Understanding the Conformational Behavior of Fluorinated Piperidines: The Origin of the Axial-F Preference.
NMR analysis
conformational behavior
fluorine
piperidines
solvation effect
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
15 May 2020
15 May 2020
Historique:
received:
18
03
2020
revised:
07
04
2020
pubmed:
10
4
2020
medline:
10
4
2020
entrez:
10
4
2020
Statut:
ppublish
Résumé
Gaining an understanding of the conformational behavior of fluorinated compounds would allow for expansion of the current molecular design toolbox. In order to facilitate drug discovery efforts, a systematic survey of a series of diversely substituted and protected fluorinated piperidine derivatives has been carried out using NMR spectroscopy. Computational investigations reveal that, in addition to established delocalization forces such as charge-dipole interactions and hyperconjugation, solvation and solvent polarity play a major role. This work codifies a new design principle for conformationally rigid molecular scaffolds.
Identifiants
pubmed: 32270524
doi: 10.1002/chem.202001355
pmc: PMC7317880
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
6141-6146Subventions
Organisme : European Research Council
ID : 788558
Pays : International
Organisme : Deutsche Forschungsgemeinschaft
ID : SPP2102
Commentaires et corrections
Type : ErratumIn
Informations de copyright
© 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.
Références
Org Biomol Chem. 2016 Jun 28;14(24):5534-8
pubmed: 26880180
Chemistry. 2017 May 2;23(25):6142-6149
pubmed: 27788283
Chemistry. 2015 Jan 19;21(4):1682-91
pubmed: 25418601
Chem Commun (Camb). 2012 Oct 7;48(77):9643-5
pubmed: 22911247
J Med Chem. 1991 Apr;34(4):1272-5
pubmed: 2016703
J Phys Chem A. 2014 Jan 16;118(2):503-7
pubmed: 24377652
Nat Chem. 2015 Jun;7(6):483-8
pubmed: 25991526
Org Biomol Chem. 2013 May 7;11(17):2885-90
pubmed: 23515623
Nat Chem. 2019 Mar;11(3):264-270
pubmed: 30664720
European J Org Chem. 2018 Aug 1;2018(27-28):3684-3687
pubmed: 30147438
J Enzyme Inhib Med Chem. 2007 Oct;22(5):527-40
pubmed: 18035820
Chem Soc Rev. 2008 Feb;37(2):308-19
pubmed: 18197347
J Am Chem Soc. 2016 Apr 20;138(15):5004-7
pubmed: 26978593
Angew Chem Int Ed Engl. 2018 Dec 10;57(50):16431-16435
pubmed: 30255972
J Med Chem. 2015 Nov 12;58(21):8315-59
pubmed: 26200936
Chem Soc Rev. 2007 Dec;36(12):2070-95
pubmed: 17982522
Chemistry. 2020 May 15;26(28):6141-6146
pubmed: 32270524
Chem Rev. 2014 Feb 26;114(4):2432-506
pubmed: 24299176
J Med Chem. 2014 Dec 26;57(24):10257-74
pubmed: 25255204
Chem Commun (Camb). 2011 Aug 7;47(29):8265-7
pubmed: 21709894
Nat Prod Rep. 2000 Oct;17(5):435-46
pubmed: 11072891
Chem Commun (Camb). 2016 Apr 14;52(29):5116-9
pubmed: 26996764
J Med Chem. 1993 Nov 26;36(24):3757-64
pubmed: 8254605
Chem Commun (Camb). 2019 Aug 29;55(71):10539-10542
pubmed: 31414105
Science. 2017 Sep 1;357(6354):908-912
pubmed: 28798044
Acc Chem Res. 2018 Jul 17;51(7):1701-1710
pubmed: 29894155
Chemistry. 2005 Feb 18;11(5):1579-91
pubmed: 15662680
Angew Chem Int Ed Engl. 2017 Jun 26;56(27):7867-7870
pubmed: 28561937
Angew Chem Int Ed Engl. 2007;46(31):5904-8
pubmed: 17610229
Chem Commun (Camb). 2018 Jul 24;54(60):8415-8418
pubmed: 29999054
Chem Soc Rev. 2008 Feb;37(2):320-30
pubmed: 18197348
Science. 2007 Sep 28;317(5846):1881-6
pubmed: 17901324