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Adamantyl-β-butyrolactones : Synthesis and ring-opening reactions


Matković, Marija; Molčanov, Krešimir; Glaser, Robert; Mlinarić-Majerski, Kata
Adamantyl-β-butyrolactones : Synthesis and ring-opening reactions // Tetrahedron, 68 (2012), 42; 8795-8804 doi:10.1016/j.tet.2012.07.102 (međunarodna recenzija, članak, znanstveni)


Naslov
Adamantyl-β-butyrolactones : Synthesis and ring-opening reactions

Autori
Matković, Marija ; Molčanov, Krešimir ; Glaser, Robert ; Mlinarić-Majerski, Kata

Izvornik
Tetrahedron (0040-4020) 68 (2012), 42; 8795-8804

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Lactonization; β-lactones; adamantyl-β-butyrolactones; C(carbonyl)—O(acyl) bond-cleavage; C(alkyl)—O(acyl) bond-cleavage

Sažetak
2-(1-Adamantyl)-β-butyrolactones 3a and 3b were synthesized using very common peptide coupling reagents under mild conditions and their ring-opening reactions were then studied. These novel lactones showed pronounced stability and were resistant to cleavage upon acidic water extraction and column chromatographic purification. The adamantane moiety plays an important function in lowering the lactone reactivity by protecting the electrophilic sites on the four-membered ring via steric hindrance. However under certain conditions, both O–C(carbonyl) and O–C(alkyl) bond-cleavage ring-opening reactions were observed. Bond-cleavage at physiological temperature makes these novel lactones especially noteworthy. Novel adamantyl-β-butyrolactones have a potential to act as biomembrane soluble amphyphiles that might exhibit a combination of stability and biological activity with the latter hopefully predominating.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
098-0982933-2911 - Kavezasti spojevi: ugradbene jedinice u molekularnim sustavima (Kata Majerski, )

Ustanove
Institut "Ruđer Bošković", Zagreb

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus


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