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Volume 2017
Issue 3
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Molbank, Volume 2017, Issue 3 (September 2017) – 13 articles

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2400 KiB  
Short Note
Crystal Structure of Bis(2,4,6-trimethylphenyl)-phosphine Oxide
by Alex J. Veinot, Ketnavi Ramgoolam, Nick A. Giffin and Jason D. Masuda
Molbank 2017, 2017(3), M957; https://doi.org/10.3390/M957 - 19 Sep 2017
Cited by 6 | Viewed by 3799
Abstract
The single crystal structure of bis(2,4,6-trimethylphenyl)phosphine oxide has been determined. All interatomic distances and angles can be considered normal. The aryl substituents adopt an intermediate configuration when compared to both sterically unhindered (e.g., diphenylphosphine oxide) and congested (e.g., bis(2,4,6-tri-tert-butylphenyl)phosphine oxide) secondary [...] Read more.
The single crystal structure of bis(2,4,6-trimethylphenyl)phosphine oxide has been determined. All interatomic distances and angles can be considered normal. The aryl substituents adopt an intermediate configuration when compared to both sterically unhindered (e.g., diphenylphosphine oxide) and congested (e.g., bis(2,4,6-tri-tert-butylphenyl)phosphine oxide) secondary phosphine oxides, illustrating the influence of steric congestion on the molecular structure. Full article
(This article belongs to the Section Structure Determination)
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954 KiB  
Short Note
(1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl 4-Aminobutyrate Hydrochloride
by Mariia Nesterkina, Svitlana Shishkina, Georgy Maltsev, Ildar Rakipov and Iryna Kravchenko
Molbank 2017, 2017(3), M956; https://doi.org/10.3390/M956 - 22 Aug 2017
Cited by 1 | Viewed by 3371
Abstract
The title ester (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 4-aminobutyrate hydrochloride was obtained in 96% yield via Steglich esterification. The structure of the target compound was established by FTIR, HR-MS, 1H-NMR, 13C-NMR spectral analysis, and single crystal X-ray diffraction study. [...] Read more.
The title ester (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl 4-aminobutyrate hydrochloride was obtained in 96% yield via Steglich esterification. The structure of the target compound was established by FTIR, HR-MS, 1H-NMR, 13C-NMR spectral analysis, and single crystal X-ray diffraction study. Single crystals of the title ester suitable for X-ray investigation were obtained by slow evaporation of the methanolic solution at room temperature. The purity of compound was assessed using HPLC coupled to mass spectrometry. Full article
(This article belongs to the Section Structure Determination)
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542 KiB  
Short Note
(E)-3′,6′-bis(Diethylamine)-2-[(2-methoxynaphthalen-1-yl)methyleneamino]spiro[isoindoline-1,9′-xanthen]-3-one
by Pierce Perkins, Angela Winstead and Fasil Abebe
Molbank 2017, 2017(3), M955; https://doi.org/10.3390/M955 - 18 Aug 2017
Cited by 1 | Viewed by 3336
Abstract
The title compound, (E)-3′,6′-bis(diethylamine)-2-[(2-methoxynaphthalen-1-yl)methyleneamino]spiro[isoindoline-1,9′-xanthen]-3-one, was synthesized in 92% isolated yield using microwave-assisted organic synthesis. This new rhodamine derivative was fully characterized by 1H-NMR, 13C-NMR, FTIR and high resolution MS. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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Scheme 1

1486 KiB  
Short Note
Ethyl 4-[5-(methoxymethyl)furan-2-yl]-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
by Hery Suwito, Salma Zulqaida, Kautsar Ul Haq, Alfinda Novi Kristanti and Indriani Indriani
Molbank 2017, 2017(3), M954; https://doi.org/10.3390/M954 - 11 Aug 2017
Cited by 2 | Viewed by 3513
Abstract
A one-pot multicomponent reaction has been used to synthesize the title compound, ethyl 4-[5-(methoxymethyl)furan-2-yl]-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate by PTSA catalyzed Biginelli reaction. The chemical structure of the product was confirmed by spectroscopic evidence, FTIR, HRESI-MS, 1D-, and 2D NMR. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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Figure 1

