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2-cyclohexenone compounds

A technology of cyclohexenones and compounds, which is applied in the field of 2-cyclohexenones and their preparation, can solve the problems of synthesis limitations and restrictions, and achieve good yield, easy operation and reasonable design

Inactive Publication Date: 2008-01-16
ZHEJIANG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

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

Method used

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Examples

Experimental program
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Embodiment 1

[0020] Embodiment 1: the preparation of 3-methyl-5,5-dimethyl carboxylate-2-cyclohexenone

[0021] Dimethyl 2,2-dipropargyl malonate (104.1 mg, 0.5 mmol), methyl gold complex (MeAuPPh 3 , 5mg, 0.01mmol), trifluoromethanesulfonic acid (100μL, 0.5mmol), water (100μL, 5.0mmol) and n-octane (50μL, internal standard substance for GC analysis) were mixed in methanol (2.0mL), and The mixed solution was heated at below 50° C. for 1 hour to react. After the reaction, according to gas chromatography analysis, the target compound was confirmed with a yield of 94%. Then, the reaction mixture was subjected to column chromatography (silica gel column; developing solvent: petroleum ether: ethyl acetate=5:1; R f =0.3) Separation and purification to obtain 95 mg of the target compound (yield 84%), and carried out boiling point, NMR, IR, mass analysis and elemental analysis, the results are as follows: Bp: 120 ° C (5mm Hg); 1 H NMR (499.10 MHz, CDCl 3 ): δ2.01(s, 3H), 2.87(s, 2H), 2.90(s, 2H...

Embodiment 2

[0022] Example 2: Preparation of 3-methyl-5,5-carbomethoxy-2-cyclohexenone

[0023] The operation was referred to Example 1, except that heterophosphotungstic acid was used instead of trifluoromethanesulfonic acid to obtain 55 mg of the target compound (yield 48%).

Embodiment 3

[0024] Example 3: Preparation of 3-methyl-5,5-carbomethoxy-2-cyclohexenone

[0025] Refer to Example 1 for the operation, except that heterophosphomolybdic acid was used instead of trifluoromethanesulfonic acid to obtain 42 mg of the target compound (yield 37%).

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Abstract

The invention provides 2-cyclohexyl ketene compounds with the following common molecular formula, wherein R1, R2, R3, R4, R5, R6, R7, and R8 are identical or different functional groups of alkyl group, carbonyl group, phosphoryl group or cyano-group. The preparation method is: use gold complex to catalyse the cyclized hydration reaction of 1,6-heptadiyne compounds and water. The refining process of the synthesizing reaction can be done with common separation and refining methods of solvent extraction, recrystallization, distillation and column chromatography. With simple and reliable operation, the method of the invention can be applied to the hydration of 1,6-dualalkyne compounds as well as to intramolecular cyclization reactions under the katalysis of special metal complex or different protonic acid to get different 2-cyclohexyl ketene compounds, thus the invention can be industrialized.

Description

[0001] This case is a divisional application with the invention name: 2-cyclohexenone compounds and their preparation method, application number: 2006100503167 technical field [0002] The invention belongs to novel compounds and their preparation methods, and mainly relates to 2-cyclohexenone compounds and their preparation methods. Background technique [0003] 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 Miche...

Claims

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Application Information

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IPC IPC(8): C07C69/75C07C49/577C07F9/42C07C255/46C07C49/543
Inventor 张辰姚立英王碧松
Owner ZHEJIANG UNIV
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