228246-74-0

Usage

Uses

Used in Organic Synthesis:
(S)-1,2-Dihydroacenaphthylen-1-amine is utilized as a chiral ligand or catalyst in asymmetric reactions, which are crucial for the synthesis of enantiomerically pure compounds. These reactions are essential in producing pharmaceuticals, agrochemicals, and other specialty chemicals that require specific stereochemistry for their desired biological activity.
Used in Pharmaceutical Development:
Due to its potential biological activity, (S)-1,2-Dihydroacenaphthylen-1-amine may be studied for its medicinal properties. It could be further investigated for its potential use in the development of new drugs, particularly in the context of its chiral nature, which may confer unique therapeutic effects.
Used in Research and Development:
(S)-1,2-Dihydroacenaphthylen-1-amine serves as a valuable compound for research purposes, particularly in the study of asymmetric synthesis and the development of novel chiral catalysts or ligands. Its unique structure and properties make it an interesting candidate for academic and industrial research aimed at advancing the field of organic chemistry and pharmaceuticals.

InChI:InChI=1/C12H11N/c13-11-7-9-5-1-3-8-4-2-6-10(11)12(8)9/h1-6,11H,7,13H2/t11-/m0/s1

Upstream product

• 6306-07-6 (R)-1,2-dihydroacenaphthylen-1-ol 
• 40745-44-6 1-aminoacenaphthene 

Downstream Products

• 228246-76-2 (S)-1-(acenaphthen-1-yl)-piperidine-4-one 
• 228246-78-4 (S)-4-phenylamino-1-(acenaphthen-1-yl)-piperidine-4-carbonitrile 

Relevant academic research and scientific papers

Identification of (S)-selective transaminases for the asymmetric synthesis of bulky chiral amines

The use of transaminases to access pharmaceutically relevant chiral amines is an attractive alternative to transition-metal-catalysed asymmetric chemical synthesis. However, one major challenge is their limited substrate scope. Here we report the creation of highly active and stereoselective transaminases starting from fold class I. The transaminases were developed by extensive protein engineering followed by optimization of the identified motif. The resulting enzymes exhibited up to 8,900-fold higher activity than the starting scaffold and are highly stereoselective (up to >99.9% enantiomeric excess) in the asymmetric synthesis of a set of chiral amines bearing bulky substituents. These enzymes should therefore be suitable for use in the synthesis of a wide array of potential intermediates for pharmaceuticals. We also show that the motif can be engineered into other protein scaffolds with sequence identities as low as 70%, and as such should have a broad impact in the field of biocatalytic synthesis and enzyme engineering.

Catalytic asymmetric hydroboration/amination and alkylamination with rhodium complexes of 1,1′-(2-diarylphosphino-1-naphthyl)isoquinoline

Catecholboronate esters formed by asymmetric hydroboration of arylalkenes are not directly converted to amines by reaction with hydroxylamine-O-sulfonic acid. Prior conversion to a trialkylborane by reaction with ZnEt2 or MeMgCl permits a subsequent amination reaction to occur with essentially complete retention of configuration, leading to a range of primary α-arylalkylamines in up to 97% enantiomeric excess (ee). Secondary, but not tertiary amines may be formed by a related pathway when in situ generated alkylchloramines are employed as the aminating agent. The catalytic asymmetric hydroboration, β-alkylation and amination steps may be combined in a single stage. Overall, this provides a practical procedure for the synthesis of enantiomerically enriched arylamines, exemplified inter alia by the synthesis of (S)-1,2,3,4-tetrahydro-1-naphthylamine in 95-97% ee and of (R)-N-(cyclohexyl)-1′-(4-methoxyphenyl)ethylamine in 93 % ee.

1,3,8-triazaspiro[4,5]decan-4-one derivatives

The present invention relates to compounds of the formula wherein R1 and R2 are each independently hydrogen, lower alkyl, lower alkoxy or halogen; R3 is phenyl, which is unsubstituted or substituted by lower alkyl, CF3, lower alkoxy or halogen; R4 is hydrogen, lower alkyl, lower alkenyl, -C(O)-lower alkyl, -C(O)-phenyl, lower alkyl-C(O)-phenyl, lower alkylene-C(O)O-lower alkyl, lower alkantriyl-di-C(O)O-lower alkyl, hydroxy-lower alkyl, lower alkyl-O-lower alkyl, lower alkyl-CH(OH)CF3, phenyl or benzyl, R5 and R6 are each independently hydrogen, phenyl, lower alkyl or di-lower alkyl or R5 and R6 together with the carbon atoms to which they are bound form a phenyl ring, or R5 and one of R1 or R2 together with the carbon atoms to which they are bound form a saturated or unsaturated 6 membered ring, A is a 4-7 membered saturated ring, their racemates and the enantiomers thereof, and the pharmaceutically acceptable acid addition salts thereof which are agonists and/or antagonists of the OFQ receptor.

8-Acenaphthen-1-yl-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one derivatives as orphanin FQ receptor agonists

A series of 8-acenaphthen-1-yl-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4- one derivatives 1 was studied with respect to the binding affinity for the orphanin FQ (OFQ) and opioid (μ, κ, δ) receptors. The influence of stereochemistry as well as the substitution pattern of the phenyl-ring in position 1 on the affinity for the orphanin FQ receptor and selectivity to opioid (μ, κ, δ) receptors is discussed. The most interesting compound 1c was tested for its anxiolytic-like properties in vivo.