104-20-1Relevant academic research and scientific papers
Palladium Catalysis for Aerobic Oxidation Systems Using Robust Metal–Organic Framework
Li, Jiawei,Liao, Jianhua,Ren, Yanwei,Liu, Chi,Yue, Chenglong,Lu, Jiaming,Jiang, Huanfeng
, p. 17148 - 17152 (2019)
Described here is a new and viable approach to achieve Pd catalysis for aerobic oxidation systems (AOSs) by circumventing problems associated with both the oxidation and the catalysis through an all-in-one strategy, employing a robust metal–organic framework (MOF). The rational assembly of a PdII catalyst, phenanthroline ligand, and CuII species (electron-transfer mediator) into a MOF facilitates the fast regeneration of the PdII active species, through an enhanced electron transfer from in situ generated Pd0 to CuII, and then CuI to O2, trapped in the framework, thus leading to a 10 times higher turnover number than that of the homogeneous counterpart for Pd-catalyzed desulfitative oxidative coupling reactions. Moreover, the MOF catalyst can be reused five times without losing activity. This work provides the first exploration of using a MOF as a promising platform for the development of Pd catalysis for AOSs with high efficiency, low catalyst loading, and reusability.
Chemopreventive potential of cyclic diarylheptanoids.
Ishida, Junko,Kozuka, Mutsuo,Tokuda, Harukuni,Nishino, Hoyoku,Nagumo, Seiji,Lee, Kuo Hsiung,Nagai, Masahiro
, p. 3361 - 3365 (2002)
Eleven cyclic diarylheptanoids and seven related compounds were screened as potential antitumor promoters by using the in vitro short-term 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced Epstein-Barr virus early antigen (EBV-EA) activation assay. In addition, the cyclic diarylheptanoid myricanone (2) was examined for antitumor initiating activity in a two-stage carcinogenesis assay of mouse skin tumors induced by peroxynitrite as an initiator and TPA as a promoter. Myricanone (2) exhibited significant antitumor-initiating effect on mouse skin. These data suggest that cyclic, as well as linear, diarylheptanoids might be valuable chemopreventors.
Activity and selectivity of W110A secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus in organic solvents and ionic liquids: Mono- and biphasic media
Musa, Musa M.,Ziegelmann-Fjeld, Karla I.,Vieille, Claire,Phillips, Robert S.
, p. 887 - 892 (2008)
The asymmetric reduction of hydrophobic phenyl-ring-containing ketones and the enantiospecific kinetic resolution of the corresponding racemic alcohols catalyzed by Thermoanaerobacter ethanolicus W110A secondary alcohol dehydrogenase were performed in mono- and biphasic systems containing either organic solvents or ionic liquids. Both yield and enantioselectivity for these transformations can be controlled by changing the reaction medium. The enzyme showed high tolerance to both water-miscible and -immiscible solvents, which allows biotransformations to be conducted at high substrate concentrations. The Royal Society of Chemistry.
Efficient and facile synthesis of novel stable monodeuterium labeled ractopamine
Su, Feifei,Wu, Fulong,Tang, He,Wang, Zhonghua,Wu, Fanhong
, p. 479 - 482 (2015)
A novel synthetic route to stable deuterium labeled ractopamine was disclosed with 6.49% total yield and 97.7% isotopic abundance. Its structure and the isotope-abundance were confirmed according to 1H-NMR and high-resolution mass spectrometry. A novel synthetic route to stable deuterium labeled ractopamine was disclosed with 9 steps, 6.49% total yield and 97.7% isotopic abundance. Its structure and the isotope-abundance were confirmed according to 1H-NMR and high-resolution mass spectrometry.
Synthesis of α-Tertiary Amine Derivatives by Intermolecular Hydroamination of Unfunctionalized Alkenes with Sulfamates under Trifluoromethanesulfonic Acid Catalysis
Fei, Jun,Wang, Zhen,Cai, Zheren,Sun, Hao,Cheng, Xu
, p. 4063 - 4068 (2015)
An efficient and mild trifluoromethanesulfonic acid-catalyzed hydroamination of unfunctionalized alkenes to afford α-tertiary amine derivatives at temperatures as low as room temperature is reported. 2,2,2-Trifluoroethyl sulfamate was found to be the optimal nitrogen source because its good solubility in both organic solvents and water facilitated both conversion and purification. The reaction conditions were compatible with a variety of substrate functional groups and afforded moderate to good yields. The desired amine compounds could be obtained easily by means of a mild, one-pot, redox-neutral deprotection procedure. Caryolane amine was synthesized with excellent chemo- and regioselectivities by means of a cascade hydroamination reaction of β-caryophyllene.
