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'''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]].
'''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]].


This compound is also considered as an [[alkaloid]] isolated from the sponge ''[[Niphates digitalis]]''.<ref>Regalado, E.L. et al., Nat. Prod. Commun., 2010, 5, 1187- 1190</ref>
This compound is also an [[alkaloid]] isolated from the sponge ''[[Niphates digitalis]]''.<ref>Regalado, E.L. et al., Nat. Prod. Commun., 2010, 5, 1187- 1190</ref>


[[File:REGALADO DBU BIOSYNTHETIC HYPOTHESIS.png|500px|center|thumb|Regalado hypothetic biosynthesis of DBU]]
[[File:REGALADO DBU BIOSYNTHETIC HYPOTHESIS.png|500px|center|thumb|Regalado hypothetic biosynthesis of DBU]]

Revision as of 18:05, 21 July 2014

The correct title of this article is 1,8-Diazabicyclo[5.4.0]undec-7-ene. The substitution of any brackets is due to technical restrictions.
1,8-Diazabicyclo[5.4.0]undec-7-ene
DBU molecule
Names
IUPAC name
2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine
Other names
DBU,Diazabicycloundecene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.027.013 Edit this at Wikidata
  • InChI=1S/C9H16N2/c1-2-5-9-10-6-4-8-11(9)7-3-1/h1-8H2 checkY
    Key: GQHTUMJGOHRCHB-UHFFFAOYSA-N checkY
  • InChI=1/C9H16N2/c1-2-5-9-10-6-4-8-11(9)7-3-1/h1-8H2
    Key: GQHTUMJGOHRCHB-UHFFFAOYAM
  • N\2=C1\N(CCCCC1)CCC/2
Properties
C9H16N2
Molar mass 152.24 g/mol
Appearance Colorless liquid
Density 1.018 g/mL liquid
Melting point −70 °C (−94 °F; 203 K)
Boiling point 80-83 °C (0.6 mmHg), 261 °C (1 atm)
Acidity (pKa) ~12 (value for protonated form, pKa of a free base is ~24 -> C-H bond dissociation)
Basicity (pKb) ? (basicity)
Hazards
Flash point 119.9 °C (247.8 °F; 393.0 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

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.

This compound is also an alkaloid isolated from the sponge Niphates digitalis.[1]

Regalado hypothetic biosynthesis of DBU

It is used as a curing agent for epoxy; it is used as a protecting agent for the synthesis of cephalosporin. It is used in fullerene purification with trimethylbenzene (it reacts to C70 and higher fullerenes but not to C60 fullerenes); and it is also used as a catalyst for polyurethane. It has a strong catalyst effect for the reactions of alicyclic and aliphatic isocyanates.

See also

References

  1. ^ Regalado, E.L. et al., Nat. Prod. Commun., 2010, 5, 1187- 1190
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