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Synthesis method of hyphantria cunea sex pheromone intermediate

A technology of American white moth and synthetic method, applied in the direction of organic chemistry, organic chemistry, etc., can solve the problems of high economic cost, difficult to guarantee safety, difficult to operate, etc., and achieve the effect of good corresponding selectivity and short route

Active Publication Date: 2019-08-09
ZHEJIANG NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

If the synthesis of (2S,3R)-2,3-epoxytetradecyl alcohol is improved, it is difficult to overcome the high economic cost of being suitable for industrial production, difficult operation, high requirements for production equipment, and difficult to guarantee safety The shortcoming of sweeping away the shortcoming that hinders its industrialized production, the route of this synthetic pheromone is extremely competitive

Method used

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  • Synthesis method of hyphantria cunea sex pheromone intermediate
  • Synthesis method of hyphantria cunea sex pheromone intermediate
  • Synthesis method of hyphantria cunea sex pheromone intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Embodiment 1: the synthesis of intermediate 3

[0041]

[0042] In a 250mL three-necked flask, add tetrahydropyran propargyl alcohol (that is, 2-(2-propargyloxy) tetrahydropyran, 1.4g, 10mmol), 40mLTHF, N 2 Protected, put in -30~-20 ℃ low-temperature tank and drop the temperature to -30 ℃, stir and cool, add n-BuLi (4.4mL 2.5M, 11mmol), after one hour of reaction, add p-toluenesulfonate undecane ( 2.6 g, 11 mmol), naturally raised to room temperature for 12 h, added 2 mL of water to quench the reaction, and then used.

Embodiment 2

[0043] Embodiment 2: the synthesis of intermediate 4

[0044]

[0045] Add p-toluenesulfonic acid (5mmol) or concentrated hydrochloric acid 0.5mL to the crude product solution of intermediate 3 in the above-mentioned example 1, heat and reflux for 5 hours, add water to terminate the reaction, remove THF by rotary evaporation, extract with ethyl acetate, dry and concentrate, and column The product was obtained by chromatography (eluent: V (ethyl acetate) / V (petroleum ether) = 1 / 10), 1.87 g, yield 89%, purity greater than 98%.

[0046] 1 H NMR (400MHz, CDCl 3 )δ 4.25 (s, 2H), 2.21 (ddd, J = 7.1, 5.0, 2.1 Hz, 2H), 1.54-1.21 (m, 19H), 0.88 (t, J = 6.8 Hz, 3H).

Embodiment 3

[0047] Embodiment 3: the synthesis of intermediate 5

[0048]

[0049] After Lindlar catalyst (2g) was suspended in triethylamine (20ml) for 1h, 2-tetradecyn-1-alcohol (21g, 100mmol) dissolved in triethylamine (80ml) was added to the above-mentioned catalytic system, Hydrogenation at room temperature under normal pressure, after the hydrogen absorption is completed, filter, and the filtrate is dried and concentrated to obtain a colorless liquid, which can be directly used for the next step reaction, 19g, yield 90%. The Z / E value is greater than 99:1.

[0050] 1 H NMR (600MHz, CDCl 3 )δ5.67-5.50 (m, 2H), 4.22 (d, J = 6.4Hz, 2H), 2.09 (dd, J = 14.6, 7.4Hz, 2H), 1.63 (d, J = 41.7Hz, 1H), 1.43-1.21 (m, 18H), 0.90 (t, J=7.0Hz, 3H).

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Abstract

The invention discloses a synthesis method of a hyphantria cunea sex pheromone intermediate. The method comprises the steps that 2-(2-propynyloxy)tetrahydropyran and a benzenesulfonate undecane compound (2) are taken as substrates, under the catalysis of a catalyst I, a reaction is carried out to obtain a compound (3), the compound (3) is hydrolyzed in an acidic environment to obtain a compound (4), the compound (4) is subjected to selective catalytic hydrogenation to obtain a cis-olefin compound (5), and finally, under the function of a catalyst II, a chiral reagent and an oxidant, (2S,3R)-2,3-epoxytetradecyl alcohol is obtained by Sharpless epoxidation. By means of the method, the hyphantria cunea sex pheromone intermediate can be efficiently and highly-selectively synthesized, and through simple crystallization treatment, the enantiomeric excess of the intermediate can reach the standard that the ee value is greater than 99%. The synthesis method has the advantages of short route and good corresponding selectivity.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a method for synthesizing a white moth sex pheromone intermediate. Background technique [0002] American white moth, also known as American lamp moth, autumn curtain caterpillar, autumn curtain moth, Lepidoptera, Diphtheridae, and white moth. The American white moth spends the winter as a pupa under the bark of trees or on the dead branches and leaves on the ground. After hatching, the larvae spin silk and form a web, and feed on the leaves in the cluster net. After the leaves are eaten up, the larvae move to another part of the branch and twig to weave a new one. network. In 1979, it was introduced to Dandong, Liaoning, China, and in 1981, it was introduced to Rongcheng County, Shandong, and spread successively in Shandong. American white moth is a worldwide quarantine pest, mainly harming fruit trees and ornamental trees, especially broad-leaved trees. It will c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D303/14C07D301/19
CPCC07B2200/07C07D301/19C07D303/14
Inventor 罗红敏陈雪珂李新生
Owner ZHEJIANG NORMAL UNIVERSITY
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