Open AccessShort Note
N-(4-Bromophenyl)methoxycarbothioamide
Molbank 2018, 2018(3), M1012; https://doi.org/10.3390/M1012 (registering DOI) -
Abstract
The synthesis, spectroscopic and crystallographic characterisation of the title compound, O-methyl-N-4-bromophenyl thiocarbamate, MeOC(=S)N(H)PhBr-4 (1), are described. Spectroscopy confirmed the formation of the compound and the molecular structure was determined crystallographically. Two independent but chemically similar molecules comprise the
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The synthesis, spectroscopic and crystallographic characterisation of the title compound, O-methyl-N-4-bromophenyl thiocarbamate, MeOC(=S)N(H)PhBr-4 (1), are described. Spectroscopy confirmed the formation of the compound and the molecular structure was determined crystallographically. Two independent but chemically similar molecules comprise the asymmetric unit of 1. The C‒S and C‒N bond lengths confirm the presence of the thioamide tautomer. The thione-S and amide-N‒H atoms are syn, enabling the formation of amide-N‒HS(thione) hydrogen bonds between the two independent molecules that generates a two-molecule aggregate via an eight-membered {HNCS}2 synthon. The aggregates are connected into a three-dimensional architecture via weak intermolecular interactions, including Brπ(4-bromophenyl), Sπ(4-bromophenyl), and weak BrS halogen bonding contacts. The overall molecular conformation, thioamide tautomer, and the presence of amide-N‒HS(thione) hydrogen bonding in the crystal conform with expectation for this class of compound. Full article
Open AccessShort Note
3-(3,5-Difluorophenyl)-1-phenyl-1H-pyrazole-4-carbaldehyde
Molbank 2018, 2018(3), M1011; https://doi.org/10.3390/M1011 -
Abstract
Vilsmeier–Haack reaction of (E)-1-[1-(3,5-difluorophenyl)ethylidene]-2-phenylhydrazine (1) using dimethyl formamide in excess of phosphorus oxychloride by conventional method, resulted in the synthesis of the title compound 3-(3,5-difluorophenyl)-1-phenyl-1H-pyrazole-4- carbaldehyde (2) in good yield and high purity. Structure characterization
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Vilsmeier–Haack reaction of (E)-1-[1-(3,5-difluorophenyl)ethylidene]-2-phenylhydrazine (1) using dimethyl formamide in excess of phosphorus oxychloride by conventional method, resulted in the synthesis of the title compound 3-(3,5-difluorophenyl)-1-phenyl-1H-pyrazole-4- carbaldehyde (2) in good yield and high purity. Structure characterization of the title compound was done by IR, 1H-NMR, 13C-NMR and HRMS spectral analysis. Full article
Open AccessCommunication
Benzyl (R)-2-(Acetylthio)Propanoate: A Promising Sulfur Isoster of (R)-Lactic Acid and Ester Precursors
Molbank 2018, 2018(3), M1010; https://doi.org/10.3390/M1010 -
Abstract
In this paper, an accessible chiral pool synthesis of benzyl (R)-2-(acetylthio)propanoate (acetylthiolactate), which is less odorous than the methyl or ethyl analogue, was performed through a clean SN2 displacement reaction using available AcSK with tris[2-(2-methoxyethoxy)]ethylamine (TDA-1), starting from commercially
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In this paper, an accessible chiral pool synthesis of benzyl (R)-2-(acetylthio)propanoate (acetylthiolactate), which is less odorous than the methyl or ethyl analogue, was performed through a clean SN2 displacement reaction using available AcSK with tris[2-(2-methoxyethoxy)]ethylamine (TDA-1), starting from commercially available benzyl (S)-lactate in 76%, 94% ee (2 steps). Deprotection of the acetyl group using N,N-dimethylethylenediamine afforded benzyl (R)-2-sulfanylpropanoate in 93% yield with 90% ee. These two sulfur-containing benzyl esters were sufficiently odorless to be purified by column chromatography. Direct HPLC analysis was applied to determine the enantiomeric excess without thiazolidin-4-one derivatizations. A complementary debenzylation of benzyl (R)-2-(acetylthio)propanoate was also performed using HBr/AcOH to afford (R)-2-(acetylthio)propanoic acid without critical racemization in 92% yield with 92% ee. Full article
