α-羟基酮类化合物参与的反应研究进展

doi:10.6023/cjoc202203007

摘要/Abstract

α-羟基酮是一类非常重要的化合物, 不仅是许多具有生物活性的天然产物的重要结构片段, 而且作为重要的合成砌块被应用于多种具有生物活性的化合物及药物的合成中. 整理和总结了α-羟基酮类化合物参与的亲核加成反应以及环加成反应.

α-Hydroxyl ketones are an important class of compounds. They are not only the key structural fragments of many biologically active natural products, but also the important synthetic building blocks, hence α-hydroxyl ketones are employed in the synthesis of various biologically active molecules and drugs. The nucleophilic addition reactions and the cycloaddition reactions involving α-hydroxyl ketones are sorted out and summarized.

Key words: α-hydroxyl ketone, nucleophilic addition reaction, cycloaddition reaction

引用此文

王君姣, 吕瑜瑜, 尚永伟, 崔振丽, 王克虎, 黄丹凤, 胡雨来. α-羟基酮类化合物参与的反应研究进展[J]. 有机化学, 2022, 42(8): 2300-2321.

Junjiao Wang, Yuyu Lv, Yongwei Shang, Zhenli Cui, Ke-Hu Wang, Danfeng Huang, Yulai Hu. Research Progress of Reactions Participated by α-Hydroxy Ketones[J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2300-2321.

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图/表 63

图式1. 以甲基酮类化合物为底物制备α-伯羟基酮类化合物

Scheme 1. Synthesis of α-primary hydroxyketones with methyl ketones as substrates

图式2. 以甲基酮类化合物为底物制备α-伯羟基酮类化合物

Scheme 2. Synthesis of α-primary hydroxyketones with methyl ketones as substrates

图式3. 以烯烃为底物制备α-伯羟基酮类化合物

Scheme 3. Synthesis of α-primary hydroxyketones with olefins as substrates

图式4. 以醛类化合物为底物制备α-伯羟基酮类化合物

Scheme 4. Synthesis of α-primary hydroxyketones with aldehydes as substrates

图式5. 以1,2-二羟基类化合物为底物制备α-伯羟基酮类化合物

Scheme 5. Synthesis of α-primary hydroxyketones with 1,2-dihydroxy compounds as substrates

图式6. 通过氧化醇类或烯醇类化合物制备α-仲羟基酮类化合物

Scheme 6. Synthesis of α-secondary hydroxyketones from alcohols or enol compounds

图式7. 通过氧化醇类或烯醇类化合物制备α-仲羟基酮类化合物

Scheme 7. Synthesis of α-secondary hydroxyketones through oxidation of alcohols or enol compounds

图式8. 通过还原炔烃制备α-仲羟基酮类化合物

Scheme 8. Synthesis of α-secondary hydroxyketones through reduction of alkynes

图式9. 通过α-羟基酯的酮重排反应制备α-仲羟基酮类化合物

Scheme 9. Synthesis of α-secondary hydroxyketones through rearrangement reaction of α-hydroxy esters

图式10. 通过氧化羰基类化合物制备α-叔羟基酮类化合物

Scheme 10. Synthesis of α-tertiary hydroxyketones through oxidation of carbonyl compounds

图式11. 通过氧化羰基类化合物制备α-叔羟基酮类化合物

Scheme 11. Synthesis of α-tertiary hydroxyketones through oxidation of carbonyl compounds

图式12. 通过氧化羰基类化合物制备α-叔羟基酮类化合物

Scheme 12. Synthesis of α-tertiary hydroxyketones through oxidation of carbonyl compouns

图式13. 通过氧化炔基醇类化合物制备α-叔羟基类化合物

Scheme 13. Synthesis of α-tertiary hydroxyketones through oxidation of alkynyl alcohol compounds

