5910-23-6Relevant academic research and scientific papers
Non-metal catalytic method for preparing 1,3-diketone compounds based on acetyenic ketone
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Paragraph 0080-0083, (2020/02/19)
The invention discloses a non-metal catalytic method for preparing 1,3-diketone compounds based on acetyenic ketone. The preparation method is a stepwise method or a one-pot method. The stepwise method comprises the following steps: mixing an acetyenic ketone compound I, a nitrogen-containing aromatic compound II and a No.1 base for a reaction, performing separation and purification to obtain an intermediate product, mixing the intermediate product and a No.2 base for a reaction, and performing separation and purification to obtain the product; and the one-pot method comprises the following steps: firstly mixing an acetyenic ketone compound I and a nitrogen-containing aromatic compound II, adding a No.1 base, performing a reaction for a period of time, adding a No.2 base, continuing a reaction for a period of time, and finally performing separation and purification to obtain the product. The method provided by the invention has mild reaction conditions, simple operation and a higher yield, wherein the yield is generally 80% or more, and the method has greater practical application value in drug synthesis.
Method of preparing 1,3-diketone compound by acetyenic ketone
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Paragraph 0153-0159, (2019/06/12)
The invention relates to a preparation method of preparing a 1,3-diketone compound by acetyenic ketone. The preparation method comprises the following steps: S1, putting alpha-alkynyl ketone compound,water, gold salt and silver salt in a reaction solvent to obtain a precursor mixture, wherein the molar ratio of the alpha-alkynyl ketone compound, water, gold salt and silver salt is 1: (1-50): (0.001-0.10): (0.002-0.15); and S2, putting the precursor mixture obtained in the S1 to react at a reaction temperature of 0-50 DEG C to obtain the 1,3-diketone compound, wherein the reaction time is 5 min to 48 h. The method is simple in reaction condition, free of acid or alkaline additives and high in yield, and can be applied to modern production on a large scale.
An effective preparation of both 1,3-diketones and nitriles from alkynones with oximes as hydroxide sources
Chen, Pei,Zhang, Qian-Qian,Guo, Jia,Chen, Lu-Lu,Wang, Yan-Bo,Zhang, Xiao
, p. 6958 - 6966 (2018/10/02)
An effective phosphine-catalyzed protocol has been established for the syntheses of 1,3-diketones and nitriles from alkynones with oximes as hydroxide surrogates. This method features the use of a phosphine catalyst, compatibility with various functional groups and ambient temperature, which makes this approach very practical. A plausible mechanism was proposed.
Room-Temperature Coupling/Decarboxylation Reaction of α-Oxocarboxylates with α-Bromoketones: Solvent-Controlled Regioselectivity for 1,2- and 1,3-Diketones
He, Zhen,Qi, Xiaotian,She, Zhijie,Zhao, Yinsong,Li, Shiqing,Tang, Junbin,Gao, Ge,Lan, Yu,You, Jingsong
supporting information, p. 1403 - 1411 (2017/02/10)
A transition-metal-free and room-temperature coupling/decarboxylation reaction between α-oxocarboxylates and α-bromoketones is reported herein. It represents the first mild and regioselective synthesis of either 1,2- or 1,3-diketones from the same starting materials. Notably, the regioselectivity is simply controlled by solvents. The preliminary experimental data and DFT calculations suggest sequential Darzens-type coupling, alkaline hydrolysis, KOH-promoted oxirane opening and decarboxylation in one pot. This method is efficient for the synthesis of α,β-epoxy-γ-butyrolactone and curcuminoids.
Synthesis, characterization and properties of furan-containing difluoroboron complexes
Liu, Chun,Zhang, Hao,Zhao, Jianzhang
, p. 92341 - 92348 (2016/10/09)
Novel difluoroboron β-diketonate complexes F1-F4 bearing a furan unit were synthesized and fully characterized. The effects of different substituents on the photoluminescence and redox properties of these new BF2 complexes were investigated systematically. The absorption and emission maxima of complexes F1-F4 were red-shifted compared to those of reference substance F0. Among them, the complexes F2 with a rigid naphthalene moiety and F3 with an electron donating methoxyl group demonstrated stronger fluorescent emission intensity, much higher quantum yields and longer lifetime values relative to other complexes. Cyclic voltammetry measurements revealed the reversible reduction waves of these BF2 complexes. DFT calculations supported the structural and spectroscopic data and confirmed the compositions of frontier molecular orbitals in the BF2 complexes. These new complexes exhibited different emission colors in solvent and might have potential applications in emitting devices.
