六氟乙酰丙酮
化合物
六氟乙酰丙酮是一種有機化合物,化學式為CF3C(O)CH2C(O)CF3,可簡寫為hfacH。它是無色液體,可作為配體並用於金屬化學氣相沉積。它只以烯醇(CF3C(OH)=CHC(O)CF3)的形式存在,而相應的乙酰丙酮僅含85%的烯醇異構。[2]相比乙酰丙酮金屬配合物,六氟乙酰丙酮和金屬形成的配合物有較高的揮發性和路易斯酸性。由於它是強親電試劑,它在水中可以形成四醇。[3]
六氟乙酰丙酮 | |
---|---|
IUPAC名 1,1,1,5,5,5-Hexafluoro-2,4-pentanedione | |
別名 | 1,1,1,5,5,5-六氟乙酰丙酮 1,1,1,5,5,5-六氟-2,4-戊二酮 HfacH |
識別 | |
CAS號 | 1522-22-1 |
PubChem | 73706 |
ChemSpider | 21106446 |
SMILES |
|
InChI |
|
InChIKey | QAMFBRUWYYMMGJ-UHFFFAOYAR |
性質 | |
化學式 | C5H2F6O2 |
摩爾質量 | 208.06 g/mol g·mol⁻¹ |
外觀 | 無色液體 |
密度 | 1.47 g·cm−3(25 °C) |
沸點 | 70—71 °C(343—344 K)[1] |
溶解性(水) | 有機溶劑 |
危險性 | |
主要危害 | 有毒 |
若非註明,所有數據均出自標準狀態(25 ℃,100 kPa)下。 |
它最初由三氟乙酸乙酯和1,1,1-三氟丙酮的縮合反應製得。[4]它和1,2-苯二胺在三氟甲磺酸鐵的催化下於DMF中加熱反應,可以得到2-三氟甲基苯並咪唑。[5]
相關物質
六氟乙酰丙酮是乙酰丙酮兩端甲基的六個氫被氟取代的產物,即1,1,1,5,5,5-六氟乙酰丙酮,儘管根據價鍵也可形成1,1,1,3,5,5-、1,1,3,3,5,5-或1,1,1,3,3,5-取代的同分異構體,但這三種物質尚未被發現。更多氟取代的1,1,1,3,5,5,5-七氟乙酰丙酮(CAS:77968-17-3)[6](異構體未知)和八氟乙酰丙酮(CAS:87291-32-5)[7]已有文獻報道。
參考文獻
- ^ Dong Hwan Lee, Sang-Eon Park, Kyuho Cho, Younsoo Kim, Taimur Athar, Ik-Mo Lee. Highly efficient microwave-accelerated preparation of β-ketoimines. Tetrahedron Letters. 2007-11, 48 (47): 8281–8284 [2021-09-20]. doi:10.1016/j.tetlet.2007.09.143. (原始內容存檔於2018-06-13) (英語).
- ^ Jane L. Burdett; Max T. Rogers. Keto-Enol Tautomerism in β-Dicarbonyls Studied by Nuclear Magnetic Resonance Spectroscopy. I. Proton Chemical Shifts and Equilibrium Constants of Pure Compounds. J. Am. Chem. Soc. 1964, 86: 2105–2109. doi:10.1021/ja01065a003.
- ^ Aygen, S.; van Eldik, R. A Spectroscopic and Mechanistic Study of the Enolization and Diol Formation of Hexafluoroacetylacetone in the Presence of Water and Alcohol. Chem. Ber. 1989, 122 (2): 315. doi:10.1002/cber.19891220218.
- ^ Henne, Albert L.; Newman, Melvin S.; Quill, Laurence L.; Staniforth, Robert A. Alkaline condensation of fluorinated esters with esters and ketones. Journal of the American Chemical Society. 1947, 69 (7): 1819–20. doi:10.1021/ja01199a075.
- ^ Yanmei Zhou, Guanshuo Shen, Yuebo Sui, Haifeng Zhou. Fe(OTf) 3 -catalyzed practical synthesis of 2-trifluoromethylarylimidazoles from o -arylenediamines and hexafluoroacetylacetone. Tetrahedron Letters. 2016-07, 57 (30): 3396–3399 [2021-09-20]. doi:10.1016/j.tetlet.2016.06.086. (原始內容存檔於2018-07-01) (英語).
- ^ Kurykin, M. A.; German, L. S.; Knunyants, I. L. Reaction of trans-perfluoro-2-pentene with ammonia(俄文). Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1980. 12: 2827-2829. ISSN 0002-3353.
- ^ Corti, Sandra; Pennington, William T.; DesMarteau, Darryl D. Trifluoromethylation of perfluorinated diacylfluorides: synthesis of the diketone CF3C(O)CF2C(O)CF3 and of new perfluorinated diol (CF3)2C(OH)CF2C(OH)(CF3)2. Acta Chimica Slovenica, 2013. 60 (3): 556-560. ISSN 1318-0207.