Molbank

3 pages, 594 KB

Open AccessShort 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^1,2, Didin Mujahidin^1,*

and Yana M. Syah¹

¹ Division of Organic Chemistry, Faculty of Mathematics and Natural Sciences, Institut Teknologi Bandung, Jl. Ganesa 10, Bandung 40132, Indonesia

² Department of Pharmacy, Faculty of Medicine and Public Health, Universitas Jenderal Soedirman, Purwokerto 53122, Indonesia

Molbank 2017, 2017(1), M922; https://doi.org/10.3390/M922 - 27 Dec 2016

Cited by 2 | Viewed by 4604

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 and Biosynthesis)

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Scheme 1

4 pages, 794 KB

Open AccessShort Note

4-Chloro-6-ethoxy-2-(methylthio)pyrimidine

by Andreas S. Kalogirou^* and Panayiotis A. Koutentis

Department of Chemistry, University of Cyprus, P. O. Box 20537, Nicosia 1678, Cyprus

Molbank 2017, 2017(1), M923; https://doi.org/10.3390/M923 - 29 Dec 2016

Cited by 1 | Viewed by 6197

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 and Biosynthesis)

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Scheme 1

6 pages, 1638 KB

Open AccessShort Note

(E)-1-(2-Aminophenyl)-3-(benzo[d][1,3]dioxol-5-yl)prop-2-en-1-one

by Rodrigo Abonia^1,*, Diana Arteaga¹, Daniel Insuasty¹, Jairo Quiroga¹

, Braulio Insuasty¹, Rodolfo Moreno-Fuquen¹ and Alan R. Kennedy²

¹ Department of Chemistry, Universidad del Valle, A.A. 25360 Santiago de Cali, Colombia

² WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, Scotland

Molbank 2017, 2017(1), M924; https://doi.org/10.3390/M924 - 30 Dec 2016

Cited by 1 | Viewed by 4443

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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4 pages, 1328 KB

Open AccessShort Note

Ethyl({[acryloyl(furan-2-ylmethyl)amino]acetyl}amino)acetate

by Shimoga D. Ganesh¹, Nabanita Saha^1,*, Ronald N. Zuckermann² and Petr Sáha¹

¹ Centre of Polymer Systems, University Institute, Tomas Bata University in Zlin, Tř. T. Bati 5678, 760 01, Zlin, Czech Republic

² Biological Nanostructures Facility, Molecular Foundry, Lawrence Berkeley National Laboratory1 Cyclotron Rd., Berkeley, CA 94720, USA

Molbank 2017, 2017(1), M925; https://doi.org/10.3390/M925 - 9 Jan 2017

Viewed by 4140

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 and Biosynthesis)

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2 pages, 271 KB

Open AccessEditorial

Acknowledgement to Reviewers of Molbank in 2016

by Molbank Editorial Office

MDPI AG, St. Alban-Anlage 66, 4052 Basel, Switzerland

Molbank 2017, 2017(1), M926; https://doi.org/10.3390/M926 - 11 Jan 2017

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Abstract

The editors of Molbank would like to express their sincere gratitude to the following reviewers for assessing manuscripts in 2016.[...] Full article

5 pages, 1309 KB

Open AccessShort Note

(Z)-4-(Carbomethoxymethylene)-2-(4-fluorophenyl)-4H-benzo[d][1,3]oxazine

by Francesco Pancrazzi¹

, Elena Motti¹, Mirco Costa¹, Raffaella Mancuso²

, Bartolo Gabriele²

and Nicola Della Ca’^1,*

¹ Department of Chemistry, University of Parma, Parco Area delle Scienze 17/A, 43124 Parma, Italy

² Laboratory of Industrial and Synthetic Organic Chemistry (LISOC), Department of Chemistry and Chemical Technologies, University of Calabria, Via Pietro Bucci 12/C, 87036 Arcavacata di Rende (CS), Italy

Molbank 2017, 2017(1), M927; https://doi.org/10.3390/M927 - 13 Jan 2017

Cited by 7 | Viewed by 3890

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 and Biosynthesis)

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6 pages, 1174 KB

Open AccessShort Note

Ethyl (1R*,10S*,12R*,15S*)-4-Hydroxy-2-oxo-15- (2-oxo-1-pyrrolidinyl)-9-oxatetracyclo[10.2.2.0^1,10.0^3,8]hexadeca-3,5,7,13-tetraene-13-carboxylate

by Jorge Heredia-Moya^1,* and Ramiro Araya-Maturana^2,*

¹ Centro de Investigación Biomédica, Facultad de Ciencias de la Salud Eugenio Espejo, Universidad Tecnológica Equinoccial, Av. Mariscal Sucre y Mariana de Jesús, Quito 170527, Ecuador

