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Journal articles on the topic 'Oxepin'

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Published: 4 June 2021

Last updated: 1 February 2022

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1

Berndt, Torsten, and Olaf Böge. "Reaction of O(3P) Atoms with Benzene." Zeitschrift für Physikalische Chemie 218, no. 4 (2004): 391–404. http://dx.doi.org/10.1524/zpch.218.4.391.29202.

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AbstractThe gas-phase reaction of O(3P) atoms with benzene was investigated in a flow system in the pressure range of 50–100mbar and a temperature of 295 ± 2K with a focus on the product formation. O2 concentrations in the carrier gas were in the range of (7.7–84) × 1014 molecule cm−3. The primary stable products detected were phenol, benzene oxide/oxepin and a not identified compound with the probable composition C5H6O. The yields of phenol and benzene oxide/oxepin were 0.12 ± 0.02 and 0.26 ± 0.06, respectively, being not affected by the experimental conditions. For benzene oxide/oxepin, a ra

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2

Florea, Stelian, Anca Nicolae, and Ovidiu Maior. "SYNTHESIS OF NEW BENZO[e]DIBENZOFURO[2,3-b]-OXEPIN-5(14H)-ONES." SOUTHERN BRAZILIAN JOURNAL OF CHEMISTRY 4, no. 4 (1996): 101–8. http://dx.doi.org/10.48141/sbjchem.v4.n4.1996.101_1996.pdf.

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The new ring systems, benzo[e]dibenzofuro[2,3-b]oxepin-5(14H)-one and benzo[e]dibenzofuro[2,1-b]oxepin-5(14H)-one were obtained by cyclizing of 2-(2-dibenzoftuyloxymethyl)benzoic acid in the presence of polyphosphoric acid ester.By cyclization of the 2-(1-methoxy-2-dibenzofuryloxymethyl) benzoic acid was obtained benzo[e]dibenzofuro[2,3-b]-oxepin-12-methoxy-5-one with a indubitable structure. The structure of the new compounds was proved by means of 1H-and 13C-NMR spectra.

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3

Li, Ning, Binrong Yao, Chunhua Wang, Qingguo Meng, and Guige Hou. "Synthesis, crystal structure and activity evaluation of novel 3,4-dihydro-1-benzoxepin-5(2H)-one derivatives as protein–tyrosine kinase (PTK) inhibitors." Acta Crystallographica Section C Structural Chemistry 73, no. 11 (2017): 1003–9. http://dx.doi.org/10.1107/s2053229617015145.

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Four new 3,4-dihydro-1-benzoxepin-5(2H)-one derivatives, namely (E)-4-(5-bromo-2-hydroxybenzylidene)-6,8-dimethoxy-3,4-dihydrobenzo[b]oxepin-5(2H)-one, (7), (E)-4-[(E)-3-(5-bromo-2-hydroxyphenyl)allylidene]-6,8-dimethoxy-3,4-dihydrobenzo[b]oxepin-5(2H)-one, (8), (E)-4-(5-bromo-2-hydroxybenzylidene)-6-hydroxy-8-methoxy-3,4-dihydrobenzo[b]oxepin-5(2H)-one, C18H15BrO5, (9), and (E)-4-[(E)-3-(5-bromo-2-hydroxyphenyl)allylidene]-6-hydroxy-8-methoxy-3,4-dihydrobenzo[b]oxepin-5(2H)-one, (10), have been synthesized and characterized by FT–IR, NMR and MS. The structure of (9) was confirmed by single-cr

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4

Klotz, Björn, Ian Barnes, Karl H. Becker, and Bernard T. Golding. "Atmospheric chemistry of benzene oxide/oxepin." Journal of the Chemical Society, Faraday Transactions 93, no. 8 (1997): 1507–16. http://dx.doi.org/10.1039/a606152d.

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5

Jasinski, Jerry P., Q. N. M. Hakim Al-arique, Ray J. Butcher, H. S. Yathirajan, and B. Narayana. "6,11-Dihydrodibenz[b,e]oxepin-11-one." Acta Crystallographica Section E Structure Reports Online 66, no. 1 (2009): o159—o160. http://dx.doi.org/10.1107/s1600536809053409.

