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Method for preparing dibenzophosphole derivants

A technology for heterocyclopentadiene and derivatives, which is applied in the field of preparation of dibenzophosphine derivatives, and can solve the problem of restricting the industrial production of dibenzophosphine derivatives and reaction substrates. Difficult to obtain, small scope of application, etc., to achieve the effect of diverse product types, short reaction time, and universality

Active Publication Date: 2013-07-24
翁后科
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] However, the reaction substrate used in the above scheme is difficult to obtain, or the price is relatively expensive, which leads to a small scope of application of the method for preparing dibenzophosphole derivatives, and the above reaction needs to be completed under anhydrous and oxygen-free conditions, Harsh reaction conditions further limit the industrial production of dibenzophosphole derivatives

Method used

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  • Method for preparing dibenzophosphole derivants
  • Method for preparing dibenzophosphole derivants
  • Method for preparing dibenzophosphole derivants

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Example 1: Synthesis of 9-methyl-phosphorene-9-oxide

[0026]

[0027] Add (biphenyl-2-yl)-methylphosphine oxide (0.22 g, 1 mmol), manganese acetate (0.27 g, 1 mmol), ethanol (10 mL) into the reaction flask, react at 40 ° C, and track with TLC The reaction was carried out until the end; the crude product obtained after the reaction was separated by column chromatography to obtain the target product (yield 78%). Main NMR test data: 1 H NMR (400 MHz, CDCl 3 ): δ7.28-7.79 (m, 8H), 3.40 (s, CH 3 ), it can be seen from the analysis that the actual synthesized product is consistent with the theoretical analysis.

Embodiment 2

[0028] Example 2: Synthesis of (9-biphenyl-2-yl)-phosphorene-9-oxide

[0029]

[0030] Add bis(biphenyl-2-yl)-phosphine oxide (0.35 g, 1 mmol), manganese acetate (0.41 g, 1.5 mmol), and acetic acid (10 mL) into the reaction flask, react at 20°C, and track the reaction by TLC Until the end; the crude product obtained after the reaction was separated by column chromatography to obtain the target product (yield 76%).

[0031] Main NMR test data: 1 H NMR (400 MHz, CDCl 3 ): δ8.60-8.72 (m, 1H), 7.45-7.57 (m, 4H), 7.20-7.33 (m, 6H), 7.01-7.02 (m, 1H), 6.85 (t, J = 7.0Hz, 1H), 6.60 (t, J = 7.0Hz, 2H), 6.24 (d, J = 7.0Hz, 2H); 13 C NMR (100MHz, CDCl 3 ): δ142.3 (d, J = 22.2Hz), 137.0 (d, J = 402.6Hz), 133.0, 132.1, 131.3 (d, J = 9.8Hz), 129.4 (d, J = 9.2Hz), 129.0 (d, J = 10.8Hz), 128.9, 127.6 (d, J= 10.8Hz), 127.1, 126.6, 121.5 (d, J =9.8Hz). HRMS (M + ): m / z (%), calcd for C 24 h 17 OP 352.1017, found 352.1005 (M + , 61.65), the analysis shows that...

Embodiment 3

[0032] Example 3: Synthesis of 9-phenyl-phosphorene-9-oxide

[0033]

[0034] (Biphenyl-2-yl)-phenylphosphine oxide (0.28 g, 1 mmol), manganese acetate (0.41 g, 1.5 mmol), acetonitrile (10 mL) were added to the reaction flask, and the reaction was carried out at 20 °C, followed by TLC The reaction was carried out until the end; the crude product obtained after the reaction was separated by column chromatography to obtain the target product (yield 85%).

[0035] Main NMR test data: 1 H NMR (400 MHz, CDCl 3 ): δ7.24-7.81 (m, 13H); 13 C NMR (100MHz, CDCl 3 ): δ142.0 (d, J = 21.8Hz), 133.6 (d, J = 2.0Hz), 133.0 (d, J = 106.7Hz), 132.4 (d, J = 2.9Hz), 131.2 (d, J = 10.4Hz), 131.0 (d, J = 103.2Hz), 130.1 (d, J = 9.6Hz), 129.7 (d, J = 9.6Hz), 128.9 (d, J = 12.6Hz), 121.4 (d, J = 10.1Hz). HRMS (M + ): m / z (%), calcd for C 18 h 13 OP 276.0704, found 276.0706 (M + , 62.04) , it can be seen from the analysis that the actual synthesized product is consis...

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Abstract

The invention discloses a method for preparing dibenzophosphole derivants. The method comprises the following steps of: taking manganese acetate as an accelerant and a diphenylphosphine oxide derivant as a reactant, and reacting in an organic solvent to obtain the dibenzophosphole derivant, wherein a structural formula of the diphenylphosphine oxide derivant is as shown in specification. According to the method, the diphenylphosphine oxide derivant which is well-sourced is used as an inhibitor to react, and therefore, various types of products can be obtained; the diphenylphosphine oxide derivant can be directly used or used for other organic synthesis reactions without anhydrous and anaerobic conditions, wherein the reaction temperature is 20-120 DEG C, the reaction conditions are mild, the reaction operation and posttreatment processes are simple, the cost is low and the yield of the target product is high.

Description

technical field [0001] The invention belongs to the technical field of preparation of phosphorus-containing organic compounds, and in particular relates to a preparation method of dibenzophosphole derivatives. Background technique [0002] At present, the research on organic π-conjugated photoelectric functional materials is very active, and they have shown broad application prospects in the fields of electroluminescent diodes, solar cells, nonlinear optics, sensors, etc., and have greatly promoted the development of organic electronics. Introducing heteroatoms into the π-conjugated system is an effective way to adjust the photoelectric properties of organic electroluminescent materials. In recent years, phosphorus, the No. 15 element in the periodic table, has received high attention. The introduction of phosphorus atoms into the organic π-conjugated system yields Phosphorus-containing organic electroluminescent materials have become one of the important research methods fo...

Claims

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Application Information

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IPC IPC(8): C07F9/6568
Inventor 邹建平李大鹏潘向强刘业业曹晓慧
Owner 翁后科
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