73744-44-2Relevant academic research and scientific papers
Fluorine-Containing sp3-Enriched Building Blocks for the Multigram Synthesis of Fluorinated Pyrazoles and Pyrimidines with (Hetero)aliphatic Substituents
Fedinchyk, Anastasiya,Herasymchuk, Maksym,Smirnov, Vladyslav O.,Melnykov, Kostiantyn P.,Yarmoliuk, Dmytro V.,Kyrylchuk, Andrii A.,Grygorenko, Oleksandr O.
, (2022/04/03)
Efficient approaches to the gram-scale synthesis of fluorinated pyrazoles and pyrimidines bearing saturated (hetero)cyclic substituents are described. The methods rely on the heterocyclizations of sp3-enriched β-bromo-α,α-difluoroketones and fl
Alpha-fluorochalcone derivative and application thereof
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, (2021/05/22)
The invention provides an alpha-fluorochalcone derivative and application thereof. The derivative comprises pharmaceutically acceptable salt of the derivative. The invention also provides an application of the derivative and the pharmaceutically acceptable salt thereof in preparation of drugs for treating PPAR receptor related diseases. The derivative provided by the invention has the characteristics of good in-vivo absorption, high bioavailability and strong drug effect, thereby having huge clinical application value.
Unbalanced-Ion-Pair-Catalyzed Nucleophilic Fluorination Using Potassium Fluoride
Hammond, Gerald B.,Li, Wangbing,Lu, Zhichao,Xu, Bo
supporting information, p. 9640 - 9644 (2021/12/14)
An unbalanced ion pair promoter (e.g., tetrabutylammonium sulfate), consisting of a bulky and charge-delocalized cation and a small and charge-localized anion, greatly accelerates nucleophilic fluorinations using easy handling KF. We also successfully converted an inexpensive and commercially available ion-exchange resin to the polymer-supported ion pair promoter (A26–SO42–), which could be reused after filtration. Moreover, A26–SO42– can be used in continuous flow conditions. In our conditions, water is well-tolerated.
Chalcone-Supported Cardiac Mesoderm Induction in Human Pluripotent Stem Cells for Heart Muscle Engineering
Raad, Farah S.,Khan, Taukeer A.,Esser, Tilman U.,Hudson, James E.,Seth, Bhakti Irene,Fujita, Buntaro,Gandamala, Ravi,Tietze, Lutz F.,Zimmermann, Wolfram
supporting information, p. 3300 - 3305 (2021/09/02)
Human pluripotent stem cells (hPSCs) hold great promise for applications in cell therapy and drug screening in the cardiovascular field. Bone morphogenetic protein 4 (BMP4) is key for early cardiac mesoderm induction in hPSC and subsequent cardiomyocyte derivation. Small-molecular BMP4 mimetics may help to standardize cardiomyocyte derivation from hPSCs. Based on observations that chalcones can stimulate BMP4 signaling pathways, we hypothesized their utility in cardiac mesoderm induction. To test this, we set up a two-tiered screening strategy, (1) for directed differentiation of hPSCs with commercially available chalcones (4’-hydroxychalcone [4’HC] and Isoliquiritigen) and 24 newly synthesized chalcone derivatives, and (2) a functional screen to assess the propensity of the obtained cardiomyocytes to self-organize into contractile engineered human myocardium (EHM). We identified 4’HC, 4-fluoro-4’-methoxychalcone, and 4-fluoro-4’-hydroxychalcone as similarly effective in cardiac mesoderm induction, but only 4’HC as an effective replacement for BMP4 in the derivation of contractile EHM-forming cardiomyocytes.
