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Stereoselective synthesis method of (Z, E)-13, 15-octadecenal

An octadecadienal and stereoselective technology, which can be used in organic chemistry methods, carbon-based compound preparation, chemical instruments and methods, etc., can solve problems such as inability to meet application requirements, and achieves low cost, simple purification, and raw materials. easy-to-get effect

Inactive Publication Date: 2020-06-19
INST OF FOREST ECOLOGY ENVIRONMENT & PROTECTION CHINESE ACAD OF FORESTRY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this component belongs to a new structural compound, and there is no commercial product at present, which cannot meet the actual application requirements

Method used

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  • Stereoselective synthesis method of (Z, E)-13, 15-octadecenal

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preparation example Construction

[0032] The invention provides a stereoselective synthesis method of (Z,E)-13,15-octadecadienal, comprising the following steps:

[0033] (1) Under the action of an oxidizing agent, 12-bromo-1-dodecanol is oxidized to obtain 12-bromo-1-dodecanal;

[0034] (2) Under the action of a catalyst, 12-bromo-1-dodecanal and triethyl orthoformate are subjected to an aldehyde protection reaction to obtain 1,1-diethoxy-12-bromododecane;

[0035] (3) Iodination reaction of sodium iodide and 1,1-diethoxy-12-bromododecane to obtain 1,1-diethoxy-12-iodododecane;

[0036] (4) Under the action of n-butyllithium, trimethylsilylacetylene and 1,1-diethoxy-12-iodododecane are subjected to a coupling reaction, and then removed under the action of potassium carbonate and methanol aqueous solution Coupling of the trimethylsilyl group in the reaction product yields 14,14-diethoxy-tetradec-1-yne;

[0037] (5) Under the catalysis of tetrakis(triphenylphosphine)palladium and cuprous iodide, the Sonogashi...

Embodiment 1

[0088] (1) Synthesis of 1,1-diethoxy-12-iodododecane

[0089] Add 12-bromo-1-dodecanol (26.5g, 0.1mol) dropwise into a solution of pyridinium chlorochromate (0.4mol) in dichloromethane (600mL) and react at room temperature for 4h to generate 12-bromo-1- Dodecanal;

[0090] The product was reacted with triethyl orthoformate (22.2g, 0.15mol) in absolute ethanol without purification, the catalyst was p-toluenesulfonic acid monohydrate (290mg), and reacted overnight at 0°C. After the reaction was completed, in the reaction solution Add saturated sodium bicarbonate solution, extract three times with ethyl acetate, combine the extracts, dry over anhydrous sodium sulfate, and evaporate the solvent to obtain the product 1,1-diethoxy-12-bromodeca dioxane;

[0091] In anhydrous acetone, 1,1-diethoxy-12-bromododecane was reacted with sodium iodide at a molar ratio of 2:1, and the bromine group was replaced by iodine; after the reaction, the organic solvent was distilled off , added di...

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Abstract

The invention provides a stereoselective synthesis method of (Z, E)-13, 15-octadecadienal, which belongs to the field of sex pheromone prevention and control of micromelalopha troglodyta. The synthesis method provided by the invention takes cheap and easily available 12-bromododecanol as an initial raw material, has the advantages of few synthesis steps, high yield and relatively high stereoselectivity, and is easy in raw material obtaining, relatively low in cost, simple and convenient in synthesis method purification and suitable for large-scale production.

Description

technical field [0001] The invention relates to the technical field of pest control, in particular to a stereoselective synthesis method of (Z,E)-13,15-octadecadienal. Background technique [0002] Poplar moth (Micromelalophasieversi (Staudinger)) belongs to Lepidoptera (Lepidoptera) boat moth family (Notodontidae), also known as poplar moth. It is distributed in Northeast my country, Central Plains, Central South, Northwest and other regions. One of the main defoliators of plantations. It is rampant in the Northeast, Northwest, Central Plains and Central South of my country. When it breaks out, it often eats up all the leaves, seriously affects the growth of trees, causes huge economic losses and environmental damage, and seriously restricts the development of forestry. [0003] The larvae of Yang Xiaozhou moth are the most serious damage. They eat up all the leaves in a short period of time. From a distance, it looks like winter, so it has the saying of "summer tree winter...

Claims

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Application Information

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IPC IPC(8): C07C45/51C07C47/21
CPCC07C45/515C07C41/50C07C41/52C07C41/56C07C45/292C07B2200/09Y02P20/55
Inventor 刘福张真孔祥波张苏芳
Owner INST OF FOREST ECOLOGY ENVIRONMENT & PROTECTION CHINESE ACAD OF FORESTRY
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