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Process for preparing 2-cyclohexenone compounds

A technology of cyclohexenones and compounds, which is applied in the field of preparation of 2-cyclohexenones, can solve problems such as constraints and synthesis restrictions, and achieve the effects of simple operation, low cost and reasonable design

Inactive Publication Date: 2007-04-25
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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  • Process for preparing 2-cyclohexenone compounds
  • Process for preparing 2-cyclohexenone compounds
  • Process for preparing 2-cyclohexenone compounds

Examples

Experimental program
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Effect test

Embodiment 1

[0019] Embodiment 1: the preparation of 3-methyl-5,5-dimethyl carboxylate-2-cyclohexenone

[0020] Dimethyl 2,2-dipropargyl malonate (104.1 mg, 0.5 mmol), mercury sulfate (HgSO 4 , 15 mg, 0.05 mmol, 10 mol%), trifluoromethanesulfonic acid (100 μL, 0.5 mmol), water (100 μL, 5.0 mmol) and n-octane (50 μL, internal standard substance for GC analysis) in methanol (2.0 mL) After mixing, the mixture 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%. 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 (400MHz, CDCl 3 ): δ 2.01(s, 3H), 2.87(s, 2H), 2.90(s, 2H), 3.75...

Embodiment 2

[0021] Example 2: Preparation of 3-methyl-5,5-carbomethoxy-2-cyclohexenone

[0022] 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

[0023] Example 3: Preparation of 3-methyl-5,5-carbomethoxy-2-cyclohexenone

[0024] 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 discloses a preparing method of 2-cyclohexenone compound, which is characterized by the following: hydrating cyclizing 1, 6-heptadiyne compound and water catalyzed by transient metal mercury salt to obtain the product; improving the receiving rate of each kind of 2-cyclohexenone compound.

Description

technical field [0001] The invention belongs to novel compounds and a preparation method thereof, and mainly relates to a preparation method of 2-cyclohexenone compounds. 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 or ketones,...

Claims

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Application Information

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IPC IPC(8): C07C69/757C07C49/753C07F9/40C07B37/10
Inventor 张辰胡永洲王碧松姚立英
Owner ZHEJIANG UNIV
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