125950-57-4Relevant academic research and scientific papers
Nucleophilic monofluoroalkylation with fluorinated phosphonium salt toward carbonyl and imine compounds
Zeng, Xian-Liang,Deng, Zu-Yong,Liu, Can,Zhao, Gang,Lin, Jin-Hong,Zheng, Xing,Xiao, Ji-Chang
, p. 17 - 23 (2017)
A fluorinated substituent on the positive phosphorus in phosphonium salt [Ph3P+CF(Me)CO2Et Br?] was found to be able to act as a nucleophile to realize monofluoroalkylation of aldehydes, ketones and imines.
Origin of the E/Z Selectivity in the Synthesis of Tetrasubstituted Olefins by Wittig Reaction of α-Fluorophosphonium Ylides: An Explanation for the Low Stereoselectivity Observed in Reactions of α-Alkoxy Aldehydes
Depré, Dominique,Vermeulen, Wim A. A.,Lang, Yolande,Dubois, Jean,Vandevivere, Jan,Vandermeersch, Jeremy,Huang, Longchuan,Robiette, Rapha?l
supporting information, p. 1414 - 1417 (2017/03/23)
A series of tetrasubstituted fluoroalkenes were synthesized in good yield and high E/Z selectivity (up to 96/4) by Wittig reaction between α-heterosubstituted ketones and α-fluorophosphonium ylides. A detailed study of factors that control stereoselectivity in these reactions shows that stereoselectivity is the result of stabilizing CH···F and N···C=O interactions in the addition TS leading to the E isomer. This analysis provides a rationale for the observed decrease in selectivity for reactions of stabilized ylides with α-alkoxy aldehydes.
Synthesis of new ligands for targeting the S1P1 receptor
Schilson, Stefanie S.,Keul, Petra,Shaikh, Rizwan S.,Sch?fers, Michael,Levkau, Bodo,Haufe, Günter
supporting information, p. 1011 - 1026 (2015/03/04)
Sphingosine-1-phosphate (S1P) influences various fundamental biological processes by interacting with a family of five G protein-coupled receptors (S1P1-5). FTY720, a sphingosine analogue, which was approved for treatment of relapsing forms of multiple sclerosis, is phosphorylated in vivo and acts as an agonist of four of the five S1P receptor subtypes. Starting from these lead structures we developed new agonists for the S1P1 receptor. The biological activity was tested in vivo and promising ligands were fluorinated at different positions to identify candidates for positron emission tomography (PET) imaging after [18F]-labelling. The radioligands shall enable the imaging of S1P1 receptor expression in vivo and thus may serve as novel imaging markers of S1P-related diseases.
NEW LIGANDS FOR TARGETING OF S1P RECEPTORS FOR IN VIVO IMAGING AND TREATMENT OF DISEASES
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Paragraph 0387; 0388; 0389; 0390; 0391; 0392; 0393, (2014/06/25)
The present invention relates to novel compounds of formulae (I) and (II) which are useful in the prevention, treatment and diagnosis, in vivo diagnosis of diseases or disorders related to S1P receptors, in particular, in diseases which are connected to the regulatory function of sphingosine-1-phosphate (S1P) and its analogues, such as inflammation, pain, autoimmune diseases and cardiovascular diseases.
IMPROVED PROCESS FOR PREPARING 2-[(2E)-2-FLUORO-2-(3-PIPERIDINYLIDENE)ETHYL]-1H-ISOINDOLE-1,3(2H)-DIONE
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Page/Page column 18, (2013/04/13)
The present invention relates to an improved process for preparing 2-[(2E)-2-fluoro-2-(3-piperidinylidene)ethyl]-1H-isoindole-1,3(2H)-dione, or a salt thereof, which is an intermediate in the synthesis route of the antibacterial compound 7-[(3E)-3-(2-amin
NEW LIGANDS FOR TARGETING OF S1P RECEPTORS FOR IN VIVO IMAGING AND TREATMENT OF DISEASES
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Page/Page column 50, (2013/03/26)
The present invention relates to novel compounds of formulae (I) and (II) which are useful in the prevention, treatment and diagnosis, in vivo diagnosis of diseases or disorders related to S1P receptors, in particular, in diseases which are connected to the regulatory function of sphingosine-1-phosphate (S1P) and its analogues, such as inflammation, pain, autoimmune diseases and cardiovascular diseases.
Alkylation of (Fluorocarbethoxymethylene)-tri-n-butylphosphorane: A Facile Entry to α-Fluoroalkanoates
Thenappan, Alagappan,Burton, Donald J.
, p. 2311 - 2317 (2007/10/02)
(Fluorocarbethoxymethyl)trialkylphosphonium bromides 6, prepared from ethyl bromofluoroacetate and tertiary phosphines, react with n-butyllithium in THF to give the corresponding phosphoranes 7.Reaction of the pregenerated (fluorocarbethoxymethylene)tri-n-butylphosphorane 7a with primary alkyl iodides and activated alkyl bromides followed by in situ hydrolysis of the alkylated salts provides the fluoroalkanoates 9 in a one-pot reaction.In the case of secondary alkyl halides, no substitution was observed, the main reaction being decomposition of the phosphorane.However, the anion obtained from diisopropyl (fluorocarbethoxymethyl)phosphonate 10 b reacts with CH3CH(Ph)Br and (CH3)2CHI to afford the corresponding alkylated phosphonates in good yields.Displacement of the phosphonate moiety either by base-induced hydrolysis or by reduction was unsuccessful.
