The method for synthesizing 2-thiabicyclo[3.1.0]-3-hexene-6-carboxylate
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A technology for formate ester and hexene, applied in the field of ester synthesis, can solve the problems of difficulty in separation, large amount of catalyst, reaction yield to be improved, etc.
Inactive Publication Date: 2015-09-09
DALIAN UNIV
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The inventor of this patent once reported that by optimizing the structure of the Cu compound, the cyclopropanation reaction of thiophene and diazoacetate was catalyzed by the Cu compound, and a yield of 30% was obtained (Li Zhengning, Wang Hongli, Shan Fengjun, Jiang Lan, Su Haibo , Chinese patent, a method for synthesizing 4-thiabicyclo[3.1.0]-2-hexene-6-carboxylate, application number, 200910188322.2, 2009.10.29), but the amount of catalyst used is large and the separation is difficult , the reaction yield still needs to be improved
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Embodiment 1
[0052] Embodiment 1: the CuCl / Al that adds in the there-necked flask that dropping funnel, reflux condensation tube are housed 2 o 3 Catalyst (0.150g, (0.002mol CuCl+0.001mol NiBr 2 ) / g Al 2 o 3 , prepared by heat dispersion method), then add thiophene (37.5mL), stir, heat to reflux temperature, drop in thiophene (10mL) solution of ethyl diazoacetate (1.71g), react for 60min, filter the catalyst and evaporate the excess solvents and thiophenes. The residue was weighed, and the product content was analyzed by the internal standard method, and the yield was 32.3%.
Embodiment 2
[0053] Embodiment 2: Add thiophene (34mL) to the there-necked flask that dropping funnel, reflux condenser are housed, Cu / HY catalyst (0.040g, 0.005mol Cu(NO 3 ) 2 / g HY, prepared by equal-volume impregnation method, calcination temperature 400°C), heated, and dripped a solution of ethyl diazoacetate in dichloroethane (8.0mL, containing 2.28g of ethyl diazoacetate) under stirring, After about 60 minutes of dripping, the reaction was carried out until the gas was exhausted, the catalyst was removed by filtration, and the solvent and excess thiophene were distilled off. The residue was weighed, and the product content was analyzed by the internal standard method, and the yield was 22.5%.
Embodiment 3
[0054]Embodiment 3: add Cu / 13X catalyst (0.250g, (0.001mol Cu(NO 3 ) 2 +0.0005mol AgNO 3 ) / g 13X, 500°C), then add thiophene (12mL), heat to 80°C under stirring, drop in the thiophene solution of butyl diazoacetate (25g, containing 3.55g of butyl diazoacetate), and react for 24min, The catalyst was removed by filtration, and the solvent and excess thiophene were distilled off. After separation by column chromatography, 1.687 g of the product of structural formula 1 (R=Bu) was obtained, with a yield of 34.1%.
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Abstract
The invention discloses a method for synthesizing 2-thiabicyclo[3.1.0]-3-hexenyl-6-formate. The method comprises the following steps: adding diazo acetate or a diazo acetate solution to a mixture of a catalyst, thiophene and a solvent in a dropwise mode under stirring at 0-140DEG C, and reacting until a gas is completely discharged; filtering to remove the catalyst, and distilling off excel thiophene and solvent; and finally separating to obtain 2-thiabicyclo[3.1.0]-3-hexenyl-6-formate, wherein the catalyst is a supported Cu catalyst which comprises a Cu active component, an assistant and a carrier. According to the invention, the cheap supported Cu catalyst is adopted, application amounts of reactants are clarified, preparation conditions of the catalyst are regulated, and the assistant is added, so performances of the catalyst are changed, and the reaction selectivity is improved; and the catalyst has the advantages of easy preparation and low cost, cyclopropanation reaction conditions are mild, the reaction selectivity and the product yield are high, and the catalyst is easy to separate after the reaction. The method is suitable for massive synthesis of 2-thiabicyclo[3.1.0]-3-hexenyl-6-formate.
Description
technical field [0001] The present invention relates to a method for synthesizing esters, more specifically, a method for synthesizing 2-thiabicyclo[3.1.0]-3-hexene-6-carboxylate (structural formula 1). Background technique [0002] The World Health Organization estimates that 1% of people worldwide suffer from schizophrenia with symptoms such as hallucinations, delusions, movement disorders, social withdrawal and cognitive deficits. At present, most anti-schizophrenia drugs exert their curative effect by reducing the level of neurotransmitter dopamine in the brain (such as chlorpromazine, haloperidol, etc.), but there are side effects such as extrapyramidal movement disorders. Others exert curative effect by inhibiting the combination of D2 receptor (such as 5-hydroxytryptamine 2A receptor, 5-HT2A) and other receptors, but there are side effects such as weight gain, prolactin and blood sugar level increase. Thus, safer antipsychotic drugs are urgently needed. [0003] Rec...
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