Open AccessShort Note
2-{[(4-Hydroxy-3,5-dimethoxyphenyl)methylidene]hydrazinylidene}-4-oxo-1,3-thiazolidin-5-yl Acetic Acid
Molbank 2018, 2018(3), M1009; https://doi.org/10.3390/M1009 -
Abstract
Thia-Michael addition of 2-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]hydrazine-1-carbothioamide (1) with maleic anhydride results in the formation of the title compound 2-{[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]hydrazinylidene}-4-oxo-1,3-thiazolidin-5-yl acetic acid 2. The precursor 1 is synthesized by the reaction of 4-hydroxy-3,5-dimethoxybenzaldehyde and thiosemicarbazide in the presence of glacial acetic acid as
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Thia-Michael addition of 2-[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]hydrazine-1-carbothioamide (1) with maleic anhydride results in the formation of the title compound 2-{[(4-hydroxy-3,5-dimethoxyphenyl)methylidene]hydrazinylidene}-4-oxo-1,3-thiazolidin-5-yl acetic acid 2. The precursor 1 is synthesized by the reaction of 4-hydroxy-3,5-dimethoxybenzaldehyde and thiosemicarbazide in the presence of glacial acetic acid as the catalyst. The structure of the title compound is determined by elemental analysis, FT-IR, 1H-NMR, 13C-NMR and mass spectral data. In order to determine the molecular interactions with the bacterial enzyme, the title compound is further docked into the active site of the MurB protein of Staphylococcus aureus (PDB ID: 1HSK). The in vitro antibacterial and antifungal activity of the title compound is carried out in order to appraise its antimicrobial efficacy by determination of zone of inhibition and minimal inhibitory concentration. The compound is also evaluated for its antioxidant property by 2,2-diphenyl-1-picryl-hydrazyl (DPPH) radical scavenging assay. Full article
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Open AccessShort Note
N-[2-(1H-Indol-3-yl)-1-(5-thioxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)ethyl]-4-methylbenzenesulfonamide
Molbank 2018, 2018(3), M1008; https://doi.org/10.3390/M1008 -
Abstract
N-[1-Hydrazinyl-3-(1H-indol-3-yl)-1-oxopropan-2-yl]-4-methylbenzenesulfonamide (1) on cyclization with carbon disulfide in ethanolic potassium hydroxide affords N-[2-(1H-indol-3-yl)-1-(5-thioxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)ethyl]-4-methylbenzenesulfonamide (2) in 84% yield. The structure of compound 2 was supported by mass spectrometry, FT-IR and 1H- and 13
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N-[1-Hydrazinyl-3-(1H-indol-3-yl)-1-oxopropan-2-yl]-4-methylbenzenesulfonamide (1) on cyclization with carbon disulfide in ethanolic potassium hydroxide affords N-[2-(1H-indol-3-yl)-1-(5-thioxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)ethyl]-4-methylbenzenesulfonamide (2) in 84% yield. The structure of compound 2 was supported by mass spectrometry, FT-IR and 1H- and 13C-NMR spectroscopy. To investigate the potential of compound 2 to act as antitubercular agent, it was docked against the enoyl reductase (InhA) enzyme of Mycobacterium tuberculosis. The docking pose and non-covalent interactions gave insights on its plausible inhibitory action. Full article
