Montmorillonite─Eco-friendly and Effective Catalyst in the Synthesis of Biologically Active Compounds with Bicyclo[3.3.1] Moiety
The result's identifiers
Result code in 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>
Result on the web
<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>
Alternative languages
Result language
angličtina
Original language name
Montmorillonite─Eco-friendly and Effective Catalyst in the Synthesis of Biologically Active Compounds with Bicyclo[3.3.1] Moiety
Original language description
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 >85% and selectivity >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.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
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OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
—
Continuities
S - Specificky vyzkum na vysokych skolach<br>I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2025
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
ACS Omega
ISSN
2470-1343
e-ISSN
2470-1343
Volume of the periodical
10
Issue of the periodical within the volume
51
Country of publishing house
US - UNITED STATES
Number of pages
11
Pages from-to
"63597–63607"
UT code for WoS article
001639290000001
EID of the result in the Scopus database
2-s2.0-105026114519