Molbank

5 pages, 2400 KB

Open AccessShort 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

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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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5 pages, 954 KB

Open AccessShort 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 3875

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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4 pages, 542 KB

Open AccessShort 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 2 | Viewed by 3698

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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5 pages, 1486 KB

Open AccessShort 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 4193

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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4 pages, 891 KB

Open AccessShort 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

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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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6 pages, 587 KB

Open AccessShort 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

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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 ∆[ν_asym(CO₂⁻) − ν_sym(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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4 pages, 1422 KB

Open AccessShort 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

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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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7 pages, 2334 KB

Open AccessShort 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 3405

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

6 pages, 900 KB

Open AccessShort 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 7 | Viewed by 3932

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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4 pages, 1083 KB

Open AccessCommunication

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 4019

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

4 pages, 528 KB

Open AccessCommunication

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 5333

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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3 pages, 497 KB

Open AccessShort 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 3422

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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6 pages, 1186 KB

Open AccessShort 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 6025

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

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