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Crowndaisy chrysanthemum analogue, synthesis method and its use

A technology of chrysanthemum chrysanthemum and halogen, which is applied in the field of synthesis of chrysanthemum chrysanthemum analogues, can solve the problems of high cost and difficult industrial production, and achieve the effect of mild reaction conditions and obvious antifeedant activity of insects

Inactive Publication Date: 2003-09-17
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] Because the synthesis of the intermediate-furandiol compound in this method must be obtained by the reaction of lithium reagents, the cost is too high and it is difficult to industrialized production

Method used

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  • Crowndaisy chrysanthemum analogue, synthesis method and its use

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Experimental program
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Effect test

Embodiment 1

[0027] Dissolve 20mmol of amine (morpholine) in 15ml of anhydrous tetrahydrofuran (THF), cool to -78°C in a dry ice-acetone bath, add 13.4ml of n-butyllithium (n-BuLi, 1.6M) n-hexyl ring solution, and slowly rise to Stir at room temperature for 2 hours, then cool to -78°C again, add garlandinin dissolved in 5ml of anhydrous THF solution. After reacting at -78°C for 10 hours, a saturated sodium bicarbonate solution was added to quench the reaction. The solid was removed by filtration, the filtrate was extracted with ethyl acetate (10ml×3), the organic layers were combined, washed with saturated sodium chloride solution, and dried over anhydrous sodium sulfate. Sodium sulfate was filtered off, the solvent was removed under reduced pressure, and the pure product was obtained by column chromatography. 1a, 12%: 1 H NMR (300MHz, CDCl 3, ppm): 7.30~7.25(2H, m), 7.18~7.08(3H, m), 5.86(1H, s), 4.08(1H, m), 3.97(1H, m), 3.73(4H, t, J =4.7Hz), 3.05~2.97(2H, m), 2.92(1H, m), 2.85~2...

Embodiment 2

[0028] Embodiment 2 is the same as embodiment 1, and the difference is that chrysanthemum chrysanthemum is 285%: 1 H NMR (300MHz, CDCl 3 , ppm): 7.61(2H, d, J=7.8Hz), 7.34~7.28(2H, m), 7.13(1H, t, J=7.2Hz), 5.29(1H, m), 4.27(1H, m) , 3.96 ~ 3.70 (9H, m). MS(m / z): 184(100.0), 112(36.7), 113(27.2), 55(26.8), 317(25.4, M + ), 41(20.1), 156(17.2), 56(14.7). IR (film, cm -1 ): 2987, 2962, 2854, 1673, 1596, 1493, 1450, 1355, 1190, 1116, 1058, 927, 888, 807, 751, 693. Elemental Analysis C 18 h 23 NO 4 Calculated: C%, 68.14, H%, 7.26, N%, 4.42, Found: C%, 68.05, H%, 7.47, N%, 4.16.

Embodiment 3

[0029] Embodiment 3 is the same as embodiment 1, and the difference is that Chrysanthemum chrysanthemum is 390%: 1 H NMR (300MHz, CDCl 3 , ppm): 7.22 (1H, d, J = 1.5Hz), 6.83 (1H, dd, J = 1.6Hz, J = 8.1Hz), 5.91 (s, 1H), 5.30 (1H, s), 4.12 (1H , m), 4.02 (1H, m), 3.74 (4H, t, J=4.7Hz), 2.98 (2H, m), 2.76 (3H, m), 2.54 (2H, m), 2.27~1.98 (3H, m), 1.98 (1H, m). MS (m / z): 345 (100.0, M + ), 168 (37.8), 346 (36.4), 55 (24.4), 204 (22.6), 127 (20.8), 140 (13.5), 41 (12.9). IR (film, cm -1 ): 2959, 2856, 2817, 1679, 1504, 1486, 1443, 1335, 1257, 1190, 1117, 1039, 956, 934, 873, 822, 756. Elemental Analysis C 18 h 23 NO 4 Calcd. C%, 66.09, H%, 6.67, N%, 4.05, Found: C%, 65.90, H%, 657, N%, 3.82.

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Abstract

A crowndaisy chrysanthemum extract which is the dioxyheterospirocycle compound with unsaturated side chain, its synthesizing process, and its application are disclosed. The said compound has obvious antifeedant activity.

Description

technical field [0001] The present invention relates to chrysanthemum chrysanthemum analogues, synthesis methods and uses thereof, that is, dioxaspirocyclic compounds with unsaturated side chains and the specific synthesis of chrysanthemum chrysanthemum compounds with unsaturated side chains as catalyzed by Lewis acid. A method for a spiro compound, and the use of the compound as a pesticide. Background technique [0002] According to relevant statistics, the annual investment in pesticide chemistry in the world exceeds four billion U.S. dollars, and more than half of the cost is used for pesticides. However, about 15% of crops are still lost due to pests and diseases every year. The resulting impact is particularly severe in developing countries. The contradiction between the growth of the world's population and the shortage of food is becoming more and more prominent. How to prevent pests and diseases and increase the yield of crops is an urgent problem to be solved at pr...

Claims

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Application Information

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IPC IPC(8): A01N43/90C07D493/10
Inventor 尹标林陈立吴毓林
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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