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Beta-hydroxyimino phosphono derivatives and preparation methods thereof

A technology of hydroxyliminophosphono and hydroxyliminodiphosphono, which is applied in the field of β-hydroxyiminophosphono derivatives and its preparation, and can solve the problem of cumbersome reaction steps, harsh reaction conditions, and multiple reaction steps. and other problems, to achieve the effect of easy-to-obtain raw materials, short reaction time and mild reaction conditions

Active Publication Date: 2018-01-12
江苏强盛功能化学股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] D. M. Mizrahi et al disclosed a synthetic method of β-aminodiphosphonic acid compounds, and tested its inhibitory activity on induced hypercalcemia, the results showed that the compound showed good activity, and the effect was better than that of clinically used anti-inflammatory drugs. Osteoporosis drug disodium clophosphate; however, the published compound synthesis route is cumbersome and requires the use of a strong corrosive reagent, thionyl chloride
In 2003, A. Obojska and others synthesized several β-aminophosphoric acid derivatives and tested their inhibitory activity against streptococcus. Inhibitory activity, in 2013, Lyzwa reported that nitrogen-containing organophosphorus compounds have activities such as inhibiting HIV protease and serine protease; however, the disclosed compound synthesis method has the disadvantages of rare raw materials, harsh reaction conditions, and many reaction steps

Method used

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  • Beta-hydroxyimino phosphono derivatives and preparation methods thereof
  • Beta-hydroxyimino phosphono derivatives and preparation methods thereof
  • Beta-hydroxyimino phosphono derivatives and preparation methods thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Example 1: Synthesis of 2-phenyl-2-hydroxyimino ethyl diphenoxyphos

[0047] Using styrene and diphenylphosphine oxide as raw materials, the reaction steps are as follows:

[0048] Add styrene (0.042 g, 0.4 mmol), diphenoxyphos (0.081 g, 0.4 mmol), tert-butyl nitrite (0.041 g, 0.4 mmol), silver nitrate (0.07 g, 0.04 mmol) in the reaction flask, Methanol (2.5 mL), react at 10°C;

[0049] TLC tracking reaction until complete completion;

[0050] The crude product obtained after the reaction was separated by column chromatography (ethyl acetate:petroleum ether=1:1) to obtain the target product (yield 80%). The analytical data of the product are as follows: 1 H NMR (400 MHz, CDCl 3 ): δ 11.47 (s, 1H), 7.80 –7.73 (m, 4H), 7.65 – 7.55 (m, 2H), 7.57 – 7.51 (m, 2H), 7.50 –7.45(m, 4H),7.32 – 7.25 (m, 3H ), 4.11 (d, J = 15.4 Hz, 2H).

Embodiment 2

[0051] Example 2: Synthesis of 2-(2-methylphenyl)-2-hydroxyiminoethyl diphenoxyphos

[0052] With 2-methylstyrene and diphenylphosphine oxide as raw materials, the reaction steps are as follows:

[0053] Add 2-methylstyrene (0.047 g, 0.4 mmol), diphenoxyphos (0.081 g, 0.4 mmol), tert-butyl nitrite (0.082 g, 0.8 mmol) and silver nitrate (0.14 g, 0.08 mmol), ethanol (2.5 mL), react at room temperature;

[0054] TLC tracking reaction until complete completion;

[0055] The crude product obtained after the reaction was separated by column chromatography (ethyl acetate:petroleum ether=1:1) to obtain the target product (yield 75%). The analytical data of the product are as follows: 1 H NMR (400 MHz, CDCl 3 ): δ 10.85 (s, 1H), 7.80 –7.71 (m, 4H), 7.53 – 7.37 (m, 6H), 7.12 – 6.97 (m, 4H), 3.78 (d, J = 11.0 Hz, 2H), 2.07 (s, 3H).

Embodiment 3

[0056] Example 3: Synthesis of 2-(4-methylphenyl)-2-hydroxyiminoethyl diphenoxyphos

[0057] With 4-methylstyrene, diphenylphosphine oxide as raw material, its reaction steps are as follows:

[0058] Add 4-methylstyrene (0.047 g, 0.4 mmol), diphenoxyphos (0.081 g, 0.4 mmol), tert-butyl nitrite (0.123 g, 1.2 mmol) and silver nitrate (0.21 g, 0.12 mmol), acetonitrile (2.5 mL), react at 30°C;

[0059] TLC tracking reaction until complete completion;

[0060] The crude product obtained after the reaction was separated by column chromatography (ethyl acetate:petroleum ether=1:1) to obtain the target product (yield 82%). The analytical data of the product are as follows: 1 H NMR (400 MHz, CDCl 3 ): δ 11.37 (s, 1H), 7.81 –7.72 (m, 4H), 7.55 – 7.47 (m, 8H), 7.08 (d, J = 7.5 Hz, 2H), 4.08 (d, J =15.4 Hz, 2H), 2.28 (s, 3H).

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Abstract

The invention discloses beta-hydroxyimino phosphono derivatives and preparation methods thereof. By the preparation methods, alkenes are used as starting materials, and raw materials are easy to obtain and wide in types; products prepared by the preparation methods are diverse in types and wide in application, can be directly used, and can be applied to synthesis of organic phosphine medicines; inaddition, the preparation methods provided by the invention are simple in steps, mild in reaction condition, high in target product yield, low in pollution and simple in reaction operation and posttreatment process, and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of preparation of organic compounds, and in particular relates to a β-hydroxyimino phosphonyl derivative and a preparation method thereof. Background technique [0002] Nitrogen-containing organophosphorus compounds have a wide range of biological activities, and have important applications in anti-hypercalcemia, anti-HIV virus, antibacterial, and as enzyme inhibitors; in addition, β-phosphoryl oxime free radical compounds can also be used in biological molecules Marker (Il'yasov A. V. Phosphorus-containing iminoxyl and nitroxyl free radicals as promising spin labels. Biophysics , 2013, 58(2): 167.). [0003] D. M. Mizrahi et al disclosed a synthetic method of β-aminodiphosphonic acid compounds, and tested its inhibitory activity on induced hypercalcemia, the results showed that the compound showed good activity, and the effect was better than that of clinically used anti-inflammatory drugs. Osteoporosis d...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/40C07F9/53C07F9/572C07F9/58C07F9/655
CPCC07F9/5333C07F9/65515C07F9/58C07F9/5728C07F9/5325C07F9/4006C07F9/4056C07F9/4009C07B2200/03
Inventor 邹建平应志耀张沛之陶泽坤李建安
Owner 江苏强盛功能化学股份有限公司
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