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3-styyl-2-cyclonene compound and preparation methods thereof
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A technology of cyclohexenones and styryls, which is applied in the field of 3-styryl-2-cyclohexenones and their preparation, can solve problems such as constraints and synthesis restrictions, and achieve rapid reaction and easy operation , design reasonable effect
Inactive Publication Date: 2010-06-16
ZHEJIANG UNIV
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However, due to the structural specificity of its functional derivatives, its synthesis is greatly limited. For example, the synthesis of 4-substituted derivatives of 2-cyclohexenones needs to introduce substituents in advance before ring closure, at least through Only 4-5 steps of chemical reaction can be completed, and if the starting material molecule has carbonyl, cyano or other functional groups, the synthesis of such compounds under alkaline conditions will be restricted
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Embodiment 1
[0018] Example 1: Preparation of (E)-3-(2,3-dimethoxystyryl)-5-phenyl-5-methylcarboxylate-2-cyclohexenone
[0019] 3-Methyl-5-phenyl-5-methylcarboxylate-2-cyclohexenone (31.7mg, 0.13mmol), bismuth trichloride (4mg, 0.013mmol), 2,3-dimethoxy Base benzaldehyde (86.3mg, 0.52mmol) is mixed, this mixed solution is reacted at power 600W, finishes reaction after 1 hour, and reaction mixture is through column chromatography (silica gel column; Developing agent: sherwood oil: ethyl acetate=5 : 1; Rf=0.2) separation and purification to obtain 41.8 mg of the target compound (yield 82%). 1 H NMR (400MHz, CDCl 3 ): δ2.95(d, J=13Hz, 1H), 3.07(d, J=13Hz, 1H), 3.30(d, J=13Hz, 1H), 3.58(d, J=13Hz, 1H), 3.64( s, 3H), 3.87(s, 3H), 6.09(s, 1H), 6.91(t, J=21Hz, 2H), 7.05(t, J=13Hz, 1H), 7.18(d, J=6Hz, 1H ), 7.30(t, J=13Hz, 1H), 7.37(t, J=12Hz, 2H), 7.41(d, J=6Hz, 2H), 7.50(d, J=13Hz, 1H); 13 C NMR (100MHz, CDCl 3 ): δ197.1, 174.0, 154.9, 153.0, 147.7, 130.3, 129.9, 129.8, 129.0, 127.8, 127.7,...
Embodiment 2
[0020] Example 2: Preparation of (E)-3-(2,3-dimethoxystyryl)-5-phenyl-5-methylcarboxylate-2-cyclohexenone
[0021] The operation was referred to Example 1, except that the reaction time was 0.5 hour, and the target compound was confirmed with a yield of 44%.
Embodiment 3
[0022] Example 3: Preparation of (E)-3-(2,3-dimethoxystyryl)-5-phenyl-5-methylcarboxylate-2-cyclohexenone
[0023] The operation was referred to Example 1, except that the reaction time was 2 hours, and the target compound was confirmed with a yield of 74%.
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Abstract
The invention provides a 3-styyl-2-cyclonene compound, which is prepared by carrying out crossed aldol condensation reaction on a 3-methyl-2-cyclonene compound and aromatic aldehyde under the catalysis of a microwave-assisted metal Lewis acid catalyst, wherein any organic solvent is not used in the reaction. The preparation method of the 3-styyl-2-cyclonene compound has reasonable design, can enable the condensation reaction of the 3-methyl-2-cyclonene compound and the aromatic aldehyde to be easily executed under the catalysis action of the microwave-assisted metal lewis acid catalyst, and obtains various kinds of 2-cyclonene compounds with a better yield; meanwhile, the organic solvent is not used in the reaction, therefore, the invention has no environment pollution, and is a typical green chemical process. The method is used for preparing the2-cyclonene compound, with simple, convenient and reliable operation, and rapid reaction. The structural formula of the 3-styyl-2-cyclonene compound is shown in the specification.
Description
technical field [0001] The invention belongs to new compounds and their preparation methods, and mainly relates to 3-styryl-2-cyclohexenone compounds and their preparation methods. Background technique [0002] Cyclohexenone compounds are a class of important chemical raw materials, which are widely used in the synthesis of medicines, pesticides, film photosensitive materials and other important chemicals or drugs. There are many synthetic methods of 2-cyclohexenone compounds reported, mainly focusing on starting from cyclohexene through oxidation reaction (see references 1, 2), 1,3-cyclohexanedione compounds through oxidation reaction Oxidative dehydrogenation reaction (see reference 3), intramolecular aldol reaction of diketones (see reference 4, 6, 7), ketones and 3,5,5-trisubstituted 2-cyclohexenones Between the Micheal addition cyclization reaction (see references 5, 7), starting from the aldehyde compound through the Wittig reaction to generate unsaturated aldehydes o...
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