Preparation method of beta-hydroxyphosphonate derivatives

A technology of hydroxyphosphonate and derivatives, which is applied in the field of preparation of β-hydroxyphosphonate derivatives, can solve the problems of poor substrate applicability, harsh reaction conditions, and high cost, and achieve stable raw materials, simplified operation steps, and high conversion rate effect

Inactive Publication Date: 2015-02-25
翁后科
View PDF3 Cites 18 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] β-hydroxyphosphonate is widely used in organic synthesis, biochemistry and other fields, so people are committed to developing new methods for the synthesis of β-hydroxyphosphonate; but existing methods have poor substrate applicability, low yield, high cost, Disadvantages of harsh reaction conditions

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation method of beta-hydroxyphosphonate derivatives
  • Preparation method of beta-hydroxyphosphonate derivatives
  • Preparation method of beta-hydroxyphosphonate derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Example 1: Synthesis of dimethyl 2-hydroxyl-2-phenylethylphosphonate

[0039] Using styrene and dimethyl phosphite as raw materials, the reaction formula and experimental steps are as follows:

[0040]

[0041] (1) Add styrene (0.11 g, 1 mmol), dimethyl phosphinate (0.11 g, 1 mmol), manganese acetate (0.41 g, 1.5 mmol) and 10 mL of acetic acid into the reaction flask, and react at 30°C Carry out, TLC follow-up reaction until the end;

[0042] (2) The reaction solution was concentrated to obtain a residue, which was separated by column chromatography (petroleum ether: ethyl acetate = 10:1) to obtain dimethyl 2-hydroxy-2-phenylethylphosphonate (yield 65%);

[0043] (3) Add dimethyl 2-hydroxy-2-phenylethylphosphonate (0.11 g, 0.5 mmol), ammonia water (0.12 g, 4.0 mmol) and 10 mL of acetonitrile obtained in (2) into the reaction flask, and react Carried out at 60°C, TLC followed the reaction until the end;

[0044] (4) The reaction solution was concentrated to remove ...

Embodiment 2

[0047] Embodiment two: the synthesis of diethyl 2-hydroxyl-2-phenylethylphosphonate

[0048] With styrene and diethyl phosphite as raw materials, its reaction formula and experimental steps are as follows:

[0049]

[0050] (1) Add styrene (0.1 g, 1 mmol), diethyl phosphite (0.20 g, 1.5 mmol), manganese acetate (0.41 g, 1.5 mmol) and 10 mL of acetonitrile into the reaction flask, and react at 40°C Carry out, TLC follow-up reaction until the end;

[0051] (2) The reaction solution was concentrated to obtain a residue, which was separated by column chromatography (petroleum ether: ethyl acetate = 10:1) to obtain diethyl 2-hydroxy-2-phenylethylphosphonate (yield 75%);

[0052] (3) Add diethyl 2-hydroxy-2-phenylethylphosphonate (0.14 g, 0.5 mmol) obtained in (2), ammonia water (0.12 g, 4.0 mmol) and 10 mL of acetonitrile into the reaction flask, and react Carried out at 60°C, TLC followed the reaction until the end;

[0053] (4) The reaction solution was concentrated to remo...

Embodiment 3

[0055] Embodiment three: two Synthesis of Isopropyl 2-Hydroxy-2-Phenylethyl Phosphonate

[0056] Taking styrene and diisopropyl phosphite as raw materials, its reaction formula and experimental steps are as follows:

[0057]

[0058] (1) Add styrene (0.1 g, 1 mmol), diisopropyl phosphite (0.25 g, 1.5 mmol), manganese acetate (0.55 g, 2 mmol) and 10 mL of dichloromethane into the reaction flask, and react Carried out at 30°C, followed by TLC until the end of the reaction;

[0059] (2) The reaction solution was concentrated to obtain a residue, which was separated by column chromatography (petroleum ether: ethyl acetate = 10:1) to obtain two Isopropyl 2-hydroxy-2-phenylethylphosphonate (74% yield);

[0060] two The analytical data for isopropyl 2-hydroxy-2-phenylethylphosphonate are as follows: 1 H NMR (300 MHz, CDCl 3 ): δ 7.41-7.27 (m, 5H), 4.73 (s, 1H), 4.75-4.70 (m, 2H), 4.48-4.38 (m, 1H), 2.23-2.13 (m, 2H), 1.27 (m, 12H).

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

Abstract

The invention discloses a preparation method of beta-hydroxyphosphonate derivatives. The preparation method comprises that an arylethene derivative, a phosphorus reagent and manganese acetate are dissolved in a solvent and the solution undergoes a reaction at a temperature of 20-60 DEG C to produce the beta-hydroxyphosphonate derivative. Under the action of ammonia water, a beta-aminophosphonate derivative is prepared from the beta-hydroxyphosphonate derivative. The preparation method utilizes the arylethene derivative as an initiator and utilizes multiple easily available raw materials. The beta-hydroxyphosphonate derivatives belong to multiple types and can be directly used and can be used for other further reactions. The preparation method has a short synthesis route, mild reaction conditions, simple reaction and aftertreatment processes and a high yield and is suitable for large-scale production.

Description

Technical field [0001] The present invention is an organic synthesis field, which involves a method of preparing a β-hydroxyl-based ester derivative. Background technique [0002] β-hydroxylceamate is an important raw material for synthetic β-cypoganate. β-cypamate is an important β-lactam inhibitor; β-hydroxyllytanate derivatives are also synthetic β-aminicateImportant raw materials for derivatives.The structure of β-aminic acid is similar to β-amino acids and has extensive physiological activity, such as antibacterial, stimulating nerves, affecting cell growth and metabolism, analgesic, regulating blood pressure, regulating plant growth, etc. Therefore, it can be used as medicine, pesticides, andAntagonists, anthocyanins synthetic inhibitors and other use. [0003] In existing technologies, the synthesis methods of β-hydroxyl-based glycogenate derivatives are mainly the following: [0004] 1. Under the existence of lithium metal reagents, the reaction of benzenedehyde and dimer...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/40C07F9/38
Inventor 邹建平李大鹏刘奎周少方
Owner 翁后科
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap