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Cyclohexyl ester compound as well as preparation method and application thereof

A cyclohexyl ester and compound technology, applied in the field of organic synthesis, can solve the problems of complicated post-processing, high reaction temperature, participation of precious metals, etc., and achieve the effects of avoiding unfriendly environment, simple preparation and wide application prospect.

Active Publication Date: 2022-01-25
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Compared with the original method, this route has changed to a greater extent in terms of raw material cost, but there are still problems such as the participation of precious metals, high reaction temperature, and complicated post-treatment.

Method used

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  • Cyclohexyl ester compound as well as preparation method and application thereof
  • Cyclohexyl ester compound as well as preparation method and application thereof
  • Cyclohexyl ester compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0073] Embodiment 1: the synthesis of 2-(4-heptyl) malononitrile

[0074] Add 30 g of 4-heptanone, 18.2 g of malononitrile, 3.05 g of ammonium acetate, 4.75 g of acetic acid and 200 mL of toluene into a three-necked flask equipped with a mechanical stirring device and a water separator, heat the system to 120 ° C, and separate the water for 2 hours. The total water content was 4.5 mL. The system was cooled down, washed with saturated brine, and concentrated to obtain crude 2-(4-heptylene)malononitrile, which was directly used in the next reaction without purification.

Embodiment 2

[0075] Embodiment 2: the synthesis of compound IV-1

[0076] Add 1.62 g (0.01 mol) of the crude product 2-(4-heptylethylene) malononitrile obtained in the above examples to 10 ml of anhydrous methanol, cool to 0° C., dropwise add 1.4 mL of 30% NaOMe solution and 2-methylpropene Aldehyde 0.7g, dropwise, stirred at room temperature for 1 hour. After concentrating under reduced pressure, add 20 mL of dichloromethane, 1.01 g of triethylamine, and 122 mg of DMAP to the oil, dropwise add 0.8 mL of acetyl chloride in an ice bath, keep warm for 2 hours in an ice bath, add water, extract and separate, and collect The organic phase was concentrated and subjected to silica gel column chromatography (petroleum ether: ethyl acetate = 10:1 (v / v)) to obtain 1.86 g of compound IV-1, yield: 67.8%. 1 H NMR (600MHz, CDCl 3 ):6.85(s,1H),3.07-3.03(m,1H),2.39-2.35(m,2H),2.23-2.19(m,1H),2.14(s,3H),2.12-2.10(m,1H ), 1.69(d,3H), 1.68-1.60(m,3H), 1.52-1.44(m,1H), 1.05(t,3H), 0.89(t,3H).

Embodiment 3

[0077] Embodiment 3: the synthesis of compound IV-1

[0078] Add 1.62g (0.01mol) of 2-(4-heptylene)malononitrile, 0.7g of 2-methacrolein, 1.01g of triethylamine, 122mg of DMAP and 20mL of 1,2-dichloroethane into the reaction flask 1.02 g of acetic anhydride was added with stirring at room temperature. After the addition was complete, the system was stirred overnight at room temperature. After adding water, extract and separate the layers, collect the organic phase, concentrate and perform silica gel column chromatography (petroleum ether: ethyl acetate = 10:1) to obtain 1.9 g of compound IV-1, yield: 69.2%.

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Abstract

The invention relates to a cyclohexyl ester compound which can be used for synthesizing a 2-phenylmalonic acid derivative. The cyclohexyl ester compound is shown as a general formula IV, wherein each substituent group in the general formula IV is defined in the specification. The compound with the general formula is cyclohexyl ester and is novel in structure; the compound is simple to prepare, a plurality of chemical reaction processes can be realized through a 'one-pot method', the preparation method is simple and easy to implement, subsequent steps (namely preparation of a pinoxaden intermediate) can be directly carried out without post-treatment, and the yield of cyclohexyl esters prepared by the method is relatively high.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a cyclohexyl ester compound, a preparation method and an application thereof. Background technique [0002] 2-Phenylmalonic acid derivatives are widely used chemical intermediates in medicine, such as thymidylate synthase inhibitors (European Journal of Medicinal Chemistry, 2019, 183, 111673), MAT2A inhibitors (WO2019191470) , barbiturates (CN110003119), IDO inhibitors (WO 2019027855) and new materials, such as thermally conductive polymer materials (CN110229318), are widely used. [0003] Pinoxaden is an important new high-efficiency herbicide (WO 9947525). It is widely used in the weed control of crops such as wheat. It has a good market prospect, and 2-phenylmalonic acid derivatives are Key intermediate in the synthesis of pinoxaden. [0004] At present, the method of synthesizing pinoxaden is through 2-(2,6-diethyl-4-methylphenyl) malonate diester or 2-(2,6-diethyl-4-methyl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/38C07C253/30C07C231/06C07C233/11C07D498/04
CPCC07C255/38C07C231/06C07D498/04C07C2601/14C07C233/11
Inventor 张帆杨辉斌裴和瑛曹巍王刚梁爽李斌
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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