6240-10-4

Usage

InChI:InChI=1/C11H17NO2/c12-11-4-7-1-8(5-11)3-10(2-7,6-11)9(13)14/h7-8H,1-6,12H2,(H,13,14)

Upstream product

• 6240-00-2 3-acetamidotricyclo[3.3.1.1^3,7]decane-1-carboxylic acid 

Downstream Products

• 16808-41-6 2-(adamantan-1-yl)isoindoline-1,3-dione 
• 1333108-08-9 3-(N-phthalimido)-1-(3-oxocyclohexyl)adamantane 
• 1333108-07-8 3-(N-phthalimido)-1-(3-methoxy-3-oxopropyl)adamantane 

Relevant academic research and scientific papers

γ-aminoadamantanecarboxylic acids through direct C-H bond amidations

Utilizing bromine-free, direct C-H bond amidations we have synthesized a large variety of adamantane amides. Depending on the precursors used these amides directly yield pharmaceutically active aminoadamantanes or γ-aminoadamantanecarboxylic acids after hydrolytic cleavage. These rigid analogues of γ-aminobutyric acid (GABA) were protected at the C- and N-termini and we synthesized a number of peptides incorporating γ-aminoadamantanecarboxylic acids in solution as well as via solid phase peptide synthesis. These peptides are promising scaffolds for applications in medicinal chemistry as well as in organocatalysis. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

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.

N-Adamantane-substituted tetrapeptide amides

N-Adamantane-substituted tetrapeptide amides and the pharmacologically acceptable salts thereof are disclosed herein. These compounds are analogs of enkephalin wherein the methionine or leucine of position 5 has been substituted by an adamantyl amide and the glycine of position 2 has been substituted by various amino acid residues. Optionally the tyrosine of position 1 and the phenylalanine of position 4 may be substituted by various amino acid residues. These compounds exhibit agonist activity at opiate receptor sites and are useful as analgesics.