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6

Warrener, RN, IG Pitt, KDV Weerasuria, and RA Russell. "Acetylene Stacking: a New Concept for the Synthesis of Cyclic Polyenes. Application to the Preparation of a 1,6-Bridged Bicyclo[4.2.0]octa-2,4,7-triene and Some Novel Oxepins." Australian Journal of Chemistry 45, no. 1 (1992): 155. http://dx.doi.org/10.1071/ch9920155.

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A new protocol for a general synthesis of cyclic polyenes is presented; in this protocol two new concepts are introduced. The first, acetylene stacking, is the generic term covering both the synthesis of a target molecule and the specific retrosynthesis upon which it is based. This retrosynthetic analysis involves conversion of the target molecule, through a series of transannular [ π2s+π2s] valence isomerizations , into a key polycyclobutanoid intermediate (24). This intermediate is cleaved, in turn, through a similar number of [ σ2s+ σ2s] electrocyclic fragmentations, to yield a set of acety

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7

Wyatt, Dorothy K., Nina M. Roscher, and Lee T. Grady. "Carbon13 NMR of Z- and E-Doxepin Hydrochloride." Applied Spectroscopy 40, no. 4 (1986): 538–42. http://dx.doi.org/10.1366/0003702864508782.

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Carbon13 chemical shift assignments are reported for Z- and E-doxepin hydrochloride [ Z- and E-N,N,-dimethyl-dibenz[b,e]oxepin-delta-11(6H)], gamma-propylamine hydrochloride, and related model compounds. Doxepin hydrochloride, a mixture of approximately 85% E- and 15% Z-isomer is of clinical importance as an antidepressant drug. Previous proton NMR studies indicated that the dibenz(b,e,)oxepin ring exists in two conformations. This study indicates that one conformation may be favored for each isomer with alkylamino olefinic substituent orientation above the most adjacent aromatic ring. Homoand

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8

Minassian, Frédéric, Nadia Pelloux-Léon, Marie-Thérèse Averbuch-Pouchot, and Yannick Vallée. "Rearrangements in the 11-Thia-9,10-dihydro-9,10-ethanoanthracene Series. Synthesis of a Bridged Thienooxepin." Journal of Chemical Research 23, no. 2 (1999): 166–67. http://dx.doi.org/10.1177/174751989902300250.

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9

KLOTZ, B., I. BARNES, K. H. BECKER, and B. T. GOLDING. "ChemInform Abstract: Atmospheric Chemistry of Benzene Oxide/Oxepin." ChemInform 28, no. 28 (2010): no. http://dx.doi.org/10.1002/chin.199728205.

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10

Hou, Yan-Jun, Shu-Lin Song, Wen-Yi Chu, and Zhi-Zhong Sun. "2,9,10-Trimethoxydibenzo[b,d]oxepin-7(6H)-one." Acta Crystallographica Section E Structure Reports Online 68, no. 1 (2011): o204. http://dx.doi.org/10.1107/s1600536811053803.

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11

Mangina, N. S. V. M. Rao, Surisetti Suresh, Balasubramanian Sridhar, and Galla V. Karunakar. "Gold(iii)-catalyzed synthesis of aroylbenzo[b]oxepin-3-ones from ortho-O-propargyl-1-one substituted arylaldehydes." Organic & Biomolecular Chemistry 14, no. 14 (2016): 3526–35. http://dx.doi.org/10.1039/c5ob02676h.

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An efficient gold-catalyzed intramolecular cyclization of ortho-O-propargyl-1-one substituted arylaldehydes has been achieved for the generation of substituted aroylbenzo[b]oxepin-3-one derivatives in moderate to good yields.

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12

Bleasdale, Christine, Richard Cameron, Christine Edwards, and Bernard T. Golding. "Dimethyldioxirane Converts Benzene Oxide/Oxepin into (Z,Z)-Muconaldehyde andsym-Oxepin Oxide: Modeling the Metabolism of Benzene and Its Photooxidative Degradation." Chemical Research in Toxicology 10, no. 12 (1997): 1314–18. http://dx.doi.org/10.1021/tx970122d.

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13

Yang, Zhen, Henry N. C. Wong, Po Ming Hon, Hson Mou Chang, and Chi Ming Lee. "A novel synthesis of the dibenz[b,f]oxepin ring system: 10,11-dihydro-11-hydroxydibenz[b,f]oxepin-10(11H)-one." Journal of Organic Chemistry 57, no. 14 (1992): 4033–34. http://dx.doi.org/10.1021/jo00040a059.