891 KiB  
Short Note
(E)-2-(1-Cyano-2-methoxy-2-oxoethylidene)-3,4-dioxo-1-(pyridin-1-ium-1-yl)cyclobutan-1-ide
by Johann Grünefeld, Conrad Kunick and Peter G. Jones
Molbank 2017, 2017(3), M953; https://doi.org/10.3390/M953 - 11 Aug 2017
Viewed by 3060
Abstract
(E)-2-(1-Cyano-2-methoxy-2-oxoethylidene)-3,4-dioxo-1-(pyridin-1-ium-1-yl)cyclobutan-1-ide was obtained by a three-component reaction of squaric acid dichloride with pyridine and methyl cyanoacetate. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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587 KiB  
Short Note
Solvent-Mediated Synthesis of M(II)-Coordination Polymer Part 1: Crystal Structure of Poly(1,2-di(4-pyridyl)ethylene-k2N,N')-bis(1,4-benzenediacetato-k4O,O′,O′′,O′′')zinc(II)], C22H18ZnN2O4
by Stephen Adie Adalikwu, Offiong E. Offiong and Ayi A. Ayi
Molbank 2017, 2017(3), M952; https://doi.org/10.3390/M952 - 6 Aug 2017
Viewed by 3346
Abstract
An interaction of water-methanol solution of sodium1,4-benzenediacetate (bda) and 4,4′-bipyridylethelene (bpee) with aqueous solution of Zn(NO3)2·6H2O at room temperature yielded colourless crystals of 1 after three weeks in a sealed glass tube. The compound with composition C [...] Read more.
An interaction of water-methanol solution of sodium1,4-benzenediacetate (bda) and 4,4′-bipyridylethelene (bpee) with aqueous solution of Zn(NO3)2·6H2O at room temperature yielded colourless crystals of 1 after three weeks in a sealed glass tube. The compound with composition C22H18ZnN2O4 crystallizes in monoclinic space group P21/c, with the following cell dimensions: a = 10.4566(2), b = 13.3085(2), c = 13.7189(2) Å, β = 101.491(1)°. In the structure of 1, two Zn(II) neighbours are connected by two bda ligands adopting chelating and bidentate-bridging coordination modes to form a dimeric unit (Zn2O8N4) with the Zn–Zn distance of 4.0432(6) Å. The carboxyl-bridged dimeric units are extended along the [001] direction by bpee co-ligands and further linked by bda ligand to form a three-dimensional network structure. The IR shows the characteristic bands of the carboxylates at 1611/1507 cm−1 and 1424/1373 cm−1, respectively, for asymmetric and symmetric stretching −CO2− vibrations. The separation ∆[νasym(CO2−) − νsym(CO2−)] values of 187 and 134 cm−1 are indicative of chelating and bidentate bridging coordination modes of the carboxylate to the metal centre. Full article
(This article belongs to the Section Structure Determination)
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1422 KiB  
Short Note
Ethyl 5-(4-Bromophenyl)-4-methyl-1H-pyrrole-2-carboxylate
by Marcus Baumann and Ian R. Baxendale
Molbank 2017, 2017(3), M951; https://doi.org/10.3390/M951 - 4 Aug 2017
Viewed by 3209
Abstract
This note describes a sequence converting an oxime-substituted pyrrolidine into a trisubstituted pyrrole structure. The synthetic route is based on a double chlorination of the pyrrolidine substrate followed by the base induced formation of both an imine and a nitrile oxide functionality. The [...] Read more.
This note describes a sequence converting an oxime-substituted pyrrolidine into a trisubstituted pyrrole structure. The synthetic route is based on a double chlorination of the pyrrolidine substrate followed by the base induced formation of both an imine and a nitrile oxide functionality. The latter reacts with an immobilized thiourea to yield an isothiocyanate which upon elimination generates the final pyrrole in an unprecedented cascade of events. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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Graphical abstract

