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Method for synthesizing pyrethroid hapten compounds

A technology of pyrethroids and synthetic methods, which is applied in the field of synthesis of pyrethroid hapten compounds, and can solve problems such as inability to obtain target compounds

Inactive Publication Date: 2008-07-09
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0013] But this kind of preparation method has only provided the knowledge of theory; The present inventor all can't obtain the target compound I

Method used

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  • Method for synthesizing pyrethroid hapten compounds
  • Method for synthesizing pyrethroid hapten compounds
  • Method for synthesizing pyrethroid hapten compounds

Examples

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Embodiment 1

[0041] The preparation of embodiment 1,3-(2,2-dimethyl-3-(2'-methacryl) cyclopropanecarbonamido) ethyl propionate (molecular structural formula is II, hereinafter referred to as II):

[0042] Add 1.582g (11mmol) γ-aminobutyric acid ethyl ester hydrochloride, 0.178g (1.45mmol) DMAP, 1.547g (15.3mmol) triethylamine and 120mL chloroform in the reaction bottle, add dropwise under ice-salt bath 1.28g (6.9mmol) of dimethyl chrysanthemum acid chloride and 30mL of chloroform were added dropwise, and reacted at 20°C for 6h. The reaction solution was washed three times with dilute hydrochloric acid, and then washed with water until neutral, anhydrous Na 2 SO 4 It was dried and concentrated to obtain 1.96 g of crude product, which was purified by silica gel column to obtain 1.71 g (6.7 mmol) of the product, Y=96.9%.

Embodiment 2

[0043] Embodiment 2, the preparation of 3-(3-ethoxy-3-oxopropanecarbonyl)-2,2-dimethylcyclopropanecarboxylic acid (molecular structural formula is III, hereinafter referred to as III):

[0044] Add 2.645g (10.3mmol) II, 0.166g (0.61mmol) ruthenium trichloride hydrate, 8.39g (39mmol) sodium periodate and 70mL (CCl 4 :CH 3 CN:H2O=10:10:15), the air was cut off and the reaction was stirred under reflux for 24h. After the reaction solution was cooled, it was filtered and the filter cake was washed with saturated sodium chloride solution, and the filtrate was extracted three times with dichloromethane, and anhydrous Na 2 SO 4 Dry, concentrate and wash with saturated NaHCO 3 Extract, adjust to pH = 2 with hydrochloric acid after liquid separation, extract with ethyl acetate, anhydrous Na 2 SO 4 It was dried, concentrated, and purified by a silica gel column to obtain 1.78 g (7.2 mmol) of the product, Y=69.7%.

Embodiment 3

[0045] The preparation of embodiment 3,2-hydroxyl-2-(3-phenoxyphenyl) acetonitrile:

[0046] After adding 4.72g (24.8mmol) sodium bisulfate and 20mL water in the reaction flask, add 4.90g (24.8mmol) m-phenoxybenzaldehyde dropwise, the dropping temperature is 20°C, and the dropping time is 40min; Continue to react at 20° C. for 3 h after completion, and white insoluble matter is produced after the reaction is completed.

[0047] Then, a solution obtained by dissolving 2.11 g (43.1 mmol) of NaCN in 20 mL of water was added dropwise to the above-mentioned white insoluble matter, and the dropping time was 30 min. After the dropwise addition was completed, the stirring reaction was continued at 15° C. for 3 h.

[0048] After the above reaction was completed, the reaction product was extracted with dichloromethane, and after washing with water, anhydrous Na 2 SO 4 After drying, the dichloromethane solution of the product 2-hydroxy-2-(3-phenoxyphenyl)acetonitrile was obtained, whi...

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Abstract

The invention discloses a synthesis process of pyrethroids hapten compound by using dimethyl trichloromethyl chloroformate, gamma-aminobutyric acid and as main material, which comprises following steps that firstly generating 3-(2, 2-dimethyl-3-(2'-methacryloyl) cyclopropyl carbonyl amino) ethyl propionate, secondly generating 3-(3-ethyoxyl-3-oxopropanecarbonic acyl radical)-2, 2-dimethyl cyclopropane aminic acid, thirdly generating 2-hydroxy-2-(3-pheonexyphenyl) acetonitrile, fourthly generating cyano-(3-phenoxy phenyl) methyl N-2-ethyoxylcarbonylethyl-2, 2-dimethylcypromethyl carbonate, fifthly generating 3-(3-(( cyano(3-phenoxyphenyl) methoxyl) carbonic acyl radical)-2, 2-phenoxy phenylcypro carbamoyl) ethylformic acid. Hapten which is prepared by the invention comprises three similarity structures of most pyrethroids pesticides, ester with-CN and three-membered ring structure.

Description

technical field [0001] The invention relates to a synthetic method for selecting a pyrethroid hapten compound having -COOH and possibly containing a pyrethroid insecticide structure. Background technique [0002] The invention belongs to the technical field of immunochemistry and residue analysis of small-molecule pesticide compounds (molecular weight less than 1000 Daltons), relates to organic synthesis, immunochemistry and biochemistry, and relies on basic principles of immunology and immunochemistry and biotechnological means to design and synthesize Small molecule target analyte hapten, and coupled with carrier protein to prepare effective artificial antigen, immunize animals to prepare specific antibody for small molecule analyte, use the specific immunological reaction of antigen and antibody and the identification of markers that are easily detected and identified Amplification, quantitative detection of ultra-trace small molecule target analytes in samples, has the c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/39C07C253/30G01N33/53
Inventor 程敬丽赵金浩王春梅朱国念
Owner ZHEJIANG UNIV
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