286-18-0

Basic information

• Product Name: 7-Aza-bicyclo[4.1.0]heptane
• Synonyms: 7-Azabicyclo[4.1.0]heptane;7-Aza-bicyclo[4.1.0]heptane
• CAS NO: 286-18-0
• Molecular Formula: C₆H₁₁N
• Molecular Weight: 97.16
• Mol File: 286-18-0.mol
• Article Data: 6

Chemical Properties

• Melting Point: 21°C
• Boiling Point: 171.72°C (rough estimate)
• Appearance: /
• Density: 0.9480
• Refractive Index: 1.4440 (estimate)
• CAS DataBase Reference: 7-Aza-bicyclo[4.1.0]heptane(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Aza-bicyclo[4.1.0]heptane(286-18-0)
• EPA Substance Registry System: 7-Aza-bicyclo[4.1.0]heptane(286-18-0)

Safety Data

• Hazardous Substances Data: 286-18-0(Hazardous Substances Data)

Usage

General Description

7-Aza-bicyclo[4.1.0]heptane, also known as 1-azabicyclo[4.1.0]heptane or tropilidine, is a chemical compound with the formula C6H9N. Its structure is based on the bicyclo[4.1.0]heptane skeleton, but one of the bridgehead carbons is replaced by a nitrogen atom. This substance is a valuable building block for the synthesis of various chemical compounds. It is relatively challenging to synthesize 7-aza-bicyclo[4.1.0]heptane compared to other bicyclic compounds, hence it may not be widely available commercially. Therefore, studies often focus on the development of practical and efficient synthetic methods for 7-aza-bicyclo[4.1.0]heptane.

Upstream product

• 623-11-0 1-methyl-4-nitrosobenzene 
• 132984-53-3 (+/-)-(trans-2-benzoylamino-cyclohexyl)-dimethyl sulfonium ; iodide 
• 132984-53-3 (+/-)-(cis-2-benzoylamino-cyclohexyl)-dimethyl sulfonium ; iodide 
• 931-16-8 (+/-)-trans-2-aminocyclohexanol 
• 3349-62-0 cyclohex-2-enone oxime 
• 28353-73-3 O-acetyl-2-cyclohexene-1-one oxime 
• 2229-00-7 cyclohexenone oxime hydrochloride 
• 2228-75-3 (Z)-cyclohex-2-en-1-one oxime 
• 64-17-5 ethanol 
• 110149-86-5 (+/-)-trans-1-benzoylamino-2-(toluene-4-sulfonyloxy)-cyclohexane 
• 141-52-6 sodium ethanolate 

Downstream Products

• 117864-55-8 N-[2-(7-aza-norcaran-7-yl)-cyclohexyl]-benzamide 
• 98289-71-5 trans-2-acetamidocyclohexanethiol 
• 69509-88-2 (+/-)-N-(trans-2-mercapto-cyclohexyl)-benzamide 
• 24417-01-4 7-Benzyl-7-aza-bicyclo[4.1.0]heptane 
• 4714-50-5 7-benzoyl-7-aza-bicyclo[4.1.0]heptane 
• 3721-20-8 N-(2-chlorocyclohexyl)benzamide 
• 96185-38-5 trans-2-(phenylsulfanyl)cyclohexan-1-amine 
• 67198-21-4 (±)-N,N-dimethyl-trans-1,2-diaminocyclohexane 
• 38361-99-8 (+/-)-N-methyl-trans-cyclohexane-1,2-diyldiamine 
• 90151-76-1 (+/-)-(trans-2-iodo-cyclohexyl)-dimethyl-amine 
• 21303-01-5 trans-2-phenoxycyclohexylamine 
• 1121-22-8 trans-1,2-Diaminocyclohexane 
• 10514-92-8 trans-2-amino-1-cyclohexanethiol 
• 931-12-4 trans-2-chloro-cyclohexylamine 

Relevant articles and documents

Efficient Direct Synthesis of Aziridine-Containing Chiral Tridentate Ligands by the Iminium-Mediated Self-Ring Opening Reaction of Enantiopure Aziridines and Salicylaldehydes

An efficient method for the direct synthesis of aziridine-containing chiral tridentate ligands was developed from enantiopure aziridines and salicylaldehydes. The method achieved the regiospecific cleavage of more substituted C?N bonds of aziridines through an iminium-mediated self-ring opening reaction of aziridines with up to 95% yield and complete inversion of configuration. The (S)-2-alkylaziridine-derived tridentate ligands displayed excellent activity and stereoselectivity in the zinc trifluoromethanesulfonate-catalyzed asymmetric aldol reactions of acetone and aromatic aldehydes. (Figure presented.).

SYNTHESIS AND REACTIONS OF ORGANIC COMPOUNDS WITH NITROGEN ATOM. PART VIII. ACTION OF DIBORANE ON SOME CYCLIC O-ACETYL α,β-UNSATURATED ALDO- AND KETOXIMES

The reaction of diborane with O-acetyl 2-cyclohexenone oxime (6), 2-methyl-2-cyclohexenone oxime (10), 3-methyl-2-cyclohexenone oxime (14), 1-cyclohexenene-1-carboxaldehyde oxime (18) and 10-(2-pinenyl)carboxaldehyde oxime (21) has been examined.The influence of the O-acetyl oxime structure on the direction and stereochemistry of the reaction is described.

Umsetzung von 2-Azidoalkoholen mit Trialkylphosphiten. Bildung von Aziridinen und Amidophosphorsaeureestern via Imidophosphorsaeureester und 1,3,2λ5-Oxazaphospholidine

The 2-azidoalcohols 1 and 2 react with trialkyl phosphites to trialkyl (2-hydroxyalkyl)imidophosphates 10, 14, and 15 respectively, whereas the 2-azidoalcohols 3-7 yield the 2,2,2-trialkoxy-1,3,2λ5-oxazaphospholidines 16-22 under the same reaction conditions (Scheme 2).The dialkyl (2-hydroxyalkyl)amidophosphates 23, 25, and 27-34 are obtained by the reaction of 10, and 14-22 with water (Scheme 3 and 4).By reaction with alcohols, however, both the imidophosphates 10, 14, and 15 and the 1,3,2λ5-oxazaphospholidines 16-22 are transformed to aziridines 24, 26, and 35-38 (S cheme 5).The reactions of the imidophosphates seem to proceed via 1,3,2λ5-oxazaphospholidines.