17160-89-3Relevant articles and documents
A green and recyclable CuSO4·5H2O/ionic liquid catalytic system for the CO2-promoted hydration of propargyl alcohols: an efficient assembly of α-hydroxy ketones
Yuan, Ye,Hu, Jia,Wang, Yu,Huang, Leilei,Zheng, Jiayun,Zhao, Yufeng,Chen, Yiyun,Chen, Cheng,Verpoort, Francis
, p. 561 - 570 (2021/12/03)
α-Hydroxy ketones are important building blocks in biological, pharmaceutical and synthetic chemistry. In this work, diverse α-hydroxy ketones were efficiently constructed through the CO2-promoted hydration process of propargyl alcohols, which was catalyzed by a system consisted of economical CuSO4·5H2O and a green 1-butyl-3-methylimidazolium acetate ionic liquid. Particularly, this catalytic system exhibited excellent activity under atmospheric CO2 or even mimetic flue gas (20 vol% of CO2). Moreover, this system employed the lowest metal loading ever reported (0.004–0.25 mol%) meanwhile reached the highest turnover number (11700) for the target hydration reaction. Additionally, this is the first reported Cu catalytic system with reliable recyclability, which could be easily reused at least 6 times with yields higher than 85%.
Synthesis and Fungicidal Activity of (E)-5-[1-(2-Oxo-1-oxaspiro[4,5]dec/non-3-en-3-yl)ethylidene]-2-aminoimidazolin-4-one Derivatives
Tang, Bo,Guan, Aiying,Zhao, Yu,Jiang, Jiazhen,Wang, Mingan,Zhou, Ligang
, p. 1133 - 1140 (2017/07/25)
The novel fungicidal agents, (E)-5-[1-(2-oxo-1-oxaspiro[4,5]dec/non-3-en-3-yl)ethylidene]-2-aminoimidazolin- 4-one derivatives, were designed and synthesized in moderate to excellent yields in four steps using α-hydroxyketone and diketene as raw materials and characterized by HR-ESI-MS, 1H NMR and X-ray diffraction. The preliminary bioassay showed that some of these compounds, such as 5e, 6a, 6e, and 7 h exhibit 87.8%, 91.3%, 89.9% and 87.8% inhibition rates against Sclerotinia scleotiorum, 3b, 3c, 4c and 7 h exhibit 96.4%, 92.5%, 90.3% and 76.9% inhibition rates against Phytophthora capsici at the concentration of 50 μg/mL, respectively. These compounds exhibited significant fungicidal activities against S. scleotiorum and P. capsici with EC50 values of 2.56–11.60 μg/mL, and compounds 6e and 7 h exhibited weak inhibition against the spore germination of S. scleotiorum, while the spore germination of P. capsici was strongly inhibited by compound 7 h solution. Scanning electron microscopy (SEM) and transmission electron microscopy (TEM) observation indicated that compound 7 h had a significant impact on the structure and function of the hyphal cell wall of P. capsici mycelium.
Electroorganic Chemistry. 140. Electroreductively Intra- and Intermolecular Couplings of Ketones with Nitriles
Shono, Tatsuya,Kise, Naoki,Fujimoto, Taku,Tominaga, Naoto,Morita, Hiroshi
, p. 7175 - 7187 (2007/10/02)
Electroreduction of γ- and δ-cyano ketones in i-PrOH with Sn cathode gave α-hydroxy ketones and their dehydroxylated ketones as the intramolecularly coupled products.Guaiazulene, (-)-valeranone, polyquinanes, dihydrojasmone, methyl dihydrojasmonate, and rosaprostol have been synthesized by utilizing this electroreductive intramolecular coupling of γ- and δ-cyano ketones in one of the key steps.Similarly, electroreduction of a mixture of ketone and nitrile gave the corresponding intermolecularly coupled product.The product obtained by the electroreductive intermolecular coupling of (+)-dihydrocarvone with acetonitrile has been found to be the precursor of an effective chiral ligand for the enantioselective addition of diethylzinc to aldehydes.
