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Volume 2024, September
 
 

Molbank, Volume 2024, Issue 4 (December 2024) – 8 articles

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0 pages, 293 KiB  
Short Note
rac-2-(2′-Ferrocenyl-2′-hydroxy-n-propyl)-1,3-benzothiazole
by Martin G. Zhen, Kathleen L. May and Robert A. Gossage
Molbank 2024, 2024(4), M1893; https://doi.org/10.3390/M1893 - 30 Sep 2024
Viewed by 189
Abstract
The synthesis and characterisation (UV-Vis, IR, HRESI-MS, 1H and 13C NMR spectroscopies, electrochemistry) is reported of the novel title material (1: alternatively named rac-1-(2′-benzothiazolyl)-2-ferrocenyl-2-propanol): a rare example of a ferrocenyl-benzothiazole hybrid species. Compound 1 is produced by the [...] Read more.
The synthesis and characterisation (UV-Vis, IR, HRESI-MS, 1H and 13C NMR spectroscopies, electrochemistry) is reported of the novel title material (1: alternatively named rac-1-(2′-benzothiazolyl)-2-ferrocenyl-2-propanol): a rare example of a ferrocenyl-benzothiazole hybrid species. Compound 1 is produced by the low temperature reaction of acetylferrocene (3) with a solution of the methyl anion derived via the deprotonation of 2-methyl-1,3-benzothiazole. The yield of 1 is moderate (34%) after purification and is an air and thermally stable solid under ambient conditions. Attempts to sublime 1, however, result in decomposition with one of the products being identified (NMR) as 3. The spectroscopic features of 1 are presented. Attempts to obtain suitable crystalline material of 1 for a single crystal X-ray diffraction study were unfortunately unsuccessful. Compound 1 also does not form stable coordination complexes with various metal salts (e.g., Ni [2+], Co[2+], etc.) under the conditions tested. Full article
(This article belongs to the Section Organic Synthesis)
0 pages, 3029 KiB  
Short Note
[(2-Chlorophenyl)-(4-fluorophenyl)methylene]-(4-fluorophenyl)amine
by Salvador Vilchis-Valdés, Alberto Cedillo-Cruz, Marco A. García-Eleno, Diego Martínez-Otero and Erick Cuevas-Yañez
Molbank 2024, 2024(4), M1892; https://doi.org/10.3390/M1892 - 30 Sep 2024
Viewed by 183
Abstract
The formation of a N,1,1-triaryl imine derived from (2-chlorophenyl)-bis-(4-fluorophenyl)methanol is reported. The title compound is formed from a consecutive process which involves a nucleophilic substitution and subsequent Schmidt reaction. A description of the synthesized compound’s NMR spectra is presented and the structure [...] Read more.
The formation of a N,1,1-triaryl imine derived from (2-chlorophenyl)-bis-(4-fluorophenyl)methanol is reported. The title compound is formed from a consecutive process which involves a nucleophilic substitution and subsequent Schmidt reaction. A description of the synthesized compound’s NMR spectra is presented and the structure was unambiguously established by X-ray analysis. A Hirshfeld surface analysis is also included, confirming the presence of intermolecular H···F interactions involved in crystal packing. Full article
6 pages, 1788 KiB  
Short Note
Benzo[d][1,3]oxathiole-2-thione
by R. Alan Aitken, David B. Cordes, Lauryne Cottineau and Aidan P. McKay
Molbank 2024, 2024(4), M1891; https://doi.org/10.3390/M1891 - 30 Sep 2024
Viewed by 147
Abstract
Although known for 120 years, the title compound has not been adequately characterised before. In this paper, it is fully characterised by 1H and 13C NMR and IR spectroscopy and its X-ray structure has been determined for the first time. Full article
(This article belongs to the Section Structure Determination)
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8 pages, 2371 KiB  
Short Note
Bis [4,4′-(1,3-Phenylenebis(azanylylidene))-bis(3,6-di-tert-butyl-2-oxycyclohexa-2,5-dien-1-one)-bis(dimethylsulfoxide)nickel(II)]
by Irina N. Meshcheryakova, Nikolay O. Druzhkov, Ilya A. Yakushev, Kseniya V. Arsenyeva, Anastasiya V. Klimashevskaya and Alexandr V. Piskunov
Molbank 2024, 2024(4), M1890; https://doi.org/10.3390/M1890 - 26 Sep 2024
Viewed by 253
Abstract
A new cage-like dimeric nickel(II) complex Ni2L2(DMSO)4 based on a ditopic redox-active hydroxy-para-iminobenzoquinone type ligand LH2 (L is 4,4′-(1,3-phenylene-bis(azaneylylidene))-bis(3,6-di-tert-butyl-2-oxycyclohexa-2,5-dien-1-one dianion) was synthesized in DMSO at 120 °C. The molecular structure of [...] Read more.
