2-hydroxy-9-fluorenone derivative as well as synthesis method and application thereof

A synthesis method and derivative technology, applied in the field of 2-hydroxy-9-fluorenone compounds and their synthesis, can solve the problems of poor functional group tolerance, complex ligands, low product yield, etc., and achieve substrate universality Good, mild reaction conditions, simple post-treatment effect

Pending Publication Date: 2021-12-21
LINYI UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The synthetic methods reported above have the following problems: some require the use of expensive noble metal catalysts, some involve relatively complex ligands, some react at high temperatures, some raw materials are not ea...

Method used

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  • 2-hydroxy-9-fluorenone derivative as well as synthesis method and application thereof
  • 2-hydroxy-9-fluorenone derivative as well as synthesis method and application thereof
  • 2-hydroxy-9-fluorenone derivative as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Embodiment 1: Synthesis of 1-phenyl-2-hydroxyl-9-fluorenone (IA)

[0029]

[0030]Under air (without inert gas protection), 0.3 mmol of o-furyl phenyl ynone, 3 mL of toluene, and 0.03 mmol of p-toluenesulfonic acid monohydrate were added to a 10 ml sealed tube. React at 100°C for 17 hours, then cool to room temperature, concentrate, and perform column chromatography to obtain the target product formula (IA), a red solid, with an isolation yield of 95%. MP 194-196°C.

[0031] Product NMR data: 1H NMR (CDCl 3 ,400MHz): δ5.32(s,1H),7.07(d,J=8.0Hz,1H),7.17(d,J=3.2Hz,1H),7.37-7.43(m,5H),7.47-7.54( m,5H); 13C NMR (CDCl 3 ,100MHz): δ119.526, 120.34, 120.84, 124.06, 127.61, 127.92, 128.98, 129.15, 129.62, 131.21, 131.60, 134.14, 134.63, 137.45, 144.05, 154.15, 192.9 z) calcd. for C 19 h 12 o 2 [M+H]+calc.: 273.0916; found: 273.0920.

Embodiment 2

[0032] Example 2: Synthesis of 1-phenyl-2-hydroxyl-6-chloro-9-fluorenone (IB)

[0033]

[0034] Under air (without inert gas protection), 0.3 mmol of chloro-substituted o-furaryl acetylenone, 3 mL of toluene, and 0.03 mmol of p-toluenesulfonic acid monohydrate were added to a sealed 10 ml tube. React at 100°C for 18 hours, then cool to room temperature, concentrate, and perform column chromatography to obtain the target product formula (IB), a dark red solid, with an isolation yield of 90%. MP 206-207°C.

[0035] Product NMR data: 1H NMR [(CD 3 ) 2 SO,400MHz]:δ7.09(d,J=8.0Hz,1H),7.27-7.31(m,3H),7.36-7.39(m,4H),7.66(d,J=8.0Hz,1H),7.80 (d, J=1.6Hz, 1H), 10.03(s, 1H); 13CNMR[(CD 3 ) 2 SO,100MHz]:δ120.11,120.44,121.77,124.92,127.28,127.43,128.92,130.03,131.56,132.02,133.09,133.97,139.80,145.87,156.86,190.99.

[0036] High resolution mass spectrometry data: HRMS(ESI,m / z)calcd.for C 19 h 11 ClO 2 [M+H]+calc.: 307.0520; found: 307.0512.

Embodiment 3

[0037] Example 3: Synthesis of 1-phenyl-2-hydroxyl-6-fluoro-9-fluorenone (IC)

[0038]

[0039] Under air (without inert gas protection), 0.3 mmol of fluorine-substituted o-furaryl acetylenone, 3 mL of toluene, and 0.03 mmol of p-toluenesulfonic acid monohydrate were added to a 10 ml sealed tube. React at 100°C for 18 hours, then cool to room temperature, concentrate, and perform column chromatography to obtain the target product formula (IC), a red solid, with an isolation yield of 100%. MP 210-213°C.

[0040] Product NMR data: 1H NMR [(CD 3 ) 2 SO,400MHz]:δ6.97-7.02(m,1H),7.09(d,J=8.0Hz,1H),7.30-7.34(m,2H),7.35-7.41(m,3H),7.43(dd, J 1 =8.2Hz,J 2 =5.6Hz,1H),7.56(dd,J 1 =9.0Hz,J 2 =2.0Hz, 1H), 7.62(d, J=8.0Hz, 1H), 10.02(s, 1H); 13C[(CD 3 ) 2 SO,100MHz]:δ107.73(d,J=24.6Hz),114.01(d,J=23.4Hz),120.27,121.66,125.84(d,J=10.4Hz),127.22,127.27,128.78,129.82,130.06 ,131.85,133.12,133.76,147.12(J=10.6Hz),156.84,166.85(d,J=250Hz),190.65.

[0041] High resolution mass spec...

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Abstract

The invention discloses a 2-hydroxy-9-fluorenone derivative as well as a synthesis method and application thereof. The synthesis of the 2-hydroxy-9-fluorenone derivative shown in the formula (I) is completed through a one-pot method by taking an o-furan aryl alkynone compound as a raw material under the action of a catalyst and utilizing the reaction processes of intramolecular D-A reaction, epoxy ring opening, aromatization and the like of the o-furan aryl alkynone compound. The preparation method provided by the invention has the advantages of simple and easily available raw materials, no metal catalyst, relatively mild reaction conditions, insensitive reaction to air, good substrate universality, simple post-treatment, excellent yield, environmental friendliness and the like. The prepared 2-hydroxy-9-fluorenone derivative can be applied to preparation of anti-virus, anti-tumor, antipyretic and anti-inflammatory drugs, fluorescent probes, sensitized dyes and other functional materials.

Description

technical field [0001] The invention belongs to the technical field of organic compounds and synthesis, and relates to 2-hydroxy-9-fluorenone compounds and a synthesis method thereof. Background technique [0002] 9-fluorenone compounds are important structural units of many drugs and natural product molecules, and are widely used in the fields of medicine and materials. In terms of medical applications, as early as 1970, Tiorone was found to have antiviral pharmacological effects in mice. Later, it was found that the compound also has the ability to enhance the phagocytic activity of natural killer cells, antipyretic, anti-fibrosis, anti-inflammatory, anti-tumor and interference. Su-induced health and so on. These pharmacodynamic effects are partly attributed to the planar structural modification of the fluorenone skeleton. Due to their unique photoelectric properties, 9-fluorenone compounds are often used as tunable synthons and are used in the field of organic semicondu...

Claims

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Application Information

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IPC IPC(8): C07C49/747C07C45/67C07C49/755
CPCC07C49/747C07C49/755C07C2603/18
Inventor 王程宇管鹏程韩玉孔令凯
Owner LINYI UNIVERSITY
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