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Molbank, Volume 2017, Issue 1 (March 2017) – 15 articles

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826 KiB  
Short Note
5,9,11-Trihydroxy-2,2-dimethyl-3-(2-methylbut-3-en-2-yl)pyrano[2,3-a]xanthen-12(2H)-one from the Stem Bark of Calophyllum tetrapterum Miq.
by Tjitjik Srie Tjahjandarie, Ratih Dewi Saputri and Mulyadi Tanjung
Molbank 2017, 2017(1), M936; https://doi.org/10.3390/M936 - 21 Mar 2017
Cited by 2 | Viewed by 3144
Abstract
A new pyranoxanthone namely 5,9,11-trihydroxy-2,2-dimethyl-3-(2-methylbut-3-en-2-yl)pyrano[2,3-a]xanthen-12(2H)-one (1) was isolated from the stem bark of Calophyllum tetrapterum Miq. The structure of compound 1 was determined by means of spectroscopic methods including UV, IR, HRESIMS, 1D and 2D NMR. Full article
(This article belongs to the Section Natural Products)
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618 KiB  
Short Note
Methyl 2,3,6-tri-O-Benzoyl-4-O-(tert-butyldimethylsilyl)-β-d-galactopyranoside
by Jack Bennett, Amélie Roux and Paul V. Murphy
Molbank 2017, 2017(1), M935; https://doi.org/10.3390/M935 - 19 Mar 2017
Viewed by 3533
Abstract
Methyl 2,3,6-tri-O-benzoyl-4-O-(tert-butyldimethylsilyl)-β-d-galactopyranoside was synthesized in 47% yield by the silylation of a partially benzoylated galactose derivative, prepared from methyl β-d-galactopyranoside. The product was characterized by 1H-NMR, 13C-NMR, IR and mass spectrometry. Full article
(This article belongs to the Section Organic Synthesis)
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Scheme 1

1930 KiB  
Communication
(5-Chloroquinolin-8-yl)-2-fluorobenzoate. The Halogen Bond as a Structure Director
by Rodolfo Moreno-Fuquen, Juan Carlos Castillo, Rodrigo Abonía, Jaime Portilla and José Antonio Henao
Molbank 2017, 2017(1), M934; https://doi.org/10.3390/M934 - 9 Mar 2017
Cited by 1 | Viewed by 3665
Abstract
Structures containing 8-hydroxyquinoline scaffold are useful for anticancer drug development. The title ester (5-chloroquinolin-8-yl)-2-fluorobenzoate was prepared by the reaction of 2-fluorobenzoyl chloride with 5-chloro-8-hydroxyquinoline. The structure of the title compound was assigned by diverse spectroscopic techniques. Moreover, a crystallographic study was undertaken and [...] Read more.
Structures containing 8-hydroxyquinoline scaffold are useful for anticancer drug development. The title ester (5-chloroquinolin-8-yl)-2-fluorobenzoate was prepared by the reaction of 2-fluorobenzoyl chloride with 5-chloro-8-hydroxyquinoline. The structure of the title compound was assigned by diverse spectroscopic techniques. Moreover, a crystallographic study was undertaken and its supramolecular characteristics were analyzed. Thus, the central ester fragment C8/O1/C10(O2)/C11 is almost planar with a root mean square (r.m.s.) deviation of 0.0612 Å and it makes dihedral angles of 76.35(6)° and 12.89(11)°, with quinoline and phenyl rings respectively. The structure shows C–H...X (X = halogen) non-classical hydrogen bonds. It also has a halogen…halogen distance less than the sum of the van der Waals radii (3.2171(15) Å). As a result of interactions with halogen atoms, chains of centrosymmetric dimer that form edge-fused R22(18) rings run parallel to the plane (100). Full article
(This article belongs to the Section Structure Determination)
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470 KiB  
Short Note
Dimethyl 7-(dimethylamino)-3,4-dihydro-1-(2-oxopropyl)-4-phenylnaphthalene-2,2(1H)-dicarboxylate
by Sung-Gon Kim
Molbank 2017, 2017(1), M933; https://doi.org/10.3390/M933 - 3 Mar 2017
Cited by 1 | Viewed by 2684
Abstract
A Friedel-Crafts–type ring-opening/intramolecular Michael addition cascade reaction of (E)-4-(3-(dimethylamino)phenyl)but-3-en-2-one with dimethyl 2-phenylcyclopropane-1,1-dicarbo-xylate catalyzed by Yb(OTf)3 has produced a new compound, dimethyl 7-(dimethylamino)-3,4-dihydro-1-(2-oxopropyl)-4-phenylnaphthalene-2,2(1H)-dicarboxylate. This reaction provided diastereoslective trans tetralin (7:3 dr) on the cyclohexyl ring. The structure of the [...] Read more.
A Friedel-Crafts–type ring-opening/intramolecular Michael addition cascade reaction of (E)-4-(3-(dimethylamino)phenyl)but-3-en-2-one with dimethyl 2-phenylcyclopropane-1,1-dicarbo-xylate catalyzed by Yb(OTf)3 has produced a new compound, dimethyl 7-(dimethylamino)-3,4-dihydro-1-(2-oxopropyl)-4-phenylnaphthalene-2,2(1H)-dicarboxylate. This reaction provided diastereoslective trans tetralin (7:3 dr) on the cyclohexyl ring. 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)
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Scheme 1

