Regio- and Enantioselective Hydromethylation of 3-Pyrrolines and Glycals Enabled by Cobalt Catalysis.

Enantioenriched 3-methylpyrrolidine, with its unique chiral nitrogen-containing core skeleton, exists widely in various functional molecules, including natural products, bioactive compounds, and pharmaceuticals. Traditional methods for synthesizing these valuable methyl-substituted heterocycles often involve enzymatic processes or complex procedures with chiral auxiliaries, limiting the substrate scope and efficiency. Efficient catalytic methylation, especially in an enantioselective manner, has been a long-standing challenge in chemical synthesis. Herein, we present a novel approach for the remote and stereoselective installation of a methyl group onto N-heterocycles, leveraging a CoH-catalyzed asymmetric hydromethylation strategy. By effectively combining a commercial cobalt precursor with a modified bisoxazoline (BOX) ligand, a variety of easily accessible 3-pyrrolines can be converted to valuable enantiopure 3-(isotopic labeling)methylpyrrolidine compounds with outstanding enantioselectivity. This efficient protocol streamlines the two-step synthesis of enantioenriched 3-methylpyrrolidine, which previously required up to five or six steps under harsh conditions or expensive starting materials.

Photo-Induced Difluoromethylation-Cyclization and Domino Amination-Defluorination to 4-(Aminomethyl)-3-fluoro-quinolinones.

Herein, we report a visible light-induced difluoromethylation cyclization and subsequent amination-defluorination reaction. This protocol allows efficient to valuable 3-fluoro-quinolinones in moderate to excellent yields. A sequential difluoromethylation-cyclization-amination-defluorination mechanism was proposed based on a mechanism study. Further density functional theory (DFT) calculations revealed that the base K2HPO4 could lower the energy due to the C═O···K+ electrostatic interaction to assist the elimination process, while the six-membered transition state located in situ was essential for the cleavage of N-H and C-F bonds during this SN2'-type process.

Two new 2-(2-phenylethyl)chromone derivatives and two sesquiterpenes from agarwood of Aquilaria sinensis with anti-inflammatory activity.

Two new 2-(2-phenylethyl)chromones (1-2), two new sesquiterpenes (12-13), and twelve known compounds (3-11, 14-16) were isolated from agarwood of Aquilaria sinensis. These structures were confirmed by HRESIMS, 1D and 2D NMR spectra. The absolute configurations of two new sesquiterpenes were determined by comparing the experimental and calculated ECD spectra. Among them, 7,8-dihydroxy-2-[2-(4'-methoxyphenyl)ethyl]chromone (2) was the first time found that the hydroxyl groups at both C-7/C-8 in agarwood. And Aseudesm B (13), the aldehyded methyl group at C-5 of eucalyptane sesquiterpenes was first discovered in natural products. In the bioassays, all compounds were evaluated for their inhibitory activity against lipopolysaccharide-activated nitric oxide (NO) production in RAW264.7 cells. Compounds 2-5, 7, 9-10, and 13-14 revealed notable inhibitory effects against NO production with IC50 values ranging from 4.0 to 13.0 µM.

Benzyl Deuteriodifluoromethyl Sulfoxide: An Easily Accessible and Stable Reagent for Direct Deuterodifluoromethylthiolation.

A new, stable and scalable reagent based on a sulfoxide skeleton for direct deuteriodifluoromethylthiolation has been developed. The reagent displays excellent reactivities toward Tf2O promoted C-H deuteriodifluoromethylthiolation of electron-rich arenes, indoles, alkenes, and intramolecular lactonization of 2-alkynylbenzoates. Moreover, high deuteration rates and good to excellent yields were achieved under metal-free reaction conditions. As a result, a wide range of deuteriodifluoromethylthilolated compounds were prepared, enabling further applications in drug discovery.

Thermal Performance Optimization of Integrated Microchannel Cooling Plate for IGBT Power Module.

In high-integration electronic components, the insulated-gate bipolar transistor (IGBT) power module has a high working temperature, which requires reasonable thermal analysis and a cooling process to improve the reliability of the IGBT module. This paper presents an investigation into the heat dissipation of the integrated microchannel cooling plate in the silicon carbide IGBT power module and reports the impact of the BL series micropump on the efficiency of the cooling plate. The IGBT power module was first simplified as an equivalent-mass block with a mass of 62.64 g, a volume of 15.27 cm3, a density of 4.10 g/cm3, and a specific heat capacity of 512.53 J/(kg·K), through an equivalent method. Then, the thermal performance of the microchannel cooling plate with a main channel and a secondary channel was analyzed and the design of experiment (DOE) method was used to provide three factors and three levels of orthogonal simulation experiments. The three factors included microchannel width, number of secondary inlets, and inlet diameter. The results show that the microchannel cooling plate significantly reduces the temperature of IGBT chips and, as the microchannel width, number of secondary inlets, and inlet diameter increase, the junction temperature of chips gradually decreases. The optimal structure of the cooling plate is a microchannel width of 0.58 mm, 13 secondary inlets, and an inlet diameter of 3.8 mm, and the chip-junction temperature of this structure is decreased from 677 °C to 77.7 °C. In addition, the BL series micropump was connected to the inlet of the cooling plate and the thermal performance of the microchannel cooling plate with a micropump was analyzed. The micropump increases the frictional resistance of fluid flow, resulting in an increase in chip-junction temperature to 110 °C. This work demonstrates the impact of micropumps on the heat dissipation of cooling plates and provides a foundation for the design of cooling plates for IGBT power modules.

[Determination of multiple chloropropanols in soy sauce by dispersive solid phase extraction-gas chromatography-high resolution mass spectrometry].

A method for the rapid screening of 1,3-dichloro-2-propanol, 2,3-dichloro-1-propanol,3-monochloropropane-1,2-diol, and 2-monochloropropane-1,3-diol in soy sauce was developed based on dispersive solid phase extraction-gas chromatography-high resolution mass spectrometry (GC-HRMS). The samples were extracted by ethyl acetate, cleaned up using N-propylethylenediamine and detected by GC-HRMS. The chloropropanols were quantified by the internal standard method. The results demonstrated that the limits of quantitation of the four chloropropanols were in the range of 0.5-10 µg/kg. The recoveries of the four chloropropanols in soy sauce spiked with three levels varied from 78% to 103%, and the relative standard deviations were no more than 8.8%. The proposed method is simple, accurate, sensitive and suitable for the rapid screening of the four chloropropanols in soy sauce.