210482-10-3

Usage

Uses

Used in Synthetic Organic Chemistry:
exo-6-[Bis(phenylmethyl)amino]-3-Azabicyclo[3.1.0]hexane is used as a chemical intermediate for the synthesis of more complex molecules. Its unique structure allows for the creation of a wide range of chemical compounds, making it a valuable asset in the field of synthetic organic chemistry.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, exo-6-[Bis(phenylmethyl)amino]-3-Azabicyclo[3.1.0]hexane is used as a building block for the development of new drugs. Its versatile structure enables the design of molecules with specific therapeutic properties, contributing to the advancement of medicinal chemistry.
Used in Chemical Research:
exo-6-[Bis(phenylmethyl)amino]-3-Azabicyclo[3.1.0]hexane is also utilized in chemical research as a model compound for studying the properties and behavior of complex organic molecules. This helps researchers gain insights into the fundamental principles of organic chemistry and develop new strategies for the synthesis of novel compounds.

Upstream product

• 164799-14-8 3α,4β,5α-4-(dibenzylamino)-3,5-cyclopiperidine-4-carbonitrile 
• 497163-57-2 tert-butyl (1R,5S,6s)-6-(N,N-dibenzylamino)-3-azabicyclo[3.1.0]hexane-3-carboxylate 
• 5464-77-7 N,N-dibenzylformamide 

Downstream Products

• 1384171-77-0 (6-(dibenzylamino)-3-azabicyclo[3.1.0]hexan-3-yl) (4,5-dichloroisothiazol-3-yl)methanone 
• 1384171-79-2 N,N-dibenzyl-3-(1-(benzotriazol-1-yl)-2-nitro-3,4,4-trichlorobuta-1,3-dienyl)-3-azabicyclo[3.1.0]hexan-6-amine 
• 1384171-78-1 N,N-dibenzyl-3-(4-(dichloromethylene)-3-nitro-4H-pyrido[1,2-a]pyrimidin-2-yl)-3-azabicyclo[3.1.0]hexan-6-amine 
• 1384171-72-5 N-(1-(6-dibenzylamino-3-azabicyclo[3.1.0]hex-3-yl)-2,3,3-trichloro-allylidene)-N'-(4-nitrophenyl)hydrazine 
• 1384171-74-7 N,N-dibenzyl-3-((E)-1,1-dichloro-3-(1-((2-chlorothiazol-5-yl)methyl)imidazolidin-2-ylidene)-3-nitroprop-1-en-2-yl)-3-azabicyclo[3.1.0]hexan-6-amine 
• 1384171-73-6 N,N-dibenzyl-3-((E)-1,1-dichloro-3-(1-((6-chloropyridin-3-yl)methyl)imidazolidin-2-ylidene)-3-nitroprop-1-en-2-yl)-3-azabicyclo[3.1.0]hexan-6-amine 
• 1384171-75-8 3,3'-((Z)-4-chloro-2,4-dinitrobuta-1,3-diene-1,1-diyl)bis(N,N-dibenzyl-3-azabicyclo-[3.1.0]hexan-6-amine) 
• 1176245-32-1 5-[3-(6-dibenzylamino-3-azabicyclo[3.1.0]hex-3-yl)phenyl]-6-oxa-4-azaspiro[2.4]hept-4-ene-7-carboxylic acid N-methyl-(3-trifluoromethylphenyl)amide 
• 1176244-83-9 5-[4-(6-dibenzylamino-3-azabicyclo[3.1.0]hex-3-yl)phenyl]-6-oxa-4-azaspiro[2.4]hept-4-ene-7-carboxylic acid N-methyl-(3-trifluoromethylphenyl)amide 
• 880545-27-7 C₃₀H₃₁FN₄O 

Relevant academic research and scientific papers

Antibacterial Agents

Naphthalene, quinoline, quinoaline and naphthyridine derivatives useful in the treatment of bacterial infections in mammals, particularly humans, are disclosed herein.

Mono- and disubstituted N,N-dialkylcyclopropylamines from dialkylformamides via ligand-exchanged titanium - Alkene complexes

Dibenzylformamide was treated with cyclohexylmagnesium bromide in the presence of either titanium tetraisopropoxide or methyltitanium triisopropoxide and a variety of cyclic and acyclic alkenes and alkadienes to give new mono- and disubstituted as well as bicyclic dialkylcyclopropylamines (Tables 1-3) in yields ranging from 18 to 90% (in most cases around 55%). 3-Benzyl-6-(N,N-dibenzylamino)-3-azabicyclo[3.1.0]hexane (10a) and the orthogonally bisprotected 3-tert-butoxycarbonyl-6-(N,N-dibenzyl)- 3-azabicyclo[3.1.0]hexane (10d) as well as the analogous 6-(N,N-dibenzylamino)bicyclo[3.1.0]hexane (12) were obtained as pure exo diastereomers in particularly high yields (87, 90, and 88%, respectively) from N-benzylpyrroline (15a), N-Boc-pyrroline (15d; Boc = tert-butyloxycarbonyl) and cyclopentene (19). 1,3-Butadiene (52) and substituted 1,3-butadienes were also aminocyclopropanated quite well to give 2-ethenylcyclopropylamines in good yields (51-64%). Except for alkenyl and aryl-substituted compounds, N,N-dibenzylcyclopropylamines can be debenzylated by catalytic hydrogenation to the primary cyclopropylamines as demonstrated for 10a and 10d to yield the fully deprotected 10e (93%) and mono-Boc-protected 10f (98%), respectively. The latter are interesting templates for combinatorial syntheses of libraries of small molecules with a well defined distance of 4.3 A between two nitrogen atoms.

Reductive decyanation of N-protected 6-amino-3-aza-bicyclo [3.1.0]hexanecarbonitriles

The cyano moiety in dibenzylamino-3-azabicyclo[3.1.0]hexane-6- carbonitriles 14c,d can be removed reductively by alkali metals: sodium in liquid ammonia at low temperatures causes a reaction with retention of configuration whilst lithium in an ethylamine - ammonia mixture at 0°C leads predominantly to inversion of configuration. The analogous diallylamino species 14e is less suitable for reductive decyanation. It can be used, however, for the synthesis of a 3-azabicyclo[3.2.0]heptane diamine 22. The solid state conformation of an N(3)-unsubstituted 3-azabicyclohexane skeleton is determined by an X-ray structural analysis.