Počet záznamů: 1
Synthesis and supramolecular properties of regioisomers of mononaphthylallyl derivatives of .gamma.-cyclodextrin
- 1.
SYSNO ASEP 0482139 Druh ASEP J - Článek v odborném periodiku Zařazení RIV J - Článek v odborném periodiku Poddruh J Článek ve WOS Název Synthesis and supramolecular properties of regioisomers of mononaphthylallyl derivatives of .gamma.-cyclodextrin Tvůrce(i) Bláhová, M. (CZ)
Filippov, Sergey K. (UMCH-V) RID, ORCID, SAI
Kováčik, L. (CZ)
Horský, Jiří (UMCH-V) RID, ORCID
Hybelbauerová, S. (CZ)
Syrová, Z. (CZ)
Křížek, T. (CZ)
Jindřich, J. (CZ)Zdroj.dok. Beilstein Journal of Organic Chemistry. - : Beilstein - Institut zur Foerderung der Chemischen Wissenschaften - ISSN 1860-5397
Roč. 13, 27 November (2017), s. 2509-2520Poč.str. 12 s. Jazyk dok. eng - angličtina Země vyd. DE - Německo Klíč. slova gamma-cyclodextrin ; naphthylallyl derivatives ; regioselective alkylation Vědní obor RIV CD - Makromolekulární chemie Obor OECD Polymer science CEP GA17-07164S GA ČR - Grantová agentura ČR 7F14009 GA MŠMT - Ministerstvo školství, mládeže a tělovýchovy Institucionální podpora UMCH-V - RVO:61389013 UT WOS 000416340800001 EID SCOPUS 85035751262 DOI 10.3762/bjoc.13.248 Anotace Monosubstituted derivatives of gamma-cyclodextrin (gamma-CD) are suitable building blocks for supramolecular polymers, and can also serve as precursors for the synthesis of other regioselectively monosubstituted gamma-CD derivatives. We prepared a set of monosubstituted 2I-O-, 3I-O-, and 6I-O-(3-(naphthalen-2-yl)prop-2-en-1-yl) derivatives of gamma-CD using two different methods. A key step of the first synthetic procedure is a cross-metathesis between previously described regioisomers of mono-O-allyl derivatives of gamma-CD and 2-vinylnaphthalene which gives yields of about 16-25% (2-5% starting from gamma-CD). To increase the overall yields, we have developed another method, based on a direct alkylation of gamma-CD with 3-(naphthalen-2-yl)allyl chloride as the alkylating reagent. Highly regioselective reaction conditions, which differ for each regioisomer in a used base, gave the monosubstituted isomers in yields between 12-19%. Supramolecular properties of these derivatives were studied by DLS, ITC, NMR, and Cryo-TEM. Pracoviště Ústav makromolekulární chemie Kontakt Eva Čechová, cechova@imc.cas.cz ; Tel.: 296 809 358 Rok sběru 2018
Počet záznamů: 1