Pyrrolines, also known under the name
dihydropyrroles, are three different heterocyclic organic chemical compounds that differ in the position of the
double bond. Pyrrolines are formally derived from the
aromaticity pyrrole by
hydrogenation. 1-Pyrroline is a cyclic
imine, whereas 2-pyrroline and 3-pyrroline are cyclic
.
|
| | | |
| 1-Pyrroline | 2-Pyrroline | 3-Pyrroline |
Substituted pyrrolines
Notable examples of pyrrolines containing various
include:
-
2-Acetyl-1-pyrroline, an aroma compound with a white bread-like smell
-
Thienamycin, a beta-lactam antibiotic
-
MTSL, a chemical used for certain NMR experiments
-
Pyrrolysine, an unusual proteinogenic amino acid
-
1-Pyrroline-5-carboxylic acid, a biosynthetic metabolite
-
Porphyrin, consisting of two alternating pairs of pyrrol and pyrroline connected via methine (=CH-) bridges
N-substituted pyrrolines can be generated by ring-closing metathesis.
[Marcelle L. Ferguson, Daniel J. O'leary, And Robert H. Grubbs "Ring-closing Metathesis Synthesis Of N-boc-3-pyrroline" Org. Synth. 2003, volume 80, p. 85. ]
See also
-
Pyrrole, the aromatic analog with two double bonds
-
Pyrrolidine, the fully saturated analog without double bonds
External links
