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Synthesis process for analogue 2R-515 of juvenile hormone

A ZR-515, juvenile hormone technology, applied in hormone peptides, animal/human proteins, specific peptides, etc., can solve the problems of expensive raw materials and reagents, environmental friendliness, unsuitable for large-scale preparation, harsh reaction conditions, etc. High target ether selectivity, lower synthesis cost, mild reaction conditions and environmental protection effects

Inactive Publication Date: 2005-01-05
GUANGZHOU INST OF GEOCHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In addition, some subsequent literature reports also provided some synthetic routes and methods of ZR-515, but there are generally problems such as cumbersome steps, harsh reaction conditions, expensive raw materials and reagents, and poor environmental friendliness, which are not suitable for large-scale preparation.

Method used

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  • Synthesis process for analogue 2R-515 of juvenile hormone
  • Synthesis process for analogue 2R-515 of juvenile hormone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] The commercially available strongly acidic cation exchange resin was treated with 2M hydrochloric acid solution at a ratio of liquid to solid mass ratio of 8 for 10 hours at 50°C, filtered and washed with deionized water until there was no chloride ion (silver nitrate solution test), at 80 °C for 24 hours to obtain a hydrogen-form strongly acidic cation exchange resin, which is ready for use.

[0025] Add 150mL of 50% aqueous sodium hydroxide solution, 120mL of dichloromethane, and tetrabutylammonium bromide (6.0g) into a 250ml three-necked flask in sequence, and add citronellal (15.6g) and dichloromethane dropwise under stirring at room temperature. A mixed solution of methane 50mL and 4-(diethoxyphosphoryl)-3-methyl-2-butenoic acid isopropyl ester (27.8g), after the dropwise addition was completed, the reaction was stirred at room temperature for 30h, and dissolved in 2M hydrochloric acid neutralize, separate liquid, extract the aqueous phase with dichloromethane (100...

Embodiment 2

[0028] Treat the commercially available strongly acidic cation exchange resin with 3M hydrochloric acid solution at a ratio of liquid to solid mass ratio of 6 for 30 hours at room temperature, filter and wash with deionized water until there is no chloride ion (tested by silver nitrate solution), and store at 90°C Dry for 12 hours to obtain a hydrogen-type strongly acidic cation exchange resin, which is set aside.

[0029]Citronellal (15.6g), 4-(diethoxyphosphoryl)-3-methyl-2-butenoic acid isopropyl ester (30.6g), dichloromethane 140mL, tetrabutylammonium bromide ( 5.0 g) was added to a 1L three-necked flask in turn, and 200 mL of 40% aqueous sodium hydroxide solution was added dropwise at room temperature under stirring. After the addition was completed, the reaction was stirred at room temperature for 36 h, neutralized with 2M hydrochloric acid until neutral, and separated. The aqueous phase was extracted with dichloromethane (100mL×3), and the organic phases were combined, ...

Embodiment 3

[0032] Treat the commercially available strongly acidic cation exchange resin with 1M hydrochloric acid solution at a ratio of liquid to solid mass ratio of 10 at room temperature for 20 hours, filter and wash with deionized water until there is no chloride ion (tested by silver nitrate solution), and store at 60°C Dry for 48 hours to obtain a hydrogen-type strongly acidic cation exchange resin, which is set aside.

[0033] Citronellal (15.6g), 4-(diethoxyphosphoryl)-3-methyl-2-butenoic acid isopropyl ester (25.0g), dichloromethane 120mL, tetrabutylammonium bromide ( 4.0g) and 180mL of 45% aqueous sodium hydroxide solution were added to a 500mL three-necked flask, stirred at room temperature for 24h, neutralized to neutral with 2M hydrochloric acid, separated, the aqueous phase was extracted with dichloromethane (100mL×3), and the organic phase, washed with water, washed with saturated sodium bicarbonate, washed with water, washed with saturated brine, dried over anhydrous mag...

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Abstract

The invention relates to a method of synthesizing juvenile hormone analoge ZR-515, including the steps: a, preparing a catalyst: using hydrochloric acid to modify strongly acidic cation exchange resin by soaking; b, preparing 3, 7, 11-trimethyl-2, 4, 10-dodecatrienoic isopropyl ester: dissolving citronellal, 4-(diethoxy phosphoryl)-3-methyl-2-butenoic acid isopropyl ester, and sodium hydroxide in dichloromethane, adding in phase transfer catalyst, stirring and reacting at room temperature -100 deg.C for 1-40 h; c, synthesizing ZR-515: mixing 3, 7, 11-trimethyl-2, 4, 10-dodecatrienoic isopropyl ester with methyl alcohol, adding in the prepared catalyst in step a, reacting for 5 h at room temperature -100 deg.C. It has the advantages of simple operation, moderate reacting conditions.

Description

technical field [0001] The present invention relates to the synthesis of juvenile hormone analog ZR-515 [(2E,4E)-11-methoxy-3,7,11-trimethyl-2,4-dodecadienoic acid isopropyl ester] method. Background technique [0002] ZR-515, chemical name (2E, 4E)-11-methoxy-3,7,11-trimethyl-2,4-dodecadienoic acid isopropyl ester, also known as Methoprene, Altosid, Altosand, Kaba et al. It is a selective, stable and potential insecticide, a conjugated diene fatty acid ester containing ether linkage, and a juvenile hormone analogue. ZR-515 does not use direct toxicity to control target pests, but interferes with insects through the growth process of insects from eggs, larvae, pupae to adults, so that insects cannot mature or reproduce, so as to inhibit the growth of insects. Therefore, it is considered a biochemical insecticide. It has the characteristics of high activity, low residual toxicity, and less environmental pollution. It is an effective inhibitor for Hemiptera, Phosphoptera, ...

Claims

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Application Information

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IPC IPC(8): C07K14/575
Inventor 江焕峰朱新海许琳赵妍冉学光
Owner GUANGZHOU INST OF GEOCHEMISTRY - CHINESE ACAD OF SCI
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