51772-30-6Relevant articles and documents
Iridium Complexes as Efficient Catalysts for Construction of α-Substituted Ketones via Hydrogen Borrowing of Alcohols in Water
Luo, Nianhua,Zhong, Yuhong,Wen, Huiling,Shui, Hongling,Luo, Renshi
, p. 1355 - 1364 (2021/03/03)
Ketones are of great importance in synthesis, biology, and pharmaceuticals. This paper reports an iridium complexes-catalyzed cross-coupling of alcohols via hydrogen borrowing, affording a series of α-alkylated ketones in high yield (86 %–95 %) and chemoselectivities (>99 : 1). This methodology has the advantages of low catalyst loading (0.1 mol%) and environmentally benign water as the solvent. Studies have shown the amount of base has a great impact on chemoselectivities. Meanwhile, deuteration experiments show water plays an important role in accelerating the reduction of the unsaturated ketones intermediates. Remarkably, a gram-scale experiment demonstrates this methodology of iridium-catalyzed cross-coupling of alcohols has potential application in the practical synthesis of α-alkylated ketones.
Photoredox/nickel-catalyzed hydroacylation of ethylene with aromatic acids
Chen, Shuai,He, Hengchi,Li, Weipeng,Xie, Jin,Zhang, Lili,Zhu, Chengjian
supporting information, p. 9064 - 9067 (2021/09/15)
We report a general, practical and scalable hydroacylation reaction of ethylene with aromatic carboxylic acids with the synergistic combination of nickel and photoredox catalysis. Under ambient temperature and pressure, feedstock chemicals such as ethylene can be converted into high-value-added aromatic ketones in moderate to good yields (up to 92%) with reaction time of 2-6 hours.
Synthetic method of 3 '-methyl propiophenone
-
, (2020/07/21)
The invention belongs to the field of organic synthesis, and discloses a synthetic method of 3 '-methyl propiophenone. The method comprises the following steps: taking m-tolualdehyde as a raw material, carrying out affinity addition reaction with an ethyl Grignard reagent to obtain 3 '-methyl phenylpropanol; and then using oxygen as an oxidizing agent, using a composite catalyst composed of nitroxide free radicals, inorganic bromide and nitrite, and performing catalytic oxidation on 3 '-methyl phenylpropanol to generate 3'-methyl propiophenone. The adopted composite catalyst is good in stability and selectivity, high in yield (up to 90% or above), reusable, safe and environment-friendly in the whole process and suitable for industrial production.
Cobalt-Catalyzed Migrational Isomerization of Styrenes
Zhao, Jiajin,Cheng, Biao,Chen, Chenhui,Lu, Zhan
supporting information, p. 837 - 841 (2020/01/31)
An efficient cobalt-catalyzed migrational isomerization of styrenes was developed using the thiazoline iminopyridine (TIP) ligand. This reaction is operationally simple and atom-economical using readily available starting materials to access trisubstituted alkenes. Even when using a 0.1 mol % catalyst loading, the reaction could be conducted in neat and completed in 1 h with excellent conversion and high E stereoselectivity.
Novel benzene-based carbamates for ache/bche inhibition: Synthesis and ligand/structure-oriented sar study
Bak, Andrzej,Kozik, Violetta,Kozakiewicz, Dariusz,Gajcy, Kamila,Strub, Daniel Jan,Swietlicka, Aleksandra,Stepankova, Sarka,Imramovsky, Ales,Polanski, Jaroslaw,Smolinski, Adam,Jampilek, Josef
, (2019/05/10)
A series of new benzene-based derivatives was designed, synthesized and comprehensively characterized. All of the tested compounds were evaluated for their in vitro ability to potentially inhibit the acetyl-and butyrylcholinesterase enzymes. The selectivity index of individual molecules to cholinesterases was also determined. Generally, the inhibitory potency was stronger against butyryl-compared to acetylcholinesterase; however, some of the compounds showed a promising inhibition of both enzymes. In fact, two compounds (23, benzyl ethyl(1-oxo-1-phenylpropan-2-yl)carbamate and 28, benzyl (1-(3-chlorophenyl)-1-oxopropan-2-yl) (methyl)carbamate) had a very high selectivity index, while the second one (28) reached the lowest inhibitory concentration IC50 value, which corresponds quite well with galanthamine. Moreover, comparative receptor-independent and receptor-dependent structure–activity studies were conducted to explain the observed variations in inhibiting the potential of the investigated carbamate series. The principal objective of the ligand-based study was to comparatively analyze the molecular surface to gain insight into the electronic and/or steric factors that govern the ability to inhibit enzyme activities. The spatial distribution of potentially important steric and electrostatic factors was determined using the probability-guided pharmacophore mapping procedure, which is based on the iterative variable elimination method. Additionally, planar and spatial maps of the host–target interactions were created for all of the active compounds and compared with the drug molecules using the docking methodology.
