|
| Identification |
| Name |
DBU |
| Synonymous |
1,8-Diazabicyclo[5.4.0]undec-7-ene; 2,3,4,6,7,8,9,10-Octahydropyrimido[1,2-a]azepine |
| Molecular Structure |
|
| Molecular Formula |
C9H16N2 |
| Molecular Weight |
152.24 |
| CAS Number |
6674-22-2 |
| Properties |
| Melting Point |
-70 ºC
|
| Boiling Point |
261 ºC; 115 °C/11 mmHg(lit.)
|
| Density |
1.019
|
| Refractive index |
1.523
|
| Flash Point |
116 ºC
|
| Solubility |
Soluble in water
|
| Safety & Transportation Data |
| Hazardous class |
8
|
| UN number |
3267
|
| Packing group |
II
|
| Harzard Symbols |
C
|
| Risk Codes |
22-34-52/53
|
| Safety Description |
26-36/37/39-45
|
| Supplier Specification |
| Purity |
99%+ (GC)
|
| Notes |
Amidine base used for dehydrohalogenation reactions to olefins[1]; Further important applications are e.g.: esterification of carboxylic acids with alkyl halides[2,3]; Alkylation and acylation of active methylene compounds[4].
Halogenated Diels-Alder adducts were dehydrohalogenated with this base, and the resulting activated 2,4-dienones were subjected to regio- and stereo-directed Michael additions, using Yamamoto′s reagent (CH3Cu · BF3).[5]
Used in a new synthesis of the ABCD ring system of Camptothecin.[6]
Application reviewed.[7].
- H. Oediger et al. Synthesis, 591, (1972)
- N. Ono et al. Bull. Chem. Soc. Jpn. 51, 2401, (1978)
- C.G. Rao Org. Prep. Proc. Int. 12, 225, (1980)
- N. Ono et al. Bull. Chem. Soc. Jpn. 52, 1716, (1979)
- Tetrahedron 60, 4821-4827, (2004)
- Org. Lett. 8, 4665, (2006)
- Synlett 3, 574-575, (2004)
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