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14

Elix, J. A., L. Xing-Wang, and J. H. Wardlaw. "Subvirensic Acid, a New Depsidone from the Lichen Flavoparmelia haysomii." Australian Journal of Chemistry 55, no. 8 (2002): 505. http://dx.doi.org/10.1071/ch02064.

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The new depsidone subvirensic acid (4-formyl-3,8-dihydroxy-1,6-dimethyl-11-oxo-11H-dibenzo[b,e][1,4]di-oxepin-7-carboxylic acid) (7) has been isolated from the lichen Flavoparmelia haysomii and the structure deduced from a combination of spectroscopic data.

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15

Pan, Chengqian, Yutong Shi, Xuegang Chen, Chen-Tung Arthur Chen, Xinyi Tao, and Bin Wu. "New compounds from a hydrothermal vent crab-associated fungus Aspergillus versicolor XZ-4." Organic & Biomolecular Chemistry 15, no. 5 (2017): 1155–63. http://dx.doi.org/10.1039/c6ob02374f.

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Three new quinazoline derivatives (1–3), one new oxepin-containing natural product (4) and four new cyclopenin derivatives (5–7 and 9) have been isolated from an EtOAc extract of the Taiwan Kueishantao hydrothermal vent crab-associated fungus Aspergillus versicolor XZ-4.

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16

Chen, Jianbo, Huifang Zhang, Li Chen, and Bin Wu. "New Stress Metabolite from Bulbophyllum kwangtungense." Natural Product Communications 6, no. 1 (2011): 1934578X1100600. http://dx.doi.org/10.1177/1934578x1100600113.

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A new dibenz[ b, f]oxepin (1) was found to be produced as a stress metabolite from the leaves and stems of Bulbophyllum kwangtungense Schlecht, in response to abiotic stress elicitation by CuCl2. The structure of 1 was established by spectroscopic and spectrometric means.

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17

Zhuravleva, Olesya I., Shamil Sh Afiyatullov, Ekaterina A. Yurchenko, Vladimir A. Denisenko, Natalya N. Kirichuk, and Pavel S. Dmitrenok. "New Metabolites from the Algal Associated Marine-derived Fungus Aspergillus Carneus." Natural Product Communications 8, no. 8 (2013): 1934578X1300800. http://dx.doi.org/10.1177/1934578x1300800809.

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The new oxepin-containing (1) and quinazolinone (2) alkaloids and new dihydrobenzofuran derivative (3) have been isolated from a marine strain of Aspergillus carneus KMM 4638. The structures of these metabolites were determined by HR-MS and 1D and 2D NMR, along with Marfey's method.

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18

Parlow, John J. "An example of a novel formation of an oxepin." Journal of Heterocyclic Chemistry 32, no. 5 (1995): 1413–16. http://dx.doi.org/10.1002/jhet.5570320501.

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19

Chattopadhyay, Shital K., Rajat Dey, and Suman Biswas. "Regioselective Synthesis of Oxepin- and Oxocin-Annulated 2-Quinolones." Synthesis 2005, no. 03 (2005): 403–6. http://dx.doi.org/10.1055/s-2005-861786.

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20

Bock, Charles W., Philip George, John J. Stezowski, and Jenny P. Glusker. "Theoretical studies of the benzene oxide?oxepin valence tautomerism." Structural Chemistry 1, no. 1 (1990): 33–39. http://dx.doi.org/10.1007/bf00675782.

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21

Morgan, Jessica, and Arthur Greenberg. "Curtin–Hammett principle: application to benzene oxide–oxepin tautomers." Structural Chemistry 24, no. 6 (2013): 1945–56. http://dx.doi.org/10.1007/s11224-013-0274-5.

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22

Yang, Zhen, Henry N. C. Wong, Po Ming Hon, Hson Mou Chang, and Chi Ming Lee. "Correction. A Novel Synthesis of the Dibenz-[b,f]oxepin Ring System: 10,11-Dihydro-11-hydroxydibenz[b,f]oxepin-10(11H)-one." Journal of Organic Chemistry 57, no. 26 (1992): 7373. http://dx.doi.org/10.1021/jo00052a602.

