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Benzodihydropyrone derivative and preparation method thereof

A technology for chromones and derivatives, applied in organic chemistry and other directions, can solve problems such as low yield, and achieve the effects of high yield, easy separation, and large application potential

Inactive Publication Date: 2018-05-18
NORTHWEST A & F UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] In view of this, the embodiment of the present invention provides a chromanone derivative and a preparation method thereof, the main purpose of which is to solve the problem of low yield

Method used

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  • Benzodihydropyrone derivative and preparation method thereof
  • Benzodihydropyrone derivative and preparation method thereof
  • Benzodihydropyrone derivative and preparation method thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0028] Prepare a dry reaction tube, dissolve 1-phenoxyhept-2-yn-4-one (0.2mmol) in 4mL chlorobenzene, add gold picolinate (PicAuCl 2 ) (3.9 mg), 2,6-dichloropyridine nitrogen oxide (49 mg), and then the reaction system was placed at 60 ° C for 2.5 h, and after separation by chromatographic column, chromanones were obtained Derivatives, the appearance of the above-mentioned chromanone derivatives is a colorless oil, and its yield is 78%; the chemical structure of the above-mentioned products is detected by nuclear magnetic resonance, as figure 1 As shown, its hydrogen spectrum 1 H NMR (500MHz, CDCl 3 ):δ16.02(s,1H),7.20(dd,J=7.5,1.5Hz,2H),7.12(dd,J=7.0,1.0Hz,1H),7.07-7.01(m,2H),4.48( s, 2H), 2.69(t, J=7.0Hz, 2H), 1.82-1.78(m, 2H), 0.1.02(t, J=7.0Hz, 3H); figure 2 As shown, its carbon spectrum 13 C NMR (125MHz, CDCl 3 ): δ193.54,187.55,152.85,126.98,125.95,122.77,121.88,117.57,106.79,70.18,37.64,19.47,14.06. The structural formula is as follows:

[0029]

Embodiment 2

[0031] Prepare a dry reaction tube, dissolve 2-methyl-6-phenoxyhex-4-yn-3-one (0.2mmol) in 4mL chlorobenzene, add PicAuCl successively at room temperature 3 (3.9mg), 2,6-dichloropyridine nitrogen oxide (49mg), and then the reaction system was placed at 60oC for 2.5h, and the substituted chromanone derivatives could be obtained through chromatography column separation; The appearance of the above-mentioned chromanone derivatives is a colorless oil, and its yield is 64%; the chemical structure of the above-mentioned product is detected by nuclear magnetic resonance method, as shown in image 3 As shown, its hydrogen spectrum 1 H NMR (500MHz, CDCl 3 ):δ15.97(s,1H),7.21(dd,J=7.5,1.5Hz,2H),7.12(dt,J=8.0,2.0Hz,1H),7.06-7.02(m,2H),4.47( s,2H),3.28-3.23(m,1H),1.28(d,J=7.0Hz,6H); Figure 4 As shown, its carbon spectrum 13 C NMR (125MHz, CDCl 3 ): δ194.92, 191.04, 153.03, 127.03, 125.90, 122.89, 121.97, 117.68, 105.47, 70.48, 32.36, 19.96; the above-mentioned proton NMR spectrum an...

Embodiment 3

[0034] Prepare a dry reaction tube, dissolve 4-phenoxy-1-phenylbut-2-yn-1-one (0.2mmol) in 4mL chlorobenzene, add PicAuCl successively at room temperature 2 (3.9mg), 2,6-dichloropyridine nitrogen oxide (49mg), and then the reaction system was placed at 60oC for 2.0h, and the substituted chromanone derivatives could be obtained through chromatography column separation; The appearance of the above-mentioned chromanone derivatives is a colorless oil, and its yield is 94%; the chemical structure of the above-mentioned product is detected by nuclear magnetic resonance method, as shown in Figure 5 As shown, its hydrogen spectrum 1 H NMR (500MHz, CDCl 3 ):δ15.68(s,1H),7.58(d,J=7.0Hz,2H),7.49(dt,J=8.0,1.5Hz,1H),7.39-7.36(m,2H),7.05-6.99( m,2H),6.69-6.62(m,2H),4.58(s,2H); Image 6 As shown, its carbon spectrum 13 C NMR (125MHz, CDCl 3 ): δ193.78, 181.50, 152.52, 135.34, 131.90, 129.04, 128.60, 127.48, 127.02, 122.22, 121.76, 117.61, 105.76, 70.02; Its chemical structural formula...

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Abstract

The invention discloses a benzodihydropyrone derivative and a preparation method thereof. The method includes: adopting a phenoxy-containing alkynone compound as the reaction raw material, taking goldtrichloride as the catalyst, using chlorobenzene as the solvent, and employing 2, 6-dichloropyridine nitrogen oxide as the oxidant, carrying out reaction at 55DEG C-65DEG C for 2h-3h to obtain the benzodihydropyrone derivative. Specifically, the alkynone compound has a chemical structural formula shown as A, and the benzodihydropyrone derivative has a chemical structural formula shown as B; R1 isselected from C1-C12 alkyl, substituted aryl, aromatic heterocycle or thick ring; R2 is selected from hydrogen atom, C1 C12 alkyl, various substituent aryl, aromatic heterocyclic or condensed ring;R2 is selected from hydrogen atom, C1-C12 alkyl, various substituted aryls, aromatic heterocycles or thick rings; the formula A is shown as the specification; and the formula B is shown as the specification. According to the method provided by the invention, the product has the advantages of easy separation, high yield, good substrate adaptability, simple reaction process and great application potential.

Description

technical field [0001] The invention relates to the technical field of organic compound synthesis, in particular to a chromanone derivative and a preparation method thereof. Background technique [0002] The chroman skeleton is a chemical unit widely present in the structure of natural products (such as: clusifoliol, brazilin, Bonducellin, etc.), with its unique chemical structure and unique biological activities (anti-HIV, anti-oxidation, Anti-osteoporosis, anti-cancer, etc.) have received extensive attention. At the same time, compounds containing the skeleton of chromanone are also important intermediate compounds in organic synthesis, and their derivatives are widely used in the synthesis of drugs , a variety of active drug candidate compounds can be obtained through modification and derivation, and its structural formula is: [0003] [0004] The current method for synthesizing chromanone derivatives has long reaction time, low yield, and fewer types of derivatives,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/58C07D405/06
CPCC07D311/58C07D405/06
Inventor 纪克攻李健
Owner NORTHWEST A & F UNIV
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