Synthesis and crystal structures of 3-hydroxy-2,4-dimethyl-2H-thiophen-5-one and 3-hydroxy-4-methyl-2H-thiophen-5-one

被引：0

作者：

Nashawi, Asma ^{[1
,2
]}

Lawson, Christopher P. ^{[1
]}

Abdel-Sattar, M. Omar ^{[2
,3
]}

ter Horst, Joop H. ^{[4
]}

Coxon, Geoffrey D. ^{[1
]}

Kennedy, Alan R. ^{[5
]}

机构：

[1] Univ Strathclyde, Strathclyde Inst Pharm & Biomed Sci, 161 Cathedral St, Glasgow G4 0RE, Lanark, Scotland

[2] King Abdulaziz Univ, Dept Pharmaceut Chem, Jeddah 21589, Saudi Arabia

[3] Al Azhar Univ, Dept Chem, Cairo 11884, Egypt

[4] Univ Strathclyde, Technol & Innovat Ctr, EPSRC Future Mfg Res Hub Continuous Manufacture &, 99 George St, Glasgow G1 1RD, Lanark, Scotland

[5] Univ Strathclyde, Dept Pure & Appl Chem, Westchem, 295 Cathedral St, Glasgow G1 1XL, Lanark, Scotland

来源：

ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS | 2020年 / 76卷

关键词：

crystal structure; hydroxy-thiophenone; hydrogen bonding; DITHIOCARBONATE REARRANGEMENT; ASYMMETRIC-SYNTHESIS; ALLYL XANTHATE; THIOLACTOMYCIN;

D O I：

10.1107/S2056989020008269

中图分类号：

O7 [晶体学];

学科分类号：

0702 ; 070205 ; 0703 ; 080501 ;

摘要：

The structures of two hydroxy-thiophenone derivatives related to the antibiotic thiolactomycin are presented. These are the racemic 3-hydroxy-2,4-dimethyl-2H-thiophen-5-one, C6H8O2S, and 3-hydroxy-4-methyl-2H-thiophen-5-one, C5H6O2S. The main structural feature of both compounds is C(6) hydrogen-bonded chains formed between the OH and C=O groups. In achiral C5H6O2S, these chains propagate only by translation, corresponding to x + 1, y, z + 1. However, in contrast, for racemic C6H8O2S the hydrogen-bonded chains propagate through a -x + 3/2, y + 1/2, z operation, giving chains lying parallel to the crystallographic b-axis direction that are composed of alternate R and S enantiomers. The crystals of 3-hydroxy-4-methyl-2H-thiophen-5-one were found to be twinned by a 180 degrees rotation about the reciprocal 001 direction. In the final refinement the twin ratio refined to 0.568 (2):0.432 (2).

引用

页码：1158 / +

页数：10

共 17 条

[1] SIR92 - a program for automatic solution of crystal structures by direct methods [J].

ALTOMARE, A ;

CASCARANO, G ;

GIACOVAZZO, G ;

GUAGLIARDI, A ;

BURLA, MC ;

POLIDORI, G ;

CAMALLI, M .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1994, 27 :435-435

[2] Thiolactomycin-Based Inhibitors of Bacterial β-Ketoacyl-ACP Synthases with in Vivo Activity [J].

Bommineni, Gopal R. ;

Kapilashrami, Kanishk ;

Cummings, Jason E. ;

Lu, Yang ;

Knudson, Susan E. ;

Gu, Chendi ;

Walker, Stephen G. ;

Slayden, Richard A. ;

Tonge, Peter J. .

JOURNAL OF MEDICINAL CHEMISTRY, 2016, 59 (11) :5377-5390

[3] AN ASYMMETRIC-SYNTHESIS OF THIOTETRONIC ACIDS USING CHIRALITY TRANSFER VIA AN ALLYL XANTHATE-TO-DITHIOCARBONATE REARRANGEMENT - X-RAY CRYSTAL-STRUCTURE OF (5R)-2,5-DIHYDRO-4-HYDROXY-5-METHYL-3-PHENYL-5-PROP-1'-ENYL-2-OXOTHIOPHENE [J].

CHAMBERS, MS ;

THOMAS, EJ ;

WILLIAMS, DJ .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (16) :1228-1230

[4] Asymmetric synthesis of 5,5-disubstituted thiotetronic acids using allyl xanthate to dithiocarbonate rearrangement: Total synthesis of (5S)-thiolactomycin with revision of the absolute configuration of the natural product [J].

Chambers, MS ;

Thomas, EJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (04) :417-431

[5] Changing and challenging times for service crystallography [J].

Coles, Simon J. ;

Gale, Philip A. .

CHEMICAL SCIENCE, 2012, 3 (03) :683-689

[6] WinGX and ORTEP for Windows: an update [J].

Farrugia, Louis J. .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 2012, 45 :849-854

[7] The Cambridge Structural Database [J].

Groom, Colin R. ;

Bruno, Ian J. ;

Lightfoot, Matthew P. ;

Ward, Suzanna C. .

ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE CRYSTAL ENGINEERING AND MATERIALS, 2016, 72 :171-179

[8] Efforts towards the development of new antitubercular agents: Potential for thiolactomycin based compounds [J].

Kamal, Ahmed ;

Azeeza, Shaik ;

Malik, M. Shaheer ;

Shaik, Ahmad Ali ;

Rao, Maddamsetty V. .

JOURNAL OF PHARMACY AND PHARMACEUTICAL SCIENCES, 2008, 11 (02) :56-80

[9] Regioselective ring opening of thiomalic acid anhydrides by carbon nucleophiles. Synthesis and X-ray structure elucidation of novel thiophenone derivatives [J].

Kikionis, Stefanos ;

McKee, Vickie ;

Markopoulos, John ;

Igglessi-Markopoulou, Olga .

TETRAHEDRON, 2009, 65 (18) :3711-3716

[10] Mercury 4.0: from visualization to analysis, design and prediction [J].

Macrae, Clare F. ;

Sovago, Ioana ;

Cottrell, Simon J. ;

Galek, Peter T. A. ;

McCabe, Patrick ;

Pidcock, Elna ;

Platings, Michael ;

Shields, Greg P. ;

Stevens, Joanna S. ;

Towler, Matthew ;

Wood, Peter A. .

JOURNAL OF APPLIED CRYSTALLOGRAPHY, 2020, 53 :226-235

← 1 2 →