2-cyclohexenones and process for preparing same

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

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

CN1827577AInactive Publication Date: 2006-09-06ZHEJIANG UNIV
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  • 2-cyclohexenones and process for preparing same
  • 2-cyclohexenones and process for preparing same
  • 2-cyclohexenones and process for preparing same

Examples

Experimental program
Comparison scheme
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), 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 the target compound 95mg (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 (499.10MHz, CDCl 3 ): δ2.01(s, 3H), 2.87(s, 2H), 2.90(s, 2H), 3....

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 provides compounds of 2-cyclohexenone with its constitutional general formula on the right, in which R1, R2, R3, R4, R5, R6, R7, and R8 may be the same or be different and their species are function groups of alkyl, carbonyl, phosphoryl, cyano and so on. The method for preparing them consists of hydrating and cyclizing 1, 6-heptadiynes and water catalyzed by transient metal-aurum complen compound to prepare 2-cyclohexenones. The subtractive process of the compound reaction of this invention can be accomplished by the usual refining partition method such as the solvent extraction, the recrystallization, the distillation and the column chromatography. The invention can obtain many kinds of compounds of 2-cyclohexenone by hydration and intermolecular cyclisation of various types of 1, 6-bis-alkynes with the accelerating effect of the given metal complen compound and groups of protonic acid. Preparing 2-cyclohexenones in this method is of simple and dependable operation and is suitable for industrial administration.

Description

technical field [0001] The invention belongs to novel compounds and their preparation methods, and mainly relates to 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 or keton...

Claims

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Application Information

Patent Timeline
06 Sep 2006
Publication
CN1827577A
IPC
C07C49/587; C07C255/45; C07F9/02; C07C45/00; C07C253/30
Inventors
张辰; 姚立英