四氢噻喃-4-酮
化合物
四氢噻喃-4-酮是化学式 C5H8OS的有机化合物，可用于合成像是红霉素的天然产物。[3]
| 四氢噻喃-4-酮 | |
|---|---|
| |
| 识别 | |
| CAS号 | 1072-72-6 
|
| PubChem | 66173 |
| SMILES |
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| EC编号 | 214-015-7 |
| 性质 | |
| 化学式 | C5H8OS |
| 摩尔质量 | 116.18 g·mol−1 |
| 外观 | 浅黄色固体[1] |
| 熔点 | 60–64 °C[1] |
| 溶解性 | 可溶于乙醇[2] |
| 若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。 | |
制备
编辑四氢噻喃-4-酮可以由3,3'-硫代二丙酸二甲酯狄克曼缩合反应成3-甲氧羰基四氢噻喃-4-酮，再皂化和脱羧而成：[4][5]
性质
编辑四氢噻喃-4-酮是浅黄色固体。[1]在气态下，它最稳定的结构是椅型结构。这个分子的键长分别是：C=O = 1.223(5) Å、C-S = 1.804(3) Å、C-C = 1.527(3) Å和C-H = 1.116(6) Å。[6]
参考资料
编辑- ^ 1.0 1.1 1.2 Datenblatt Tetrahydro-4H-thiopyran-4-one, 99% bei AlfaAesar, abgerufen am 2021-07-23.
- ^ Stephenson, Richard Montgomery; Malanowski, Stanisław; Ambrose, D. Handbook of the thermodynamics of organic compounds. New York: Elsevier. 1987. ISBN 978-94-009-3173-2. OCLC 610431280.
- ^ Woodward, R. B.; Logusch, E.; Nambiar, K. P.; Sakan, K.; Ward, D. E.; Au-Yeung, B. W.; Balaram, P.; Browne, L. J.; Card, P. J.; Chen, C. H. Asymmetric total synthesis of erythromcin. 1. Synthesis of an erythronolide A secoacid derivative via asymmetric induction. Journal of the American Chemical Society (American Chemical Society (ACS)). 1981, 103 (11): 3210–3213. ISSN 0002-7863. doi:10.1021/ja00401a049.
- ^ Matsuyama, Haruo; Miyazawa, Yasuyuki; Takei, Yuji; Kobayashi, Michio. Regioselective synthesis of cyclopentenones from 4-thianone. The Journal of Organic Chemistry (American Chemical Society (ACS)). 1987, 52 (9): 1703–1710. ISSN 0022-3263. doi:10.1021/jo00385a011.
- ^ Fehnel, Edward A.; Carmack, Marvin. Studies in the Thiapyran Series. The Preparation, Properties and Reactions of 1,4-Thiapyrone-1-dioxide. Journal of the American Chemical Society (American Chemical Society (ACS)). 1948, 70 (5): 1813–1817. ISSN 0002-7863. doi:10.1021/ja01185a048.
- ^ Seip, R.; Seip, H.M.; Smith, Z. Structure of gaseous 4-thiacyclohexanone studied by electron diffraction. Journal of Molecular Structure (Elsevier BV). 1976, 32 (2): 279–284. ISSN 0022-2860. doi:10.1016/0022-2860(76)85006-5.