1248 KiB  
Short Note
3-{4-[(E)-{4-[(E)-Phenyldiazenyl]phenyl}diazenyl]phenoxy}propane-1,2-diol
by Vladimir V. Chupin and Ivan A. Boldyrev
Molbank 2017, 2017(1), M932; https://doi.org/10.3390/M932 - 22 Feb 2017
Viewed by 3381
Abstract
Title compound was designed to be a black quencher of pyrene fluorescence. It was made amphiphilic to serve as a membrane-bound probe. The synthesis is a two-step procedure. The first step is a Mitsunobu reaction of [{(phenyldiazenyl)phenyl}diazenyl]phenol with 1,2-O-isopropylideneglycerol. The second [...] Read more.
Title compound was designed to be a black quencher of pyrene fluorescence. It was made amphiphilic to serve as a membrane-bound probe. The synthesis is a two-step procedure. The first step is a Mitsunobu reaction of [{(phenyldiazenyl)phenyl}diazenyl]phenol with 1,2-O-isopropylideneglycerol. The second step is the cleavage of the isopropylidene protecting group. The title compound has the extinction coefficient 59,000 at λmax = 380 nm. The Forster distance between the title compound and the pyrene was found to be 37.8 Å. Full article
(This article belongs to the Section Organic Synthesis)
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500 KiB  
Short Note
Copper 5,10,15,20-Tetrakis-(3,4-dibenzyloxyphenyl)porphyrin
by L. Dalila Mathews, Cynthia P. Tidwell, Prakash Bharara, Glenn Stephens, Ting Yu Su and Alexia Carter
Molbank 2017, 2017(1), M931; https://doi.org/10.3390/M931 - 16 Feb 2017
Cited by 1 | Viewed by 3160
Abstract
The copper complex of 5,10,15,20-tetrakis-(3,4-dibenzyloxyphenyl)porphyrin (CuTDBOPP) was synthesized and characterized with electronic absorption spectroscopy and ESI high-resolution spectrometry. In the electronic spectrum, there was a shift in the Soret band from 424 nm to 420 nm that indicated that the insertion of the [...] Read more.
The copper complex of 5,10,15,20-tetrakis-(3,4-dibenzyloxyphenyl)porphyrin (CuTDBOPP) was synthesized and characterized with electronic absorption spectroscopy and ESI high-resolution spectrometry. In the electronic spectrum, there was a shift in the Soret band from 424 nm to 420 nm that indicated that the insertion of the metal ion was successful. Additionally, the number of Q bands decreased from four peaks to a single peak at 541 nm. The molar absorptivity of the Soret and Q band are 3.4 × 105 cm−1·M−1 and 1.8 × 105 cm−1·M−1, respectively. The ESI HRMS was in excellent agreement with simulated isotopic distribution spectra. CuTDBOPP was incorporated into a series of Gratzel cells where the open current voltage was recorded. Full article
(This article belongs to the Section Organic Synthesis)
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Graphical abstract

1751 KiB  
Short Note
2-(tert-Butyl)-4-phenyloxetane
by Filippo Maria Perna, Paola Vitale, Simona Summa and Vito Capriati
Molbank 2017, 2017(1), M930; https://doi.org/10.3390/M930 - 10 Feb 2017
Cited by 1 | Viewed by 3372
Abstract
The two geometric isomers of 2-(tert-butyl)-4-phenyloxetane have, for the first time, been prepared starting from the commercially available 4,4-dimethyl-1-phenylpentane-1,3-dione. The latter was reduced with NaBH4 to give a mixture of diastereomeric syn and anti diols which were then stereospecifically cyclized [...] Read more.
The two geometric isomers of 2-(tert-butyl)-4-phenyloxetane have, for the first time, been prepared starting from the commercially available 4,4-dimethyl-1-phenylpentane-1,3-dione. The latter was reduced with NaBH4 to give a mixture of diastereomeric syn and anti diols which were then stereospecifically cyclized into the corresponding oxetanes with an overall yield for the two steps of 69.6%. The newly synthesized stereoisomeric four-membered oxygenated heterocycles were separated by column chromatography on silica gel and fully spectroscopically characterized. Full article
(This article belongs to the Section Organic Synthesis)
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Graphical abstract

