Optimization of Nazarov Cyclization of 2,4-Dimethyl-1,5-diphenylpenta-1,4-dien-3-one in Deep Eutectic Solvents by a Design of Experiments Approach
Abstract
:1. Introduction
2. Results and Discussion
3. Materials and Methods
3.1. General
3.2. Preparation of DES1
3.3. Preparation of DES2
3.4. General Procedure for the Nazarov Cyclization Reaction.
3.5. Statistical analysis
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Conflicts of Interest
Abbreviations
AA | Acetic Acid |
ANOVA | ANalysis Of Variance |
BA | Bronsted Acid |
BBD | Box–Behnken Design |
CPME | CycloPentyl Methyl Ether |
DCE | 1,2-DiChloroEthane |
DES | Deep Eutectic Solvent |
DoE | Design of Experiment |
DW | Durbin-Watson |
EG | Ethylene Glycol |
HBA | Hydrogen Bond Acceptor |
HBD | Hydrogen Bond Donor |
LA | Lewis Acid |
MAE | Mean Absolute Error |
NaDES | Natural Deep Eutectic Solvent |
SRA | Surface Responding Analysis |
TPMPBr | TriPhenylMethyl Phosphonium Bromide |
VOC | Volatile Organic Compound |
References and Note
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Entry | Promoter | Solvent | S1 (%) 2 | P1 (%) 2 | cis-P1 (%) 2 | P2 (%) 2 |
---|---|---|---|---|---|---|
1 | TPMPBr | CPME | 91 | - | - | - |
2 | AA | CPME | 41 | 10 | 60 | 22 |
3 | TPMPBr | DCE | 2 | 78 | 9 | - |
4 | AA | DCE | 5 | 17 | 59 | 30 |
5 | TPMPBr | EG | 82 | 62 | 94 | - |
6 | AA | EG | 0 | 30 | 57 | 22 |
Factor | Level − 1 | Level + 1 | Unit |
---|---|---|---|
Temperature | 25 | 60 | °C |
Time | 2 | 16 | h |
Substrate concentration | 1.0 | 0.2 | mmol S1/g DES |
DES | DES11 | DES22 | |
Responses | |||
Total conversion | % of consumed S1 | ||
Conversion to P1 | % of P1 formed |
Factor | Level − 1 1 | Level + 1 1 | Unit |
---|---|---|---|
Temperature | 25 | 60 | °C |
Time | 1 | 5 | h |
Amount of DES | 0.2 | 1.0 | g DES for 0.2 mmol S1 |
Responses | |||
Total conversion | % of consumed S1 | ||
Conversion to P1 | % of P1 formed | ||
Selectivity | % of cis isomer |
Response Variables | |||||
Name | Unit | Analyse | Goal | Impact | Sensitivity |
Conv. to P1 | % | Mean | Maximize | 3.0 | Medium |
Cis selectivity | % | Mean | Maximize | 3.0 | Medium |
Total Conv. | % | Mean | Maximize | 3.0 | Medium |
Experimental variable factors | |||||
Name | Unit | Type | Role | Low | High |
A: temperature | °C | Continuous | Controllable | 25.0 | 60.0 |
B: time | h | Continuous | Controllable | 1.0 | 5.0 |
C: DES amount | g | Continuous | Controllable | 0.2 | 1.0 |
Theoretical | Experimental | |
---|---|---|
Total conversion | 96.55% | 96% |
Conversion to P1 | 85.28% | 82% |
Sample Availability: Samples of the compounds are not available from the authors.
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Nejrotti, S.; Mannu, A.; Blangetti, M.; Baldino, S.; Fin, A.; Prandi, C. Optimization of Nazarov Cyclization of 2,4-Dimethyl-1,5-diphenylpenta-1,4-dien-3-one in Deep Eutectic Solvents by a Design of Experiments Approach. Molecules 2020, 25, 5726. https://doi.org/10.3390/molecules25235726
Nejrotti S, Mannu A, Blangetti M, Baldino S, Fin A, Prandi C. Optimization of Nazarov Cyclization of 2,4-Dimethyl-1,5-diphenylpenta-1,4-dien-3-one in Deep Eutectic Solvents by a Design of Experiments Approach. Molecules. 2020; 25(23):5726. https://doi.org/10.3390/molecules25235726
Chicago/Turabian StyleNejrotti, Stefano, Alberto Mannu, Marco Blangetti, Salvatore Baldino, Andrea Fin, and Cristina Prandi. 2020. "Optimization of Nazarov Cyclization of 2,4-Dimethyl-1,5-diphenylpenta-1,4-dien-3-one in Deep Eutectic Solvents by a Design of Experiments Approach" Molecules 25, no. 23: 5726. https://doi.org/10.3390/molecules25235726