A new cage-like dimeric nickel(II) complex Ni2L2(DMSO)4 based on a ditopic redox-active hydroxy-para-iminobenzoquinone type ligand LH2 (L is 4,4′-(1,3-phenylene-bis(azaneylylidene))-bis(3,6-di-tert-butyl-2-oxycyclohexa-2,5-dien-1-one dianion) was synthesized in DMSO at 120 °C. The molecular structure of the synthesized compound was determined by X-ray diffraction analysis. The complex Ni2L2(DMSO)4 is almost insoluble in all organic solvents, probably due to the presence of a large number of intermolecular contacts in its structure. The electronic spectrum and thermal stability of the crystalline compound have been studied. Full article
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6 pages, 941 KiB  
Short Note
Methyl 6,7-Difluoro-2-[(4-fluorobenzyl)sulfanyl]-4-hydroxyquinoline-3-carboxylate
by Vladimir A. Potapov, Irina A. Novokshonova, Maxim V. Musalov, Svetlana V. Amosova and Oleg A. Rakitin
Molbank 2024, 2024(4), M1889; https://doi.org/10.3390/M1889 - 26 Sep 2024
Viewed by 195
Abstract
A convenient synthesis of a novel fluoroquinolone precursor, methyl 6,7-difluoro-2-[(4-fluorobenzyl)sulfanyl]-4-hydroxyquinoline-3-carboxylate, at a 78% yield starting from 3,4-difluorophenyl isothiocyanate was developed. The structure of the product was established by 1H, 13C, and 19F NMR spectroscopy, mass spectrometry, IR spectroscopy and confirmed [...] Read more.
A convenient synthesis of a novel fluoroquinolone precursor, methyl 6,7-difluoro-2-[(4-fluorobenzyl)sulfanyl]-4-hydroxyquinoline-3-carboxylate, at a 78% yield starting from 3,4-difluorophenyl isothiocyanate was developed. The structure of the product was established by 1H, 13C, and 19F NMR spectroscopy, mass spectrometry, IR spectroscopy and confirmed by elemental analysis. The title compound, containing the pharmacophoric 4-fluorobenzyl group, will be used in the synthesis of novel fluoroquinolone derivatives. Full article
(This article belongs to the Section Organic Synthesis)
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6 pages, 1731 KiB  
Short Note
(R)-2-Amino-1-hydroxyethylphosphonic Acid
by Majid Motevalli, Isaac Abrahams, Peter Blakskjær, Caroline E. Wyatt and Peter B. Wyatt
Molbank 2024, 2024(4), M1888; https://doi.org/10.3390/M1888 - 26 Sep 2024
Viewed by 258
Abstract
(R)-2-Amino-1-hydroxyethylphosphonic acid 2 was prepared by hydrolytic kinetic resolution of rac-diethyl oxiran-2-ylphosphonate followed by reaction with benzylamine, acid hydrolysis, catalytic hydrogenolysis, and anion-exchange chromatography. Recrystallization from water-ethanol gave pure 2, which was characterized by IR, 1H NMR, 13 [...] Read more.
