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).
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页码：1158 / +
页数：10
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