228246-73-9

Usage

Uses

Used in Pharmaceutical Industry:
(R)-1,2-Dihydroacenaphthene-1-amine is used as an intermediate in the synthesis of W 212393 (W400090), a small-molecule opioid receptor-like 1 (ORL1) receptor agonist. This application is significant because ORL1 receptor agonists have potential therapeutic applications in treating various pain conditions and other disorders. (R)-1,2-DIHYDROACENAPHTHYLEN-1-AMINE's role in the synthesis process is crucial for the development of effective and targeted 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-/m1/s1

Upstream product

• 40745-44-6 1-aminoacenaphthene 

Downstream Products

• 228246-77-3 (R)-4-phenylamino-1-(acenaphthen-1-yl)-piperidine4-carbonitrile 
• 228246-75-1 (R)-1-(acenaphthen-1-yl)-piperidine-4-one 

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.