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23

YANG, Z., H. N. C. WONG, P. M. HON, H. M. CHANG, and C. M. LEE. "ChemInform Abstract: A Novel Synthesis of the Dibenz(b,f)oxepin Ring System: 10,11-Dihydro- 11-hydroxydibenz(b,f)oxepin-10(11H)-one." ChemInform 23, no. 51 (1992): no. http://dx.doi.org/10.1002/chin.199251216.

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24

Muhammad, Aminu, and Hasnah Mohd Sirat. "Potent Microbial and Tyrosinase Inhibitors from Stem Bark of Bauhinia Rufescens (Fabaceae)." Natural Product Communications 8, no. 10 (2013): 1934578X1300801. http://dx.doi.org/10.1177/1934578x1300801025.

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The stem bark extracts of Bauhinia rufescens Lam. (Fabaceae) yielded 6-methoxy-7-methyl-8-hydroxydibenz[ b,f]oxepin, α-amyrin acetate, β-sitosterol 3- O-β-D-xylopyranoside, 4-(2′-Hydroxyphenethyl)-5-methoxy-2-methylphenol, menisdaurin and sequoyitol. Their structures were determined using spectroscopic methods and comparisons with the literature data. For the antimicrobial assay Gram-positive and Gram-negative bacterial and fungal strains were tested, while the tyrosinase inhibition assay utilized L-DOPA as a substrate for the tyrosinase enzyme. 6-Methoxy-7-methyl-8-hydroxydibenz[ b,f]oxepin,

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25

Li, Haoxin, Stéphanie Jean, Duncan Webster, et al. "Dibenz[b,f]oxepin and Antimycobacterial Chalcone Constituents ofEmpetrum nigrum." Journal of Natural Products 78, no. 11 (2015): 2837–40. http://dx.doi.org/10.1021/acs.jnatprod.5b00627.

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26

Prateeptongkum, Saisuree, Wiratchanee Mahavorasirikul, and Nongnaphat Duangdee. "Synthesis and anti-proliferative activity of novel oxepin-annulated coumarins." Arkivoc 2018, no. 7 (2018): 73–85. http://dx.doi.org/10.24820/ark.5550190.p010.547.

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27

Zheng, Liujuan, Haowen Wang, Lena Ludwig-Radtke, and Shu-Ming Li. "Oxepin Formation in Fungi Implies Specific and Stereoselective Ring Expansion." Organic Letters 23, no. 6 (2021): 2024–28. http://dx.doi.org/10.1021/acs.orglett.1c00166.

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28

Cleve, A., and F. Bohlmann. "Synthesis of (±)-senoxepin - the first naturally occurring anti-hückel oxepin derivative." Tetrahedron Letters 30, no. 10 (1989): 1241–44. http://dx.doi.org/10.1016/s0040-4039(00)72725-0.

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29

Baur, Benjamin, Dieter Schollmeyer, and Stefan Laufer. "3-(2,4-Dimethoxyanilino)-8-methoxydibenz[b,e]oxepin-11(6H)-one." Acta Crystallographica Section E Structure Reports Online 67, no. 2 (2011): o487. http://dx.doi.org/10.1107/s1600536811002637.

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30

PARLOW, J. J. "ChemInform Abstract: An Example of a Novel Formation of an Oxepin." ChemInform 27, no. 13 (2010): no. http://dx.doi.org/10.1002/chin.199613184.

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31

Baur, Benjamin, Dieter Schollmeyer, and Stefan Laufer. "3-(2,4-Difluoroanilino)-9-nitrodibenzo[b,e]oxepin-11(6H)-one." Acta Crystallographica Section E Structure Reports Online 67, no. 3 (2011): o555. http://dx.doi.org/10.1107/s1600536811002881.

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32

Paz, Cristian, Matthias Heydenreich, Bernd Schmidt, Nahir Vadra та Ricardo Baggio. "Three new dihydro-β-agarofuran sesquiterpenes from the seeds of Maytenus boaria". Acta Crystallographica Section C Structural Chemistry 74, № 5 (2018): 564–70. http://dx.doi.org/10.1107/s2053229618005429.

