1,8-diazabicyclo[5.4.0]undec-7-ene
Also known as DBU
1,8-Diazabicyclo[5.4.0]undec-7-ene, or more commonly DBU, is a chemical compound and belongs to the class of amidine compounds. It is used in organic synthesis as a catalyst, a complexing ligand, and a non-nucleophilic base.
Chemical data
- Formula
- C9H16N2
- Molecular weight
- 152.24 g/mol
- IUPAC name
- 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine
- SMILES
- C1CCC2=NCCCN2CC1
- InChIKey
- GQHTUMJGOHRCHB-UHFFFAOYSA-N
- XLogP
- 1.4
- Polar surface area
- 15.6 Ų
- H-bond donors
- 0
- H-bond acceptors
- 1
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 152.131
~2 min read
Article
5 sectionsContents
- Synthesis
- Occurrence
- Applications
- See also
- References
1,8-Diazabicyclo[5.4.0]undec-7-ene, or more commonly DBU, is a chemical compound and belongs to the class of amidine compounds. It is used in organic synthesis as a catalyst, a complexing ligand, and a non-nucleophilic base.
==Synthesis== DBU can be synthesised in three steps from caprolactam and acrylonitrile. First, the nitrile undergoes an addition reaction at the caprolactam nitrogen, producing N-(2-cyanoethyl)-caprolactam. This is then hydrogenated to N-aminopropyl-caprolactam, followed by an intramolecular carbonyl condensation to form the imine. Water is removed by fractional distillation.