Synthesis and supramolecular properties of regioisomers of mononaphthylallyl derivatives of .gamma.-cyclodextrin

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61389013%3A_____%2F17%3A00482139" target="_blank" >RIV/61389013:_____/17:00482139 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/00216208:11310/17:10367090 RIV/00216208:11110/17:10367090

Výsledek na webu

<a href="http://dx.doi.org/10.3762/bjoc.13.248" target="_blank" >http://dx.doi.org/10.3762/bjoc.13.248</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.3762/bjoc.13.248" target="_blank" >10.3762/bjoc.13.248</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Synthesis and supramolecular properties of regioisomers of mononaphthylallyl derivatives of .gamma.-cyclodextrin

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

Synthesis and supramolecular properties of regioisomers of mononaphthylallyl derivatives of .gamma.-cyclodextrin

Popis výsledku anglicky

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.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10404 - Polymer science

Projekt

Výsledek vznikl pri realizaci vícero projektů. Více informací v záložce Projekty.

Návaznosti

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Rok uplatnění

2017

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

Beilstein Journal of Organic Chemistry

ISSN

1860-5397

e-ISSN

—

Svazek periodika

13

Číslo periodika v rámci svazku

27 November

Stát vydavatele periodika

DE - Spolková republika Německo

Počet stran výsledku

12

Strana od-do

2509-2520

Kód UT WoS článku

000416340800001

EID výsledku v databázi Scopus

2-s2.0-85035751262