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Synthetic method of sex pheromone intermediate of Hyphantria cunea

A technology of American white moth and synthetic method, which is applied in the direction of organic chemistry, organic chemistry, etc., can solve the problems of difficult control of the reaction process, difficult operation, high reactivity, etc., and achieve strong reaction operability, lower production costs, and better reaction conditions mild effect

Active Publication Date: 2018-07-20
ZHEJIANG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Lindella catalyst has high catalytic hydrogenation reaction activity, strict requirements on reaction temperature (0-5°C), reaction time (30-60 minutes) and reaction pressure, poor applicability of reaction conditions, and extremely difficult to control the reaction process
The Sharpless asymmetric epoxidation reaction requires many types of catalysts, the feeding process is cumbersome, the reaction time (4 days) is long, and it is always carried out at low temperature (-30~-25°C), the economic cost is high, and it is not easy to operate
At the same time, both these two-step reactions have the disadvantages of high requirements for production equipment and difficulty in ensuring safety, and are difficult to meet the needs of industrial production.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Embodiment 1, a kind of preparation method of white moth sex pheromone intermediate (2S, 3R)-2,3-epoxy-1-tetradecyl alcohol, carries out the following steps successively:

[0037] Step 1, Synthesis of (Z)-2-enetetradec-1-alcohol (3)

[0038]

[0039] At 20°C, add nickel acetate tetrahydrate (2.5mmol, 623mg), sodium borohydride (11mmol, 418mg), ethylenediamine (13.5mmol, 0.9mL) and 150mL 95% ethanol to a 500mL hydrogenation reaction kettle in sequence, mix and stir 20 minutes. Then add 100 mL of 95% ethanol solution dissolved in 2-alkynetetradec-1-ol (2) (25 mmol, 5.25 g) to replace the hydrogen, and the reaction pressure is 0.2 MPa, and the reaction is continued for 20 hours.

[0040] After the reaction is complete, the reaction solution is filtered to remove the catalyst (nickel boride), the filter cake is washed with ethyl acetate (10ml), and the filtrate is concentrated and dried under reduced pressure (at a pressure of 0.1Mpa and at a temperature of 40°C for 120...

Embodiment 2

[0050] Embodiment 2, a kind of preparation method of white moth sex pheromone intermediate (2S, 3R)-2,3-epoxy-1-tetradecyl alcohol, the following steps are carried out in sequence:

[0051] Step 1, Synthetic (Z)-2-enetetradecan-1-alcohol (3)

[0052]

[0053] 95% ethanol in step 1) of embodiment 1 is changed into methanol (volume constant), reaction temperature is changed into 25 ℃, reaction pressure is changed into 0.5MPa, all the other are equal to embodiment 1.

[0054] The purity of compound 3 is 82%, Z / E>85.

[0055] Step 2. Synthesis of (2S,3R)-2,3-epoxy-1-14 carbon alcohol (4)

[0056]

[0057] The dichloromethane in step 2) of Example 1 was changed to chloroform (volume constant), the reaction temperature was changed to 25° C., and the rest were the same as in Example 1.

[0058] Compound 4 has dr>10, ee=80%.

Embodiment 3

[0059] Embodiment 3, " sodium bicarbonate " solution in embodiment 1 step 2) is correspondingly changed into " potassium bicarbonate, sodium carbonate, potassium carbonate or cesium carbonate " solution, concentration is constant, and volume is also constant; Identical to step 2) of Example 1; The results obtained are shown in Table 1 below.

[0060] Table 1

[0061] carbonate

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Abstract

The invention discloses a synthetic method of sex pheromone intermediate (2S,3R)-2,3-epoxy-1-tetradecanol (4) of Hyphantria cunea. According to the method, firstly, nickel acetate tetrahydrate, sodiumborohydride, ethylenediamine as well as an alcohol as a solvent are added to a hydrogenation reactor for a reaction, then, an alcoholic solution with 2-tetradecynol dissolved is added continuously, areaction is performed after hydrogen replacement, and (Z)-2-tetradecene-1-ol is obtained; (Z)-2-tetradecene-1-ol is dissolved in a halogenated hydrocarbon solvent, a carbonate solution and a halogenated hydrocarbon solution of 3-chloroperoxybenzoic acid are added for a reaction, and (2S,3R)-2,3-epoxy-1-tetradecanol is obtained. The method is environmentally friendly and suitable for industrial production, cost is low, and reaction conditions are mild.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a method for synthesizing an important intermediate (2S, 3R)-2,3-epoxy-1-tetradecyl alcohol of the white moth sex pheromone. Background technique [0002] The American white moth Hyphantria cunea (Drury), also known as the American lamp moth, belongs to the family Lepidoptera and is native to North America, mainly distributed in the southern United States and Canada. The insect is a worldwide quarantine pest, which seriously affects the growth of trees, and even invades farmland, endangering crops, resulting in reduced production and income, or even extinction. It is called "smokeless fire". In 1979, the insect was introduced into my country from the border of China and North Korea, and quickly developed into one of the seven major forest pests. The American white moth once broke out in a large area in North China on the eve of the Beijing Olympic Games, so it is urgent to prev...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D303/14C07D301/14
CPCC07B2200/07C07D301/14C07D303/14
Inventor 赵金浩杨勇程敬丽杜永均
Owner ZHEJIANG UNIV
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