图式14. α-羟基酮与醛的不对称aldol反应

Scheme 14. Asymmetric aldol reaction of α-hydroxyl ketones with aldehydes

图式15. α-羟基酮与醛的不对称aldol反应

Scheme 15. Asymmetric aldol reaction of α-hydroxyl ketones with aldehydes

图式16. α-羟基酮与醛的不对称aldol反应

Scheme 16. Asymmetric aldol reaction of α-hydroxyl ketones with aldehydes

图式17. α-羟基酮与乙醛酸乙酯的不对称aldol反应

Scheme 17. Cycloaddition reaction of α-hydroxyl ketones with ethyl glyoxylates

图式18. α-羟基酮与亚胺的不对称Mannich反应

Scheme 18. Asymmetric Mannich reaction of α-hydroxyl ketones with imines

图式19. α-羟基酮与亚胺的不对称Mannich反应

Scheme 19. Asymmetric Mannich reaction of α-hydroxyl ketones with imines

图式20. α-羟基酮与靛红亚胺的不对称Mannich反应

Scheme 20. Asymmetric Mannich reaction of α-hydroxyl ketones with indigo imines

图式21. α-羟基酮与N-芳基甘氨酸酯的交叉脱氢偶联反应

Scheme 21. Cross dehydrogenation coupling reaction of α-hydroxyl ketones with N-arylglycine esters

图式22. α-羟基酮与N-芳基甘氨酸酯的交叉脱氢偶联反应

Scheme 22. Cross dehydrogenation coupling reaction of α-hydroxyl ketones with N-arylglycine esters

图式23. α-羟基酮与硝基烯烃的不对称Michael反应

Scheme 23. Asymmetric Michael reaction of α-hydroxyl ketones with nitroolefins

图式24. α-羟基酮与硝基烯烃的不对称Michael反应

Scheme 24. Asymmetric Michael reaction of α-hydroxyl ketones with nitroolefins

图式25. α-羟基酮与烯烃衍生物的不对称Michael反应

Scheme 25. Asymmetric Michael reaction of α-hydroxyl ketones with olefins

图式26. α-羟基茚二酮与烯烃衍生物的不对称Michael反应

Scheme 26. Asymmetric Michael reaction of α-hydroxy indanones with olefins

图式27. α-羟基酮与对亚甲基苯醌的不对称Michael反应

Scheme 27. Asymmetric Michael reaction of α-hydroxyl ketones with p-methylene benzoquinones

图式28. α-羟基酮与氰胺的环加成反应

Scheme 28. Cycloaddition reaction of α-hydroxyl ketones with cyanamide

图式29. α-羟基酮与氰胺的环加成反应

Scheme 29. Cycloaddition reaction of α-hydroxyl ketones with cyanamide

图式30. α-羟基酮与α-氰基酰胺的环加成反应

Scheme 30. Cycloaddition reaction of α-hydroxyl ketones with α-cyanamides

图式31. α-羟基酮与腈类的环加成反应

Scheme 31. Cycloaddition reaction of α-hydroxyl ketones with nitriles

图式32. α-羟基酮与腈类的环加成反应

Scheme 32. Cycloaddition reaction of α-hydroxyl ketones with nitriles

图式33. α-羟基酮与腈类的环加成反应

Scheme 33. Cycloaddition reactions of α-hydroxyl ketones with nitriles

图式34. α-羟基酮与硫氰酸钾的环加成反应

Scheme 34. Cycloaddition reaction of α-hydroxyl ketones with potassium thiocyanate

图式35. α-羟基酮与异氰酸酯的环加成反应

Scheme 35. Cycloaddition reaction of α-hydroxyl ketones with isocyanates

图式36. α-羟基酮与异氰酸酯的环加成反应

Scheme 36. Cycloaddition reaction of α-hydroxyl ketones with isocyanates

图式37. α-羟基酮与炔烃的环加成反应

Scheme 37. Cycloaddition reaction of α-hydroxyl ketones with alkynes

图式38. α-羟基酮与炔烃的环加成反应

Scheme 38. Cycloaddition reaction of α-hydroxyl ketones with alkynes

图式39. α-羟基酮与炔烃的环加成反应

Scheme 39. Cycloaddition reaction of α-hydroxyl ketones with alkynes

图式40. α-羟基酮与硫醇酯的环加成反应

Scheme 40. Cycloaddition reaction of α-hydroxyl ketones with Mercaptan esters

图式41. α-羟基酮与二胺类化合物的环加成反应

Scheme 41. Cycloaddition reaction of α-hydroxyl ketones with diamine compounds

图式42. α-羟基酮与邻苯二胺类化合物的环加成反应

Scheme 42. Cycloaddition reaction of α-hydroxyl ketones with O-phenylenediamine compounds