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Open AccessShort Note
5,7-Dihydroxy-3,6-Dimethoxy-3′,4′-Methylendioxyflavone
Molbank 2018, 2018(3), M1007; https://doi.org/10.3390/M1007 -
Abstract
A new flavonoid derivative, namely 5,7-dihydroxy-3,6-dimethoxy-3′,4′-methylenedioxyflavone (1), was isolated from the leaves of Melicope glabra (Blume) T.G. Hartley. The structure of 1 was elucidated based on their UV, IR, HRESIMS, and 1D and 2D NMR spectral data. Full article
Open AccessFeature PaperShort Note
Quercetin-3-oleate
Molbank 2018, 2018(3), M1006; https://doi.org/10.3390/M1006 -
Abstract
Polyphenols are well-known health promoting agents, but they have some limitations due to their spontaneous oxidation. This evidence has limited their use as drugs in recent years. In this field, several chemical modifications have been proposed to overcome these restrictions; among these, esterification
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Polyphenols are well-known health promoting agents, but they have some limitations due to their spontaneous oxidation. This evidence has limited their use as drugs in recent years. In this field, several chemical modifications have been proposed to overcome these restrictions; among these, esterification seems to be the preferred modification. Ester derivatives may be able to reduce the bioavailability problems connected to polyphenols. On the other hand, the presence of esterase enzymes in the body guarantees ester hydrolysis, which in turn frees the two molecules that make it up. Lipase-catalyzed esterifications gave birth to several derivatives of flavonoids glycosides, in green conditions. In this short paper, pancreatic porcine lipase was firstly used as a cheap bio-catalyst, to synthesize oleoyl derivatives of quercetin in aglycone form. The results demonstrated how the enzyme is able to promote a regioselective acylation on C-3 position, with high yields and easy purification processes. Full article
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Open AccessShort Note
1-(4-Hexylbenzoyl)-3-methylthiourea
Molbank 2018, 2018(3), M1005; https://doi.org/10.3390/M1005 -
Abstract
The 1-(4-hexylbenzoyl)-3-methylthiourea compound has been successfully synthesized by reacting 4-hexylbenzoyl chloride and 1-methylthiourea via the reflux method using a triethylamine catalyst. The 1-(4-hexylbenzoyl)-3-methylthiourea compound was identified by UV-visible, FT-IR, 13C/1H-NMR and Mass spectrophotometry. From the activity test on four cancer
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The 1-(4-hexylbenzoyl)-3-methylthiourea compound has been successfully synthesized by reacting 4-hexylbenzoyl chloride and 1-methylthiourea via the reflux method using a triethylamine catalyst. The 1-(4-hexylbenzoyl)-3-methylthiourea compound was identified by UV-visible, FT-IR, 13C/1H-NMR and Mass spectrophotometry. From the activity test on four cancer cell lines (HeLa, T47D, WiDr and MCF7 cell), it could be seen that it had better activity on four cancer cells than the control, hydroxyurea. Full article
Open AccessShort Note
5-Hydroxy-3-(4-hydroxyphenyl)-8,8-dimethyl-6-(3-methylbut-2-enyl)pyrano[2,3-h]chromen-4-one
Molbank 2018, 2018(3), M1004; https://doi.org/10.3390/M1004 -
Abstract
Natural and semi-synthetic compounds are being studied as novel phosphodiesterase 5 (PDE5) inhibitors for the treatment of erectile dysfunction, pulmonary hypertension, and lower urinary symptoms. Maclura pomifera is a source of flavonoids, one of the main classes of molecules investigated for these purposes.
