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2(5H)-furan-2-one derivative, preparation method thereof and application of 2(5H)-furan-2-one derivative in inhibition of rice tillering

A technology of derivatives and furan, which is applied in the field of 2(5H)-furan-2-one derivatives and its preparation and in the application field of inhibiting rice tillering, and achieves the effect of low preparation price and simple structure

Active Publication Date: 2020-08-14
NANJING AGRICULTURAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are no reports or patents of cheap and easy-to-synthesize strigolactone analogues

Method used

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  • 2(5H)-furan-2-one derivative, preparation method thereof and application of 2(5H)-furan-2-one derivative in inhibition of rice tillering
  • 2(5H)-furan-2-one derivative, preparation method thereof and application of 2(5H)-furan-2-one derivative in inhibition of rice tillering
  • 2(5H)-furan-2-one derivative, preparation method thereof and application of 2(5H)-furan-2-one derivative in inhibition of rice tillering

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036]

[0037] Weigh K 2 CO3 3 (2.5mmol, 1.25equiv) and tetra-n-butylammonium bromide (0.2mmol, 0.1equiv), add water (10ml), stir until completely dissolved, add and dissolve in CH 2 Cl 2 (5ml) in 2,4-dichlorophenol (2mmol, 1equiv), stirred at room temperature for 10min, dissolved in CH 2 Cl 2 5-Bromo-furan-2(5H)-one (2mmol, 1 equiv) in (5ml) was added dropwise to the above system, stirred at room temperature for 8h, and the reaction solution was washed with CH 2 Cl 2 (3×5ml) extraction, dried with anhydrous sodium sulfate, distilled off the solvent under reduced pressure, mixed with silica gel in a dry method, loaded the sample, and used (petroleum ether / ethyl acetate=6:1v / v) as the eluent to separate Compound 1 (white solid, yield 84%), identified as 5-(2,4-dichlorobenzene)furan-2(5H)-one.

[0038] 1 H NMR (400MHz, CDCl 3 )δ7.57(dd, J=5.6,1.2Hz,1H),7.37(d,J=8.1Hz,2H),7.13(t,J=8.1Hz,1H),6.45(s,1H),6.39( dd,J=5.6,1.0Hz,1H). 13 C NMR (101MHz, CDCl 3 )δ151.6, 149....

Embodiment 2

[0040]

[0041] With 2,6-dichlorophenol instead of 2,4-dichlorophenol in Example 1, others are the same as in Example 1 to obtain compound 2 (white solid, yield 81%), identified as 5-(2, 6-Dichlorophenoxy)furan-2(5H)-one.

[0042] 1 H NMR (400MHz, CDCl 3 )δ7.48(dd, J=5.7,1.2Hz,1H),7.43(d,J=2.3Hz,1H),7.28–7.24(m,2H),6.39(dd,J=5.7,1.1Hz,1H ),6.35(d,J=1.1Hz,1H). 13 C NMR (101MHz, CDCl 3 )δ169.9, 149.6, 148.2, 129.3, 126.8, 125.4, 103.0.

Embodiment 3

[0044]

[0045] Replace 2,4-dichlorophenol in Example 1 with 2-bromophenol, and others are the same as in Example 1 to obtain compound 3 (white solid, yield is 96%), identified as 5-(2-bromophenoxy base) furan-2(5H)-one.

[0046] 1 H NMR (400MHz, CDCl 3 )δ7.53(d, J=7.6Hz, 1H), 7.44(dd, J=5.7, 1.2Hz, 1H), 7.27–7.26(m, 2H), 7.00–6.96(m, 1H), 6.33(s ,1H),6.29(dd,J=5.7,1.1Hz,1H). 13 C NMR (101MHz, CDCl 3 )δ169.8, 152.9, 149.8, 133.6, 128.9, 125.4, 118.6, 113.5, 101.3.

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Abstract

The invention discloses a 2(5H)-furan-2-one derivative as shown in a formula I which is described in the specification. R is substituted or unsubstituted phenyl, or substituted or unsubstituted naphthyl as shown in a formula. The invention also discloses a preparation method of the 2(5H)-furan-2-one derivative. ROH and 5-bromo-furan-2 (5H)-one are used as raw materials, water and an organic solvent are used as reaction solvents, and a target compound is obtained through a reaction in the presence of an inorganic base and a phase transfer catalyst. The 2(5H)-furan-2-one derivative has the effect of inhibiting rice tillering, compared with strigolactones GR24, the 2(5H)-furan-2-one derivative is simple in structure and low in preparation price, the cost is less than one ten thousandth of thecommercialized price of GR24, and the 2(5H)-furan-2-one derivative has potential commercialized prospects.

Description

technical field [0001] The invention relates to a class of 2(5H)-furan-2-one derivatives, a preparation method thereof and an application in inhibiting rice tillering. Background technique [0002] Strigolactone (SL) is a class of phytohormone compounds, which have the functions of inducing the germination of strigolite and genus plant seeds, promoting the mycelium branching of arbuscular mycorrhizal fungi, inhibiting the formation of plant branches and mediating It has attracted much attention due to its biological functions such as guiding the resistance response of plants to adversity stress. In particular, it can inhibit excessive tillering in rice, which is conducive to the cultivation of high-quality ideal plants. Therefore, it is expected to increase rice yield by controlling ineffective tillering. [0003] Due to the extremely low content of SL in plants (the detection limit of strigolactone in rice roots is 20ng / kg), it is difficult to obtain by means of separation ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/60C07D417/12C07D405/12C07F7/08A01N43/08A01N43/78A01N43/36A01N55/10A01P21/00
CPCA01N43/08A01N43/36A01N43/78A01N55/00C07D307/60C07D405/12C07D417/12C07F7/0812C07F7/083
Inventor 吴磊吴金金刘月欣罗凯丁承强丁艳锋
Owner NANJING AGRICULTURAL UNIVERSITY
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