Английская Википедия:Azetidine

Материал из Онлайн справочника
Перейти к навигацииПерейти к поиску

Шаблон:Distinguish Шаблон:Chembox

Azetidine is a saturated heterocyclic organic compound containing three carbon atoms and one nitrogen atom. It is a liquid at room temperature with a strong odor of ammonia and is strongly basic compared to most secondary amines.

Synthesis and occurrence

Файл:MugineicAcid.svg
Mugineic acid, an iron-binding azetidine.

Azetidines can be prepared by reduction of azetidinones (β-lactams) with lithium aluminium hydride. Even more effective is a mixture of lithium aluminium hydride and aluminium trichloride, a source of "AlClH2" and "AlCl2H".[1] Azetidine can also be produced by a multistep route from 3-amino-1-propanol.[2]

Regio- and diastereoselective synthesis of 2-arylazetidines could be performed from appropriately substituted oxiranes via ring transformation. It is controlled by Baldwin's Rules with remarkable functional group tolerance. Шаблон:Cn

Azetidine and its derivatives are relatively rare structural motifs in natural products. They are a component of mugineic acids and penaresidins. Perhaps the most abundant azetidine containing natural product is azetidine-2-carboxylic acid - a toxic mimic of proline.[3]

See also

  • Azete, the unsaturated analog

References

Шаблон:Reflist

External links


Шаблон:Heterocyclic-stub