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Natural and semi-synthetic compounds are being studied as novel phosphodiesterase 5 (PDE5) inhibitors for the treatment of erectile dysfunction, pulmonary hypertension, and lower urinary symptoms. Maclura pomifera is a source of flavonoids, one of the main classes of molecules investigated for these purposes. The extraction of the natural isoflavone osajin and its modification to obtain a semi-synthetic derivative are described in this short note. 1H and 13C-nuclear magnetic resonance spectroscopy (NMR), mass spectrometry, high-performance liquid chromatography (HPLC) and spectroscopic characterization of the title compound are also hereby provided. Two-dimensional (2D) nuclear Overhauser effect spectroscopy (NOESY) NMR, supported by in silico conformational studies, was used to achieve a complete assignment of the proton signals, assessing the correct chemical structure of the compound. Heteronuclear single quantum coherence spectroscopy (HSQC) and heteronuclear multiple bond correlation (HMBC) NMR experiments were performed to assign 13C chemical shifts. Calculated chemical properties and preliminary in silico docking suggest that this molecule might be a promising candidate as PDE5 inhibitor. Full article
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Open AccessShort Note
3,3′-(Diazene-1,2-diyl)bis[4-(nitroamino)-1,2,5-oxadiazole 2-oxide]
Molbank 2018, 2018(3), M1003; https://doi.org/10.3390/M1003 -
Abstract
The nitramino derivatives of furoxans are of specific interest as precursors for the preparation of high energy salts with nitrogen-rich cations. In this communication, the 3,3′-(diazene-1,2-diyl)bis[4-(nitroamino)-1,2,5-oxadiazole 2-oxide] was prepared via nitration of available 4,4′-diamino-3,3′-diazenofuroxan; the best yield of the target compound was achieved
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The nitramino derivatives of furoxans are of specific interest as precursors for the preparation of high energy salts with nitrogen-rich cations. In this communication, the 3,3′-(diazene-1,2-diyl)bis[4-(nitroamino)-1,2,5-oxadiazole 2-oxide] was prepared via nitration of available 4,4′-diamino-3,3′-diazenofuroxan; the best yield of the target compound was achieved under the action of nitrating system HNO3/(CF3CO)2O in molar ratio 15:3 in CCl4 at −5 °C. The structure of 3,3′-(diazene-1,2-diyl)bis[4-(nitroamino)-1,2,5-oxadiazole 2-oxide] was confirmed by means of 1H, 13C,14N-NMR, IR spectroscopy and high resolution mass spectra (HRMS). Full article
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Open AccessCommunication
2-[2-Methyl-5-phenyl-1-(3,4,5-trimethoxyphenyl)-1H-pyrrol-3-yl]-2-oxo-N-(pyridin-4-yl) acetamide
Molbank 2018, 2018(3), 1002; https://doi.org/10.3390/M1002 -
Abstract
We synthesized 2-[2-methyl-5-phenyl-1-(3,4,5-trimethoxyphenyl)-1H-pyrrol-3-yl]-2-oxo-N-(pyridin-4-yl) acetamide 4 as a novel compound derived from the indibulin and combretastatin scaffolds, which are known anti-mitotic agents, using a multistep reaction. We tested its cytotoxic activity against three breast cancer cell lines, namely, MCF-7, T47-D,
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We synthesized 2-[2-methyl-5-phenyl-1-(3,4,5-trimethoxyphenyl)-1H-pyrrol-3-yl]-2-oxo-N-(pyridin-4-yl) acetamide 4 as a novel compound derived from the indibulin and combretastatin scaffolds, which are known anti-mitotic agents, using a multistep reaction. We tested its cytotoxic activity against three breast cancer cell lines, namely, MCF-7, T47-D, and MDA-MB 231 as well as normal cell line NIH-3T3, by 3-(4,5-dimethylthiazoyl-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay. The biological activity results showed good cytotoxicity on cancerous cell lines (IC50 value 27.7–39.2 µM) and low toxicity on normal cell line (NIH-3T3, IC50 value > 100 µM). Full article
