羟基醛

在有机化学中，羟基醛（英文：Aldol，简称：羟醛）是一种由3-羟基酮或3-羟基醛组成的结构片段。由3-羟基酮构成的羟基酮称为β-羟基酮，由3-羟基醛构成的羟醛称为β-羟基醛。术语“羟醛”一般可指3-羟基丁醛。^[1]^[2]

合成与反应

羟醛通常是羟醛加成的产物，即两个醛通过缩合反应的产物。^[1]醛醇的立体选择性合成是不对称合成的一个活跃领域。

羟醛可发生的化学反应主要为一类反应，即脱水反应：

RC(O)CH ₂ CH(OH)R' → RC(O)CH=CHR' + H ₂ O

应用

当两个醛分子反应形成羟醛（β-羟基醛）时，羟醛通常会因不稳定产生二级化合物。^[1]二级化合物可以是二醇、不饱和醛或不饱和醇。^[1]羟醛中的3-羟基丁醛是喹哪啶的前体化合物，喹哪啶则是染料喹啉黄SS的前体。^[1]

羟醛还可用作合成天然产物和药物的中间体。^[3]^[4]用于治疗流感的抗病毒药物奥司他韦的合成路线，涉及羟醛反应。^[5]

羟醛的结构片段通常存在于天然产物聚酮化合物中，其可用于制造抗生素。^[3]

羟基新戊醛是相对稳定的羟醛，这种化合物较为罕见。^[6]

参考

^ ^1.0 ^1.1 ^1.2 ^1.3 ^1.4 Kohlpainter, Christian; Schulte, Markus; Falbe, Jürgen; Lappe, Peter; Weber, Jürgen; Frey, Guido D. Aldehydes, Aliphatic. Ullmann's Encyclopedia of Industrial Chemistry. 15 January 2013, (7) [1 April 2023]. ISBN 9783527303854. doi:10.1002/14356007.a01_321.pub3. （原始内容存档于2023-04-01） –通过Wiley Online Library.
^ PubChem. CID 21282929. National Center for Biotechnology Information. [2023-04-15]. （原始内容存档于2023-04-16）（英语）.
^ ^3.0 ^3.1 Schetter, Bernd; Mahrwald, Rainer. Modern aldol methods for the total synthesis of polyketides. Angewandte Chemie International Edition. 2006, 45 (45): 7506–25. PMID 17103481. doi:10.1002/anie.200602780.
^ Ghosh, Arun K.; Dawson, Zachary L. Synthesis of Bioactive Natural Products by Asymmetric syn- and anti-Aldol Reactions. Synthesis. 2009, 2009 (17): 2992–3002. PMC 6233898 . PMID 30443084. doi:10.1055/s-0029-1216941 –通过Thieme.
^ Ko, Ji S.; Keum, Ji E.; Ko, Soo Y. A synthesis of oseltamivir (Tamiflu) starting from D-mannitol. J Org Chem. 15 October 2010, 75 (20): 7006–9 [2023-06-04]. PMID 20866058. doi:10.1021/jo101517g. （原始内容存档于2023-04-20） –通过National Library Of Medicine.
^ Zhang, Yanping; Mu, Hongliang; Pan, Li; Wang, Xuling; Li, Yuesheng. Robust Bulky [P,O] Neutral Nickel Catalysts for Copolymerization of Ethylene with Polar Vinyl Monomers. ACS Catal. 21 May 2018, 8 (7): 5963–5976. doi:10.1021/acscatal.8b01088 –通过ACS Publications.

[:0-1] 1.0 ^1.1 ^1.2 ^1.3 ^1.4 Kohlpainter, Christian; Schulte, Markus; Falbe, Jürgen; Lappe, Peter; Weber, Jürgen; Frey, Guido D. Aldehydes, Aliphatic. Ullmann's Encyclopedia of Industrial Chemistry. 15 January 2013, (7) [1 April 2023]. ISBN 9783527303854. doi:10.1002/14356007.a01_321.pub3. （原始内容存档于2023-04-01） –通过Wiley Online Library.

[2] PubChem. CID 21282929. National Center for Biotechnology Information. [2023-04-15]. （原始内容存档于2023-04-16）（英语）.

[:1-3] 3.0 ^3.1 Schetter, Bernd; Mahrwald, Rainer. Modern aldol methods for the total synthesis of polyketides. Angewandte Chemie International Edition. 2006, 45 (45): 7506–25. PMID 17103481. doi:10.1002/anie.200602780.

[4] Ghosh, Arun K.; Dawson, Zachary L. Synthesis of Bioactive Natural Products by Asymmetric syn- and anti-Aldol Reactions. Synthesis. 2009, 2009 (17): 2992–3002. PMC 6233898 . PMID 30443084. doi:10.1055/s-0029-1216941 –通过Thieme.

[5] Ko, Ji S.; Keum, Ji E.; Ko, Soo Y. A synthesis of oseltamivir (Tamiflu) starting from D-mannitol. J Org Chem. 15 October 2010, 75 (20): 7006–9 [2023-06-04]. PMID 20866058. doi:10.1021/jo101517g. （原始内容存档于2023-04-20） –通过National Library Of Medicine.

[6] Zhang, Yanping; Mu, Hongliang; Pan, Li; Wang, Xuling; Li, Yuesheng. Robust Bulky [P,O] Neutral Nickel Catalysts for Copolymerization of Ethylene with Polar Vinyl Monomers. ACS Catal. 21 May 2018, 8 (7): 5963–5976. doi:10.1021/acscatal.8b01088 –通过ACS Publications.

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