2334 KiB  
Short Note
(OC-6-35-A)-Aquadicarbonylchlorido[2-(2-pyridyl)-1,8-naphthyridine-κ;2N1,N2]ruthenium(II) hexafluoridophosphate 2,2′-Bipyridine
by Tsugiko Takase, Ryosuke Abe and Dai Oyama
Molbank 2017, 2017(3), M950; https://doi.org/10.3390/M950 - 3 Aug 2017
Cited by 1 | Viewed by 3110
Abstract
A dicarbonylruthenium(II) complex containing bidentate 2-(2-pyridyl)-1,8-naphthyridine, as well as monodentate aqua and chlorido ligands, were isolated and characterized using spectroscopic techniques and single crystal X-ray diffraction. These data indicate that geometrical isomerization occurs during the substitution reaction involving a superacid. Density functional theory [...] Read more.
A dicarbonylruthenium(II) complex containing bidentate 2-(2-pyridyl)-1,8-naphthyridine, as well as monodentate aqua and chlorido ligands, were isolated and characterized using spectroscopic techniques and single crystal X-ray diffraction. These data indicate that geometrical isomerization occurs during the substitution reaction involving a superacid. Density functional theory (DFT) calculations were performed on the plausible geometrical isomers. The DFT-optimized structures and calculated infrared spectra suggest that the experimentally obtained structure is stable. Full article
(This article belongs to the Section Structure Determination)
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Graphical abstract

900 KiB  
Short Note
2-[(2,6-Dimethylmorpholin-4-yl)methyl]-4-[(E)-2-{3-[(E)-2-{3-[(2,6-dimethylmorpholin-4-yl)methyl]-4-hydroxy-5-methoxyphenyl}ethenyl]-1H-pyrazol-5-yl}ethenyl]-6-methoxyphenol
by Joko Untung, Iskandarsyah Iskandarsyah and Hayun Hayun
Molbank 2017, 2017(3), M949; https://doi.org/10.3390/M949 - 3 Aug 2017
Cited by 6 | Viewed by 3334
Abstract
A novel di-Mannich derivative of curcumin pyrazole, 2-[(2,6-dimethyl morpholin-4-yl)methyl]-4-[(E)-2-{3-[(E)-2-{3-[(2,6-dimethylmorpholin-4-yl)methyl]-4-hydroxy-5-methoxyphenyl}ethenyl]-1H-pyrazol-5-yl}ethenyl]-6-methoxyphenol (2), has been synthesized through a Mannich reaction of curcumin pyrazole (1), formaldehyde, and 2,6-dimethylmorpholine. The structure of the synthesized compound was confirmed on [...] Read more.
A novel di-Mannich derivative of curcumin pyrazole, 2-[(2,6-dimethyl morpholin-4-yl)methyl]-4-[(E)-2-{3-[(E)-2-{3-[(2,6-dimethylmorpholin-4-yl)methyl]-4-hydroxy-5-methoxyphenyl}ethenyl]-1H-pyrazol-5-yl}ethenyl]-6-methoxyphenol (2), has been synthesized through a Mannich reaction of curcumin pyrazole (1), formaldehyde, and 2,6-dimethylmorpholine. The structure of the synthesized compound was confirmed on the basis of FTIR, 1H-NMR, 13C-NMR, 2D Heteronuclear Single-Quantum Correlation (HSQC) and 2D Heteronuclear Multiple Bond Correlation (HMBC), and mass spectral data. The water solubility was evaluated and the result showed that compound 2 was three times more soluble than that of curcumin pyrazole (1) and curcumin. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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1083 KiB  
Communication
Rac-2′,3a,6,6,6′,6′-Hexamethyl-3a,3b,6,7-tetra-hydrospiro-[benzo[2,3]cyclopropa[1,2-c]pyrazole-1,1′-cyclo-hepta[2,4]diene]
by Marcus Baumann, Sophie Lapraille and Ian R. Baxendale
Molbank 2017, 2017(3), M948; https://doi.org/10.3390/M948 - 1 Aug 2017
Cited by 1 | Viewed by 3708
Abstract
This note describes a novel reaction cascade in which a tosylhydrazone derivative of eucarvone undergoes a non-classical dimerization process under basic conditions. The key step in this sequence is a dipolar cycloaddition between a diazo species and a transient cyclopropene. A proposed mechanism [...] Read more.
This note describes a novel reaction cascade in which a tosylhydrazone derivative of eucarvone undergoes a non-classical dimerization process under basic conditions. The key step in this sequence is a dipolar cycloaddition between a diazo species and a transient cyclopropene. A proposed mechanism for this sequence is presented that is supported by single crystal X-ray analysis of the resulting dimer. We believe this unique transformation is of note as it highlights a neat and efficient entry to complex polycyclic architectures containing an embedded pyrazoline moiety. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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Graphical abstract

