73166-52-6Relevant academic research and scientific papers
PALLADIUM-PROMOTED REACTION OF ALLYL TRIMETHYLSILYL ETHERS WITH ARYL IODIDES
Hirao, Toshikazu,Enda, Jun,Ohshiro, Yoshiki,Agawa, Toshio
, p. 403 - 406 (1981)
Allyl trimethylsilyl ether reacts with aryl iodides in the presence of palladium acetate and lithium chloride to afford selectively β-aryl (E)-α,β-unsaturated carbonyl compound.
Preparation method of alpha-deuterated olefine aldehyde
-
Paragraph 0026; 0097-0100; 0109; 0110, (2022/03/27)
The invention relates to a preparation method of alpha-deuterated olefine aldehyde, which comprises the following steps: by taking alpha, beta-olefine aldehyde as a raw material, carrying out a reversible Michael addition mechanism under the action of deuterium water, a nucleophilic reagent and an organic catalyst to obtain an alpha-deuterated olefine aldehyde compound. The method has high selectivity, and does not generate deuterated by-products at other positions. The alpha-deuterated olefine aldehyde compound prepared by the invention has great application value, can be further widely converted to prepare mono (poly) deuterated olefin and derivatives, olefine acid, conjugated olefine aldehyde, eneyne and other compounds, and has important significance in drug synthesis.
Fluorinated Sulfinates as Source of Alkyl Radicals in the Photo-Enantiocontrolled β-Functionalization of Enals
Alemán, José,Rodríguez, Ricardo I.,Sicignano, Marina
supporting information, (2022/01/22)
The generation of sulfonyl radicals has long been known as a flexible strategy in a wide range of different sulfonylative transformations. Meanwhile their use in alkylation processes has been somehow limited due to their inherent difficulty in evolving to less-stable radicals after sulfur dioxide extrusion. Herein we report a convenient strategy that involves gem-difluorinated sulfinates as an “upgrading-mask”, allowing these precursors to decompose into their corresponding alkyl radicals. The electron–donor character of sulfinates in the formation of an electron donor–acceptor (EDA) complex with transient iminium ions is displayed, achieving the first example of a stereocontrolled light-driven insertion of gem-difluoro derivatives into unsaturated aldehydes. This methodology is compatible with flow conditions, maintaining identical levels of enantiocontrol.
Structure-Based Design of Dual-Acting Compounds Targeting Adenosine A2AReceptor and Histone Deacetylase as Novel Tumor Immunotherapeutic Agents
Cheng, Jianjun,Jiang, Hualiang,Ling, Lijun,Liu, Ruiquan,Wu, Yiran,Xie, Chengying,Yan, Wenzhong,Yang, Kexin,Zhang, Jinfeng,Zhao, Simeng,Zhao, Suwen,Zhong, Guisheng
, p. 16573 - 16597 (2021/12/02)
Adenosine is an immunosuppressive factor in the tumor microenvironment mainly through activation of the A2A adenosine receptor (A2AR), which is a mechanism hijacked by tumors to escape immune surveillance. Small-molecule A2AR antagonists are being evaluat
Gold-Catalyzed Formal Hexadehydro-Diels-Alder/Carboalkoxylation Reaction Cascades
Wang, Hong-Fa,Guo, Lin-Na,Fan, Zhi-Bo,Tang, Tian-Hua,Zi, Weiwei
supporting information, p. 2676 - 2681 (2021/04/12)
A dual gold-catalyzed hexadehydro-Diels-Alder/carboalkoxylation cascade reaction is reported. In this transformation, the gold catalyst participated in the hexadehydro-Diels-Alder step, switching the mechanism from a radical type to a cationic one, and then the catalyst activated the resulting aryne to form an ortho-Au phenyl cation species, which underwent a carboalkoxylation rearrangement rather than the expected aryne-ene reaction.
Aromatic aldehyde synthesis method
-
Paragraph 0078-0084, (2019/07/04)
The invention provides an aromatic aldehyde synthesis method. Aryl halide serves as a starting material, glyoxylic acid serves as a carbonyl source, proper palladium catalysts and phosphine-containingorganic ligands are used, and aromatic aldehyde serving as a target product is prepared by heating and sealing reaction. Raw materials of the synthesis method are easily obtained, operation is simple, the product is easily separated, total reaction rate is high, process cost is low, and the yield of the target product is easily adjusted. Therefore, the aromatic aldehyde synthesis method is beneficial to large-scale industrial production of the aromatic aldehyde.
Evolution of physical and photocatalytic properties of new Zn(II) and Ru(II) complexes
Gugulothu, Venkanna,Ahemed, Jakeer,Subburu, Mahesh,Yadagiri, Bhongiri,Mittal, Ritu,Prabhakar, Chetti,Pola, Someshwar
, p. 412 - 423 (2019/06/27)
Synthesis of Zn(II) and Ru(II) complexes were reported by using N4-macrocyclic Schiff base ligands under solvothermal conditions. The newly synthesized Zn(II) and Ru(II) complexes have been characterized by various physico-chemical techniques such as elemental analysis, molar conductance, HRMS, TGA, FESEM, UV–Vis, FT-IR, 1H NMR, and cyclic voltammetry. By using molar conductance studies, the complexes are formulated as [Zn(TPTTP)]Cl2 and [Ru(TPTTP)Cl2]. C–H bond activation of an sp3 group of methylstyrenes (converted into cinnamaldehydes) and C–H bond activation of the sp2 bond of polycyclic aromatic hydrocarbons through photooxidation was examined in the presence of Zn(II) and Ru(II) complexes. Reusable activity studies and photostability of catalyst are investigated by using UV–Vis spectra. Based on the results, higher catalytic activity of [Ru(TPTTP)Cl2] complex than [Zn(TPTTP)]Cl2 complex in both C–H bond activation and photooxidation of aromatic hydrocarbons has been reported.