Open AccessShort Note
(E)-3-[3-(2-Butoxyquinolin-3-yl)acryloyl]-2-hydroxy-4H-chromen-4-one
Molbank 2018, 2018(3), 1001; https://doi.org/10.3390/M1001 -
Abstract
The coumarinyl-quinolinylchalcone hybrid (E)-3-[3-(2-butoxyquinolin-3-yl)acryloyl]-2-hydroxy-4H-chromen-4-one 3b was prepared in good yield from a Claisen-Schmidt condensation reaction between 3-acetyl-4-hydroxy-2H-chromen-2-one 1 and 2-butoxyquinoline-3-carbaldehyde 2 in methanol at reflux and catalyzed by KOH pellets. The structure of the synthesized compound 3b
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The coumarinyl-quinolinylchalcone hybrid (E)-3-[3-(2-butoxyquinolin-3-yl)acryloyl]-2-hydroxy-4H-chromen-4-one 3b was prepared in good yield from a Claisen-Schmidt condensation reaction between 3-acetyl-4-hydroxy-2H-chromen-2-one 1 and 2-butoxyquinoline-3-carbaldehyde 2 in methanol at reflux and catalyzed by KOH pellets. The structure of the synthesized compound 3b was fully confirmed by FTIR-ATR, (1D and 2D) NMR experiments, EIMS and elemental analysis. Full article
Open AccessShort Note
1-[5-(4-Ethoxyphenyl)-3-(naphthalen-1-yl)-4,5-dihydro-1H-pyrazol-1-yl]ethan-1-one
Molbank 2018, 2018(2), M1000; https://doi.org/10.3390/M1000 -
Abstract
The cyclization reaction of 3-(4-ethoxyphenyl)-1-(naphthalen-1-yl)prop-2-en-1-one (1) using hydrazine hydrate in acetic acid medium culminates, resulting in the title compound 1-[5-(4-ethoxyphenyl)-3-(naphthalen-1-yl)-4,5-dihydro-1H-pyrazol-1-yl]ethan-1-one (2). The structure of the newly synthesized compound is determined by IR, 1H-NMR, 13C-NMR and
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The cyclization reaction of 3-(4-ethoxyphenyl)-1-(naphthalen-1-yl)prop-2-en-1-one (1) using hydrazine hydrate in acetic acid medium culminates, resulting in the title compound 1-[5-(4-ethoxyphenyl)-3-(naphthalen-1-yl)-4,5-dihydro-1H-pyrazol-1-yl]ethan-1-one (2). The structure of the newly synthesized compound is determined by IR, 1H-NMR, 13C-NMR and mass spectral data. In order to evaluate the putative molecular interactions, the title compound (2) is docked against the active site of Cytochrome P450 14α-sterol demethylase (CYP51) from Mycobacterium tuberculosis. Full article
Open AccessShort Note
[(η5-pentamethylcyclopentadienyl)(3-fluoro-N-methylbenzylamine-к1,N)dichlorido]iridium(III)
Molbank 2018, 2018(2), M999; https://doi.org/10.3390/M999 -
Abstract
A half-sandwich iridium(III) complex containing 3-fluoro-N-methylbenzylamine ligands has been obtained by reaction of one equivalent of [(η5-Cp*)IrCl2]2 (Cp* = pentamethylcyclopentadienyl) with two equivalent of 3-fluoro-N-methylbenzylamine in very good yield. The structure of this
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A half-sandwich iridium(III) complex containing 3-fluoro-N-methylbenzylamine ligands has been obtained by reaction of one equivalent of [(η5-Cp*)IrCl2]2 (Cp* = pentamethylcyclopentadienyl) with two equivalent of 3-fluoro-N-methylbenzylamine in very good yield. The structure of this complex was confirmed by X-ray crystallography, 1H-NMR, 13C-NMR spectroscopy, and elemental analysis. Full article
Open AccessShort Note
Ethyl 5-methyl-7-(4-morpholinophenyl)-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate
Molbank 2018, 2018(2), M998; https://doi.org/10.3390/M998 -
Abstract
