220247-74-5

Basic information

• Product Name: 1-(N,N-dibenzylamino)-2-ethenylcyclopropane
• Synonyms: 1-(N,N-dibenzylamino)-2-ethenylcyclopropane
• CAS NO: 220247-74-5
• Molecular Weight: 263.382
• Mol File: 220247-74-5.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 1-(N,N-dibenzylamino)-2-ethenylcyclopropane(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(N,N-dibenzylamino)-2-ethenylcyclopropane(220247-74-5)
• EPA Substance Registry System: 1-(N,N-dibenzylamino)-2-ethenylcyclopropane(220247-74-5)

Safety Data

• Hazardous Substances Data: 220247-74-5(Hazardous Substances Data)

Upstream product

• 5464-77-7 N,N-dibenzylformamide 
• 7103-09-5 4-but-1-enylmagnesium bromide 
• 106-99-0 buta-1,3-diene 
• 139527-25-6 bis(4-chlorobutyl)zinc 

Relevant articles and documents

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.

Unexpected titanium shifts during cyclopropanation of N,N- dibenzylformamide with ligand-exchanged titanium-alkadiene complexes

A number of readily available dienes and a triene were applied to exchange the alkene ligand on the in situ generated titanium-alkene complexes which react with N,N-dialkylcarboxamides to give N,N- dialkylcyclopropylamines. The ligand-exchanged intermedia