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A kind of benzyl phosphine oxide compound and its preparation method and application

A technology of benzylphosphine oxide and compounds, which is applied in the field of phosphorus-containing organic synthesis, can solve the problems of harsh preparation conditions and unfavorable industrial production, and achieve the effects of simple and mild reaction conditions, easy industrial production, and wide application prospects

Active Publication Date: 2022-04-19
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In order to solve the problem that the preparation conditions of existing benzylphosphine oxide compounds are harsh and unfavorable for industrial production, the object of the present invention is to provide a benzylphosphine oxide compound

Method used

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  • A kind of benzyl phosphine oxide compound and its preparation method and application
  • A kind of benzyl phosphine oxide compound and its preparation method and application
  • A kind of benzyl phosphine oxide compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] (1) (hydroxyl (phenyl) methyl) diphenylphosphine oxide has a molecular structure as shown in formula (1):

[0048]

[0049] (2) the preparation method of (hydroxyl (phenyl) methyl) diphenyl phosphorus oxide, comprises the following steps:

[0050]Take a 10mL pressure-resistant reaction tube, add 40mg (0.2mmol) of diphenylphosphine oxide, 2.5mL (20mmol) of benzyl methyl ether, place the reaction tube under the irradiation of a 600nm LED lamp in an air atmosphere, and stir at 60°C for 36 hours . The reaction was purified by flash column chromatography on silica gel with dichloromethane to give the product 50mg, 81% yield, as a white solid.

[0051] Depend on figure 1 with figure 2 It can be seen that 1 H NMR and figure 2 13 C NMR shows that the δ (ppm) of the prepared compound is 1 H NMR (400MHz, CDCl3) δ7.81-7.72 (m, 2H), 7.63-7.56 (m, 2H), 7.51-7.31 (m, 6H), 7.24-7.08 (m, 5H), 5.49 (d, J =4.9Hz,1H); 13 C NMR (100MHz, CDCl3) δ 136.2, 132.3, 132.2, 132.0, 12...

Embodiment 2

[0053] (1) (4-bromophenyl (hydroxyl) methyl) diphenylphosphine oxide has a molecular structure as shown in formula (2):

[0054]

[0055] (2) The preparation method of (4-bromophenyl (hydroxyl) methyl) diphenyl phosphorus oxide may further comprise the steps:

[0056] Take a 10mL pressure-resistant reaction tube, add 40mg (0.2mmol) of diphenylphosphine oxide, 2.5mL (17mmol) of 4-bromobenzyl methyl ether, and place the reaction tube under the irradiation of a 600nm LED lamp in an air atmosphere, at 60°C Stir for 36 hours. The residue was purified by flash column chromatography on silica gel with dichloromethane to give the product 58mg, 75% yield, as a white solid.

[0057] Depend on image 3 with Figure 4 It can be seen that the δ (ppm) of the prepared compound is 1H NMR (400MHz, CDCl3) δ7.77 (ddt, J=11.0,6.9,1.3Hz, 2H), 7.64 (ddt, J=11.1,6.9,1.4Hz, 2H ),7.59-7.36(m,6H),7.29(d,J=8.4Hz,2H),7.05-6.99(m,2H),5.44(t,J=5.5Hz,1H),4.30(s,1H) ; 13C NMR (100MHz, CDCl3) δ 135.3,...

Embodiment 3

[0059] (1) Hydroxyl (4-methoxyphenyl) methyl) diphenylphosphine oxide has a molecular structure as shown in formula (3):

[0060]

[0061] (2) the preparation method of hydroxy (4-methoxyphenyl) methyl) diphenyl phosphorus oxide, comprises the following steps:

[0062] Take a 10mL pressure-resistant reaction tube, add 40mg (0.2mmol) of diphenylphosphine oxide, 2.5mL (17mmol) of (4-methoxybenzyl) methyl ether, and place the reaction tube under the irradiation of a 600nm LED lamp in an air atmosphere , and stirred at 60°C for 36 hours. The reactant was purified by flash column chromatography on silica gel with dichloromethane to obtain 45 mg of the desired product hydroxy(4-methoxyphenyl)methyl)diphenylphosphine oxide as a white solid in a yield of 67%.

[0063] Depend on Figure 5 with Image 6 It can be seen that 1H NMR (400MHz, CDCl3) δ7.89-7.80 (m, 4H), 7.58-7.47 (m, 6H), 7.36-7.30 (m, 2H), 6.97-6.92 (m, 2H), 5.86 (ddt , J=11.5, 9.5, 1.0Hz, 1H), 3.80 (s, 3H); 13CNMR (...

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Abstract

The invention discloses a benzyl phosphine oxide compound, a preparation method and application thereof. The benzyl phosphine oxide compound has heterocyclic aromatic hydrocarbon phosphine oxide and a highly active hydroxyl group, so that it has high biological activity, can be effectively used as a pharmaceutical intermediate, and has broad application prospects in the medical field. Moreover, the benzyl phosphine oxide compound is easy to prepare, has high conversion rate under relatively mild conditions, and the highest product yield can reach 81%.

Description

technical field [0001] The invention belongs to the technical field of phosphorus-containing organic synthesis, and more specifically relates to a benzylphosphine oxide compound and its preparation method and application. Background technique [0002] Organophosphorus compounds have rich physiological activities, special chemical reactivity and excellent photoelectric properties, and have extensive and important applications in the fields of medicine, pesticides, fertilizers, industrial extractants, chemical weapons, reaction ligands and organic flame retardant materials. Value. Especially because of their various biological activities, such as antiviral, antitumor, antibacterial, enzyme inhibitory, etc., their wide application as ligands in synthetic chemistry and their important biological and pharmacological properties have attracted widespread attention from chemists. [0003] Usually, the synthesis of benzylphosphine oxide compounds needs to react at a relatively high ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/53
CPCC07F9/5333
Inventor 刘波霍延平陈迁赵经纬
Owner GUANGDONG UNIV OF TECH
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