Montmorillonite─Eco-friendly and Effective Catalyst in the Synthesis of Biologically Active Compounds with Bicyclo[3.3.1] Moiety

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22310%2F25%3A43932609" target="_blank" >RIV/60461373:22310/25:43932609 - isvavai.cz</a>

Výsledek na webu

<a href="https://pubs.acs.org/doi/full/10.1021/acsomega.5c10876" target="_blank" >https://pubs.acs.org/doi/full/10.1021/acsomega.5c10876</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1021/acsomega.5c10876" target="_blank" >10.1021/acsomega.5c10876</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Montmorillonite─Eco-friendly and Effective Catalyst in the Synthesis of Biologically Active Compounds with Bicyclo[3.3.1] Moiety

Popis výsledku v původním jazyce

Prins cyclization is a key method for synthesizing oxygen-containing heterocycles with biological activity involving the reaction of alkenes and aldehydes under mild acidic conditions. This process is valuable for producing compounds such as 2,2,6-trimethyl-4-(1-propenyl)-3-oxabicyclo[3.3.1]non-6-ene, a bioactive bicyclic ether synthesized from limonene and crotonaldehyde. Compounds with bicyclo[3.3.1]nonene structures are interesting due to their fragrance properties and potential estrogen receptor activity. This study evaluates montmorillonite (MMT), a low-cost, environmentally friendly clay, as a heterogeneous acid catalyst for this reaction. Acid treatment of MMT (treated with HNO3, HCl, H2SO4, and H3PO4) had a positive influence on limonene conversion compared with nonmodified MMT, and limonene conversions &gt;85% and selectivity &gt;70% were obtained (24 h). Reaction parameters such as temperature, solvent, catalyst amount, and limonene-to-crotonaldehyde ratio significantly influenced conversion and selectivity. Higher temperatures and lower crotonaldehyde ratios improved the achieved limonene conversion, though selectivity decreased with temperature. Montmorillonite-supported heteropoly acids (HPW and HPMo) increased conversion but reduced selectivity and showed inefficient catalyst utilization at higher loadings. The initial reaction rate increased and selectivity decreased with catalyst acidity. Overall, acid-treated MMTs are more effective and economical than heteropoly acid-modified variants, offering a viable path for synthesizing bicyclic ethers via green chemistry.

Název v anglickém jazyce

Montmorillonite─Eco-friendly and Effective Catalyst in the Synthesis of Biologically Active Compounds with Bicyclo[3.3.1] Moiety

Popis výsledku anglicky

Prins cyclization is a key method for synthesizing oxygen-containing heterocycles with biological activity involving the reaction of alkenes and aldehydes under mild acidic conditions. This process is valuable for producing compounds such as 2,2,6-trimethyl-4-(1-propenyl)-3-oxabicyclo[3.3.1]non-6-ene, a bioactive bicyclic ether synthesized from limonene and crotonaldehyde. Compounds with bicyclo[3.3.1]nonene structures are interesting due to their fragrance properties and potential estrogen receptor activity. This study evaluates montmorillonite (MMT), a low-cost, environmentally friendly clay, as a heterogeneous acid catalyst for this reaction. Acid treatment of MMT (treated with HNO3, HCl, H2SO4, and H3PO4) had a positive influence on limonene conversion compared with nonmodified MMT, and limonene conversions &gt;85% and selectivity &gt;70% were obtained (24 h). Reaction parameters such as temperature, solvent, catalyst amount, and limonene-to-crotonaldehyde ratio significantly influenced conversion and selectivity. Higher temperatures and lower crotonaldehyde ratios improved the achieved limonene conversion, though selectivity decreased with temperature. Montmorillonite-supported heteropoly acids (HPW and HPMo) increased conversion but reduced selectivity and showed inefficient catalyst utilization at higher loadings. The initial reaction rate increased and selectivity decreased with catalyst acidity. Overall, acid-treated MMTs are more effective and economical than heteropoly acid-modified variants, offering a viable path for synthesizing bicyclic ethers via green chemistry.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10401 - Organic chemistry

Projekt

—

Návaznosti

S - Specificky vyzkum na vysokych skolach<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2025

Kód důvěrnosti údajů

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

Název periodika

ACS Omega

ISSN

2470-1343

e-ISSN

2470-1343

Svazek periodika

10

Číslo periodika v rámci svazku

51

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

11

Strana od-do

"63597–63607"

Kód UT WoS článku

001639290000001

EID výsledku v databázi Scopus

2-s2.0-105026114519