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Synthetic method of tea geometrid tea geometrid

A synthesis method and pheromone technology, applied in organic chemistry methods, organic chemistry and other directions, can solve problems such as harsh reaction conditions, and achieve the effect of simple operation and mild conditions

Inactive Publication Date: 2017-07-21
CHANGZHOU UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the key step of the Sharpless asymmetric epoxidation is harsh reaction conditions, which need to be carried out at low temperature for a long time (two days).

Method used

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  • Synthetic method of tea geometrid tea geometrid
  • Synthetic method of tea geometrid tea geometrid
  • Synthetic method of tea geometrid tea geometrid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0065] Example 1: Dissolve AD-mix-alpha (20g) in t-BuOH:H 2 O=1:1 (140mL) solution, cooled to 0°C, added (2E)-2-alkenyl-5-ynyl-1-octanol (1.8g, 14.5mmol) and MeSO 4 NH 2 (1.4g, 14.5mmol), reacted at 0°C for 3 days. After the reaction, NaHSO was added at 0°C 3 (18g) quenched, suction filtered, and the filtrate was extracted with ethyl acetate, washed with saturated brine, and the organic phase was collected, washed with Na 2 SO 4 dry. Spin-dried and passed through the column to obtain (2R,3R)-5-alkynyl-1,2,3-trioctanol (1.9 g, yield 85%) as a white solid. 1 H-NMR (400MHz, CDCl 3 ): δ1.12(t, J=7.5Hz, 3H), 2.17(q, J=7.5Hz, 2H), 2.47(t, J=16.8Hz, 2H), 3.75(m, 4H), 4.01(s ,1H); 13 C-NMR (400MHz, CDCl 3 ): δ83.4, 76.3, 76.0, 75.7, 74.0, 71.7, 70.0, 63.5, 23.0, 13.0, 11.3.

[0066] Step 2: Preparation of (6R,7R)-7,8-epoxy-6-p-toluenesulfonate-3-octyne

Embodiment 2

[0067] Example 2: Add NaH (2.87g, 72mmol) to THF (240mL), add (2R,3R)-5-alkynyl-1,2,3-trioctanol (3.78g, 24mmol) at 0°C , Tos-Im (19.98 g, 59 mmol). The reaction was performed at 0°C and detected by TLC. After the reaction is complete, add H at 0°C 2 O quenched, extracted with ethyl acetate, washed with saturated brine, collected the organic phase, and washed with Na 2 SO 4 dry. Spin-dried and passed through the column to obtain (6R,7R)-7,8-epoxy-6-p-toluenesulfonate-3-octyne (4 g, yield 41%) as a colorless transparent liquid. 1 H-NMR (300MHz, CDCl 3 ): δ1.07(t, J=7.5Hz, 3H), 2.10(qt, J=7.5, 2.4Hz, 2H), 2.45(s, 3H), 2.61-2.65(m, 2H), 2.73(dd, J=4.8,2.5Hz,2H),2.83(m,1H),3.20(m,1H),4.32(dd,J=13.4,6.3Hz,1H),7.34(d,J=8.0Hz,2H), 7.82(d, J=8.3Hz, 2H); 13 C-NMR (400MHz, CDCl 3 ): δ143.8, 132.8, 128.9, 128.7, 127.0, 126.9, 79.6, 71.5, 66.9, 51.2, 44.3, 21.8, 20.6, 12.8, 11.2.

[0068] Step 3: Preparation of (6S,7S)-3,9-diyne-6-p-toluenesulfonate-7-octadecyl alcohol

Embodiment 3

[0069] Embodiment 3: Take 1-decyne (580mg, 4.2mmol) in THF, N 2 For protection, add n-BuLi (1.2mL, 2.8mmol, 2.5M in hexane) at room temperature, react at room temperature for 15min, cool down to -78°C, add (7R,8R)-7,8-epoxy-6-p-toluene Sulfonate-3-octyne (569mg, 2.4mmol), BF 3 ·Et 2 O (0.264mL), reacted overnight. After the reaction was completed, it was quenched by adding saturated ammonium chloride at -78°C, raised to room temperature and stirred for 30 minutes, spin-dried THF, extracted with ethyl acetate, washed with saturated brine, collected the organic phase, and washed with Na 2 SO 4 dry. Spin-dried and passed through the column to obtain a slightly oily liquid (398 mg, yield 51%). 1 H-NMR (300MHz, CDCl 3 ): δ0.88(t, J=6.7Hz, 3H), 1.08(t, J=7.5Hz, 3H), 1.27(m, 10H), 1.42-1.50(m, 2H), 2.05-2.17(m, 4H),2.25-2.40(m,2H),2.45(s,3H),2.50-2.59(m,1H),2.74(qt,J=8.1,2.4Hz,1H),3.98-4.05(m,1H) ,4.61-4.67(m,1H),7.34(d,J=8.0Hz,2H),7.82(d,J=8.3Hz,2H); 13 C-NMR (300MHz, CDCl ...

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Abstract

The invention discloses a synthetic method of tea geometrid tea geometrid, and belongs to the drug synthesis field. Particularly, (2E)-2- alkenyl-5-alkynyl-1-octanol is prepared to be chirality 5- alkynyl-1, 2, 3-trioctanol under the function of cinchona alkaloid catalyst. Under the alkali condition, the trioctanol and para-toluene formyl chloride are reacted to generate 1, 2-epoxy-3- tosylate-5- octyne; under the alkali condition, the 1, 2-epoxy-3- tosylate-5- octyne and 1-decyne, boron trifluoride are reacted to generate 3, 9-diyne-6-tosylate-7-octadecanol. Then the 3, 9-diyne-6-tosylate-7-octadecanol is reacted with potassium carbonate to generate 6, 7-epoxy-3, 9-diyne octodecane; at last, tea geometrid tea geometrid is acquired through catalytic hydrogenation. The synthetic method of tea geometrid tea geometrid is simple in operation, gentle in condition, and suitable for massive production.

Description

technical field [0001] The invention relates to a new synthesis method of tea geometrid sex pheromone components which are insect-attractive and non-toxic and harmless natural products, and belong to the field of drug synthesis. Background technique [0002] Tea geometrid, belonging to Lepidoptera, Geometridae, is one of the important leaf-eating pests on tea trees. Widely distributed in my country's tea areas, it is the main pest of tea trees in Zhejiang, Jiangsu, and Anhui in my country. The insect damage is common and the damage is serious. There are 6-7 generations in a year, the generations overlap, and the amount of eggs laid is large, often breaking out into disasters. For many years, tea farmers have used organophosphorus pesticides to control the pest, resulting in pesticide residues in tea and environmental pollution, and it is easy to develop resistance. With the rapid increase in productivity and the continuous improvement of living conditions, people have high...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D303/04C07D301/00C07D301/02
CPCC07D303/04C07B2200/07C07D301/00C07D301/02
Inventor 陈新徐凯赵帅张成芳王玉波
Owner CHANGZHOU UNIV
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