常用保护基试剂---2,2-二甲氧基丙烷

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【英文名称】2,2-Dimethoxypropane

【分子式】C5H12O2

【分子量】104.15

【 CA登录号】77-76-9

【缩写和别名】Acetone Dimethyl Acetal

【物理性质】有刺激性的液体，bp 83 °C，0.847 g/cm3。溶于大多数有机溶剂，可以在多种溶剂中使用。

【制备和商品】国内外化学试剂公司均有销售。

【注意事项】有刺激性的可燃液体，须在通风橱中使用。


2,2-二甲氧基丙烷常被用于制备缩醛、缩酮和烯醇醚，还可以用于羧酸的甲基化反应。它是一种十分有效的1,2-和1,3-二醇的保护基团，对碱和氧化试剂都很稳定，非常适合对糖羟基的保护。在酸性催化条件下，它还可以与烯醇硅醚发生羟醛缩合反应。

在酸的催化下，该试剂可以与醛和酮反应生成相应的缩醛和缩酮(式1)[1]。

在酸性催化条件下，该试剂可以将醛和酮转化成烯醇甲基醚。如式2和式3所示[2,3]:该反应是经过半缩醛脱水机理完成的。

该试剂可以吸收酯化反应中产生的水分子，生成丙酮和甲醇。在盐酸的催化下，该试剂与氨基酸反应生成甲基酯的盐酸盐（式4和式5)[4,5]。

该试剂是一种很好的二羟基保护基团，可以选择性地保护糖分子上的1,2-二醇（式6和式7)[6,7]和1,3-二醇（式8和式9)[8,9]结构，生成相应的五元环或六元环的缩酮。生成的缩酮保护基在碱性和中性条件下稳定，一般不受氧化剂的影响。但是，可以在酸性条件下去保护。

在催化计量酸的存在下，该试剂可以与烯醇硅醚发生羟醛缩合反应(式 10)[10]。

参考文献

1. Roeschlaub, C. A.; Samraes，P. G. J.Chem. Soc”Perkin Tram. 1 2000,2243.

2. Nussbaum, A. L.; Yuan, E.; Dincer, D.; Olivetto, E. P. J. Org. Chem. 1961,26,3925.

3. Liu, Q.; Ferreira, E. M.; Stoltz, B. M. J. Org. Chem. 2007, 72,7352.

4. Corey, E. J.; Lee, D.-H.; Sarshar, S. Tetrahedron: Asymmetry 1995, 6,3.

5.(a)Hsu, F.-L.; Hamada, A.; Booher, M. E.; Fuder, H.; Patil, P. N.; Miller, D. D. J. Med. Chem. 1980,23, 1232. (b) Rachele, J. R. 1 Org. Chem. 1963,28, 2898.

6. Chavre, S. N.; Ullapu, P. R.; Min, S.-J.; Lee, J. K.; Pae, A. N.; Kim, Y.; Cho, Y. S. Org. Lett. 2009,11,3834.

7. Chang, Y.-K.; Lo, H.-J.; Yan, T.-H. Org. Lett‘2009,11,4278.

8. Tian, G.-Q.; Kaiser, T.; Yang, J. Org. Lett. 2010,12,288.

9. Busse, H.; Hakoda, M.; Stanley, M.; Streicher, H. 1 Carbohydr. Chem. 2007, 26,159.

10. Miirata, S.; Suzuki, M.; Noyori, R. Tetrahedron 1988,44,4259.


本文摘自---现代有机合成试剂


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