Palladium-catalyzed hydroformylation of terminal arylacetylenes with glyoxylic acid
Liu, Yang,Cai, Liangzhen,Xu, Sheng,Pu, Weiwen,Tao, Xiaochun
supporting information, p. 2166 - 2168 (2018/03/06)
A simple, practical and governable palladium-catalyzed hydroformylation of terminal arylacetylenes has been disclosed. The reaction proceeds under syngas-free conditions, using readily available glyoxylic acid as the formyl source, under mild conditions, giving rise to a broad range of α,β-unsaturated aldehydes.
Hendrickson reagent induced rearrangement of aryl propargyl alcohols to α,β-unsaturated aldehydes
Moussa, Ziad,Aljuhani, Ateyatallah
, p. 845 - 853 (2018/11/06)
The Hendrickson reagent (triphenylphosphonium anhydride trifluoromethanesulfonate), prepared from the reaction of triphenylphosphine oxide (Ph3PO) and triflic anhydride (Tf2O) (2:1 stoichiometry), promotes dehydrations and various coupling reactions. The reagent has been used to transform oximes to nitriles and to prepare esters, amides and many other functional groups through the intermediacy of an alkoxyphosphonium salt. The reagent proved useful in heterocycle synthesis of thiazolines, imidazolines, quinoline precursors, isoquinolines, β-carbolines, phenanthridines, 11H-indolo[3,2-c]quinolines, quinoline-lactones, furoquinolinones, and indolizino[1,2-b]quinolin-9(11H)-ones. Moreover, the reagent has been key to the successful total synthesis of several natural products. Aryl propargyl alcohols with a terminal α-acetylenic group undergo rapid conversion to the corresponding α,β-unsaturated aldehydes at room temperature in dichloromethane in the presence of one equivalent of triphenylphosphonium anhydride trifluoromethanesulfonate. The reaction involved adding freshly distilled Tf2O (1.0 mmol) to a solution of Ph3PO (2.0 mmol) in CH2Cl2 (10 mL) at 0oC under N2 atmosphere. After stirring for 10 min, the propargyl alcohol (1.0 mmol) was added as a CH2Cl2 solution (2 mL), followed by the addition of water and Et3N (2.0 mmol) and further stirring at room temperature for 1h. Subsequent workup with 5% NaHCO3 (20 mL) and purification afforded α,β-unsaturated aldehydes. Eighteen aryl propargyl alcohol substrates with a terminal α-acetylenic group were transformed in good to excellent yields (71-85%) to enals. The methodology proved successful with secondary and tertiary alcohols with stereoselectivity favouring exclusively the E isomer. All the synthesized compounds are known and were characterized (1H,13C, and M.P) and compared to literature values. The method offers several advantages such as exclusive stereoselectivity, short reaction time, good yield, mild reaction conditions, and simple operational procedure.
Novel Inhibitors of Staphyloxanthin Virulence Factor in Comparison with Linezolid and Vancomycin versus Methicillin-Resistant, Linezolid-Resistant, and Vancomycin-Intermediate Staphylococcus aureus Infections in Vivo
Ni, Shuaishuai,Wei, Hanwen,Li, Baoli,Chen, Feifei,Liu, Yifu,Chen, Wenhua,Xu, Yixiang,Qiu, Xiaoxia,Li, Xiaokang,Lu, Yanli,Liu, Wenwen,Hu, Linhao,Lin, Dazheng,Wang, Manjiong,Zheng, Xinyu,Mao, Fei,Zhu, Jin,Lan, Lefu,Li, Jian
supporting information, p. 8145 - 8159 (2017/10/18)
Our previous work (Wang et al. J. Med. Chem. 2016, 59, 4831-4848) revealed that effective benzocycloalkane-derived staphyloxanthin inhibitors against methicillin-resistant Staphylococcus aureus (S. aureus) infections were accompanied by poor water solubility and high hERG inhibition and dosages (preadministration). In this study, 92 chroman and coumaran derivatives as novel inhibitors have been addressed for overcoming deficiencies above. Derivatives 69 and 105 displayed excellent pigment inhibitory activities and low hERG inhibition, along with improvement of solubility by salt type selection. The broad and significantly potent antibacterial spectra of 69 and 105 were displayed first with normal administration in the livers and hearts in mice against pigmented S. aureus Newman, Mu50 (vancomycin-intermediate S. aureus), and NRS271 (linezolid-resistant S. aureus), compared with linezolid and vancomycin. In summary, both 69 and 105 have the potential to be developed as good antibacterial candidates targeting virulence factors.