² Instituto de Química de Recursos Naturales, Universidad de Talca, Av. Lircay s/n, Casilla 747, Talca 3460000, Chile

Molbank 2017, 2017(1), M928; https://doi.org/10.3390/M928 - 18 Jan 2017

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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 and Biosynthesis)

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Scheme 1

7 pages, 1948 KB

Open AccessCommunication

Oxidative Radical Cyclization–Cyclization Reaction Leading to 1H-Benzo[f]isoindole Derivatives

by Eito Yoshioka and Hideto Miyabe^*

School of Pharmacy, Hyogo University of Health Sciences, Minatojima, Kobe 650-8530, Japan

Molbank 2017, 2017(1), M929; https://doi.org/10.3390/M929 - 4 Feb 2017

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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 and Biosynthesis)

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Graphical abstract

6 pages, 1751 KB

Open AccessShort Note

2-(tert-Butyl)-4-phenyloxetane

by Filippo Maria Perna^*

, Paola Vitale

, Simona Summa and Vito Capriati^*

Dipartimento di Farmacia-Scienze del Farmaco, Università di Bari “A. Moro”, Consorzio C.I.N.M.P.I.S., Via E. Orabona 4, I-70125 Bari, Italy

Molbank 2017, 2017(1), M930; https://doi.org/10.3390/M930 - 10 Feb 2017

Cited by 1 | Viewed by 4045

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 and Biosynthesis)

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Graphical abstract

4 pages, 500 KB

Open AccessShort 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

Department of Biology, Chemistry, and Mathematics, University of Montevallo, UM Station 6480, Montevallo, AL 35115, USA

Molbank 2017, 2017(1), M931; https://doi.org/10.3390/M931 - 16 Feb 2017

Cited by 1 | Viewed by 3936

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 and Biosynthesis)

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Graphical abstract

4 pages, 1248 KB

Open AccessShort Note

3-{4-[(E)-{4-[(E)-Phenyldiazenyl]phenyl}diazenyl]phenoxy}propane-1,2-diol

by Vladimir V. Chupin¹ and Ivan A. Boldyrev^2,*

¹ Moscow Institute of Physics and Technology, 9 Institutskiy per., Dolgoprudny 141701, Moscow Region, Russian Federation

² Shemyakin–Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, ul. Miklukho-Maklaya 16/10, Moscow 117997, Russia

Molbank 2017, 2017(1), M932; https://doi.org/10.3390/M932 - 22 Feb 2017

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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 and Biosynthesis)

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4 pages, 470 KB

Open AccessShort Note

Dimethyl 7-(dimethylamino)-3,4-dihydro-1-(2-oxopropyl)-4-phenylnaphthalene-2,2(1H)-dicarboxylate

by Sung-Gon Kim

Department of Chemistry, Kyonggi University, 154-42, Gwanggyosan-ro, Yeongtong-gu, Suwon 16227, Korea

Molbank 2017, 2017(1), M933; https://doi.org/10.3390/M933 - 3 Mar 2017

Cited by 1 | Viewed by 3248

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 and Biosynthesis)

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Scheme 1

7 pages, 1930 KB

Open AccessCommunication

(5-Chloroquinolin-8-yl)-2-fluorobenzoate. The Halogen Bond as a Structure Director

by Rodolfo Moreno-Fuquen^1,*, Juan Carlos Castillo²

, Rodrigo Abonía¹, Jaime Portilla²

and José Antonio Henao³

¹ Department of Chemistry, Universidad del Valle, A.A. 25360, Santiago de Cali, Colombia

² Department of Chemistry, Universidad de los Andes, Bogotá 111711, Colombia

³ Escuela de Química, Facultad de Ciencias, Universidad Industrial de Santander, Apartado 678, Bucaramanga, Colombia

Molbank 2017, 2017(1), M934; https://doi.org/10.3390/M934 - 9 Mar 2017

Cited by 1 | Viewed by 4476

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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4 pages, 618 KB

Open AccessShort Note

Methyl 2,3,6-tri-O-Benzoyl-4-O-(tert-butyldimethylsilyl)-β-d-galactopyranoside

by Jack Bennett

, Amélie Roux and Paul V. Murphy^*

School of Chemistry, National University of Ireland, Galway H91 TK33, Ireland

Molbank 2017, 2017(1), M935; https://doi.org/10.3390/M935 - 19 Mar 2017

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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 and Biosynthesis)

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