1948 KiB  
Communication
Oxidative Radical Cyclization–Cyclization Reaction Leading to 1H-Benzo[f]isoindole Derivatives
by Eito Yoshioka and Hideto Miyabe
Molbank 2017, 2017(1), M929; https://doi.org/10.3390/M929 - 4 Feb 2017
Viewed by 4252
Abstract
The synthesis of 1H-benzo[f]isoindole derivatives was achieved by the cascade radical cyclization–cyclization reaction of the active methine substrate having an allyl group and phenyl group as different two radical acceptors. This oxidative transformation proceeded by using iron(III) chloride FeCl [...] Read more.
The synthesis of 1H-benzo[f]isoindole derivatives was achieved by the cascade radical cyclization–cyclization reaction of the active methine substrate having an allyl group and phenyl group as different two radical acceptors. This oxidative transformation proceeded by using iron(III) chloride FeCl3 as a mild oxidant via the intramolecular radical addition to the allyl group followed by the second radical addition to the phenyl group. Full article
(This article belongs to the Section Organic Synthesis)
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Graphical abstract

1174 KiB  
Short Note
Ethyl (1R*,10S*,12R*,15S*)-4-Hydroxy-2-oxo-15- (2-oxo-1-pyrrolidinyl)-9-oxatetracyclo[10.2.2.01,10.03,8]hexadeca-3,5,7,13-tetraene-13-carboxylate
by Jorge Heredia-Moya and Ramiro Araya-Maturana
Molbank 2017, 2017(1), M928; https://doi.org/10.3390/M928 - 18 Jan 2017
Viewed by 3444
Abstract
N-Vinylpirrolidinone reacts with (E)-ethyl 5-hydroxy-3-(4-oxo-4H-chromen-3-yl) acrylate (1) through a domino reaction similar to that reported reaction for ethyl vinyl ether. Inverse electron demand Diels–Alder (IEDDA)–elimination-IEDDA generates isomeric tetracycles 5 and 6. The assignment of the [...] Read more.
N-Vinylpirrolidinone reacts with (E)-ethyl 5-hydroxy-3-(4-oxo-4H-chromen-3-yl) acrylate (1) through a domino reaction similar to that reported reaction for ethyl vinyl ether. Inverse electron demand Diels–Alder (IEDDA)–elimination-IEDDA generates isomeric tetracycles 5 and 6. The assignment of the relative stereochemistry of the products was made by comparing the proton couplings with those obtained by reaction with ethyl vinyl ether. Full article
(This article belongs to the Section Organic Synthesis)
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Scheme 1