Double Enzyme-Catalyzed One-Pot Synthesis of Enantiocomplementary Vicinal Fluoro Alcohols
Fan, Jiajie,Lin, Xianfu,Peng, Yongzhen,Wang, Anlin,Wu, Qi,Xu, Jian,Xu, Weihua,Yu, Huilei
, (2020/07/24)
A double-enzyme-catalyzed strategy for the synthesis of enantiocomplementary vicinal fluoro alcohols through a one-pot, three-step process including lipase-catalyzed hydrolysis, spontaneous decarboxylative fluorination, and subsequent ketoreductase-catalyzed reduction was developed. With this approach, β-ketonic esters were converted to the corresponding vicinal fluoro alcohols with high isolated yields (up to 92percent) and stereoselectivities (up to 99percent). This new cascade process addresses some issues in comparison with traditional methods such as environmentally hazardous reaction conditions and low stereoselectivity outcome.
Copper(I)-Mediated Borofluorination of Alkynes
Jordan, Abraham J.,Thompson, Percie K.,Sadighi, Joseph P.
, p. 5242 - 5246 (2018/09/12)
The electrophilic fluorination of N-heterocyclic carbene (NHC) copper(I) vinyls results in fluoroalkene formation. Alkynes can be converted to cis-(β-fluorovinyl)boronates by a reaction with an (NHC)copper(I) boryl generated in situ, followed by N-fluorobenzenesulfonimide (NFSI). This sequence gives rise to anti-Markovnikov fluorination products from terminal alkynes. Oxidation of a cis-(β-fluorovinyl)trifluoroboronate yields an α-fluoroketone, whereas a palladium-catalyzed Suzuki-Miyaura coupling yields a tetrasubstituted monofluoroalkene.
Α - fluoro acetophenone derivative
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Paragraph 0029; 0034, (2018/08/28)
PROBLEM TO BE SOLVED: To provide a new production method of an α-fluoroacetophenone derivative by a simple one-step fluorination reaction with an acetophenone derivative under a mild condition.SOLUTION: An acetophenone derivative represented by formula (I) is reacted with a hydrogen fluoride/amine complex in the presence of a hypervalent iodine compound, (in the formula, a ring A indicates an aromatic ring of 1-3 members; Rindicates a hydrogen atom or an aromatic ring of 1-3 members that may be substituted; Rindicates a hydrogen atom or an alkyl group of 1-6 carbons; and Rindicates a hydrogen atom, an alkyl group of 1-6 carbons, an alkoxy group of 1-6 carbons or a halogen atom). The H part in formula (I) is substituted and fluorinated.
Decarboxylative fluorination of β-Ketoacids with N-fluorobenzenesulfonimide (NFSI) for the synthesis of α-fluoroketones: Substrate scope and mechanistic investigation
Zhang, Rui,Ni, Chuanfa,He, Zhengbiao,Hu, Jinbo
, p. 166 - 172 (2017/09/18)
Cesium carbonate (Cs2CO3)-mediated decarboxylative fluorination of β-ketoacids using NFSI in the MeCN/H2O mixed solvent system affords α-fluoroketones with a broad scope. Both electron-rich and electron-deficient α-non-substituted β-ketoacids are amenable to this protocol. The mechanistic study indicates that the reaction proceeds through electrophilic fluorination followed by decarboxylation, which is different from the decarboxylative fluorination of normal carboxylic acids.
Palladium-catalyzed direct mono-α-arylation of α-fluoroketones with aryl halides or phenyl triflate
Zhou, Jun,Fang, Xiang,Shao, Tongle,Yang, Xueyan,Wu, Fanhong
, p. 54 - 62 (2016/10/05)
A palladium catalyzed Negishi-type α-arylation of α-fluoroketones with electron-rich and electron-deficient aryl halides or phenyl triflate has been developed. This direct mono-α-arylation method generate a variety of ternary α-aryl-α-monofluoroketones easily in good to excellent yields using XPhos as ligand and Cs2CO3as mild base.
Synthesis of α-Fluoroketones from Vinyl Azides and Mechanism Interrogation
Wu, Shu-Wei,Liu, Feng
supporting information, p. 3642 - 3645 (2016/08/16)
An efficient and mild fluorination of vinyl azides for the synthesis of α-fluoroketones is described. The mechanistic studies indicated that a single-electron transfer (SET) and a subsequent fluorine atom transfer process could be involved in the reaction.
