214557-84-3

Basic information

• Product Name: 3,5,7-trifluoroadaMantane-1-carboxylic acid Methyl ester
• Synonyms: 3,5,7-trifluoroadaMantane-1-carboxylic acid Methyl ester
• CAS NO: 214557-84-3
• Molecular Formula: C₁₂H₁₅F₃O₂
• Molecular Weight: 248.2415096
• Mol File: 214557-84-3.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3,5,7-trifluoroadaMantane-1-carboxylic acid Methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5,7-trifluoroadaMantane-1-carboxylic acid Methyl ester(214557-84-3)
• EPA Substance Registry System: 3,5,7-trifluoroadaMantane-1-carboxylic acid Methyl ester(214557-84-3)

Safety Data

• Hazardous Substances Data: 214557-84-3(Hazardous Substances Data)

Upstream product

• 1426-93-3 methyl 3-fluoroadamantane-1-carboxylate 
• 214557-81-0 methyl 3,5-difluoroadamantane-1-carboxylate 
• 214557-80-9 methyl 3-fluoro-5-hydroxyadamantane-1-carboxylate 
• 68435-07-4 1-methoxycarbonyl-3-hydroxyadamantane 
• 711-01-3 methyl adamantane-1-carboxylate 
• 214557-86-5 methyl 3,5-difluoro-7-hydroxyadamantane-1-carboxylate 

Downstream Products

• 214557-89-8 3,5,7-trifluoroadamantane-1-carboxylic acid 
• 214557-91-2 benzyl 3,5,7-trifluoroadamantane-1-carbamate 

Relevant articles and documents

Selective introduction of fluorine atoms to the tert-carbons of functionalized adamantanes by BrF3

The direct fluorination reaction of the functionalized adamantanes was achieved by using BrF3. In the reaction with methyl adamantane-1-caroxylate 1 and dimethyl adamantane-1,3-dicarboxylate 3, three and two fluorine atoms, respectively, were i

Pharmacological Evaluation of Novel Bioisosteres of an Adamantanyl Benzamide P2X7 Receptor Antagonist

Adamantanyl benzamide 1 was identified as a potent P2X7R antagonist but failed to progress further due to poor metabolic stability. We describe the synthesis and SAR of a series of bioisosteres of benzamide 1 to explore improvements in the pharmacological properties of this lead. Initial efforts investigated a series of heteroaromatic bioisosteres, which demonstrated improved physicochemical properties but reduced P2X7R antagonism. Installation of bioisosteric fluorine on the adamantane bridgeheads was well tolerated and led to a series of bioisosteres with improved physicochemical properties and metabolic stability. Trifluorinated benzamide 34 demonstrated optimal physicochemical parameters, superior metabolic stability (ten times longer than lead benzamide 1), and an improved physicokinetic profile and proved effective in the presence of several known P2X7R polymorphisms.

Selective fluorination of adamantanes by an electrochemical method

(Chemical Equation Presented) Selective fluorination of adamantanes was achieved by the electrochemical fluorination method, using Et3N-5HF as electrolyte and a fluorine source. Mono-, di-, tri-, and tetrafluoroadamantanes were selectively prepared from adamantanes by controlling the oxidation potential, and the fluorine atoms were introduced selectively at the tertiary carbons. Adamantanes that have functional groups such as ester, cyano, and acetoxymethyl were also fluorinated selectively.