.png){kind=icon}
.png){kind=icon}
Return
Synthesis of Levoglucosenone-Based Amphiphilic Molecules via Microwave-Assisted Michael Additions
.png){kind=icon}
OA
AI
M
B
L
D
J
G
J
C
A
DOI：10.1002/cmtd.70129.png)
.png){kind=icon}
.png){kind=icon}
Share.png){kind=icon}
Save
Abstract
En 中文
Aligning with the objectives of the EU chemicals strategy for sustainability, an ultrarapid, safe and sustainable method for producing a library of levoglucosenone (LGO)-based amphiphilic molecules was developed. LGO and a series of alkyl malonates were employed as renewable building blocks to synthesize a series of structurally diverse adducts via Michael addition. The use of a nontoxic, inexpensive heterogeneous base catalyst (Ca(OH)2) enables the reaction to proceed through base activation of the Michael donors, namely the series of malonates employed. This process generates the carbon-based nucleophiles, the enolates, in situ. These intermediates subsequently react with levoglucosenone, the Michael acceptor, via a 1,4-conjugate addition. The microwave-enhanced procedure provides a rapid, selective and energy-efficient heating source, enabling a solventless and low-impact process. Reaction conditions were optimized through a multivariate Design of Experiments (D-optimal) approach, affording reproducible gravimetric yields above 80% with high selectivity and stereochemical control. The configuration of the newly formed chiral center was confirmed by X-ray characterization of the dimethyl derivative. The physical properties of the four synthesized adducts were investigated through an integrated set of methods, including theoretical tools such as the hydrophilic–lipophilic balance calculations and COnductor like Screening MOdel for Real Solvents simulations. n-Octanol/water partition coefficients, contact angle measurements, and emulsion tests further revealed the potential of these molecules as wetting and emulsifying agents. Overall, the results highlight how it is possible to synthesize LGO-based adducts with clear and tunable structure–property features using an ultrarapid, solventless protocol.
Keywords:
amphiphilic molecules
emulsifying agents
levoglucosenone
Michael addition
microwave chemistry
AI Summary
Key information extracted from the uploaded paper, including a brief overview, abstract, background, key highlights, visual analysis, and future outlook.
Journal
IF:
6.1
Papers:
104
Citations:
694
Organization
Cited Papers