Method for generating ketone through rearranging diazo compounds under catalysis condition of ferrous sulfate heptahydrate
-
Paragraph 0018; 0019; 0020; 0021; 0023; 0027; 0028; 0029, (2018/09/08)
The invention provides a method for generating ketone through rearranging diazo compounds to remove one molecule of nitrogen gas and one molecule of carbon dioxide under a certain condition. The method comprises the following steps of adding diazo compound 2-diazo-1-phenylbutane-1,3-diketone and iron sulfate heptahydrate into a reaction container; then adding methylbenzene; performing stirring reaction for 12 hours at 100 DEG C; after the reaction is completed, performing filtering by a kieselguhr sand core funnel; after rotary drying, performing column separation to obtain pure products. Thepreparation method is simple and convenient; the cost is low; the conditions are mild; the yield can reach 80 percent or higher. The method belongs to a novel method for generating ketone. A positiveresearch is provided for the application of the compound.
Enantioselective Hydrogen Atom Transfer: Discovery of Catalytic Promiscuity in Flavin-Dependent 'Ene'-Reductases
Sandoval, Braddock A.,Meichan, Andrew J.,Hyster, Todd K.
supporting information, p. 11313 - 11316 (2017/08/30)
Flavin has long been known to function as a single electron reductant in biological settings, but this reactivity has rarely been observed with flavoproteins used in organic synthesis. Here we describe the discovery of an enantioselective radical dehalogenation pathway for α-bromoesters using flavin-dependent 'ene'-reductases. Mechanistic experiments support the role of flavin hydroquinone as a single electron reductant, flavin semiquinone as the hydrogen atom source, and the enzyme as the source of chirality.
General, Simple, and Chemoselective Catalysts for the Isomerization of Allylic Alcohols: The Importance of the Halide Ligand
Erbing, Elis,Vázquez-Romero, Ana,Bermejo Gómez, Antonio,Platero-Prats, Ana E.,Carson, Fabian,Zou, Xiaodong,Tolstoy, P?ivi,Martín-Matute, Belén
supporting information, p. 15659 - 15663 (2016/10/25)
Remarkably simple IrIIIcatalysts enable the isomerization of primary and sec-allylic alcohols under very mild reaction conditions. X-ray absorption spectroscopy (XAS) and mass spectrometry (MS) studies indicate that the catalysts, with the general formula [Cp*IrIII], require a halide ligand for catalytic activity, but no additives or additional ligands are needed.
The genetic incorporation of thirteen novel non-canonical amino acids
Tuley, Alfred,Wang, Yane-Shih,Fang, Xinqiang,Kurra, Yadagiri,Rezenom, Yohannes H.,Liu, Wenshe R.
supporting information, p. 2673 - 2675 (2014/03/21)
Thirteen novel non-canonical amino acids were synthesized and tested for suppression of an amber codon using a mutant pyrrolysyl-tRNA synthetase-tRNAPylCUA pair. Suppression was observed with varied efficiencies. One non-canonical amino acid in particular contains an azide that can be applied for site-selective protein labeling. The Royal Society of Chemistry 2014.
Rhodium-catalyzed ketone methylation using methanol under mild conditions: Formation of α-branched products
Chan, Louis K. M.,Poole, Darren L.,Shen, Di,Healy, Mark P.,Donohoe, Timothy J.
supporting information, p. 761 - 765 (2014/01/23)
The rhodium-catalyzed methylation of ketones has been accomplished using methanol as the methylating agent and the hydrogen-borrowing method. The sequence is notable for the relatively low temperatures that are required and for the ability of the reaction system to form α-branched products with ease. Doubly alkylated ketones can be prepared from methyl ketones and two different alcohols by using a sequential one-pot iridium- and rhodium-catalyzed process. Uniquely effective for making branched alkyl products from ketones (see scheme): The scope of the presented reaction includes aromatic and aliphatic ketones and consecutive one-pot double alkylation reactions to provide a convenient route to branched ketones from simple methyl ketones. A brief study into the mechanism of the reaction has given evidence for an aldol-based reaction pathway.
