Literature DB >> 31414105

Fluorine containing cyclopropanes: synthesis of aryl substituted all-cis 1,2,3-trifluorocyclopropanes, a facially polar motif.

Zeguo Fang1, David B Cordes, Alexandra M Z Slawin, David O'Hagan.   

Abstract

The syntheses of substituted all-cis-1,2,3-trifluorocyclopropanes are described for the first time. The three fluorines located on each of the cyclopropyl carbons with a stereochemistry where they are all on the same face of the cyclopropane, imparts a significant polarity to the molecule, and the inherent conformational rigidity and lowering of log P makes this motif attractive for exploration as a substituent for pharmaceuticals and agrochemicals research.

Entities:  

Year:  2019        PMID: 31414105     DOI: 10.1039/c9cc05749h

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN: 1359-7345            Impact factor:   6.222


  6 in total

1.  Janus All-Cis 2,3,4,5,6-Pentafluorocyclohexyl Building Blocks Applied to Medicinal Chemistry and Bioactives Discovery Chemistry.

Authors:  Joshua L Clark; Rifahath M Neyyappadath; Cihang Yu; Alexandra M Z Slawin; David B Cordes; David O'Hagan
Journal:  Chemistry       Date:  2021-10-06       Impact factor: 5.020

2.  Trifluorinated Tetralins via I(I)/I(III)-Catalysed Ring Expansion: Programming Conformation by [CH2 CH2 ] → [CF2 CHF] Isosterism.

Authors:  Jessica Neufeld; Timo Stünkel; Christian Mück-Lichtenfeld; Constantin G Daniliuc; Ryan Gilmour
Journal:  Angew Chem Int Ed Engl       Date:  2021-05-01       Impact factor: 15.336

3.  Understanding the Conformational Behavior of Fluorinated Piperidines: The Origin of the Axial-F Preference.

Authors:  Zackaria Nairoukh; Felix Strieth-Kalthoff; Klaus Bergander; Frank Glorius
Journal:  Chemistry       Date:  2020-05-12       Impact factor: 5.236

4.  Synthesis of organic liquid crystals containing selectively fluorinated cyclopropanes.

Authors:  Zeguo Fang; Nawaf Al-Maharik; Peer Kirsch; Matthias Bremer; Alexandra M Z Slawin; David O'Hagan
Journal:  Beilstein J Org Chem       Date:  2020-04-14       Impact factor: 2.883

5.  Regio- and Enantioselective Intermolecular Aminofluorination of Alkenes via Iodine(I)/Iodine(III) Catalysis.

Authors:  Michael Schäfer; Timo Stünkel; Constantin G Daniliuc; Ryan Gilmour
Journal:  Angew Chem Int Ed Engl       Date:  2022-06-28       Impact factor: 16.823

6.  Lipophilicity trends upon fluorination of isopropyl, cyclopropyl and 3-oxetanyl groups.

Authors:  Benjamin Jeffries; Zhong Wang; Robert I Troup; Anaïs Goupille; Jean-Yves Le Questel; Charlene Fallan; James S Scott; Elisabetta Chiarparin; Jérôme Graton; Bruno Linclau
Journal:  Beilstein J Org Chem       Date:  2020-09-02       Impact factor: 2.883

  6 in total

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