环丙醇
化合物
环丙醇（英语：Cyclopropanol）化学式C3H6O，包含一个环丙基和一个羟基。它可以由乙基溴化镁和环氧氯丙烷的反应合成[1]，而其衍生物则能通过库林科维奇反应制备。[3]环丙醇由于三元环的张力很不稳定，易开环生成丙醛。[4][5]因此环丙醇可作为烯醇化丙醛的合成子。环丙醇还被用来在分子中引入环丙基，合成环丙基酯、磺酸酯和胺。含环丙基的化合物作为潜在抗病毒药物，[6]亦用于蛋白质运输的控制研究。[7]
| 环丙醇 | |
|---|---|
| |
| IUPAC名 Cyclopropanol | |
| 别名 | Cyclopropyl alcohol, Hydroxycyclopropane |
| 识别 | |
| CAS号 | 16545-68-9 
|
| PubChem | 123361 |
| ChemSpider | 109961 |
| SMILES |
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| 性质 | |
| 化学式 | C3H6O |
| 摩尔质量 | 58.08 g·mol−1 |
| 密度 | 0.917 g/mL[1] |
| 沸点 | 101–102 °C[2] |
| 若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。 | |
参考资料
编辑- ^ 1.0 1.1 Roberts, J. D.; Chambers, V. C. Small-Ring Compounds. VI. Cyclopropanol, Cyclopropyl Bromide and Cyclopropylamine. J. Am. Chem. Soc. 1951, 73 (7): 3176–3179. doi:10.1021/ja01151a053.
- ^ Jongejan, J. A.; Duine, J. A. Enzymatic hydrolysis of cyclopropyl acetate. A facile method for medium- and large-scale preparations of cyclopropanol. Tetrahedron Lett. 1987, 28 (24): 2767–2768. doi:10.1016/S0040-4039(00)96204-X.
- ^ Eisch, John J.; Adeosun, Adetenu A.; Gitua, John N. Mechanism of the Kulinkovich Cyclopropanol Synthesis: Transfer-Epititanation of the Alkene in Generating the Key Titanacyclopropane Intermediate. European Journal of Organic Chemistry (Wiley). 2003, 2003 (24): 4721–4727. ISSN 1434-193X. doi:10.1002/ejoc.200300588.
- ^ Magrane, J. K.; Cottle, D. L. The Reaction of Epichlorohydrin with the Grignard Reagent. J. Am. Chem. Soc. 1942, 64 (3): 484–487. doi:10.1021/ja01255a004.
- ^ Stahl, G. W.; Cottle, D. L. The Reaction of Epichlorohydrin with the Grignard Reagent. Some Derivatives of Cyclopropanol. J. Am. Chem. Soc. 1943, 65 (9): 1782–1783. doi:10.1021/ja01249a507.
- ^ WO application 2009005677,Cottell, J. J.; Link, J. O. Schroeder, S. D.; Taylor, J.; Tse, W.; Vivian, R. W.; Yang, Z.-Y.,“Antiviral compounds”,发表于2009-01-08
- ^ WO application 2009062118,Bulawa, C. E.; Devit, M.; Elbaum, D.,“Modulators of protein trafficking”,发表于2009-05-14