528 KiB  
Communication
1,2,3,4-Tetra-O-Acetyl-β-d-Mannuronic Acid
by Laura Beswick and Gavin J. Miller
Molbank 2017, 2017(3), M947; https://doi.org/10.3390/M947 - 14 Jul 2017
Cited by 3 | Viewed by 4692
Abstract
1,2,3,4-Tetra-O-acetyl-β-d-mannuronic acid was synthesized in three steps from commercial d-mannose in 21% yield. Regioselective 6-O-tritylation followed by per-acetylation and 6-OTr removal using HBr/AcOH gave the required primary alcohol substrate, which was then oxidised to the target [...] Read more.
1,2,3,4-Tetra-O-acetyl-β-d-mannuronic acid was synthesized in three steps from commercial d-mannose in 21% yield. Regioselective 6-O-tritylation followed by per-acetylation and 6-OTr removal using HBr/AcOH gave the required primary alcohol substrate, which was then oxidised to the target compound using TEMPO/BAIB. None of the synthetic steps required column chromatography and the product was fully characterized by 1H-NMR, 13C-NMR, 2D NMR, MS and IR. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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Graphical abstract

497 KiB  
Short Note
Ethyl 2-[2-(4-Nitrobenzoyl)-1H-indol-3-yl]acetate
by Sunyoung Choi and Sung-Gon Kim
Molbank 2017, 2017(3), M945; https://doi.org/10.3390/M945 - 12 Jul 2017
Cited by 1 | Viewed by 3058
Abstract
Ethyl 2-[2-(4-nitrobenzoyl)-1H-indol-3-yl]acetate was prepared in good yield and characterized by the aza-alkylation/intramolecular Michael cascade reaction of (E)-ethyl 3-[2-(tosylamino)phenyl]acrylate with 2-bromo-4′′-nitroacetophenone, followed by desulfonative dehydrogenation with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) The structure of the newly synthesized compound was determined using 1H-, [...] Read more.
Ethyl 2-[2-(4-nitrobenzoyl)-1H-indol-3-yl]acetate was prepared in good yield and characterized by the aza-alkylation/intramolecular Michael cascade reaction of (E)-ethyl 3-[2-(tosylamino)phenyl]acrylate with 2-bromo-4′′-nitroacetophenone, followed by desulfonative dehydrogenation with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) The structure of the newly synthesized compound was determined using 1H-,13C-NMR, IR and mass spectral data. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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1186 KiB  
Short Note
Ethyl (E)-4-(2,4-Dimethoxyphenyl)-6-(2,4-dimethoxystyryl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
by Hery Suwito, Lutfan Zulianto, Kautsar Ul Haq, Erwanto Erwanto, Abdulloh Abdulloh, Alfinda Novi Kristanti and Indriani Indriani
Molbank 2017, 2017(3), M946; https://doi.org/10.3390/M946 - 11 Jul 2017
Cited by 3 | Viewed by 4918
Abstract
A new compound belonging to the “heterostilbene” derivative, namely ethyl (E)-4-(2,4-dimethoxyphenyl)-6-(2,4-dimethoxystyryl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate (2), has been successfully synthesized as an unprecedented side product of the Biginelli reaction between 2,4-dimethoxybenzaldehyde, ethyl acetoacetate and urea, employing PTSA as catalyst in reflux conditions and [...] Read more.
A new compound belonging to the “heterostilbene” derivative, namely ethyl (E)-4-(2,4-dimethoxyphenyl)-6-(2,4-dimethoxystyryl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate (2), has been successfully synthesized as an unprecedented side product of the Biginelli reaction between 2,4-dimethoxybenzaldehyde, ethyl acetoacetate and urea, employing PTSA as catalyst in reflux conditions and using ethanol as solvent. The molecular structure of compound (2) was established by FTIR, HRESIMS, 1D and 2D NMR. Full article
(This article belongs to the Section Organic Synthesis and Biosynthesis)
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Figure 1

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