(R)-2-Amino-1-hydroxyethylphosphonic acid 2 was prepared by hydrolytic kinetic resolution of rac-diethyl oxiran-2-ylphosphonate followed by reaction with benzylamine, acid hydrolysis, catalytic hydrogenolysis, and anion-exchange chromatography. Recrystallization from water-ethanol gave pure 2, which was characterized by IR, 1H NMR, 13C NMR, 31P NMR, polarimetry, elemental microanalysis, high-resolution mass spectrometry, and single-crystal X-ray diffraction. The acid 2 crystallized in the orthorhombic noncentrosymmetric space group P212121 with cell parameters a = 6.303 (2) Å, b = 7.104 (2) Å, c = 11.627 (3) Å. The X-ray crystal structure confirmed the (R)-configuration of 2 and revealed that 2 is zwitterionic in the solid state, with extensive intermolecular hydrogen bonding between the hydroxyl, ammonium cation, and phosphonate anion groups. Full article
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5 pages, 1385 KiB  
Short Note
Ac-[K-Aib-C(3,9-Acm; 6,12-DFLC(Acm)KKESEK)]4-NH2
by Vasiliki Moulasioti, Evgenia Fotou, Vassilios Moussis and Vassilios Tsikaris
Molbank 2024, 2024(4), M1887; https://doi.org/10.3390/M1887 - 25 Sep 2024
Viewed by 197
Abstract
Chemoselective reactions have played a crucial role in the development of high-molecular-weight (>3000 Da) macromolecules with a branched architecture, particularly as peptides and epitope-based vaccines have emerged as promising tools for drug development. Based on this, in this study, we designed and synthesized [...] Read more.
Chemoselective reactions have played a crucial role in the development of high-molecular-weight (>3000 Da) macromolecules with a branched architecture, particularly as peptides and epitope-based vaccines have emerged as promising tools for drug development. Based on this, in this study, we designed and synthesized the peptide macromolecule CH3CO-[K-Aib-C(3,9-CH2NHCOCH3; 6,12-DFLC(CH2NHCOCH3)KKESEK)]4-NH2 [Ac-K-Aib-C(3,9-Acm); 6,12-epitope)]4-NH2] using chemoselective thioether bond formation between the peptide carrier CPSOC (3,9 Acm) and the IAc-DFLC(Acm)KKESEK-NH2 peptide epitope. The conjugate was purified via RP-HPLC and characterized via HR-ESI-MS. The epitope D128FLCKKESEK137 derives from the lethal toxin, ammodytoxin A, from the V. ammodytes snake species, and it was synthesized using the SPPS Fmoc/tBu methodology and characterized via HR-ESI-MS and NMR techniques. Full article
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5 pages, 1538 KiB  
Communication
Synthesis and Characterization of N-Nitroso-3-morpholinosydnonimine as NO Radical Donor
by Nathalie Saffon-Merceron, Christian Lherbet and Pascal Hoffmann
Molbank 2024, 2024(4), M1886; https://doi.org/10.3390/M1886 - 24 Sep 2024
Viewed by 234
Abstract
N-Nitroso-3-morpholinosydnonimine 3 was prepared by nitrosation of SIN-1 and characterized by 1H-NMR, 13C-NMR, and HRMS. Its structure, confirmed by single crystal X-ray diffraction analysis, was found to be in agreement with its mesoionic and aromatic character. Unlike 3-morpholino-sydnonimine (SIN-1), which [...] Read more.
N-Nitroso-3-morpholinosydnonimine 3 was prepared by nitrosation of SIN-1 and characterized by 1H-NMR, 13C-NMR, and HRMS. Its structure, confirmed by single crystal X-ray diffraction analysis, was found to be in agreement with its mesoionic and aromatic character. Unlike 3-morpholino-sydnonimine (SIN-1), which releases both nitric oxide and superoxide radical, decomposition of this nitrosylated sydonimine could yield nitric oxide as the only decomposition product, and thus without the formation of toxic peroxynitrite. Full article
(This article belongs to the Section Organic Synthesis)
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