图式43. α-羟基酮与邻苯二胺类化合物的环加成反应

Scheme 43. Cycloaddition reaction of α-hydroxyl ketones with O-phenylenediamine compounds

图式44. α-羟基酮与2-乙烯酮的环加成反应

Scheme 44. Cycloaddition reaction of α-hydroxyl ketones with 2-vinyl ketone

图式45. α-羟基酮与烯酮的环加成反应

Scheme 45. Cycloaddition reaction of α-hydroxyl ketones with ketene derivatives

图式46. α-羟基酮与烯酮的环加成反应

Scheme 46. Cycloaddition reaction of α-hydroxyl ketones with ketene derivatives

图式47. α-羟基酮与酯类的环加成反应

Scheme 47. Cycloaddition reaction of α-hydroxyl ketones with esters

图式48. 3-羟基吲哚酮与α,β-不饱和酯的环加成反应

Scheme 48. Cycloaddition reaction of 3-hydroxyindole ketones with α,β-unsaturated esters

图式49. α-羟基酮与β,γ-不饱和-α-酮酯的环加成反应

Scheme 49. Cycloaddition reaction of α-hydroxyl ketones with β,γ-unsaturated-α-ketone esters

图式50. α-羟基-1-茚酮与α,β-不饱和酯的环加成反应

Scheme 50. Cycloaddition reaction of α-hydroxy-1-windanones with α,β-unsaturated esters

图式51. α-羟基-1-茚酮与β,γ-不饱和α-酮酰胺的环加成反应

Scheme 51. Cycloaddition reaction of α-hydroxy-1-indanones with β,γ-unsaturated α-ketoamides

图式52. α-羟基-1-茚酮与邻酯基查尔酮的环加成反应

Scheme 52. Cycloaddition reaction of α-hydroxy-1-indanones with o-ester chalcones

图式53. α-羟基芳基酮与β,γ-不饱和α-酮酰胺的环加成反应

Scheme 53. Cycloaddition reaction of α-hydroxyl ketones with β,γ-unsaturated α-ketoamides

图式54. α-羟基芳基酮与β,γ-不饱和α-酮酰胺的环加成反应

Scheme 54. Cycloaddition reaction of α-hydroxyl ketones with β,γ-unsaturated α-ketoamides

图式55. α-羟基酮与间苯二酚衍生物的环加成反应

Scheme 55. Cycloaddition reaction of α-hydroxyl ketones with resorcinol derivatives

图式56. α-羟基酮与邻羟基苯乙酮衍生物的环加成反应

Scheme 56. Cycloaddition reaction of α-hydroxyl ketones with O-hydroxyacetophenone derivatives

图式57. α-羟基酮与乙酸铵的环加成反应

Scheme 57. Cycloaddition reaction of α-hydroxyl ketones with ammonium acetate

图式58. α-羟基酮与磺酰胺的环加成反应

Scheme 58. Cycloaddition reaction of α-hydroxyl ketones with ammonium sulfonamides

图式59. α-羟基酮参与的三组分环加成反应

Scheme 59. Three tomponent cycloaddition reaction involving α-hydroxyl ketones

图式60. α-羟基-1-茚酮与亚烷基氮内酯的环加成反应

Scheme 60. Cycloaddition reaction of α-hydroxy-1-indanones with alkylene nitrogen lactones

图式61. α-羟基酮与炔烃的氧化偶联反应

Scheme 61. Oxidative coupling reaction of α-hydroxyl ketones with alkynes

图式62. α-羟基酮与环丙烷的交叉偶联反应

Scheme 62. Cross coupling reaction of α-hydroxyl ketones with cyclopropanes

图式63. α-羟基酮的重排反应

Scheme 63. Rearrangement of α-hydroxyl ketones

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