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Attempted Synthesis of 3-Carboxy-4-hydroxy-4-(trifluoromethyl)tetralone

✍ Scribed by Ukerun, Sylvester Ohwevwo

Publisher
John Wiley and Sons
Year
1989
Tongue
English
Weight
172 KB
Volume
1989
Category
Article
ISSN
0947-3440

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✦ Synopsis

Tetralone 1 Pentanoic acid, 3-carboxy 1 Furandione The synthesis of 3-carboxy-4-(trifluoromethyl)tetralone'~2~, a model compound which is important for the preparation of perfluoroalkyl-substituted tetracyclines, is an offshoot of an attempted synthesis of the hydroxytetralone 2. Some of the results obtained in the course of the research work are revealed in this article.

The reaction of the hydroxy diacid 1 with polyphosphoric acid (PPA) did not give the anticipated hydroxytetralone 2, but 3'). Consequently, methylation of the 4-OH group of 1, prior to cyclisation

📜 SIMILAR VOLUMES

N-[4-Cyano-3-(trifluoro­meth­yl)phen­yl]
N-[4-Cyano-3-(trifluoro­meth­yl)phen­yl]-3-(4-fluoro­phenyl­sulfan­yl)-2-hydr­oxy-2-methyl­propionamide
✍ Hu, Xiu-Rong ;Wang, Li-Li ;Gu, Jian-Ming 📂 Article 📅 2006 🏛 International Union of Crystallography 🌐 English ⚖ 201 KB

Single-crystal X-ray study T = 296 K Mean (C-C) = 0.004 A Disorder in main residue R factor = 0.065 wR factor = 0.175 Data-to-parameter ratio = 16.3 For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.

N-[4-Cyano-3-(trifluoro­meth­yl)phen­yl]
N-[4-Cyano-3-(trifluoro­meth­yl)phen­yl]-3-(4-fluoro­phenyl­sulfon­yl)-2-hydr­oxy-2-methyl­propionamide
✍ Hu, Xiu-Rong ;Gu, Jian-Ming 📂 Article 📅 2005 🏛 International Union of Crystallography 🌐 English ⚖ 254 KB

The structure of the title compound, C 18 H 14 F 4 N 2 O 2 S, consists of molecules that pack in a linear hydrogen-bonded chain along the c axis. This hydrogen-bonding arrangement involves the hydroxy group and one of the sulfonyl O atoms.

N-[4-Cyano-3-(trifluoro­methyl)phenyl]-3
N-[4-Cyano-3-(trifluoro­methyl)phenyl]-3-(4-fluoro­phenyl­sulfanyl)-2-hydroxy-2-methyl­propionamide chloro­form solvate
✍ Tang, Gu-Ping ;Gu, Jian-Ming 📂 Article 📅 2005 🏛 International Union of Crystallography 🌐 English ⚖ 250 KB

The title compound, C 18 H 14 F 4 N 2 O 2 SÁCHCl 3 , forms a onedimensional hydrogen-bonded chain via a single O-HÁ Á ÁN interaction; the chain runs approximately along the [110] axis. The two benzene rings are almost parallel to one another, forming a dihedral angle of 8.43 (8) .

Enthalpies of combustion of the pyridine
Enthalpies of combustion of the pyridine N-oxide derivatives: 4-methyl-, 3-cyano-, 4-cyano-, 3-hydroxy-, 2-carboxy-, 4-carboxy-, and 3-methyl-4-nitro, and of the pyridine derivatives: 2-carboxy-, and 4-carboxy-. The dissociation enthalpies of the N-O bonds
✍ Maria D.M.C. Ribeiro da Silva; M. Agostinha; R. Matos; M.Cláudia Vaz; Luı&#x 📂 Article 📅 1998 🏛 Elsevier Science 🌐 English ⚖ 155 KB

The standard pЊ s 0.1 MPa molar enthalpies of formation ⌬ H cr at T s 298.15 K were 2 4-CO HPyNO y381.2 " 1.3 136.1 " 1.2 259.5 " 5.0 2 3-Me4NO PyNO y19.5 " 3.4 106.7 " 2.0 263.4 " 7.1 2 2-CO HPy y341.0 " 1.2 98.0 " 2.3 2 4-CO HPy y348.7 " 1.6 113.9 " 4.4 2 T Ž . Comparison has been made with D N-O