A new compound belonging to a dihydrotetrazolopyrimidine derivative, that is, ethyl 5-methyl-7-(4-morpholinophenyl)-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate, was successfully synthesized using a Biginelli reaction between 4-morpholinobenzaldehyde, ethyl acetoacetate, and 5-aminotetrazole with p-toluenesulfonic acid (pTSA) as a catalyst in ethanol under reflux. The molecular
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A new compound belonging to a dihydrotetrazolopyrimidine derivative, that is, ethyl 5-methyl-7-(4-morpholinophenyl)-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylate, was successfully synthesized using a Biginelli reaction between 4-morpholinobenzaldehyde, ethyl acetoacetate, and 5-aminotetrazole with p-toluenesulfonic acid (pTSA) as a catalyst in ethanol under reflux. The molecular structure of the title compound was characterized on the basis of spectroscopic evidence, using FTIR, HRESI-MS, 1H- and 13C-NMR, and 2D NMR. Full article
Open AccessFeature PaperCommunication
5,6,7,8-Tetrafluoro-1-(2-nitrophenyl)-3-phenyl-1H-benzo[e][1,3,4]oxadiazine
Molbank 2018, 2018(2), M997; https://doi.org/10.3390/M997 -
Abstract
Treating 1-fluoro-2-nitrobenzene (6) with N′-pentafluorophenylbenzohydrazide (7) and K2CO3 (1.1 equiv) in EtOH at ca. 110 °C (sealed tube) for 24 h affords 5,6,7,8-tetrafluoro-1-(2-nitrophenyl)-3-phenyl-1H-benzo[e][1,3,4]oxadiazine (5) (36%) and N′-(2-nitrophenyl)-N
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Treating 1-fluoro-2-nitrobenzene (6) with N′-pentafluorophenylbenzohydrazide (7) and K2CO3 (1.1 equiv) in EtOH at ca. 110 °C (sealed tube) for 24 h affords 5,6,7,8-tetrafluoro-1-(2-nitrophenyl)-3-phenyl-1H-benzo[e][1,3,4]oxadiazine (5) (36%) and N′-(2-nitrophenyl)-N′-(perfluorophenyl)benzohydrazide (3) (37%). The X-ray crystallography of 5,6,7,8-tetrafluoro-1-(2-nitrophenyl)-3-phenyl-1H-benzo[e][1,3,4]oxadiazine (5) is provided. Microwave irradiation (100 W) of perfluorophenylbenzohydrazide 3 with K2CO3 (1.1 equiv) in THF at ca. 120 °C (sealed tube, 80 PSI) for 3 h gives oxadiazine 5 (85%), while reduction of the nitro group using Sn (4 equiv) in glacial acetic acid at ca. 20 °C for 30 min, followed by cyclodehydration at ca. 118 °C for 20 min and treatment with 2 M NaOH for 24 h resulted in 1-(perfluorophenyl)-3-phenyl-1,2,4-benzotriazin-4-yl (4) with 93% yield. Full article
Open AccessShort Note
2,4-Bis[(2,6-diisopropylphenyl)imino]-3-methylpentan-3-ol
Molbank 2018, 2018(2), M995; https://doi.org/10.3390/M995 -
Abstract
The compound 2,4-bis[(2,6-diisopropylphenyl)imino]-3-methylpentan-3-ol was synthesized with a yield of approximately 80% by the reaction of 2,4-bis(2,6-diisopropylphenylimino)pentan-3-one with trimethylaluminum, which was followed by hydrolysis with an aqueous NaOH solution. A chemoselective addition to the C=O bond occurred in this reaction. The structure was confirmed
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The compound 2,4-bis[(2,6-diisopropylphenyl)imino]-3-methylpentan-3-ol was synthesized with a yield of approximately 80% by the reaction of 2,4-bis(2,6-diisopropylphenylimino)pentan-3-one with trimethylaluminum, which was followed by hydrolysis with an aqueous NaOH solution. A chemoselective addition to the C=O bond occurred in this reaction. The structure was confirmed by X-ray crystallography. This new compound was also fully characterized by 1H, 13C-NMR spectroscopy and 1H-13C HSQC spectroscopy, mass spectrometry and elemental analysis. Full article
Open AccessShort Note
(E)-3-[4-(Pent-4-en-1-yloxy)phenyl]acrylicc Acid
Molbank 2018, 2018(2), M996; https://doi.org/10.3390/M996 -
