1,4-二氢吡啶衍生物中的分子内 C-H···O 氢键
Intramolecular C-H···O hydrogen bonding in 1,4-dihydropyridine derivatives.
机构信息
Latvian Institute of Organic Synthesis Aizkraukles 21 Street, Riga LV-1006, Latvia.
出版信息
Molecules. 2011 Sep 19;16(9):8041-52. doi: 10.3390/molecules16098041.
Abstract
The diastereotopy of the methylene protons at positions 2 and 6 in 1,4-dihydropiridine derivatives with various substituents has been investigated. NMR spectroscopy and quantum chemistry calculations show that the CH···O intramolecular hydrogen bond is one of the factors amplifying the chemical shift differences in the 1H-NMR spectra.
摘要
本文研究了具有不同取代基的 1,4-二氢吡啶衍生物中 2 位和 6 位亚甲基质子的非对映异构性。NMR 光谱和量子化学计算表明，CH···O 分子内氢键是放大 1H-NMR 光谱中化学位移差异的因素之一。
相似文献
1
Intramolecular C-H···O hydrogen bonding in 1,4-dihydropyridine derivatives.
Molecules. 2011 Sep 19;16(9):8041-52. doi: 10.3390/molecules16098041.
2
Two 1,4-dihydropyridine derivatives with potential calcium-channel antagonist activity.
Acta Crystallogr C. 2011 Feb;67(Pt 2):o80-4. doi: 10.1107/S0108270111003362. Epub 2011 Jan 27.
3
Three methoxy-substituted diethyl 4-phenyl-2,6-dimethyl-1, 4-dihydropyridine-3,5-dicarboxylate compounds.
Acta Crystallogr C. 2000 Oct;56 ( Pt 10):1228-31. doi: 10.1107/s0108270100008416.
4
Synthetic Diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylates Induce Apoptosis.
Med Chem. 2018;14(8):851-862. doi: 10.2174/1573406414666180418143048.
5
Quantifying weak hydrogen bonding in uracil and 4-cyano-4'-ethynylbiphenyl: a combined computational and experimental investigation of NMR chemical shifts in the solid state.
J Am Chem Soc. 2008 Jan 23;130(3):945-54. doi: 10.1021/ja075892i. Epub 2008 Jan 1.
6
The hydrogen bonding and hydration of 2'-OH in adenosine and adenosine 3'-ethyl phosphate.
J Org Chem. 2002 Mar 22;67(6):1852-65. doi: 10.1021/jo010960j.
7
Solid state and solution study of some phosphoramidate derivatives containing the P(O)NHC(O) bifunctional group: crystal structures of CCl(2)HC(O)NHP(O)(NCH(3)(CH(2)C(6)H(5)))(2), p-ClC(6)H(4)C(O)NHP(O)(NCH(3)(CH(2)C(6)H(5)))(2), CCl(2)HC(O)NHP(O)(N(CH(2)C(6)H(5))(2))(2) and p-BrC(6)H(4)C(O)NHP(O)(N(CH(2)C(6)H(5))(2))(2).
Spectrochim Acta A Mol Biomol Spectrosc. 2010 Apr;75(4):1236-43. doi: 10.1016/j.saa.2009.12.033. Epub 2010 Jan 4.
8
Intramolecular Hydrogen Bonding Involving Organic Fluorine: NMR Investigations Corroborated by DFT-Based Theoretical Calculations.
Molecules. 2017 Mar 7;22(3):423. doi: 10.3390/molecules22030423.
9
Intramolecular hydrogen bonds in 1,4-dihydropyridine derivatives.
R Soc Open Sci. 2018 Jun 13;5(6):180088. doi: 10.1098/rsos.180088. eCollection 2018 Jun.
10
Synthesis, structural and conformational properties, and gas phase reactivity of 1,4-dihydropyridine ester and ketone derivatives.
Org Biomol Chem. 2010 Dec 7;8(23):5339-44. doi: 10.1039/c0ob00494d. Epub 2010 Sep 27.
引用本文的文献
1
Highly Efficient Electrocarboxylation Method to Synthesize Novel Acid Derivatives of 1,4-Dihydropyridines and to Study Their Antimicrobial Activity.
ACS Omega. 2022 Apr 28;7(18):16055-16062. doi: 10.1021/acsomega.2c01316. eCollection 2022 May 10.
2
Pleiotropic Properties of Amphiphilic Dihydropyridines, Dihydropyridones, and Aminovinylcarbonyl Compounds.
Oxid Med Cell Longev. 2020 Dec 31;2020:8413713. doi: 10.1155/2020/8413713. eCollection 2020.
3
Intramolecular hydrogen bonds in 1,4-dihydropyridine derivatives.
R Soc Open Sci. 2018 Jun 13;5(6):180088. doi: 10.1098/rsos.180088. eCollection 2018 Jun.
4
Dihydropyridine Derivatives as Cell Growth Modulators In Vitro.
Oxid Med Cell Longev. 2017;2017:4069839. doi: 10.1155/2017/4069839. Epub 2017 Apr 3.
本文引用的文献
1
Dihydropyridines: evaluation of their current and future pharmacological applications.
Drug Discov Today. 2009 Nov;14(21-22):1058-66. doi: 10.1016/j.drudis.2009.08.004. Epub 2009 Sep 1.
2
The chemist as astronaut: searching for biologically useful space in the chemical universe.
Biochem Pharmacol. 2009 Aug 1;78(3):217-23. doi: 10.1016/j.bcp.2009.02.015. Epub 2009 Mar 5.
3
Novel cationic amphiphilic 1,4-dihydropyridine derivatives for DNA delivery.
Biochim Biophys Acta. 2000 Dec 20;1509(1-2):451-66. doi: 10.1016/s0005-2736(00)00327-8.
Zotero 插件