The preparation method of cis-conjugated enynes
A conjugated enyne and cis technology, which is applied in the field of preparation of cis conjugated enyne, can solve the problems of unsuitability for industrial production, low reaction yield, long reaction time and the like, and achieves low cost, simple and convenient reaction operation, Stable performance
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[0032] The invention provides a method for preparing a cis-conjugated enyne with a structure shown in formula (I), comprising: in the presence of a protective gas and an organic solvent, making a cis-enyne with a structure shown in formula (II) Bromine, the terminal alkyne of structure shown in formula (III), catalyzer, weakly basic compound and o-phenanthroline carry out contact reaction to prepare the cis-conjugated enyne of structure shown in formula (I),
[0033]
[0034] Among them, R 1 is H, alkyl, alkoxy, halogen or trifluoromethyl, R 2 is H, alkyl, alkoxy or halogen; the catalyst is selected from one or more of nano-copper oxide, nano-cuprous oxide and nano-cuprous iodide. Preferably, R 1 Is H, C1-C3 alkyl, C1-C3 alkoxy, halogen or trifluoromethyl, R 2 is H, C1-C6 alkyl, C1-C3 alkoxy or halogen.
[0035] In the preparation method provided by the invention, R 1 , R 2 The specific choice of can be selected in a wide range, but considering the yield of the produc...
Embodiment 1
[0045] Preparation of cis 1-fluoro-4-(4-(p-tolyl)-3-butene-1-ynyl)benzene:
[0046] Weigh 0.05mmol of shuttle-shaped nano-copper oxide (100-250nm in diameter), 0.15mmol of phenanthroline, and 2mmol of potassium carbonate into a clean and dry reaction tube, and place the reaction tube in an anhydrous and oxygen-free system. Evacuate and cycle three times with argon. Then, under argon protection, 1 mmol cis 1-(2-bromovinyl)-4-methylbenzene, 1.2 mmol 1-(4-fluoro-phenyl)acetylene and 3 mL diethylene glycol dimethyl were added successively. ether. Then stirred and refluxed at 140°C for 20h. Finally, after stopping the reaction, it was cooled to 25°C, extracted with petroleum ether (3×10 mL), and the obtained organic phase was dried over anhydrous magnesium sulfate and concentrated. Purification by column chromatography using petroleum ether as a developing agent yielded a white solid with a yield of 90% and a melting point of 72-73°C.
[0047] The characterization data is: 1 H...
Embodiment 2
[0050] Preparation of cis 1-bromo-4-(4-(p-tolyl)-3-butene-1-ynyl)benzene:
[0051] Weigh 0.025mmol of nano-copper oxide particles (particle size is 5-8nm), 0.075mmol of phenanthroline, and 1mmol of potassium carbonate into a clean and dry reaction tube, and place the reaction tube in an anhydrous and oxygen-free system. Evacuate and cycle three times with argon. Under the protection of argon, add 0.5mmol cis-1-(2-bromovinyl)-4-methylbenzene, 0.6mmol 1-(4-bromo-phenyl)acetylene and 2mL diethylene glycol dimethyl ether. Stir and reflux at 140°C for 20h. After stopping the reaction, it was cooled to 25°C, extracted with petroleum ether (3×10 mL), and the obtained organic phase was dried over anhydrous magnesium sulfate and concentrated. Using petroleum ether as a developer for column chromatography separation and purification to obtain a yellow solid, cis-1-bromo-4-(4-(p-tolyl)-3-butene-1-ynyl)benzene, with a yield of 82%. The melting point is 64-65°C.
[0052] The character...
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