Process for producing 1,3-enyne compounds

Abstract

The invention discloses a method for preparing a 1, 3-eneyne compound. The method is characterized in that at the room temperature and under the protection of nitrogen, an alkenyl iodine compound, substituent end alkyne, catalyst, cesium carbonate and a ligand are mixed in the mol proportion of 1-1.5:1:1-3:0.1-0.15:0.1-0.3; then a mixture is put into the solvent of toluene and dimethylbenzene to react for 36 to 72 hours with the temperature increased to 110 DEG C; and the 1, 3-eneyne compound is obtained after separating and purifying. Compared with the prior art, the invention has simple synthesis method, easily obtained raw materials, low reaction cost, high yield and no environmental pollution, and a generated product is kept with a double-bond configuration.

Description

technical field [0001] The invention relates to the technical field of organic chemical synthesis, in particular to a preparation method of 1,3-enyne compounds. Background technique [0002] 1,3-enyne compounds (1,3-enyne) are an important class of unsaturated compounds, which are important structural units and synthetic building blocks of many natural products and pharmaceutical intermediates. At present, the synthesis of 1,3-enynes has been reported in the literature, for example: Literature (1) Yue, D.; Yao, T.; Larock, R.C.J.Org.Chem.2006, 71, 62; (2) Mino, T.; Shirae, Y.; Saito, T.; Sakamoto, M.; Fujita, T.J.Org.Chem.2006, 71, 9499; (3) Silva, S.; Sylla, B.; Suzenet, F. ; Tatibouet, A.; Pauter, A.P.; Rollin, P. Org. Lett. 2008, 10, 853.; , G.; Hoefsloot, H.C.J.Chem.Eur.J.2008, 14, 2857. (5) Yin, L.; Liebscher, J.Chem.Rev.2007, 107, 133. (6) Chinchilla, R.; Najera , C.Chem..Rev.2007,107,874. The synthetic methods reported in the above literatures all use expensive met...

AI Technical Summary

Problems solved by technology

At present, the synthesis of 1,3-enynes has been reported in the literature, for example: Literature (1) Yue, D.; Yao, T.; Larock, R.C.J.Org.Chem.2006, 71, 62; (2) Mino, T.; Shirae, Y.; Saito, T.; Sakamoto, M.; Fujita, T.J.Org.Chem.2006, 71, 9499; (3) Silva, S.; Sylla, B.; Suzenet, F. ; Tatibouet, A.; Pauter, A.P.; Rollin, P. Org. Lett. 2008, 10, 853.; , G.; Hoefsloot, H.C.J.Chem.Eur.J.2008, 14, 2857. (5) Yin, L.; Liebscher, J.Chem.Rev.2007, 107, 133. (6) Chinchilla, R.; Najera , C.Chem..Rev.2007,107,874. The synthetic methods reported in the above literatures all use expensive metal catalysts such as palladium, copper, etc., which not only increases the cost of the reaction, but also metals such as palladium have certain toxicity and are easily cause environmental pollution

Images