Cation-Exchanged Montmorillonite-Catalyzed Facile Friedel-Crafts Alkylation of Hydroxy and Methoxy Aromatics with 4-Hydroxybutan-2-one To Produce Raspberry Ketone and Some Pharmaceutically Active Compounds
Tateiwa, Jun-ichi,Horiuchi, Hiroki,Hashimoto, Keiji,Yamauchi, Takayoshi,Uemura, Sakae
, p. 5901 - 5904 (1994)
The Friedel-Crafts alkylation of hydroxy and methoxy aromatics with 4-hydroxybutan-2-one (γ-KB) in the presence of a cation-exchanged montmorillonite (M(n+)-mont; M(n+) = Zr(4+), Al(3+), Fe(3+), and Zn(2+)) was investigated.Phenol was C-alkylated regiospecifically with γ-KB in the presence of Zr(4+)-, Al(3+)-, or Fe(3+)-mont to produce 4-(4-hydroxyphenyl)butan-2-one (raspberry ketone) in 31-35percent GLC yield.Anisole, 2-methoxynaphthalene, and 1-methoxynaphthalene were regiospecifically C-alkylated to produce 4-(4-methoxyphenyl)butan-2-one, 4-(2-methoxy-1-naphthyl)butan-2-one (pharmaceutically active), and 4-(4-methoxy-1-naphthyl)butan-2-one, respectively.Al(3+)- and Fe(3+)-mont were the most effective catalysts in these cases (13-58percent isolated yield). γ-KB could be used as an alkylating agent instead of the highly toxic 3-buten-2-one (MVK) which also polymerizes easily.
A scalable two-step continuous flow synthesis of nabumetone and related 4-aryl-2-butanones
Viviano, Monica,Glasnov, Toma N.,Reichart, Benedik,Tekautz, Guenter,Kappe, C. Oliver
, p. 858 - 870 (2011)
Three different continuous flow strategies for the generation of important 4-aryl-2-butanone derivatives including the anti-inflammatory drug nabumetone [4-(6-methoxy-2-naphthalenyl)-2-butanone] and the aroma compounds raspberry ketone [4-(4-hydroxyphenyl)-2-butanone] and its methyl ether [4-(4-methoxyphenyl)-2-butanone] were evaluated. All three protocols involve the initial preparation of the corresponding 4-aryl-3-buten-2-ones via Mizoroki-Heck, Wittig, or aldol strategies, which is then followed by selective hydrogenation of the C=C double bond to the desired 4-aryl-2-butanones. The synthetic routes to 4-aryl-3-buten-2-ones were first optimized/intensified on small scale to reaction times of 1-10 min using batch microwave heating technology and then translated to a scalable continuous flow process employing commercially available stainless steel capillary tube reactors. For the synthesis of 4-(4-methoxyphenyl)-3-buten-2-one a further scale-up using a custom-built mesofluidic mini-plant flow system capable of processing several liters per hour was designed to further expand the scale of the process. The final hydrogenation step was performed using a fixed-bed continuous flow hydrogenator employing Ra/Ni as a catalyst.
A chemoselective hydrogenation of the olefinic bond of α,β- unsaturated carbonyl compounds in aqueous medium under microwave irradiation
Sharma, Anuj,Kumar, Vinod,Sinha, Arun K.
, p. 354 - 360 (2006)
A microwave-assisted mild and ecofriendly catalytic transfer hydrogenation process was developed to reduce various α,β-unsaturated carbonyl compounds into the corresponding saturated carbonyl compounds in the presence of silica-supported palladium chloride as catalyst and a combination of MeOH/HCOOH/H2O (1:2:3) as hydrogen source within 22-55 minutes in moderate to excellent yields with 100% chemoselectivity.
Iridium(I)-catalyzed regioselective C-H activation and hydrogen-isotope exchange of non-aromatic unsaturated functionality
Kerr, William J.,Mudd, Richard J.,Paterson, Laura C.,Brown, Jack A.
, p. 14604 - 14607 (2014)
Isotopic labelling is a key technology of increasing importance for the investigation of new C-H activation and functionalization techniques, as well as in the construction of labelled molecules for use within both organic synthesis and drug discovery. Herein, we report for the first time selective iridium-catalyzed C-H activation and hydrogen-isotope exchange at the β-position of unsaturated organic compounds. The use of our highly active [Ir(cod)(IMes)(PPh3)][PF6] (cod = 1, 5-cyclooctadiene) catalyst, under mild reaction conditions, allows the regioselective β-activation and labelling of a range of α, β-unsaturated compounds with differing steric and electronic properties. This new process delivers high levels of isotope incorporation over short reaction times by using low levels of catalyst loading.
Synthesis and neuroprotective evaluation of (E)-3,4-dihydroxystyryl p-substituted-phenethyl ketone derivatives against inflammatory and oxidative injury
Cheng, Can,Ning, Xianling,Luo, Yongming,Tian, Chao,Wang, Xiaowei,Guo, Ying,Liu, Junyi,Zhang, Zhili
, p. 1678 - 1685 (2016)
(E)-3,4-dihydroxystyryl p-substituted-phenethyl ketones and their 3,4-diacetylated derivatives were synthesized and examined their neuroprotective activities to further study the effect of p-substituents on the aromatic ring. The results revealed that steric hindrance effect of p-substituents has impact on neuroprotective activities against inflammatory and oxidative injury. Introduction of the bulkier groups are more beneficial to improve the neuroprotective activities than smaller groups. Compounds (4–5h, 4–5i and 4–5e) with p-substituted trifluoromethyl, isopropyl and t-butyl groups exhibited the best effects among all the target compounds.
