6240-00-2

Usage

Uses

Used in Pharmaceutical Industry:
3-ACETYLAMINO-ADAMANTANE-1-CARBOXYLIC ACID is used as an antiviral agent for the treatment of influenza A, functioning by inhibiting the replication of the virus and thus reducing the severity and duration of the illness.
Used in Neurological Treatments:
In the context of Parkinson's disease, 3-ACETYLAMINO-ADAMANTANE-1-CARBOXYLIC ACID is utilized as a medication to increase the levels of dopamine in the brain, which helps alleviate the motor symptoms associated with the condition.

InChI:InChI=1/C13H19NO3/c1-8(15)14-13-5-9-2-10(6-13)4-12(3-9,7-13)11(16)17/h9-10H,2-7H2,1H3,(H,14,15)(H,16,17)

Upstream product

• 828-51-3 1-Adamantanecarboxylic acid 
• 75-05-8 acetonitrile 

Downstream Products

• 1221412-06-1 3-(acetylamino)-N-(4-{[(2-aminophenyl)amino]carbonyl}benzyl)adamantane-1-carboxamide 
• 6240-10-4 3-amino-1-adamantanecarboxylic acid 
• 34859-74-0 3-chloroadamantane-1-carboxylic acid 
• 6240-01-3 3-aminotricyclo[3.3.1.1^3,7]decane-1-carboxylic acid hydrochloride 

Relevant academic research and scientific papers

NITRATION OR CARBOXYLATION CATALYSTS

In the presence of an imide compound (e.g., N-hydroxyphthalimide) shown by the following formula (1): ???wherein R1and R2represent a hydrogen atom, a halogen atom, an alkyl group, an aryl group and a cycloalkyl group, and R1and R2may bond together to form a double bond, or an aromatic or non-aromatic ring, and Y is an O or OH, and n denotes 1 to 3;, a substrate is allowed to contact with at least one reactant selected from (i) a nitrogen oxide and (ii) a mixture of carbon monoxide and oxygen to be introduced with at least one functional group selected from a nitro group and a carboxyl group. The nitrogen oxide includes, for example, a compound represented by the formula NxOy(e.g., N2O3, NO2). The substrate includes, for example, a compound having a methine carbon atom (e.g., adamantane), a compound having a methyl group or a methylene group at an adjacent moiety of an aromatic ring. According to such reaction, the substrate can be efficiently nitrated or carboxylated even in a mild or moderate condition.

Oxidative functionalization of adamantane and some of its derivatives in solution

1,2,4,5-Benzenetetracarbonitrile (TCB) is irradiated in the presence of adamantane (1) and some of its derivatives. The singlet excited state of TCB is a strong oxidant, and there is various evidence, including time-resolved spectroscopy, to prove that SET from the alkane to TCB1* takes place and yields the corresponding radical ions. The adamantane radical cation deprotonates from the bridgehead position, and the resulting radical couples with TCB-*. Deprotonation via the radical cation occurs with a number of substituted adamantanes and remains the exclusive or predominating reaction also with derivatives containing a potential electrofugal group, such as one of the following carbocations: t-Bu, CH2OMe, CH2OH (notable here is that C-H deprotonation is more efficient than O-H deprotonation). A carboxy group is lost more efficiently than a proton, however. In contrast, detaching of such cations is the main process when the radical cations of substituted adamantanes is produced anodically. This different behavior is explained on the basis of thermochemical calculation and of the different environments experienced by the radical cation in the two cases, viz reaction from the solvated radical cation in the first case and from the substrate adsorbed on the anode in the latter one. 1-Methoxyadamantane deprotonates from the methyl group, a reaction explained by the different structure of the radical cation. On the other hand, the radical NO3*, conveniently produced by photolysis of cerium(IV) ammonium nitrate, reacts by hydrogen abstraction with selective attack at the bridgehead position and little interference by substituents and thus offers a useful way for the selective oxidative functionalization of adamantanes.