Abstract
(E)-3-[4-(Pent-4-en-1-yloxy)phenyl]acetic acid is one of the useful components of liquid crystal materials which can be produced through Williamson ether synthesis by synthesizing 4-hydroxy-cinnamic acid and 5-bromo-1-pentene. Although Williamson ether synthesis is generally slow under conventional external heating conditions, microwave irradiation was
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(E)-3-[4-(Pent-4-en-1-yloxy)phenyl]acetic acid is one of the useful components of liquid crystal materials which can be produced through Williamson ether synthesis by synthesizing 4-hydroxy-cinnamic acid and 5-bromo-1-pentene. Although Williamson ether synthesis is generally slow under conventional external heating conditions, microwave irradiation was effective for significant acceleration of the etherification. Furthermore, we demonstrated the rapid and continuous synthesis of (E)-3-[4-(pent-4-en-1-yloxy)phenyl]acetic acid, using a microwave-assisted flow reactor developed by us, in which the blockage by salt precipitation was suppressed by the continuous addition of an aqueous methanol solution after the reaction cavity. Full article
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Open AccessShort Note
N-(1-Deoxy-α-d-tagatopyranos-1-yl)-N-methylaniline (“d-Tagatose-N-methylaniline”)
Molbank 2018, 2018(2), M994; https://doi.org/10.3390/M994 -
Abstract
Tagatosamines form in thermally-processed dairy products and contribute to the foods’ organoleptic and nutritional value. d-Tagatose-N-methylaniline (N-(1-deoxy-d-tagatos-1-yl)-N-methylaniline, 1-deoxy-1-(N-methylphenylamino)-d-tagatose) was synthesized from d-galactose via the Amadori rearrangement. In aqueous solution,
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Tagatosamines form in thermally-processed dairy products and contribute to the foods’ organoleptic and nutritional value. d-Tagatose-N-methylaniline (N-(1-deoxy-d-tagatos-1-yl)-N-methylaniline, 1-deoxy-1-(N-methylphenylamino)-d-tagatose) was synthesized from d-galactose via the Amadori rearrangement. In aqueous solution, it established an anomeric equilibrium consisting of 62.8% α-pyranose, 21.3% β-pyranose, 1.5% α-furanose, 8.1% β-furanose, and 6.2% acyclic keto tautomer. The crystalline α-pyranose anomer of d-tagatose-N-methylaniline adopted the 5C2 chair conformation. All hydroxyl and ring oxygen atoms and the amino nitrogen are involved in an extensive H-bonding network dominated by infinite homodromic chains. The Hirshfeld surface analysis suggests a significant contribution of non-polar intermolecular contacts to the crystal structure. Full article
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Open AccessFeature PaperShort Note
Octahydro-1H,5H,7H-dipyrrolo[1,2-c:1′,2′-f][1,3,6]oxadiazocine-5-thione
Molbank 2018, 2018(2), M993; https://doi.org/10.3390/M993 -
Abstract
A minor byproduct in the reaction of (S)-prolinol with thiophosgene in the presence of triethylamine is identified as a novel tricyclic dipyrrolidino-1,3,6-oxadiazocane-2-thione, the first example of such a ring system, and a representative of the uncommon, but useful 1,3,6-oxadiazocanes. A mechanism
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A minor byproduct in the reaction of (S)-prolinol with thiophosgene in the presence of triethylamine is identified as a novel tricyclic dipyrrolidino-1,3,6-oxadiazocane-2-thione, the first example of such a ring system, and a representative of the uncommon, but useful 1,3,6-oxadiazocanes. A mechanism is proposed for its formation. Full article
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