1309 KiB  
Short Note
(Z)-4-(Carbomethoxymethylene)-2-(4-fluorophenyl)-4H-benzo[d][1,3]oxazine
by Francesco Pancrazzi, Elena Motti, Mirco Costa, Raffaella Mancuso, Bartolo Gabriele and Nicola Della Ca’
Molbank 2017, 2017(1), M927; https://doi.org/10.3390/M927 - 13 Jan 2017
Cited by 7 | Viewed by 3319
Abstract
The title compound, (Z)-4-(carbomethoxymethylene)-2-(4-fluorophenyl)-4H-benzo[d][1,3]oxazine, was synthesized in 68% isolated yield by palladium-catalyzed oxidative cyclization-methoxycarbonylation of 4-fluoro-N-(2-((trimethylsilyl)ethynyl)phenyl)benzamide. This new heterocyclic derivative was fully characterized by IR, 1H-NMR, 13C-NMR spectroscopies, MS spectrometry, and elemental analysis. [...] Read more.
The title compound, (Z)-4-(carbomethoxymethylene)-2-(4-fluorophenyl)-4H-benzo[d][1,3]oxazine, was synthesized in 68% isolated yield by palladium-catalyzed oxidative cyclization-methoxycarbonylation of 4-fluoro-N-(2-((trimethylsilyl)ethynyl)phenyl)benzamide. This new heterocyclic derivative was fully characterized by IR, 1H-NMR, 13C-NMR spectroscopies, MS spectrometry, and elemental analysis. The Z configuration around the double bond was unequivocally established by 2D NOESY experiments. Full article
(This article belongs to the Section Organic Synthesis)
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271 KiB  
Editorial
Acknowledgement to Reviewers of Molbank in 2016
by Molbank Editorial Office
Molbank 2017, 2017(1), M926; https://doi.org/10.3390/M926 - 11 Jan 2017
Viewed by 2265
Abstract
The editors of Molbank would like to express their sincere gratitude to the following reviewers for assessing manuscripts in 2016.[...] Full article
1328 KiB  
Short Note
Ethyl({[acryloyl(furan-2-ylmethyl)amino]acetyl}amino)acetate
by Shimoga D. Ganesh, Nabanita Saha, Ronald N. Zuckermann and Petr Sáha
Molbank 2017, 2017(1), M925; https://doi.org/10.3390/M925 - 9 Jan 2017
Viewed by 3467
Abstract
Ethyl({[acryloyl(furan-2-ylmethyl)amino]acetyl}amino)acetate was synthesized via Ugi four component (4C) reaction at ambient temperature. The protocol employs a reaction between formaldehyde, furfurylamine, acrylic acid, and ethyl 2-isocyanoacetate. The course of the reaction was found to be high yielding, and the resulting glycine ester derivative was [...] Read more.
Ethyl({[acryloyl(furan-2-ylmethyl)amino]acetyl}amino)acetate was synthesized via Ugi four component (4C) reaction at ambient temperature. The protocol employs a reaction between formaldehyde, furfurylamine, acrylic acid, and ethyl 2-isocyanoacetate. The course of the reaction was found to be high yielding, and the resulting glycine ester derivative was well characterized by elemental analysis, FTIR, NMR spectroscopy, and mass spectrometric techniques. Full article
(This article belongs to the Section Organic Synthesis)
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1638 KiB  
Short Note
(E)-1-(2-Aminophenyl)-3-(benzo[d][1,3]dioxol-5-yl)prop-2-en-1-one
by Rodrigo Abonia, Diana Arteaga, Daniel Insuasty, Jairo Quiroga, Braulio Insuasty, Rodolfo Moreno-Fuquen and Alan R. Kennedy
Molbank 2017, 2017(1), M924; https://doi.org/10.3390/M924 - 30 Dec 2016
Cited by 1 | Viewed by 3538
Abstract
The title chalcone (E)-1-(2-aminophenyl)-3-(benzo[d][1,3]dioxol-5-yl)prop-2-en-1-one was obtained in 76% yield from a NaOH catalyzed Claisen–Schmidt condensation reaction between o-aminoacetophenone and piperonal. This product will be used as a key precursor for the development of an alternative route for the [...] Read more.
The title chalcone (E)-1-(2-aminophenyl)-3-(benzo[d][1,3]dioxol-5-yl)prop-2-en-1-one was obtained in 76% yield from a NaOH catalyzed Claisen–Schmidt condensation reaction between o-aminoacetophenone and piperonal. This product will be used as a key precursor for the development of an alternative route for the total synthesis of the alkaloid Graveoline. Single crystals of the title compound suitable for X-ray diffraction were grown via slow evaporation in ethanol at room temperature. A complete crystallographic study was performed in depth to unequivocally confirm its structure. The crystal structure of the title o-aminochalcone, C16H13NO3, shows two molecules per asymmetric unit (Z = 4) and adopts an E configuration about the C=C double bond. In the title compound, the mean plane of the non-H atoms of the central chalcone fragment C—C(O)—C—C—C is as follow: [root-mean-square (r.m.s.) deviation = 0.0210 Å for A–B and 0.0493 for C–D molecules]. In the crystal, molecules are linked by N–H...O and C–H...O, hydrogen bonds forming S(6), R22(6) and edge-fused R44(24)rings along with C(18) chains running parallel to (110). Full article
(This article belongs to the Section Structure Determination)
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794 KiB  
Short Note
4-Chloro-6-ethoxy-2-(methylthio)pyrimidine
by Andreas S. Kalogirou and Panayiotis A. Koutentis
Molbank 2017, 2017(1), M923; https://doi.org/10.3390/M923 - 29 Dec 2016
Cited by 1 | Viewed by 3797
Abstract
4,6-Dichloro-2-(methylthio)pyrimidine (3) reacts with EtONa in EtOH, at ca. 20 °C, for 2 h, to give exclusively 4-chloro-6-ethoxy-2-(methylthio)pyrimidine (5) in 89% yield. The latter is presented as a useful multifunctionalised pyrimidine scaffold. Full article
(This article belongs to the Section Organic Synthesis)
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Scheme 1

594 KiB  
Short Note
(2E,2′E)-3-(4-{[4-(4-Hydroxy-3-methoxyphenyl)but-2-en-1-yl]oxy}phenyl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one
by Muhamad S. Fareza, Didin Mujahidin and Yana M. Syah
Molbank 2017, 2017(1), M922; https://doi.org/10.3390/M922 - 27 Dec 2016
Cited by 2 | Viewed by 3854
Abstract
A hybrid of eugenol and a chalcone has been synthesized in good yield via cross olefin metathesis. The title compound (3) was characterized by spectroscopic data including NMR, infrared, and ESI-MS. Full article
(This article belongs to the Section Organic Synthesis)
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Scheme 1

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