研究目的
The research objective was directed towards using continuous-flow photochemistry as a scaling-up tool in preparative organic synthesis, specifically for UV-mediated Intramolecular-Photo-Dehydro-Diels-Alder (IMPDDA) reactions.
研究成果
The developed annular continuous-flow reactor demonstrated high performance in scaling up UV-mediated IMPDDA reactions, achieving a daily productivity of 102.2 g of product. The reactor's design allowed for efficient cooling, minimized hazards from UV irradiation, and flexibility in using different UV wavelengths. Future work will focus on simplifying the reactor design and applying the IMPDDA transformation in natural product synthesis.
研究不足
The study was limited by the need for high substrate dilutions in batch reactions, leading to long reaction times and potential over-irradiation of products. The flow reactor required careful temperature control and optimization of flow parameters to maximize product yield and minimize degradation.
1：Experimental Design and Method Selection:
The study involved designing and constructing an annular continuous-flow reactor for UV-mediated IMPDDA reactions. The reactor was optimized for different UV wavelengths and flow rates.
2：Sample Selection and Data Sources:
The model system chosen was a macrocyclic structure with an overall tether length of 16 atoms for IMPDDA reactions.
3：List of Experimental Equipment and Materials:
The reactor consisted of a non-corrosive metal casing, quartz tubes with UV lamps, FEP tubing, aluminum foil for reflection, and a preparative HPLC pump. Cooling was achieved with silicon tubes and water.
4：Experimental Procedures and Operational Workflow:
The reaction was conducted in DCM as solvent, with variations in solvent concentration, flow rates, and excitation wavelengths. The system was cooled to maintain a constant temperature.
5：Data Analysis Methods:
Product yields were determined using HNMR with 1,3,5-trimethoxybenzene as an internal standard.
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