A kind of anti-marine vibrio monoterpene derivative and its preparation method and application
A technology of marine vibrio and derivatives, applied in the field of monoterpene derivatives, can solve the problems of bacterial resistance to drugs, achieve strong inhibitory activity, low synthesis cost, and easy control of conditions
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Embodiment 1
[0024] Example 1: Synthesis of 3-hydroxy-3,7-dimethyloctanoic acid methyl ester (hereinafter referred to as compound 1)
[0025] Step 1: Reformatsky reaction
[0026]
[0027] Dissolve 3.27g (50mmol) of Zn powder in dry 50mL THF solution, and heat to reflux. Dissolve 3.77mL (25mmol) methylheptenone and 4.83mL (50mmol) methyl bromoacetate in dry 50mL THF solution, slowly add dropwise to the refluxing THF solution of suspended zinc powder, and continue the reflux reaction, Until the color of the zinc powder turns from gray to brown, the reaction solution turns green (about 2h). After the reaction, the reaction solution was cooled to room temperature, and the reaction was extracted with 10% acetic acid, the solution turned yellow and transparent, and the zinc powder was dissolved. The reaction solution was diluted with ethyl acetate, the aqueous layer was extracted twice with ethyl acetate, 50 mL each time, the organic layers were combined, anhydrous MgSO 4 Dry, concentrate...
Embodiment 2
[0031] Example 2: Synthesis of ethyl 3-hydroxy-3,7-dimethyloctanoate (hereinafter referred to as compound 2)
[0032] Step 1: Reformatsky reaction
[0033]
[0034] Dissolve 1.47g (22.5mmol) of Zn powder in dry 50mL THF solution, and heat to reflux. Dissolve 1.89g (15mmol) methylheptenone and 3.76g (22.5mmol) ethyl bromoacetate in dry 20mL THF solution, slowly add dropwise to the refluxing THF solution of suspended zinc powder, and continue the reflux reaction , until the color of the zinc powder turns from gray to brown, and the reaction solution turns green (about 2h). After the reaction, the reaction solution was cooled to room temperature, and the reaction was extracted with 100 mL of 10% AcOH, the solution turned yellow and transparent, and the zinc powder was dissolved. The reaction solution was diluted with ethyl acetate, the aqueous layer was extracted twice with EtOAc, 100 mL each time, the organic layers were combined, anhydrous MgSO 4 It was dried, concentrate...
Embodiment 3
[0038] Example 3: Synthesis of ethyl 3-hydroxyl-3,7-dimethyloctanoic anhydride (hereinafter referred to as compound 3)
[0039] Step 1: Allylic Oxidation Reaction
[0040]
[0041] Dissolve 31.04g (144.8mmol) of compound 5 in 250mL CH 2 Cl 2 In the solution, 1.61g (14.5mmol) of SeO was added dropwise at room temperature 2 and 41.6 mL (290 mmol) of tert-butyl hydroperoxide in 50 mL of CH 2 Cl 2 The solution was stirred at room temperature for 12h. After the reaction, add 100mL10% NaOH solution to wash, 100mL distilled water to wash, anhydrous Na 2 SO 4 Drying, concentrated silica gel column chromatography, elution with ethyl acetate and petroleum ether (the volume ratio of the two is 1:7) gave 620.91 g of compound 620.91 g as a colorless oil, with a yield of 80.8%. Rf0.2 (ethyl acetate: petroleum ether, 1:3 (v / v)). Compound 6: 1 H NMR (500MHz, CDCl 3 )δ5.39-5.36(t,J=6.7Hz,1H,CH 2 C H =),4.18-4.14(q,2H,OC H 2 CH 3 ),3.97(s,2H,C H 2 OH),2.50(d,J=15.6Hz,1H,C H...
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