4-Oxoadamantane-1-carboxylic acid

Base Information

• Chemical Name: 4-Oxoadamantane-1-carboxylic acid
• CAS No.: 56674-87-4
• Molecular Formula: C10H14O3
• Molecular Weight: 194.23
• Hs Code.: 2918300090
• European Community (EC) Number: 689-257-3
• DSSTox Substance ID: DTXSID80385706
• Mol file: 56674-87-4.mol

Synonyms:4-Oxoadamantane-1-carboxylic acid;56674-87-4;2-Adamantanone-5-carboxylic acid;4-OXO-1-ADAMANTANECARBOXYLIC ACID;2-Adamantone-5-carboxylic acid;Tricyclo[3.3.1.13,7]decane-1-carboxylic acid, 4-oxo-;5-Carboxy-2-Adamantanone;ChemDiv3_000437;MFCD01825769;1-carboxy-4-adamantanone;1-carboxyadamantan-4-one;Oprea1_199202;SCHEMBL328950;4-Oxoadamantane-1-carboxylicacid;4-Oxoadamantan-1-carboxylic acid;DTXSID80385706;HMS1474D19;4-Oxo-adamantane-1-carboxylic acid;AKOS001031984;AKOS016344196;CS-W001595;FS-3056;NCGC00174864-01;NCGC00174864-02;SY021305;AM20070535;BB 0259746;FT-0650477;EN300-53672;AB01225109-03;Not available;4-Oxo-1-adamantanecarboxylic Acid;A851735;SR-01000400502;J-515913;SR-01000400502-1;BRD-A69621249-001-01-7;Z56762234

Chemical Property of 4-Oxoadamantane-1-carboxylic acid

Chemical Property:

• Vapor Pressure: 2.07E-06mmHg at 25°C
• Melting Point: 169.5-171.0 °C(Solv: ethyl ether (60-29-7))
• Refractive Index: 1.591
• Boiling Point: 367.6 °C at 760 mmHg
• PKA: 4.45±0.20(Predicted)
• Flash Point: 190.3 °C
• PSA: 54.37000
• Density: 1.358g/cm³
• LogP: 1.46640
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 194.094294304
• Heavy Atom Count: 14
• Complexity: 303

Purity/Quality:

99%min ^*data from raw suppliers

2-Adamantanone-5-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2CC3CC(C2)(CC1C3=O)C(=O)O
• Uses: 2-Adamantanone-5-carboxylic Acid is a reactant used in the synthesis of potent inhibitors targeting the drug-resistant mutant of Influenze A. Starting material for Saxagliptin impurities.

Technology Process of 4-Oxoadamantane-1-carboxylic acid

There total 2 articles about 4-Oxoadamantane-1-carboxylic acid 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: 12.0%

1-Adamantanecarboxylic acid (828-51-3) → 4-oxoadamantane-1-carboxylic acid (56674-87-4) + 4-hydroxyadamantane-1-carboxylic acid (81968-77-6) + 3-hydroxyadamantane-1-carboxylic acid (42711-75-1)

Guidance literature:

With sodium hydroxide; phosphate buffer; oxygen; iron(II) sulfate; In water; at 40 ℃; for 3h; Product distribution; investigation of the oxy-functionalization of adamantane-1-carboxylic acid;

Reference yield:

1-Adamantanecarboxylic acid (828-51-3) → 4-oxoadamantane-1-carboxylic acid (56674-87-4) + 3-hydroxyadamantane-1-carboxylic acid (42711-75-1)

Guidance literature:

With tert.-butylhydroperoxide; C₆₀H₆₆N₁₈*3Fe⁽²⁺⁾*3O₄S^(2-); In water; at 60 ℃; for 24h;

DOI:10.1080/10610278.2016.1177184

Reference yield: 89.0%

4-oxoadamantane-1-carboxylic acid (56674-87-4) + benzyl bromide (100-39-0) → (phenylmethyl) 4-oxo-1-adamantanecarboxylate

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

upstream raw materials:

1-Adamantanecarboxylic acid

Downstream raw materials:

methyl 4-oxoadamantane-1-carboxylate

4-hydroxyadamantane-1-carboxylic acid

trans-4-aminoadamantane-1-carboxylic acid

4-amino-adamantane-1-carboxylic acid methyl ester

Refernces

• 1、 Miura, Toshiaki,Shibata, Kunihiko,Sawaya, Takuji,Kimura, Michiya. "Oxy-Functionalization of Adamante-1-acetic Acid and Adamantane-1-carboxylic Acid by the Ferrous Iron-Molecular Oxygen System in Aqueous Solution". . p. 67 - 73. Retrieved 2007/10/02.