3,5-Diazatetracyclo[7.3.1.17,11.01,6]tetradecan-4-one

Base Information

• Chemical Name: 3,5-Diazatetracyclo[7.3.1.17,11.01,6]tetradecan-4-one
• CAS No.: 27174-89-6
• Molecular Formula: C12H18N2O
• Molecular Weight: 206.28
• DSSTox Substance ID: DTXSID101201406
• Mol file: 27174-89-6.mol

Synonyms:27174-89-6;DTXSID101201406;Decahydro-2H-4a,8:6,10-dimethanocyclooctapyrimidin-2-one

Chemical Property of 3,5-Diazatetracyclo[7.3.1.17,11.01,6]tetradecan-4-one

Chemical Property:

• XLogP3: 1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 206.141913202
• Heavy Atom Count: 15
• Complexity: 314

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1C2CC3CC1CC4(C2)C3NC(=O)NC4

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.