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A kind of preparation method of benzo [c] fluorenone

A technology of benzo and fluorenone, which is applied in the field of synthetic medicinal chemistry to achieve the effect of mild reaction conditions and great application value

Active Publication Date: 2016-02-24
BASILEA PHARM CHINA LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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  • A kind of preparation method of benzo [c] fluorenone
  • A kind of preparation method of benzo [c] fluorenone
  • A kind of preparation method of benzo [c] fluorenone

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] 2,9-Dimethoxybenzo[c]fluorenone (A)

[0027]

[0028] 6-Methoxy-1-indenenone A1 (80mg, 0.5mmol) was dissolved in toluene (8ml), and the reaction solution was refluxed for 36 hours under the protection of argon. Cool to room temperature, concentrate the reaction solution to obtain a crude product, and then purify it by column chromatography (ethyl acetate / petroleum ether: 1:8~1:4) to obtain a red oily product A (68 mg, 85%), which solidifies in the refrigerator to obtain a red color solid. Melting point 144~146°C; 1 HNMR (400MHz, Acetone-d 6 )δppm: 7.51(d,J=8.4Hz,1H),7.23(d,J=8.4Hz,1H),7.22(s,1H),7.18(s,1H),7.07(d,J=8.0Hz, 1H),6.84(dd,J=8.0and2.0Hz,1H),6.40(dd,J=9.6and2.0Hz,1H),5.62(dd,J=9.2and3.2Hz,1H),4.67(d,J =8.4Hz,1H),3.90(s,3H),3.85(s,3H),3.81(dd,J=5.2and3.2Hz,1H); 13 CNMR (100MHz, Acetone-d 6 )δppm:201.05,179.17,160.14,159.88,148.65,136.30,136.00,128.99,126.98,126.87,124.56,123.64,121.84,115.37,112.50,105.22,55.36,55.07,51.18,40.79;MS-ESI(m / z ,%):291.1([...

Embodiment 2

[0030]3,9-Dichlorobenzo[c]fluorenone (B)

[0031]

[0032] 5-Chloro-1-indenenone (66mg, 0.40mmol) B1 was dissolved in N,N-dimethylformamide (5ml), and the reaction solution was reacted at 80°C for 5 hours. After cooling to room temperature, the solvent was removed under reduced pressure, and the crude product was directly purified by column chromatography (ethyl acetate / petroleum ether: 1:8) to obtain yellow solid B (54 mg, 90%). 1 HNMR (400MHz, CDCl 3 )δppm:8.37(d,J=9.2Hz,1H),7.95(d,J=1.6Hz,1H),7.92(d,J=2.0Hz,1H),7.81~7.75(m,2H),7.66~ 7.60(m,2H),7.36(dd,J=8.0and1.2Hz,1H). 13 CNMR (100MHz, CDCl 3 )δppm: 192.0, 145.6, 141.1, 140.2, 138.2, 134.2, 132.1, 131.9, 129.3, 128.6, 128.3, 128.0, 126.4, 125.5, 124.6, 123.4, 120.6.

Embodiment 3

[0034] 3-methoxy-9-chlorobenzo[c]fluorenone (C)

[0035]

[0036] 5-Methoxy-1-indenenone C1 (32mg, 0.2mmol) and 5-chloro-1-indenenone (34mg, 0.2mmol) were dissolved in xylene (6ml), and the reaction solution was heated under argon Reflux for 20 hours. After cooling to room temperature, the reaction solution was concentrated to obtain a crude product, which was purified by column chromatography (ethyl acetate / petroleum ether: 1:8) to obtain yellow solid C (41 mg, 70%). 1 HNMR (400MHz, CDCl 3 )δppm:8.07(d,J=8.4Hz,1H),7.88(d,J=1.6Hz,1H),7.81(d,J=2.0Hz,1H),7.72~7.62(m,3H),7.49( s,1H),7.08(dd,J=8.0and1.2Hz,1H). 13 CNMR (100MHz, CDCl 3 )δppm: 191.5, 157.6, 140.8, 138.6, 136.2, 134.2, 132.1, 131.9, 131.3, 130.9, 127.8, 127.2, 126.4, 123.5, 122.5, 118.4, 110.6.

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Abstract

The present invention provides a benzo[C]fluorenone preparation method. According to the method, 1-indene olefine ketone is adopted as a raw material and is subjected to a heating reaction in an organic solvent to obtain a benzo[C]fluorenone crude product, and the crude product is purified with column chromatography or re-crystallization to obtain the benzo[C]fluorenone. According to the present invention, the easily available 1-indene olefine ketone is adopted as the raw material to prepare the benzo[C]fluorenone, the continuous Diels-Alder reaction, a CO removing reaction and a H2 removing reaction are adopted to conveniently and efficiently prepare the benzo[C]fluorenone, the required reaction conditions are mild, the preparation method is suitable for industrial production, and great application values are provided.

Description

technical field [0001] The invention relates to synthetic medicinal chemistry, in particular to drug synthesis, and in particular to a method for preparing benzo[C]fluorenone by using 1-indenone as a raw material. Background technique [0002] Fluorenone derivatives are a class of compounds with strong biological activity. They are not only the basic skeleton of many drug molecules, but also the core structure of many natural products. Such as natural products dengibsin, dengibsinin, dendroflorin and kinobscurinone and so on. Fluorenone derivatives can also be used as photosensitizers in organic photosensitive devices, and have important electrical and optical properties. Benzo[C]fluorenone is an important series of fluorenone derivatives. Many biologically active compounds use it as the core structure, such as 5-(dimethylaminoethoxy)benzo[C] 】Fluorenone-VUFB13468 (Benfluron, Formula 1) and 5-(diethylaminoethoxy)-6-(diethylaminoethoxyformyl)benzo[C]fluorenone (VUFB13431, F...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C45/74C07C49/753C07C49/697
CPCC07C45/74C07C2603/18C07C49/755C07C49/697
Inventor 沈征武郑书岩李小平
Owner BASILEA PHARM CHINA LTD