Knoevenagel 冷凝反應

反應

Knoevenagel縮合反應是一種經典的有機合成反應，由 Emil Knoevenagel 在 1890 年代描述。Knoevenagel 反應是一種改良的 Aldol Condensation，在基本催化劑的作用下，醛或酮與活性氫化合物之間會產生親核加成，形成 C-C 鍵。活性氫化合物含有一個 C-H 鍵，可被基本催化劑去離子化。反應後通常會自發脫水，產生不飽和的產品。

圖 1. Knoevenagel 冷凝反應

Z, Z' (取電基) = CO₂R, COR, CHO, CN, NO₂, etc.

Knoevenagel使用伯胺和仲胺及其鹽類作為催化劑，為氨基催化劑的研究奠定了早期基礎。² 使用 Knoevenagel 冷凝的合成方法的研究仍在繼續，新的催化劑和反應活化也不斷被報導：

微波和超聲波照射反應^3-6
無溶劑條件^7,8
固相合成⁹
10,11

注意事項

請參閱安全資料表，以瞭解有關危害和安全處理實務的資訊。

材料

抱歉，發生意外錯誤。

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參考資料

1. March J. 1968. in Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, McGraw-Hill. 693697-698.

2. List B. 2010. Emil Knoevenagel and the Roots of Aminocatalysis. Angew. Chem. Int. Ed.. 49(10):1730-1734. https://doi.org/10.1002/anie.200906900

3. Vass A, Földesi A, Lóránd T. 2006. Reactions of 3-isochromanone with aromatic aldehydes?microwave assisted condensations performed on solid basic inorganic supports. Journal of Biochemical and Biophysical Methods. 69(1-2):179-187. https://doi.org/10.1016/j.jbbm.2006.03.011

4. Senguttuvan S, Hemalatha T, Nagarajan S. 2013. Microwave-Assisted Synthesis and Antimicrobial Activities of Some Indenones. Advanced Chemistry Letters. 1(2):187-191. https://doi.org/10.1166/acl.2013.1029

5. Palmisano G, Tibiletti F, Penoni A, Colombo F, Tollari S, Garella D, Tagliapietra S, Cravotto G. 2011. Ultrasound-enhanced one-pot synthesis of 3-(Het)arylmethyl-4-hydroxycoumarins in water. Ultrasonics Sonochemistry. 18(2):652-660. https://doi.org/10.1016/j.ultsonch.2010.08.009

6. Lidström P, Tierney J, Wathey B, Westman J. 2001. Microwave assisted organic synthesis?a review. Tetrahedron. 57(45):9225-9283. https://doi.org/10.1016/s0040-4020(01)00906-1

7. Ware M. 2007. DBU: An Efficient Catalyst for Knoevenagel Condensation under Solvent-free Condition.. Bull. Catal. Soc. India. 6104.

8. Pasha MA, Manjula K. 2011. Lithium hydroxide: A simple and an efficient catalyst for Knoevenagel condensation under solvent-free Grindstone method. Journal of Saudi Chemical Society. 15(3):283-286. https://doi.org/10.1016/j.jscs.2010.10.010

9. Guo G, Arvanitis EA, Pottorf RS, Player MR. 2003. Solid-Phase Synthesis of a Tyrphostin Ether Library. J. Comb. Chem.. 5(4):408-413. https://doi.org/10.1021/cc030003i

10. Pal R. Visible light induced Knoevenagel condensation: A clean and efficient protocol using aqueous fruit extract of tamarindus indica as catalyst. 2(1): https://doi.org/10.14419/ijac.v2i1.1703

11. Pal R, Sarkar T. 2014. Visible Light Induced Knoevenagel Condensation Catalyzed by Starfruit Juice of <i>Averrhoa carambola</i>. IJOC. 04(02):106-115. https://doi.org/10.4236/ijoc.2014.42012