Decoupling Activation of Heme Biosynthesis from Anaerobic Toxicity in a Molecule Active in Staphylococcus aureus
Dutter, Brendan F.,Mike, Laura A.,Reid, Paul R.,Chong, Katherine M.,Ramos-Hunter, Susan J.,Skaar, Eric P.,Sulikowski, Gary A.
, p. 1354 - 1361 (2016/06/09)
Small molecules active in the pathogenic bacterium Staphylococcus aureus are valuable tools for the study of its basic biology and pathogenesis, and many molecules may provide leads for novel therapeutics. We have previously reported a small molecule, 1, which activates endogenous heme biosynthesis in S. aureus, leading to an accumulation of intracellular heme. In addition to this novel activity, 1 also exhibits toxicity towards S. aureus growing under fermentative conditions. To determine if these activities are linked and establish what features of the molecule are required for activity, we synthesized a library of analogs around the structure of 1 and screened them for activation of heme biosynthesis and anaerobic toxicity to investigate structure-activity relationships. The results of this analysis suggest that these activities are not linked. Furthermore, we have identified the structural features that promote each activity and have established two classes of molecules: activators of heme biosynthesis and inhibitors of anaerobic growth. These molecules will serve as useful probes for their respective activities without concern for the off target effects of the parent compound.
2-Hydroxylation of 1,3-Diketones with Atmospheric Oxygen
Li, Zheng,Li, Tianpeng,Li, Jiasheng,He, Lili,Jia, Xianggui,Yang, Jingya
supporting information, p. 2863 - 2865 (2015/12/18)
An efficient method for the 2-hydroxylation of 1,3-diketones by using atmospheric oxygen as an oxidant under transition-metal-free condition is described. The protocol has the advantages of using an inexpensive and stable oxidant, producing high yields, and requiring ecofriendly conditions.
Variations in the blaise reaction: Conceptually new synthesis of 3-amino enones and 1,3-diketones
Rao, H. Surya Prakash,Muthanna, Nandurka
supporting information, p. 1525 - 1532 (2015/03/04)
Organic compounds with 3-amino enone or 1,3-diketone functional groups are extremely important, as they can be converted into a plethora of heterocyclic or carbocyclic compounds, or can be used as ligands in metal complexes. We have achieved a new, easy, straightforward and convenient synthesis of 3-amino enones and 1,3-diketones starting from aryl/heteroaryl/alkyl nitriles and 1-aryl/alkyl 2-bromoethanones. The reaction is a variation of the classical Blaise reaction, and it works with zinc and trimethylsilyl chloride as an activator. By running the hydrolysis of the reaction intermediate with HCl (3 N aq.) at 0-30 °C or at 100 °C, it is possible to form either 3-amino enones or 1,3-diketones, respectively. The newly developed method was used for the synthesis of avobenzone, an ingredient of sun-screen lotions. Furthermore, an easy synthesis of (Z)-3-amino-1-[4-(tertbutyl) phenyl]-3-(4-methoxyphenyl)prop-2-en-1-one, with UV/Vis absorption characteristics similar to those of avobenzone, was also achieved.
FLUORIDE ION INDUCED REACTIONS OF ORGANOSILANES: THE PREPARATION OF MONO AND DICARBONYL COMPOUNDS FROM β-KETOSILANES.
Fiorenza, Mariella,Mordini, Alessandro,Papaleo, Sandro,Pastorelli, Stefania,Ricci, Alfredo
, p. 787 - 788 (2007/10/02)
β-ketosilanes react with a variety of carbon electrophiles in the presence of CsF to give mono- and dicarbonyl derivatives in reasonably good yields.
