. N.,Skomorokhov, M. Yu.. "Kinetic Study of the Nitrolysis of Haloadamantanes". . . Retrieved 2020.
• 9、 Schmidt, Kerstin,Margaretha, Paul. "Photochemistry of spiro[6H-[1,3]oxathiin-2,2′-tricyclo[3.3.1.1 3.7]decan]-6-one". . p. 1906 - 1911. Retrieved 2004.
• 10、 Adam, Waldemar,Bronstein, Irena,Edwards, Brooks,Engel, Thomas,Reinhardt, Dirk,Schneider, Friedemann W.,Trofimov, Alexei V.,Vasil'ev, Rostislav F.. "Electron exchange luminescence of spiroadamantane-substituted dioxetanes triggered by alkaline phosphatases. Kinetics and elucidation of pH effects". . p. 10400 - 10407. Retrieved 1996.