06078cam a2200625 i 4500 on1055049972 OCoLC 20210423014331.0 m o d cr cnu---unuuu 180929s2019 enka ob 001 0 eng d EBLCP eng rda pn EBLCP N$T OPELS N$T YDX OCLCF OTZ LVT OCLCQ D6H YDXIT UKMGB LQU ESU OCLCQ SNK OCLCQ S2H OCLCO VT2 OCLCQ OCLCO OCLCQ OCLCA (S GBB978886 bnb 019066057 Uk 1054829672 1098218012 1155235042 1235837329 9780128127346 (electronic book) 0128127341 (electronic book) 9780128127339 (paperback) 0128127333 (paperback) (OCoLC)1055049972 (OCoLC)1054829672 (OCoLC)1098218012 (OCoLC)1155235042 (OCoLC)1235837329 QD181.F1 F58 2019 2019 E-939 QV 282 SCI 013030 bisacsh PNN bicssc 546/.731 23 Fluorine in life sciences : pharmaceuticals, medicinal diagnostics, and agrochemicals / edited by Günter Haufe, Frédéric R. Leroux. London, United Kingdom ; San Diego, CA : Academic Press, [2019] 1 online resource (xviii, 667 pages) text txt rdacontent computer c rdamedia online resource cr rdacarrier Progress in fluorine science series Includes bibliographical references and index. 4.3.1 Fluorination of the a-position of carbonyl compounds4.3.2 Electrophilic fluorination of enolates; 4.4 From carboxylic acids; 4.5 From diazo compounds/olefins; 5. Aromatic C-H fluorination; 5.1 Electrophilic aromatic fluorination; 5.2 Transition metal-catalyzed aromatic C-H fluorination; 6. Benzylic C-H fluorination; 6.1 Transition metal-catalyzed C-H fluorination; 6.2 Metal free-radical initiated fluorination; 6.3 Photocatalyzed C-H fluorination; 7. Fluorination of unactivated aliphatic C-H bonds; 7.1 Transition metal-catalyzed C-H fluorination; 7.2 Radical-initiated fluorination. 880-01 Front Cover; Fluorine in Life Sciences:Pharmaceuticals, Medicinal Diagnostics, and Agrochemicals; Fluorine in Life Sciences:Pharmaceuticals, Medicinal Diagnostics, and Agrochemicals; Contents; List of contributors; About the editors; Preface; 1 -- Emerging fluorination methods in organic chemistry relevant for life science application; 1. Introduction; 2. Common reagents; 2.1 Nucleophilic fluorination sources; 2.2 Electrophilic fluorination sources; 3. Fluorination of prefunctionalized aromatic/heteroaromatic substrates; 3.1 Balz-Schiemann reaction; 3.2 The Halex reaction. 3.3 Transition metal-catalyzed fluorination of aryl halides and pseudo-halides3.4 Aromatic deoxyfluorination: PhenoFluor/PhenoFluor Mix; 3.5 Decarboxylative fluorination of heterocycles; 3.6 Fluorination of aryl boron derivatives; 3.7 Fluorination of aryl stannanes; 3.8 Fluorination of aryl silanes; 3.9 Fluorination of diaryliodonium salts; 4. Fluorination of prefunctionalized aliphatic substrates; 4.1 Nucleophilic displacement of halides/activated alcohols; 4.2 Deoxyfluorination-a new era!; 4.3 Direct replacement from aldehydes/ketones. 7.3 Photocatalyzed fluorination of unactivated aliphatic C-H bonds8. Conclusions and outlook; References; 2 -- Fluorination patterns in small alkyl groups: their impact on properties relevant to drug discovery; 1. Introduction; 2. Effective and intrinsic lipophilicity; 3. Basicity modulation by fluorine in aliphatic amines; 4. Modulation of lipophilicity by partially fluorinated alkyl groups; 5. Partially fluorinated alkyl groups attached to aryl carbon; 6. Partially fluorinated alkyl groups attached to ether oxygen; 7. Partially fluorinated alkyl groups attached to saturated amine nitrogen. 8. Aqueous solubility related to lipophilicity and crystal lattice energy9. In vitro oxidative metabolism related to lipophilicity; 10. Conclusions and outlook; References; 3 -- Polyfluorinated scaffolds in drug discovery; 1. Introduction; 1.1 Properties of fluorine; 2. Fluorine chemistry and drug discovery; 2.1 Fluorinated natural products; 2.2 "Early" perfluoroalkyl group-containing compounds; 2.3 Metabolism and toxicity of polyfluorinated compounds; 3. Polyfluorinated drugs; 3.1 Central nervous system agents; 3.2 Anticancer agents; 3.3 Metabolic disorder agents. 3.3.1 Fenfluramine (1973, 70) and Tiflorex (Flutiorex, 71). Online resource; title from digital title page (viewed on April 24, 2019). Fluorine. Fluorine Physiological effect. Fluorine pharmacology. (DNLM)D005461Q000494 SCIENCE Chemistry Inorganic. bisacsh Fluorine. fast (OCoLC)fst00928151 Fluorine Physiological effect. fast (OCoLC)fst00928157 Electronic books. Haufe, Günter, editor. Leroux, Frederic, editor. Print version: Haufe, Günter. Fluorine in Life Sciences: Pharmaceuticals, Medicinal Diagnostics, and Agrochemicals. San Diego : Elsevier Science & Technology, ©2018 9780128127339 Progress in fluorine science series. ScienceDirect https://www.sciencedirect.com/science/book/9780128127339 505-01/(S 4.3.1 Fluorination of the α-position of carbonyl compounds4.3.2 Electrophilic fluorination of enolates; 4.4 From carboxylic acids; 4.5 From diazo compounds/olefins; 5. Aromatic C-H fluorination; 5.1 Electrophilic aromatic fluorination; 5.2 Transition metal-catalyzed aromatic C-H fluorination; 6. Benzylic C-H fluorination; 6.1 Transition metal-catalyzed C-H fluorination; 6.2 Metal free-radical initiated fluorination; 6.3 Photocatalyzed C-H fluorination; 7. Fluorination of unactivated aliphatic C-H bonds; 7.1 Transition metal-catalyzed C-H fluorination; 7.2 Radical-initiated fluorination.