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As part of a project studying the secondary metabolites extracted from the Chilean flora, we report herein three new β-agarofuran sesquiterpenes, namely (1S,4S,5S,6R,7R,8R,9R,10S)-6-acetoxy-4,9-dihydroxy-2,2,5a,9-tetramethyloctahydro-2H-3,9a-methanobenzo[b]oxepine-5,10-diyl bis(furan-3-carboxylate), C27H32O11, (II), (1S,4S,5S,6R,7R,9S,10S)-6-acetoxy-9-hydroxy-2,2,5a,9-tetramethyloctahydro-2H-3,9a-methanobenzo[b]oxepine-5,10-diyl bis(furan-3-carboxylate), C27H32O10, (III), and (1S,4S,5S,6R,7R,9S,10S)-6-acetoxy-10-(benzoyloxy)-9-hydroxy-2,2,5a,9-tetramethyloctahydro-2H-3,9a-methanobenzo[b]oxepin

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33

Matsuzawa, E. S., N. Hirayama, E. Ohshima, and H. Obase. "Structural aspects of the 6,11-dihydro-11-oxodibenz[b,e]oxepin skeleton." Acta Crystallographica Section C Crystal Structure Communications 48, no. 11 (1992): 2016–19. http://dx.doi.org/10.1107/s0108270192002701.

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34

Stok, Jeanette E., Sharon Chow, Elizabeth H. Krenske, et al. "Direct Observation of an Oxepin from a Bacterial Cytochrome P450-Catalyzed Oxidation." Chemistry - A European Journal 22, no. 13 (2016): 4408–12. http://dx.doi.org/10.1002/chem.201600246.

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35

Ilkhani, Ali Reza. "Pseudo Jahn-Teller effect in oxepin, azepin, and their halogen substituted derivatives." Russian Journal of Physical Chemistry A 91, no. 9 (2017): 1743–51. http://dx.doi.org/10.1134/s0036024417090035.

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36

Li, Qiang, ShaoPing Sun, and XianFeng Gong. "Dinitrodibenzo [B,D]Oxepin-7(6h)-One Antiproliferative Activity Against Hepg2 Cells." Pharmaceutical Chemistry Journal 53, no. 7 (2019): 624–27. http://dx.doi.org/10.1007/s11094-019-02050-8.

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37

Bhutia, Tshering Doma, Karin M. Valant-Vetschera, and Lothar Brecker. "Orphan Flavonoids and Dihydrochalcones from Primula Exudates." Natural Product Communications 8, no. 8 (2013): 1934578X1300800. http://dx.doi.org/10.1177/1934578x1300800812.

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Two orphan flavonoids containing an oxepin structure in ring A and named as Primcortusin (1) and 3’-OH-Primcortusin (2) were isolated from leaf exudates of Primula cortusoides, while P. glutinosa exudates yielded two dihydrochalcone derivatives (3,4). These novel structures have not been detected in other species of Primula so far. Chemical structures were elucidated by 2D NMR and mass spectrometry. The nature of compounds 1 and 2 is discussed, and ideas about their possible origin and that of unsubstituted flavone and other irregular substituted Primula flavones are presented.

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38

Yamazaki, Hiroyuki, Henki Rotinsulu, Tsuyoshi Kaneko, et al. "A New Dibenz[b,e]oxepine Derivative, 1-Hydroxy-10-methoxy-dibenz[b,e]oxepin-6,11-dione, from a Marine-Derived Fungus, Beauveria bassiana TPU942." Marine Drugs 10, no. 12 (2012): 2691–97. http://dx.doi.org/10.3390/md10122691.

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39

Moreno, David, Giorgio Giorgi, Cristian Salas, and Ricardo Tapia. "New Short Strategy for the Synthesis of the Dibenz[b,f]oxepin Scaffold." Molecules 18, no. 12 (2013): 14797–806. http://dx.doi.org/10.3390/molecules181214797.

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40

Garbicz, Damian, Damian Mielecki, Michal Wrzesinski, et al. "Evaluation of Anti-cancer Activity of Stilbene and Methoxydibenzo[b,f] oxepin Derivatives." Current Cancer Drug Targets 18, no. 7 (2018): 706–17. http://dx.doi.org/10.2174/1568009617666170623120742.

