呫吨-2-酚

呫吨-2-酚
识别
CAS号	30414-78-9
性质
化学式	C13H10O2
摩尔质量	198.22 g·mol−1
外观	白色固体
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

呫吨-2-酚是一种有机化合物，化学式为C₁₃H₁₀O₂，它是呫吨醇的同分异构体之一。

合成

呫吨-2-酚可以2,5-二羟基苯甲醛和2-环己烯酮为原料反应制得。反应的第一步先生成4-羟基-2,3,4,4a-四氢呫吨酮，第二步是用硼氢化钠将其还原为2,3,4,4a-四氢呫吨-1,7-二酚，第三步是将得到的二酚和三氯化铁六水合物研磨，再用乙酸乙酯萃取得到。^[1]

反应以三氟甲磺酸钪为催化剂，在氯苯中于180 °C反应，可一步得到呫吨-2-酚。^[2]

在十钨二钒磷酸的季铵盐催化下，它也可由30%过氧化氢在乙腈-叔丁醇混合溶剂中氧化呫吨得到，副产物为少量的呫吨醇和呫吨酮。^[3]以一种吡啶亚胺螯合的铁配合物为催化剂，得到的主产物则是呫吨酮。^[4]

反应

在碳量子点催化下，它可以被过氧化叔丁醇氧化为2-羟基呫吨酮。^[5]在甲磺酸、四丁基氟硼酸铵存在下，于1,2-二氯乙烷中通电，它和取代芳烃（如苯甲醚）反应，可以生成9-芳基呫吨-2-酚。^[6]

参考文献

^ ^1.0 ^1.1 Hülya Sahin, Martin Nieger, Stefan Bräse. Probing the Oxidation of Functionalized (Hexahydro)xanthenols. European Journal of Organic Chemistry. 2009-11, 2009 (32): 5576–5586 [2022-10-19]. doi:10.1002/ejoc.200900635 （英语）.
^ Esther Böβ, Tim Hillringhaus, Jacqueline Nitsch, Martin Klussmann. Lewis acid-catalysed one pot synthesis of substituted xanthenes. Organic & Biomolecular Chemistry. 2011, 9 (6): 1744 [2022-10-19]. ISSN 1477-0520. doi:10.1039/c0ob00954g （英语）.
^ Keigo Kamata, Taiyo Yamaura, Noritaka Mizuno. Chemo- and Regioselective Direct Hydroxylation of Arenes with Hydrogen Peroxide Catalyzed by a Divanadium-Substituted Phosphotungstate. Angewandte Chemie International Edition. 2012-07-16, 51 (29): 7275–7278 [2022-10-19]. doi:10.1002/anie.201201605. （原始内容存档于2022-10-19）（英语）.
^ Barbara Ticconi, Giorgio Capocasa, Andrea Cerrato, Stefano Di Stefano, Andrea Lapi, Beatrice Marincioni, Giorgio Olivo, Osvaldo Lanzalunga. Insight into the chemoselective aromatic vs. side-chain hydroxylation of alkylaromatics with H 2 O 2 catalyzed by a non-heme imine-based iron complex. Catalysis Science & Technology. 2021, 11 (1): 171–178 [2022-10-19]. ISSN 2044-4753. doi:10.1039/D0CY01868F （英语）.
^ Daisy Sarma, Biju Majumdar, Tridib K. Sarma. Carboxyl-Functionalized Carbon Dots as Competent Visible Light Photocatalysts for Aerobic Oxygenation of Alkyl Benzenes: Role of Surface Functionality. ACS Sustainable Chemistry & Engineering. 2018-12-03, 6 (12): 16573–16585 [2022-10-19]. ISSN 2168-0485. doi:10.1021/acssuschemeng.8b03811. （原始内容存档于2022-10-21）（英语）.
^ Hui Gao, Xinyu Chen, Pei-Long Wang, Meng-Meng Shi, Ling-Long Shang, Heng-Yi Guo, Hongji Li, Pinhua Li. Electrochemical benzylic C–H arylation of xanthenes and thioxanthenes without a catalyst and oxidant. Organic Chemistry Frontiers. 2022, 9 (7): 1911–1916 [2022-10-19]. ISSN 2052-4129. doi:10.1039/D1QO01925B （英语）.

[Sahin-1] 1.0 ^1.1 Hülya Sahin, Martin Nieger, Stefan Bräse. Probing the Oxidation of Functionalized (Hexahydro)xanthenols. European Journal of Organic Chemistry. 2009-11, 2009 (32): 5576–5586 [2022-10-19]. doi:10.1002/ejoc.200900635 （英语）.

[2] Esther Böβ, Tim Hillringhaus, Jacqueline Nitsch, Martin Klussmann. Lewis acid-catalysed one pot synthesis of substituted xanthenes. Organic & Biomolecular Chemistry. 2011, 9 (6): 1744 [2022-10-19]. ISSN 1477-0520. doi:10.1039/c0ob00954g （英语）.

[3] Keigo Kamata, Taiyo Yamaura, Noritaka Mizuno. Chemo- and Regioselective Direct Hydroxylation of Arenes with Hydrogen Peroxide Catalyzed by a Divanadium-Substituted Phosphotungstate. Angewandte Chemie International Edition. 2012-07-16, 51 (29): 7275–7278 [2022-10-19]. doi:10.1002/anie.201201605. （原始内容存档于2022-10-19）（英语）.

[4] Barbara Ticconi, Giorgio Capocasa, Andrea Cerrato, Stefano Di Stefano, Andrea Lapi, Beatrice Marincioni, Giorgio Olivo, Osvaldo Lanzalunga. Insight into the chemoselective aromatic vs. side-chain hydroxylation of alkylaromatics with H 2 O 2 catalyzed by a non-heme imine-based iron complex. Catalysis Science & Technology. 2021, 11 (1): 171–178 [2022-10-19]. ISSN 2044-4753. doi:10.1039/D0CY01868F （英语）.

[5] Daisy Sarma, Biju Majumdar, Tridib K. Sarma. Carboxyl-Functionalized Carbon Dots as Competent Visible Light Photocatalysts for Aerobic Oxygenation of Alkyl Benzenes: Role of Surface Functionality. ACS Sustainable Chemistry & Engineering. 2018-12-03, 6 (12): 16573–16585 [2022-10-19]. ISSN 2168-0485. doi:10.1021/acssuschemeng.8b03811. （原始内容存档于2022-10-21）（英语）.

[6] Hui Gao, Xinyu Chen, Pei-Long Wang, Meng-Meng Shi, Ling-Long Shang, Heng-Yi Guo, Hongji Li, Pinhua Li. Electrochemical benzylic C–H arylation of xanthenes and thioxanthenes without a catalyst and oxidant. Organic Chemistry Frontiers. 2022, 9 (7): 1911–1916 [2022-10-19]. ISSN 2052-4129. doi:10.1039/D1QO01925B （英语）.

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