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Method for continuously synthesizing 9-phenol phenanthrene compound under promotion of visible light

A visible light and compound technology, applied in the preparation of organic compounds, chemical instruments and methods, formation/introduction of hydroxyl groups, etc., can solve the problems of harsh reaction conditions, long reaction time, high cost, etc., and achieves simple operation and reaction time. The effect of shortening and increasing conversion rate

Pending Publication Date: 2022-07-05
NANJING ADVANCED BIOLOGICAL MATERIALS & PROCESS EQUIP INST CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] According to existing literature reports, the method for synthesizing 9-phenanthrene compounds mainly includes: (1) under heating conditions, use oxides to oxidize alkynes and then cyclize, refer to the literature (J.Org.Chem.2017,82,7070 -7076; J.Am.Chem.Soc.2021,143,15420-15426); (2) Under acidic conditions, low-temperature reduction carbonyl ring closure reaction, refer to the literature (Eur.J.Org.Chem.2017,2017 ,262-265); in addition, although many schemes have been reported, there are some obvious shortcomings in these schemes: harsh reaction conditions, need to use toxic and harmful substances and oxidants, long reaction time, etc.
These defects not only bring safety hazards to experimental production or industrial production, but also bring high costs to industrial production.

Method used

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  • Method for continuously synthesizing 9-phenol phenanthrene compound under promotion of visible light
  • Method for continuously synthesizing 9-phenol phenanthrene compound under promotion of visible light
  • Method for continuously synthesizing 9-phenol phenanthrene compound under promotion of visible light

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Synthesis of Example 1 Compound 2a:

[0039] 0.3 mmol (0.0763 g) of compound 1a, 0.3 mmol (0.0655 g) of diphenyl disulfide and 0.6 mmol (0.0360 g) of acetic acid were dissolved in 3 mL of acetonitrile to obtain a homogeneous solution, which was added to a syringe; the syringe was set to inject pump, and inject the mixed solution in the syringe at a flow rate of 0.3mL / min, and then uniformly mix with air through the gas pressure regulating valve and flow into the microchannel reaction device; place the microchannel reaction device in a 30W blue LED lamp Irradiation; the reaction volume of the microchannel reaction device is V=3mL, and the reaction time is 10min; after the reaction in the microchannel reactor goes through one cycle, the reaction liquid is collected, and the product yield calculated by HPLC is 81%, and the volume ratio is 2:1 Extract with ethyl acetate / saturated aqueous sodium chloride solution (V=10 mL×3), and after concentration, the product 2a is obtain...

Embodiment 2

[0040] Synthesis of Example 2 Compound 2a:

[0041] 0.3 mmol (0.0763 g) of compound 1a, 0.3 mmol (0.0655 g) of diphenyl disulfide and 0.6 mmol (0.0684 g) of trifluoroacetic acid were dissolved in 3 mL of acetonitrile to obtain a homogeneous solution, which was added to a syringe; syringe set up On the syringe pump, inject the mixed solution in the syringe at a flow rate of 0.3mL / min, and then uniformly mix it with air through the gas pressure regulating valve and flow into the microchannel reaction device; place the microchannel reaction device in a 30W blue light LED light irradiation; the reaction volume of the microchannel reaction device is V=3mL, and the reaction time is 10min; after the reaction in the microchannel reactor goes through one cycle, the reaction liquid is collected, and the product yield is 70% calculated by the HPLC method, and the volume ratio is 2 : 1 ethyl acetate / saturated aqueous sodium chloride solution (V=10mL×3) for extraction, and after concentrat...

Embodiment 3

[0042] Synthesis of Example 3 Compound 2a:

[0043] 0.3 mmol (0.0763 g) of compound 1a, 0.3 mmol (0.0655 g) of diphenyl disulfide and 0.6 mmol (0.0900 g) of trifluoromethanesulfonic acid were dissolved in 3 mL of acetonitrile to obtain a homogeneous solution, which was added to a syringe; The syringe is placed on the syringe pump, and the mixed solution in the syringe is injected at a flow rate of 0.3mL / min, and then uniformly mixed with air through the gas pressure regulating valve and then flows into the microchannel reaction device; the microchannel reaction device is placed in 30W The reaction volume of the microchannel reaction device was V=3mL, and the reaction time was 10min; after the reaction in the microchannel reactor went through a cycle, the reaction liquid was collected, and the product yield was calculated by HPLC as 56%, and the volume was 56%. Extracted with 2:1 ethyl acetate / saturated aqueous sodium chloride solution (V=10 mL×3), concentrated and separated by...

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Abstract

The invention discloses a method for continuously synthesizing a 9-phenol phenanthrene compound promoted by visible light, which comprises the following steps: by taking an alkynyl compound 1 as a reaction raw material, carrying out continuous reaction in a micro-channel reaction device in the presence of a free radical initiator, an additive and oxidizing gas to obtain a target compound 2. According to the invention, a micro-reaction device continuous synthesis method is adopted, so that the preparation of 9-phenol phenanthrene in a visible light promotion manner is proposed for the first time; by using the microchannel reactor device, the reaction time is greatly shortened, the conversion rate of the reaction is improved, and the method has a series of advantages of low process operation cost, greenness, high efficiency, safety, no toxicity, mild reaction conditions, simplicity in operation, high safety coefficient and the like.

Description

technical field [0001] The invention belongs to the field of synthesis of 9-phenanthrene compounds, in particular to a method for continuously synthesizing 9-phenanthrene compounds promoted by visible light. Background technique [0002] PAHs are an important class of compounds with various physicochemical properties and biological activities. phenanthrene is derived from its widespread presence in biologically active molecules including natural products, and exhibits various biological activities (J.Pharm.Sci.1993,82,571-574; J.Org,Chem.2003,68,2099- 2108), such as anti-cancer, antibacterial, anti-HIV virus, etc., so it is widely known in polycyclic aromatic hydrocarbons. Furthermore, phenanthrene derivatives are widely used for the fabrication of valuable organic materials due to their optoelectronic properties (Chem. Rev. 2007, 107, 1066-1096), such as organic semiconductors, organic solar cells and organic light-emitting diodes. In conclusion, phenanthrene-containing s...

Claims

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Application Information

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IPC IPC(8): C07B41/02C07C37/58C07C39/12C07C39/40C07C41/26C07C43/23C07C201/12C07C205/20
CPCC07B41/02C07C37/58C07C41/26C07C201/12C07C39/12C07C39/40C07C43/23C07C205/20Y02E10/549
Inventor 乔凯马涛方正李玉光沈磊郭凯
Owner NANJING ADVANCED BIOLOGICAL MATERIALS & PROCESS EQUIP INST CO LTD
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