羥基醛

在有機化學中，羥基醛（英文：Aldol，簡稱：羥醛）是一種由3-羥基酮或3-羥基醛組成的結構片段。由3-羥基酮構成的羥基酮稱為β-羥基酮，由3-羥基醛構成的羥醛稱為β-羥基醛。術語「羥醛」一般可指3-羥基丁醛。^[1]^[2]

合成與反應

羥醛通常是羥醛加成的產物，即兩個醛通過縮合反應的產物。^[1]醛醇的立體選擇性合成是不對稱合成的一個活躍領域。

羥醛可發生的化學反應主要為一類反應，即脫水反應：

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

應用

當兩個醛分子反應形成羥醛（β-羥基醛）時，羥醛通常會因不穩定產生二級化合物。^[1]二級化合物可以是二醇、不飽和醛或不飽和醇。^[1]羥醛中的3-羥基丁醛是喹哪啶的前體化合物，喹哪啶則是染料喹啉黃SS的前體。^[1]

羥醛還可用作合成天然產物和藥物的中間體。^[3]^[4]用於治療流感的抗病毒藥物奧司他韋的合成路線，涉及羥醛反應。^[5]

羥醛的結構片段通常存在於天然產物聚酮化合物中，其可用於製造抗生素。^[3]

羥基新戊醛是相對穩定的羥醛，這種化合物較為罕見。^[6]

參考

^ ^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. （原始內容存檔於2023-04-01） –透過Wiley Online Library.
^ PubChem. CID 21282929. National Center for Biotechnology Information. [2023-04-15]. （原始內容存檔於2023-04-16）（英語）.
^ ^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 –透過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. （原始內容存檔於2023-04-20） –透過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 –透過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. （原始內容存檔於2023-04-01） –透過Wiley Online Library.

[2] PubChem. CID 21282929. National Center for Biotechnology Information. [2023-04-15]. （原始內容存檔於2023-04-16）（英語）.

[: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 –透過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. （原始內容存檔於2023-04-20） –透過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 –透過ACS Publications.

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