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Background: Stilbenes, 1,2-diphenylethen derivatives, including resveratrol and combretastatins, show anticancer features especially against tumor angiogenesis. Fosbretabulin, CA-4, in combination with carboplatin, is in the last stages of clinical tests as an inhibitor of thyroid cancer. The mode of action of these compounds involves suppression of angiogenesis through interfering with tubulin (de)polymerization. Objective: We have previously synthesized five E-2-hydroxystilbenes and seven dibenzo [b,f]oxepins in Z configuration, with methyl or nitro groups at varied positions. The aim of the

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41

Tyurin, R. V., A. A. Milov, A. N. Bezuglov, A. N. Antonov, L. G. Minyaeva, and V. V. Mezheritskii. "Synthesis and structure of 2-aryl-4H-acenaphth[5,6-bc]oxepin-4-ones." Russian Journal of Organic Chemistry 43, no. 10 (2007): 1466–70. http://dx.doi.org/10.1134/s1070428007100090.

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42

YAMAMOTO, I., K. NAGAI, K. WATANABE, T. MATSUNAGA, and H. YOSHIMURA. "A Novel Metabolite, an Oxepin Formed from Cannabidiol with Guinea-pig Hepatic Microsomes." Journal of Pharmacy and Pharmacology 47, no. 8 (1995): 683–86. http://dx.doi.org/10.1111/j.2042-7158.1995.tb05860.x.

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43

Ohshima, Etsuo, Shizuo Otaki, Hideyuki Sato, et al. "Synthesis and antiallergic activity of 11-(aminoalkylidene)-6,11-dihydrodibenz[b,e]oxepin derivatives." Journal of Medicinal Chemistry 35, no. 11 (1992): 2074–84. http://dx.doi.org/10.1021/jm00089a020.

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44

Glukhov, A. A., N. F. Kirillov, A. A. Potapova, R. R. Makhmudov, and L. G. Mardanova. "Synthesis and analgesic activity of 4-aroyl-1H-benzo[c]oxepin-3-ones." Pharmaceutical Chemistry Journal 44, no. 9 (2010): 483–85. http://dx.doi.org/10.1007/s11094-010-0497-3.

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45

Majumdar, Krishna, Pradip Debnath, and Abu Taher. "Regioselective Synthesis of Oxepin and Oxocin Annulated Quinoline Heterocycles by Ring-Closing Metathesis." Letters in Organic Chemistry 5, no. 3 (2008): 169–73. http://dx.doi.org/10.2174/157017808783955871.

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46

OHSHIMA, Etsuo, Hideyuki SATO, Hiroyuki OBASE, Tatsuo UCHIMURA, Takashi KUWABARA, and Satoshi KOBAYASHI. "Synthesis of a Dibenz(b,e)oxepin-Bovine Serum Albumin Conjugate for Radioimmunoassay of KW-4679((Z)-11-(3-(Dimethylamino)propylidene)-6,11-dihydrodibenz(b,e)oxepin-2-acetic Acid Hydrochloride)." CHEMICAL & PHARMACEUTICAL BULLETIN 40, no. 9 (1992): 2552–54. http://dx.doi.org/10.1248/cpb.40.2552.

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47

Kulesza, Anna, Frank H. Ebetino, and Adam W. Mazur. "Synthesis of 1-substituted 2,3-dihydro-7H-oxepin-4-one from an amino acid." Tetrahedron Letters 44, no. 29 (2003): 5511–14. http://dx.doi.org/10.1016/s0040-4039(03)01226-7.

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48

Pye, Cory C., James D. Xidos, Raymond A. Poirier, and D. Jean Burnell. "Examination of the Valence Tautomers Benzene Oxide and Oxepin and Two Derivative Systems byabInitioMethods." Journal of Physical Chemistry A 101, no. 18 (1997): 3371–76. http://dx.doi.org/10.1021/jp9623498.

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49

Kudoh, Mitsutaka, Susumu Sudoh, Shigeyoshi Katagiri, et al. "X-ray Structures and Dipole Moments of Tropones Annulated with Furan, Benzene, and Oxepin." Bulletin of the Chemical Society of Japan 79, no. 8 (2006): 1240–47. http://dx.doi.org/10.1246/bcsj.79.1240.

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MATSUZAWA, E. S., N. HIRAYAMA, E. OHSHIMA, and H. OBASE. "ChemInform Abstract: Structural Aspects of the 6,11-Dihydro-11-oxodibenz(b,e)oxepin Skeleton." ChemInform 24, no. 9 (2010): no. http://dx.doi.org/10.1002/chin.199309035.

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